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Development of highly efficient, selective, and practical synthetic method of pseudo-peptides possessing anti-tumour activity.

Research Project

Project/Area Number 09557179
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section展開研究
Research Field Chemical pharmacy
Research InstitutionKYOTO UNIVERSITY

Principal Investigator

FUJII Nobutaka (1999)  Kyoto University, Graduate School of Pharmaceutical Sciences, Professor, 薬学研究科, 教授 (60109014)

井深 俊郎 (1997-1998)  京都大学, 薬学研究科, 教授 (80025692)

Co-Investigator(Kenkyū-buntansha) OHTAKA Akira  Kyoto University, Graduate School of Pharmaceutical Sciences, Associate Professor, 薬学研究科, 助教授 (20201973)
YAMAMOTO Yoshinori  Tohoku University, Graduate School of Sciences, Professor, 理学研究科, 教授 (60029519)
IBUKA Toshiro  Kyoto University, Graduate School of Pharmaceutical Sciences, Professor, 薬学研究科, 教授 (80025692)
TANAKA Hirokazu  Fujisawa Pharmaceutical Co., Ltd., Manager of Research Information, 研究情報部, 研究情報担当部長
HOSOTANI Ryo  Kyoto University, Graduate School of Medical Sciences, Associate Professor, 医学研究科, 助教授 (00139908)
玉村 啓和  京都大学, 薬学研究科, 講師 (80217182)
藤井 信孝  京都大学, 薬学研究科, 教授 (60109014)
Project Period (FY) 1997 – 1999
Project Status Completed (Fiscal Year 1999)
Budget Amount *help
¥13,000,000 (Direct Cost: ¥13,000,000)
Fiscal Year 1999: ¥3,500,000 (Direct Cost: ¥3,500,000)
Fiscal Year 1998: ¥3,500,000 (Direct Cost: ¥3,500,000)
Fiscal Year 1997: ¥6,000,000 (Direct Cost: ¥6,000,000)
KeywordsOrganocopper Compound / Bombesin Antagonist / SN2-type Ring-Opening / Alkene Isostere / Aziridinylenoate / Vinylaziridine / Organopalladium Compound / Allylpalladium Complex / トリプトファン・イソスター / トリプトフアン・イソスター
Research Abstract

1.We found a convenient method for the transformation of undesired anti-amino alcohols into desired cis-2-vinylaziridines, which are key synthetic intermediates for biologically active(E)-alkene peptide-isosteres, via trans-2-vinylaziridines by Pd(0)-catalyzed equilibration reaction.
2.Various cis-aziridine derivatives were efficiently synthesized from 4-alkyl-5-vinyloxazilidin-2-ones and β-aziridinyl-α, β-unsaturated esters by the Pd(0)-mediated equilibration reaction.
3.The ab initio calculations revealed that cis-β-aziridinyl-α, β-unsaturated esters, possessing cis-(E)-configuration, are more stable than their diastereoisomers. These results are compatible with the experimental results.
4.In combination with Pd(0)-mediated isomerization and the regio- and stereo-specific SN2-type ring-opening reactions of β-aziridinyl-α,β-unsaturated esters with Brφnsted acids, the completely stereocontrolled synthetic process for(L,L)-, (L,D)-, (D,D)-, and (D,L)-type(E)-alkene dipeptide isosteres starting from amino acids has been established.
5.Various peptide-isosteres containing Trp-, Asp-, Cys-, and Glu-analogues were synthesized by the reductive alkylation with organocopper reagents or by the nucleophilic alkylation with zinc-copper mixed reagents.
6.Several bombesin analogues with(E)-alkene bond were prepared by replacing a constituent amino acid of bombesin with the synthesized peptide-isosteres, and these compounds were revealed to be potent bombesin receptor antagonists.

Report

(4 results)
  • 1999 Annual Research Report   Final Research Report Summary
  • 1998 Annual Research Report
  • 1997 Annual Research Report
  • Research Products

    (124 results)

All Other

All Publications (124 results)

  • [Publications] H.Ohno et al.: "A Synthesis of Chiral Amino Allenes via an Organocyanocuprate-Mediated Ring-Opening Reaction of Enantiopure Ethynylaziridines"Tetrahedron Letters. 40. 349-352 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H.Ohno et al.: "The First Palladium-Catalyzed Aziridination Reaction of Amino Allenes"J. Org. Chem.. 64. 2992-2993 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H.Ohno et al.: "Sterically Congested Activated Aziridines : Highly Stereoselective Synthesis of Both 2.3-Cis-and 2.3-Trans-2-Alkenvl-3-alkvlaziridines from Common Intermediates"Tetrahedron Letters. 40. 1331-1334 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H.Tamamura et al.: "Regiospecific Ring-opening Reactions of β-Aziridiny1-α, β-enoates with Acids : Application to the Stereoselective Synthesis of a Couple of Diastereoisomeric(E)-"J. Chem. Soc., Perkin Trans. 1. 2983-2996 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] R.Yanada et al.: "Diastereoselective Allylation and Alkylation of Optically Active Imines with Metallic Samarium and a Catalytic Amount of Iodine"Tetrahedron. 55. 13947-13956 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] M.Okaniwa et al.: "Enantioselective addition of diethylzinc to aldehydes with novel chiral C2-symmetric dimeric ligands"Tetrahedron Letters. 41. 1047-1050 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] K.Ishii et al.: "Selective synthesis of Nonracemic 3-Pyrrolines and 2,3-cis-2vinylaziridines from(Z)-Amino Allylic Alcohols : New Synthetic Route to Chiral 3,4-Dehydroproline"Synlett. 228-230 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] K.Ishii et al.: "Selective synthesis of 2,3-cis-2-Vinyl-3-alkylaziridines and 3-Pyrrolines from Common Intermediates(Z)-4-N-Arvlsulfonvlaminoalk-2-en-1-ols"J. Chem. Soc., Perkin Trans. 1. 2155-2163 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H.Ohno et al.: "Convenient syntheses of chiral 3-substituted 2-ethynylaziridines"J. Chem. Soc., Perkin Trans. 1. 2949-2962 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] M.Anzai et al.: "Palladium-catalyzed Regio-and Stereoselective Synthesis of N-Protected 2,4-Dialkylated Azacyclobutanes from Amino Allenes"Tetrahedron Letters. 40. 7393-7397 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Y.Takemoto et al.: "Utility of a Diene-tricarbonyliron Complex as a Chiral Auxiliary : Regio-and Stereocontrolled Functionalization of Acyclic Diene Ligands"J. Am. Chem. Soc. 121. 9143-9154 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Y.Takemoto et al.: "CAN-Indced Double Ether Formation : Synthesis of trans-and cis-Fused Tricyclic Ethers from 3-Oxabicyclo[3. 1. 0]hexyl Sulfides"Chem. Commun.. 2515-2516 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Y.Takemoto et al.: "Stereospecific Migration of an Fe(CO)3 Group on Acyclic Conjugated Treines bearing an Electron-withdrawing Group"Tetrahedron Letters. 41. 85-88 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H.Ohno et al.: "Stereoselective Synthesis of Chiral Amino Allenes by Organocopper-Mediated anti SN2'-Substitution Reaction of Chiral Ethynylaziridines"Tetrahedron. (印刷中).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H.Tamamura et al.: "Unambiguous Synthesis of Stromal Cell-derived Factor-1 by Regioselective Disulfide Bond Formation using DMSO-aqueous HCI System"Chem. Commun.. 151-152 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H.Tamamura et al.: "Effective Lowly Cytotoxic Analogs of an HIV-Cell Fusion Inhibitor T22(「Tvr5,12,Lvs7」-polvphemusin II)"Bioorg. Med. Chem.. 6. 231-238 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H.Tamamura et al.: "Convenient One-pot Synthesis of Cystine-Containing Peptides Using the Trimethylsilyl Chloride-Dimethylsulfoxide/trifluoroacetic Acid System and"J. Chem. Soc., Perkin Trans. 1. 495-500 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H.Habashita et al.: "A New Synthesis of the Central Substracture of Botryococcenes"J. Org. Chem.. 63. 2391-2396 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H.Tamamura et al.: "Downsizing of an HIV-Cell Fusion Inhibitors T22([Tyr5,12,Lys7]-Polyphemusin II), with the Maintenance of Anti-HIV Activity and Solution Structure"Bioorg. Med. Chem.. 6. 473-479 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H.Tamamura et al.: "Pharmacophore Identification of a Chemokine Receptor (CXCR4) Antagonist, T22(「Tvr5,12,Lvs7」-Polvphemusin II), which Specifically Blocks T Cell-Line-"Bioorg. Med. Chem.. 6. 1033-1041 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] A.Toda et al.: "Reactons of N-Arylsulfony1-2, 3-cis-and trans-3-Alkyl-2-Vinylaziridines with Organocopper Reagents ; Imortance of 2,3-cis-Stereochemistry in controlling"J. Org. Chem.. 63. 7053-7061 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] A.Honda et al.: "Rhodium(I)-or Iridium(I)-Mediated Equilibrated Reactions of Activated 2,3-cis and trans-3-Alkyl-2-vinylaziridines"Synlett. 969-970 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Y.Takemoto et al.: "Utility of a diene-tricarbonyliron complex as mobile chiral auxiliary : iterative use for constructing contiguous chirl centers"Chem. Commun.. 1911-1912 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H.Ohno et al.: "A 2,3-Selective Synthesis of Aziridines Bearing a Vinyl Group from Allyl Methyl Carbonates and Allyl Mesylates"J. Chem. Soc., Perkin Trans. 1. 3703-3716 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H.Ohno et al.: "A convenient Synthesis of Activated Enantionerically Pure Ethynyl-aziridenes"Tetrahedron : Asymmetry. 9. 3929-3933 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Y.Takemoto et al.: "Stereoselective Synthesis of Cis-Fused Chlorinated Bicyclic Ethers via CAN-Mediated Ring-Opening of Cyclopropylsulfides"Tetrahedron Letters. 39. 7454-7548 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Y.Takemoto et al.: "Asymmetric Synthesis of (Diene) Fe (CO)_3 Complexes by a Catalytic Enantioselective Alkylation using Dialkylzincs"Tetrahedron. 54. 15567-15580 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H.Tamamura et al.: "A Low-molecular-weight Inhibitor against the Chemokine Receptor CXCR4 : A Strong Anti-HIV Peptide T 140"Biochem. Biophys. Res. Commun.. 253. 877-882 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] K.Miyasaka et al.: "Cholinergic Involvement in Cholecystokinin (CCK) Release by Luminal Oleic Acid"J. of Autonomic Nervous System. 63. 179-182 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] K.Fujimoto et al.: "Effects of Structural Modulation on Biological Activity of Bombesin Analogues with (E)-Alkene Bond"Life Science. 60. 29-34 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] M.Noda et al.: "Synthesis of (E)-Alkene Dipeptide Isosters of Tryptophan-Valine"Shimadzu Review. 54. 231-234 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] T.Ibuka et al.: "A Thermodynamic Preference of Chiral N-Methanesulfonyl and N-Arylsulfonyl 2,3-cis-3-Alkyl-2-Vinylaziridines over Their 2,3-trans-Isomers : Usefl"J. Org. Chem.. 62. 999-1015 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] T.Ibuka et al.: "Palladium(0)-catalyzed Isomerization Reaction of Aziridines bearing an α,β-Unsaturated Ester Group : A Thermodynamic Prefernce for Chiral"J. Org. Chem.. 62. 2982-2991 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Y.Chounan et al.: "A Chemical Scale for Evaluating the Electron Transfer Ability of Alkylcopper Reagents"Bull. Chem. Soc. Jpn.. 70. 1953-1959 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] N.Masaki et al.: "A highly Stereoselective Synthesis of the Functionalized (E)-Alkene Dipeptide Isosteres of Trp-Val via Organocvanocopper-Lewis Acid Mediated Reaction"Chem. Pharm. Bull.. 45. 1259-1264 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H.Ohno et al.: "Palladium-catalyzed Reductive ring Opening with Formic Acid of Aziridines Bearing an α,β-Unsaturated Ester Group"Tetrahedron. 53. 12933-12946 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H.Aoyama et al.: "Regio-and Stereoselectivity in Reactions of 2,3-cis-and trans-3-Alkyl-2-Vinylaziridines with Organocopper Reagents : Importance of 2,3-cis-"Tetrahedron Letters. 38. 7383-7386 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H.Habashita et al.: "One-Pot Transformation of p-Toluenesulfonates of 2,3-Epoxy Alcohols into Allylic Alcohols"Tetrahedron Letters. 38. 8307-8310 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H.Tamamura et al.: "Regiospecific Ring-Opening Reactions of Aziridines Bearing an α,β-Unsaturated Ester group with Trifluoroacetic Acid : Application to"Chem. Commun.. 2327-2328 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H. Ohno et al.: "A Synthesis of Chiral Amino Allenes via an Organocyanocupurprate-Mediated Ring-Opening Reaction of Enantiopure Ethynylaziridines."Tetrahedron Letters. 40. 349-352 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H. Ohno et al.: "The First Palladium-Catalyzed Aziridination Reaction of Amino Allenes."J. Org. Chem.. 64. 2992-2993 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H. Ohno et al.: "Sterically Congested Activated Aziridines : Highly Stereoselective Synthesis of Both 2,3-Cis-and 2,3-Trans-2-Alkenyl-3-alkylaziridines from Common Intermediates."Tetrahedron Letters. 40. 1331-1334 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H. Tamamura et al.: "Regiospecific Ring-opening Reactions of β-Aziridinyl-α,β-enoates with Acids : Application to the Stereoselective Synthesis of a Couple of Diastereoisomeric (E)-Akene Dipeptide Isosteres from a Single β-Aziridino-α,β-enoate and to the Convenient Preparation of Amino Alcohols bearing α,β-Unsaturated Ester Groups."J. Chem. Soc., Perkin Trans. 1. 2983-2996 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] R. Yanada et al.: "Diastereoselective Allylation and Alkylation of Optically Active Imines with Metallic Samarium and a Catalytic Amount of Iodine."Tetrahedron. 55. 13947-13956 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] M. Okaniwa et al.: "Enantioselective addition of diethylzinc to aldehydes with novel chiral CィイD22ィエD2-symmetric dimeric ligands."Tetrahedron Letters. 41. 1047-1050 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] K. Ishii et al.: "Selective Synthesis of Nonracemic 3-Pyrrolines and 2,3-cis-2-vinylaziridines from (Z)-Amino Allylic Alcohols : New Synthetic Route to Chiral 3,4-Dehydroproline."Synlett. 228-230 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] K. Ishii et al.: "Selective Synthesis of 2,3-cis-2-Vinyl-3-alkylaziridines and 3-Pyrrolines from Common Intermediates(Z)-4-N-Arylsulfonylaminoalk-2-en-1-ols."J. Chem. Soc., Perkin Trans. 1. 2155-2163 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H. Ohno et al.: "Convenient syntheses of chiral 3-substituted 2-ethynylaziridines."J. Chem. Soc., Perkin Trans.1. 2949-2962 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] M. Anzai et al.: "Palladium-catalyzed Regio-and Stereoselective Synthesis of N-Protected 2,4-Dialklated Azacyclobutanes from Amino Allenes."Tetrahedron Letters. 40. 7393-7397 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Y. Takemoto et al.: "Utility of a Diene-tricarbonyliron Complex as a Chiral Auxiliary : Regio-and Stereocontrolled Functionalization of Acyclic Diene Ligands"J. Am. Chem. Soc.. 121. 9143-9154 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Y. Takemoto et al.: "CAN-Indced Double Ether Formation : Synthesis of trans-and cis-Fused Tricyclic Ethers from 3-Oxabicyclo[3.1.0]hexyl Sulfides"Chem. Commun. 2515-2516 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Y. Takemoto et al.: "Stereospecific Migration of an Fe(CO)ィイD23ィエD2 Group on Acyclic Conjugated Trienes bearing an Electron-withdrawing Group."Tetrahedron Lettters. 41. 85-88 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H. Ohno et al.: "Stereoselective Synthesis of Chiral Amino Allenes by Organocopper-Mediated anti SィイD2NィエD22'-Substitution Reaction of Chiral Ethynylaziridines."Tetrahedron. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H. Tamamura et al.: "Unambiguous Synthesis of Stromal Cell-derived Factor-1 by Regioselective Disulfide Bond Formation using DMSO-aqueous HC1 System."Chem. Commun.. 151-152 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H. Tamamura, et al.: "Effective Lowly Cytotoxic Analogs of an HIV-Cell Fusion Inhibitor, T22 ([Tyr5,12,Lys7]-polyphemusin II)."Bioorg. Med. Chem.. 6. 231-238 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H. Tamamura, et al.: "Convenient One-pot Synthesis of Cystine-Containing Peptides Using the Trimethylsilyl Chloride-Dimethylsulfoxide/trifluoroacetic Acid System and Its Application to the Synthesis of Bifunctional Anti-HIV Compounds."J. Chem. Soc., Perkin Trans 1. 495-500 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H. Habashita, et al.: "A New Synthesis of the Central Substracture of Botryococcenes."J. Org. Chem.. 63. 2391-2396 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H. Tamamura et al.: "Downsizing of an HIV-Cell Fusion Inhibitors, T22([Tyr5,12,Lys7]-Polyphemusin II), with the Maintenance of Anti-HIV Activity and Solution Streucture."Bioorg. Med. Chem.. 6. 473-479 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H. Tamamura et al.: "Pharmacophore Identification of a Chemokine Receptor(CXCR4)Antagonist, T22 ([Tyr5,12,Lys7]-Plyphemusin II), Which Specifically Blocks T Cell-Line-Tropic Infection."Bioorg. Med. Chem.. 6. 1033-1041 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] A. Toda et al.: "Reactions of N-Arylsulfony1-2,3-cis-and trans-3-Alky1-2-Vinylaziridines with Organocopper Reagents : Importance of 2,3-cis-Stereochemistry in Controlling Regio-and Stereoselectivity."J. Org. Chem.. 63. 7053-7061 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] A. Honda et al.: "Rhodium(I)-or Iridium(I)-Mediated Equilibrated Reactions of Activated 2,3-cis and trans-3-Alkyl-2-vinylaziridines."Synlett. 969-970 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Y. Takemoto et al.: "Utility of a diene-tricarbonyliron complex as mobile chiral auxiliary : iterative use for constructing contiguous chiral centers."Chem. Commun.. 1911-1912 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H. Ohno et al.: "A 2,3-Selective Synthesis of Aziridines Bearing a Vinyl Group from Allyl Methyl Carbonates and Allyl Mesylates."J. Chem. Soc., Perkin Trans. 1. 3703-3716 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H. Ohno et al.: "A Convenient Synthesis of Activated Enantionerically Pure Ethynyl-aziridines."Tetrahedron : Asymmetry. 9. 3929-3933 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Y. Takemoto et al.: "Stereoselective Synthesis of Cis-Fused Chlorinated Bicyclic Ethers via CAN-Mediated Ring-Opening of Cyclopropylsulfides."Tetrahedron Letters. 39. 7545-7548 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Y. Takemoto et al.: "Asymmetric Synthesis of (Diene)Fe(CO)ィイD23ィエD2 Complexes by a Catalytic Enantioselective Alkylation using Dialkylzincs."Tetrahedron. 54. 15567-15580 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H. Tamamura et al.: "A Low-molecular-weight Inhibitor against the Chemokine Receptor CXCR4 : A Strong Anti-HIV Peptide T 140."Biochem. Biophys. Res. Commun. 253. 877-882 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] K. Miyasaka et al.: "Cholinergic Involvement in Cholecystokinin (CCK) Release by Luminal Oleic Acid."J. of Autonomic Nervous System. 63. 179-182 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] K. Fujimoto et al.: "Effects of Structural Modulation on Biological Activity of Bombesin Analogues with (E) -Alkene Bond."Life Science. 60. 29-34 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] M. Noda et al.: "Synthesis of (E) -Alkene Dipeptide Isosteres of Tryptophan-Valine."Shimadzu Review. 54. 231-234 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] T. Ibuka et al.: "A Thermody namic Preference of Chiral N-Methanesulfonyl and N-Arylsulfonyl 2,3-cis-3-Alkyl-2-Vinylaziridines over Their 2,3-trans-Isomers : Useful Palladium(0)-Catalyzed Equilibration Reactions for the Synthesis of (E)-Alkene Dipeptide Isosteres."J. Org. Chem.. 62. 999-1015 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] T. Ibuka et al.: "Palladium (0) -catalyzed Isomerization Reaction of Aziridines bearing an α,β-Unsaturated Ester Group : A Thermodynamic Preference for Chiral Alkyl(2E)-4,5-cis-4,5-epimino-N-(alkyl or arylsulfonyl)-2-enoates over Other Three Stereoisomers."J. Org. Chem.. 62. 2982-2991 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Y. Chounan et al.: "A Chemical Scale for Evaluating the Electron Transfer Ability of Alkylcopper Reagents."Bull. Chem. Soc. Jpn.. 70. 1953-1959 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] N. Masaki et al.: "A highly Stereoselective Synthesis of the Functionalized(E)-Alkene Dipeptide Isosteres of Trp-Val via Organocyanocopper-Lewis Acid Mediated Reaction."Chem. Pharm. Bull.. 45. 1259-1264 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H. Ohno et al.: "Palladium-catalyzed Reductive Ring Opening with Formic Acid of Aziridines Bearing an α,β-Unsaturated Ester Group."Tetrahedron. 53. 12933-12946 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H. Aoyama et al.: "Regio-and Stereoselectivity in Reactions of 2,3-cis-and trans-3-Alkyl-2-Vinylaziridines with Organocopper Reagents : Importance of 2,3-cis-Stereochemistry in Controlling Selectivity."Tetrahedron Letters. 38. 7383-7386 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H. Habashita et al.: "One-Pot Transformation of p-Toluenesulfonates of 2,3-Epoxy Alcohols into Allylic Alcohols."Tetrahedron Letters. 38. 8307-8310 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H. Tamamura et al.: "Regiospecific Ring-Opening Reactions of Aziridines Bearing an α,β-Unsaturated Ester Group with Trifluoroacetic Acid : Application to Stereoselective Synthesis of(E)-Alkene Dipeptide Isosteres."Chem. Commun.. 2327-2328 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H.Ohno et al.: "A Synthesis of Chiral Amino Allenes via an Organocyanocuprate-Mediated Ring-Opening Reaction of Enantiopure Ethynylaziridines"Tetrahedron Letters. 40. 349-352 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] H.Ohno et al.: "The First Palladium-Catalyzed Aziridination Reaction of Amino Allenes"J.Org.Chem.. 64. 2992-2993 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] H.Ohno et al.: "Sterically Congested Activated Aziridines : Highly Stereoselective Synthesis of Both 2.3-Cis-and 2,3-Trans-2-Alkenvl-3-alkvlaziridines from Common Intermediates"Tetrahedron Letters. 40. 1331-1334 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] H.Tamamura et al.: "Regiospecific Ring-opening Reactions of β-Aziridinyl-α,β-enoates with Acids : Application to the Stereoselective Synthesis of a Couple of Diastereoisomeric (E)-"J.Chem.Soc.Perkin Trans.1. 2983-2996 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] R.Yanada et al.: "Diastereoselective Allylation and Alkylation of Optically Active Imines with Metallic Samarium and a Catalytic Amount of Iodine"Tetrahedron. 55. 13947-13956 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] M.Okaniwa et al.: "Enantioselective addition of diethylzinc to aldehydes with novel chiral C2-symmetric dimeric ligands"Tetrahedron Letters. 41. 1047-1050 (2000)

    • Related Report
      1999 Annual Research Report
  • [Publications] K.Ishii et al.: "Selective Synthesis of Nonracemic 3-Pyrrolines and 2,3-cis-2-vinylaziridines from (Z)-Amino Allylic Alcohols : New Synthetic Route to Chiral 3,4-Dehydroproline"Synlett. 228-230 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] K.Ishii et al.: "Selective Synthesis of 2,3-cis-2-Vinyl-3-alkylaziridines and 3-Pyrrolines from Common Intermediates (Z)-4-N-Arvlsulfonvlaminoalk-2-en-1-ols"J.Chem.Soc.,Perkin Trans.1. 2155-2163 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] H.Ohno et al.: "Convenient syntheses of chiral 3-substiuted 2-ethynylaziridines"J.Chem.Soc.,Perkin Trans.1. 2949-2962 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] M.Anzai et al.: "Palladium-catalyzed Regio-and Stereoselective Synthesis of N-Protected 2,4-Dialkylated Azacyclobutanes from Amino Allenes"Tetrahedron Letters. 40. 7393-7397 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Y Takemoto et al.: "Utility of a Diene-tricarbonyliron Complex as a Chiral Auxiliary : Regio-and Stereocontrolled Functionalization of Acyclic Diene Ligands"J.Am.Chem.Soc,. 121. 9143-9154 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Y.Takemoto et al.: "CAN-Indced Double Ether Formation : Synthesis of trans-and cis-Fused Tricyclic Ethers from 3-Oxabicyclo[3.1.0]hexyl Sulfides"Chem.Commun. 2515-2516 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Y.Takemoto et al.: "Stereospecific Migration of an Fe(CO)3 Group on Acyclic Conjugated Trienes bearing an Electron-withdrawing Group"Tetrahedron Letters. 41. 85-88 (2000)

    • Related Report
      1999 Annual Research Report
  • [Publications] H.Ohno et al.: "Stereoselective Synthesis of Chiral Amino Allenes by Organocopper-Mediated anti SN2'-Substitution Reaction of Chiral Ethynylaziridines"Tetrahedron. (印刷中).

    • Related Report
      1999 Annual Research Report
  • [Publications] Hirokazu Tamamura: "Unambiguous synthesis of stromal cell-derived factor-1 by regioselective disulfide bond formation using DMSO-aqueous HCl system" Chemical Communications. 1号. 151-152 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Hirokazu Tamamura: "Effective lowly cytotoxic analogs of an HIV-cell fusion inhibitor,T22([Tyr5,12,Lys7]-polyphemusin II)" Bioorganic & Medicibnal Chemistry. 6巻. 231-238 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Hirokazu Tamamura: "Convenient one-pot synthesis of cystine-containing peptides using the trimethylsilyl chloride-dimethylsulfoxide/trifluoroacetic acid system." J.Chem.Soc.,. 495-500 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Toshiro Ibuka: "The Aza-Payne Rearrangement: A Synthetically Valuable Equlibration" Chemical Society Reviews. 27巻. 145-154 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Hiromu Habashita: "A New Synthesis of the Central Substracture of Botryococcenes" Journal of Organic Chemistry. 63巻. 2391-2396 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Hirokazu Tamamura: "Downsizing of an HIV-Cell Fusion Inhibitors,T22([Tyr5,12,Lys7]-Polyphemusin II),with the Maintenance of Anti-HIV Activity and Solution Streucture" Bioorganic & Medicinal Chemistry. 6巻. 473-479 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Hirokazu Tamamura: "Pharmacophore identification of a chemokine receptor (CXCR4)antagonist,T22([Tyr5,12,Lye7]-plyphemusin II)." Bioorgic & Madicinal Chemistry. 6巻. 1033-1041 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Asami Honda: "Rhodium(I)-or Iridium(I)-Mediated Equilibrated Reactions of Activated 2,3-cis and trans-3-Alkyl-2-vinylaziridines" Synlett. 969-970 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Yoshiji Takemoto: "Utility of a diene-tricarbonyiron complex as mobile chiral auxiliary: iterative use for constructing contiguous chiral centers" Chemical Communications. 1911-1912 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Hiroaki Ohno: "A 2,3-Cis Selective Synthesis of Aziridines bearing a Vinyl Group from Allyl Methyl Carbonates and Allyl Mesylates" J.Chem.Soc.,Perkin Trans.1. 3703-3716 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Hiroaki Ohno: "A Convenient Synthesis of Activated Enantionerically Pure 2-Ethynylaziridines" Tetrahedron:Asymmetry. 9巻. 3929-3933 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Yoshiji Takemoto: "Stereoselective synthesis of cis-fused chlorinated bicyclic ethers via CAN-mediated ring-opening of cycloprophysulfides" Tetrahedron Letters. 39巻. 7545-7548 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Yoshiji Takemoto: "Asymmetric synthesis of (diene)Fe(CO)_3 complexes by a catalytic enantioselective alkylation using diakylzincs" Tetrahedron. 54巻. 15567-15580 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Hirokazu Tamamura: "A low-molecular-weight inhibitor against the chemokine receptor CXCR4: A strong anti-HIV peptide T140" Biochem.Biophys.Res.Commun.253巻. 877-882 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Hiroaki Ohno: "A Synthesis of Chiral Amino Allenes via an Organocyanocupreate-Mediated Ring-Opening Reaction of Enantiopure Ethynylaziridines" Tetrahedron Letters. 40巻. 349-352 (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] Hiroaki Ohno: "Sterically Congested Activated Aziridines: Highyl Stereoselective Synthesis of Both 2,3-Cis- and 2,3-Trans-1-Alkenyl-3-alkylaziridines from Common Intermediates" Tetrahedron Letters. 40巻. 1331-1334 (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] Hiroaki Ohno: "Selective Synthesis of Nonracemic 3-Pyrolines and 2,3-cis-2-vinylaziridines from(Z)- Amino Allylic Alcohols: New Synthetic Route to Chiral 3,4-Dehydroproline" Synlett. (in press). (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] Hiroaki Ohno: "The first palladium-catalyzed aziridination reaction of amino allenes" Journal of Organic Chemistry. (in print). (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] Kyoko Miyasaka: "Cholinergic Involvement in Cholecystokinin (CCK) Release by Luminal Oleic Aci" J.of Autonomic Nervous System. 63巻,1号. 179-182 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Koji Fujimoto: "Effects of Structural Modulation on Biological Activity of Bombesin Analogues with (E)-Alkene Bond" Life Science. 60巻,1号. 29-34 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Masaki Noda: "Synthesis of (E)-Alkene Dipeptide Isosteres of Tryptophan-Valine" Shimadzu Review. 54巻,3号. 231-234 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Toshiro Ibuka: "A Thermodynamic Preference of Chirai N-Methanesulfonyl and N-Arylsulfonyl 2,3-cis-3-Alkyl-2-Vinylaziridines over their 2,3-trans-Isomers :" Journal of Organic Chemistry. 62巻,4号. 999-1015 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Toshiro Ibuka: "Palladium (0)-catalyzed Isomerization Reaction of Aziridines bearing an α,β-Unsaturated Ester group." Journal of Organic Chemistry. 62巻,9号. 2982-2991 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Yukiyasu Chounan: "A Chemical Scale for Evaluating the Electron Transfer Ability of Alkylcopper Reagents" Bull.Chem.Soc.Jpn.70巻,8号. 1953-1959 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Noda Masaki: "A Highly Stereoselective Synthesis of the Functionalized (E)-Alkene" Chem.Pharm.Bull.45巻,8号. 1259-1264 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Hiroaki Ohno: "Palladium-catalyzed Reductive Ring Opening with Formic Acid of Aziridines Bearing an α,β-Unsaturated Ester Group" Tetrahedron. 53巻,38号. 12933-12946 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Hiroshi Aoyama: "Regio-and Stereoselectivity in Reactions of 2,3-cis and trans-3-Alkyl-2-Vinylaziridines with Organocopper Reagents." Tetrahedron Letters. 38巻,42号. 3783-3786 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Hiromu Habashita: "One-Pot Transformation of p-Toluenesulfonates of 2,3-Epoxy Alcohols into Allylic Alcohols" Tetrahedron Letters. 38巻,48号. 8307-8310 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Hirokazu Tamamura: "Regiospecific Ring-Opening Reactions of Aziridines Bearing an α,β-Unsaturated Ester Group with Trifluoroacetic Acid." Chemical Communications. 23号. 2327-2328 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Hirokazu Tamamura: "Unambiguous synthesis of stromal cell-derived factor-1 by regioselective disulfide bond formation using DMSO-aqueous HCI system" Chemical Communications. 1号. 151-152 (1998)

    • Related Report
      1997 Annual Research Report
  • [Publications] Toshiro Ibuka: "The Aza-Payne Rearrangement : A Synthetically Valuable Equlibration" Chemical Society Reviews. (in press). (1998)

    • Related Report
      1997 Annual Research Report
  • [Publications] Hiromu Habashita: "A New Synthesis of the Central Substracture of Botryococcenes" Journal of Organic Chemistry. 63巻(in press). (1998)

    • Related Report
      1997 Annual Research Report

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Published: 1997-04-01   Modified: 2016-04-21  

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