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Shynthesis of Carbocyclic Nucleosides Having Biological Function

Research Project

Project/Area Number 06672230
Research Category

Grant-in-Aid for General Scientific Research (C)

Allocation TypeSingle-year Grants
Research Field 医薬分子機能学
Research InstitutionTOHOKU UNIVERSITY

Principal Investigator

KATAGIRI Nobuya  Tohoku Univ. Pharmaceutical Institute, associate, Professor, 薬学部, 助教授 (60089787)

Co-Investigator(Kenkyū-buntansha) TOYOTA Akemi  Tohoku University, Pharmaceutical Institute, Instructor, 薬学部, 教務職員 (80237148)
Project Period (FY) 1994 – 1995
Project Status Completed (Fiscal Year 1995)
Budget Amount *help
¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 1995: ¥800,000 (Direct Cost: ¥800,000)
Fiscal Year 1994: ¥1,300,000 (Direct Cost: ¥1,300,000)
Keywordscarbocylic nucleoside / nitrone / anti-HIV activity / bicyclic amide / asymmetric synthesis / cis-difluoro compound / Diels-Alder reaction / adenosine deaminase / 抗ウイルス剤 / キラルルイス酸 / アミノ酸 / 炭素環ホモヌクレオシド / 抗HIV剤 / フッ素化 / シクロペンテン / 含フッ素炭素環ヌクレオシド
Research Abstract

1. The cis-dihydroxylation of cis-3,5-disubstituted cyclopentenes leading to carbocyclic nucleosides was examined. Its stereoselectivity was found to be attibutable to the conformation of substituents of cyclopentenes.
2. Addition of molecular fluorine to bicyclo [2.2.1] hept-2-ene derivatives and conversion to fluorine-containing carbocyclic nucleosides were carried out. Biological evaluation of these nucleosides did not show any anti-HIV activity.
3. Asymmetric hetero Diels-Alder reaction of benzenesulfonyl cyanide with cyclopentadiene using chiral Lewis acids was investigated to give opticaliy active 2-azabicyclo [2.2.1] hept-5-en-3-one, which was a synthon of chiral carbocyclic nucleosides.
4. The 1,3-dipolar cycloaddition reaction of bornadiene or bicycloamides with cyclic nitrones obtained from nitrosoketene with ketones gave stereoselectively the exocycloadducts, which would be intermediates for the synthesis of carbocyclic nucleosides containing an alpha-amino acid residue.
5. A new dienophile, dimethyl trifluoroacetylaminomethylenemalonate, was created. The dienophile reacted readily with cyclopentadiene to give a bicyclic compound leading to carbocyclic homo-nucleosides.
6. Deamination of carbocyclic adenine nucleosides by adenosine deaminase under highpressure revealed that the deamination was a useful procedure for the kinetical resolution of racemic carbocyclic nucleosides.

Report

(3 results)
  • 1995 Annual Research Report   Final Research Report Summary
  • 1994 Annual Research Report
  • Research Products

    (44 results)

All Other

All Publications (44 results)

  • [Publications] Nobuya Katagiri: "A novel synthesis of cyclic mitrones via a nitrosoketene intermediate" J. Chem. Soc. Chem. Commun.,. 281-282 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Nobuya Katagiri: "Synthesis of 5-isonitroso-1, 3-dioxane-4, 6-diones and their reactions" Chem. Pharm. Bull.42. 1251-1257 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Akemi Toyota: "Synthesis of 9-(C-5-hydroxy-C-4-hydroxymethyl-cyclopent-2-en-r-l-yl)-9H-adenine [(±)-epinor-BCA]" Heterocycles. 38. 27-30 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Kenji Kitano: "Dimethyl 2-[3, 3-bis (methoxycarbonyl) bicyclo [2. 2. 1] hept-5-en-2-yl] malonate : Synthesis and base-catalyzed C-C bond cleavage reaciton" Chem. Lett.1285-1288 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Nobuya Katagiri: "Selective protection of the hydroxyl groups of oxetanocin A directed towards the oliganucleotide synthesis" Nucleic Acid, Symp. Ser.31. 13-14 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Akemi Toyota: "Addition of molecular fluorine to bicyclo [2. 2. 1]-hept-2-ene derivatives and conversion to fluorine-containiny carbocyclic nucleosides" Tetrahedron Lett.35. 5665-5688 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Nobuya Katagiri: "Explanation for stereoselectivity of the cis-dihydroxylation of cis-3, 5-disubstituted cyclopentenes" Chem. Pharm. Bull.42. 2653-2655 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Nobuya Katagiri: "A new synthesis of highly functional nitrones through nitrosoketene intermediate and their use for the stereoselective synthesis of amino acids" J. Org. Chem.59. 8101-8106 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Nobuya Katagiri: "Selective protection of the primary hydroxyl groups of oxetanocin A and conformational analysis of O-protected oxetanocin A" Chem. Pharm. Bull.43. 884-886 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Akemi Toyota: "Addition of molecular fluorine to bicyclo [2. 2. 1] hept-2-ene derivatives and synthesis of fluorine-containing carbocyclic nucleosides" Tetrahedron Lett.51. 8783-8797 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Nobuya Katagiri: "Synthesis of carbocyclic nucleoside precursors from bicyclo [2. 2. 1] hept-5-enes using a novel reductive C-C bond cleavage reaction" Nucleic Acids, Symp. Ser.34. 157-158 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] 片桐 信弥: "新規ヌクレオシド分子の構築-炭素環ヌクレオシドを中心に-" 蛋白質 核酸 酵素. 40. 1219-1231 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Nobuya Katagiri: "Deamination of 9-(hydroxymethylated cycloalkyl) adenines (carbocyclic adenine nucleosides) by adenosine deaminase : Effect of high-pressure upon deamination rate and enantioselectivity" Nucleosides & Nucleotides. 15. 631-647 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Nobuya Katagiri: "Hetero Diels-Alder reaction of benzenesulfonyl cyanide with cyclopentadiene using chiral Lewis acids" Chem. Pharm. Bull.44. 850-852 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] 片桐 信弥: "ゴ-ドン会議に参加して-炭素環ヌクレオシドのトピックスを中心に-" 化学と生物. 34. 54-59 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Nobuya Katagiri: "Synthesis of chiral cyclic nitrones via nitrosoketent intermediate and their use for the complete EPC Synthesis of nonpooteinogenic amino acids" Tetrahedron Lett.,. (in press).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] N.Katagiri, A.Kurimoto, A.Yamada, H,Sato, T.Katsuhara, Y.Takagi, and C.Kaneko: "A novel synthesis of cyclic nitrones via a nitrosoketene intermediate" J.Chem. Soc. Chem. Commun. 281-282 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] N.Katagiri, H.Nochi, A.Kurimoto, H.Sato, and C.Kaneko: "Synthesis of 5-isonitroso-1,3-dioxane-4,6-diones and their reactions" Chem. Pharm. Bull. 42. 1251-1257 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] A.Toyota, N.Katagiri, and C.Kaneko: "Synthesis of 9-(c-5-hydroxy-c-4-hydroxymethylcyclopent-2-en-r-1-yl)-9H-adenine [(+)-epinor-BCA]." Heterocycles. 38. 27-30 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] K.Kitano, N.Katagiri, and C.Kaneko: "Dimethyl 2-[3,3-bis (methoxycarbonyl) bicyclo [2.2.1] hept-5-en-2-yl] malonate : Synthesis and base-catalyzed C-C bond cleavage reaction" Chem. Lett. 1285-1288 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] N.Katagiri, S.Makino, and C.Kaneko: "Selective protection of the hydroxyl groups of oxetanocin A directed towards the oligonucleotide synthesis" Nucleic Acids, Symp. Ser. 31. 13-14 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] A.Toyota, C.Habutani, N.Katagiri, and C.Kaneko: "Addition of molecular fluorine to bicyclo [2.2.1] hept-2-ene derivatives and conversion to fluorine-containing carbocyclic nucleosides" Tetrahedron Lett. 35. 5665-5688 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] N.Katagiri, Y.Ito, K.Kitano, A.Toyota, and C.Kaneko: "Synthesis of nucleosides and related compounds. XXXVI : Explanation for stereoselectivity of the cis-dihydroxylation of cis-3,5-disubstituted cyclopentenes" Chem. Pharm. Bull. 42. 2653-2655 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] N.Katagiri, H.Sato, A.Kurimoto, M.Okada, A.Yamada, and C.Kaneko: "A new synthesis of highly functional nitrones throught nitrosoketene intermediate and their use for the stereoselective synthesis of amino acids." J.Org. Chem. 59. 8101-8106 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] N.Katagiri, M.Makino, and C.Kaneko: "Selective protection of the primary hydroxyl groups of oxetanocin A and conformational analysis of O-protected oxetanocin A." Chem. Pharm. Bull. 43. 884-886 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] A.Toyota, M.Aizawa, C,Habutani, N.Katagiri, and C.Kaneko: "Addition of molecular fluorine to bicyclo [2.2.1] hept-2-ene derivatives and synthesis of fluorinecontaining carbocyclic nucleosides." Tetrahedron. 51. 8783-8797 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] N.Katagiri, M.Makino, H.Nakajima, and C.Kaneko: "Synthesis of carbocyclic nucleoside precursors from bicyclo [2.2.1] hept-5-enes using a novel reductive C-C bond cleavage reaction." Nucleic Acids, Symp. Ser. 34. 157-158 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] N.Katagiri, and C.Kaneko: "Synthesis of novel nucleosides" : Carbocyclic nucleosides" Protein, Nucleic Acid and Enzyme. 40. 1219-1231 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] 片桐信弥: "新規ヌクレオシド分子の構築-炭素環ヌクレオシドを中心に" 蛋白質核酸酵素. 40. 1219-1231 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Nobuya Katagiri: "Selective protection of the primary hydroxyl groups of oxetanoclnA and conformational analysis of O-protected oxetanocinA" Chem. Pharm. Bull.43. 884-886 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Akemi Toyota: "Addition of molecular fluorine to bicyclo[2. 2. 1]hept-2-ene derivatives and systhesis of fluorine-containing carbocyclic nucleosides" Tetraheolron. 51. 8783-8797 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Nobuya Katagiri: "Synthesis of carbocyclic nucleoside precursors from bicyclo[2. 2. 1]hept-5-enes using a novel reductive C-C bond cleavoge reaction" Nuclelc Acids, Symp. Ser.34. 157-158 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Akemi Toyota: "Iodofluorination of 2-ajabicyclo[2. 2. 1]hept-5-en-3-ones and related compounds : Regio-and stereoselectivities" Tetrahedron Lett.36. 6123-6126 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Nobuya Katagiri: "Deamination of 9-chydroxymethylated(ycloalkyl) adenines(carbocyclic adenine nucleosides) by adenosine deaminase" Nucleosides & Nucleotides. 15. 631-647 (1996)

    • Related Report
      1995 Annual Research Report
  • [Publications] Nobuya Katagiri: "Hetero Dielo-Alder reaction of benzenesulfonyl cyanide with cyclopentadiene using chiral Lewis acids" Chem. Pharm. Bull.(in press).

    • Related Report
      1995 Annual Research Report
  • [Publications] Nobuya Katagiri: "Synthesis of chiral cyclic nitrones via nitrosoketene intermediate and their use for the complete EPC Synthesis of nonproteinogenic aminoacds" Tetrahedron Lett.(in press).

    • Related Report
      1995 Annual Research Report
  • [Publications] Nobuya Katagiri: "A Novel Synthesis of Cyclic Nitrones via a Nitrosoketene Intermediate" J.Chem.Soc.,Chem.Commun.281-282 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Kenji Kitano: "Dimethyl2-{3,3-Bis(methoxycarbonyl)bicyclo〔2.2.1〕hept-5-en-2-tl}malonate.Synthesis and Base-Catalyzed C-C Bond Cleaction" Chemistry Letters. 1285-1288 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Nobuya Kstagiri: "Synthesis of5-Isomitroso-1,30dioxane-4,6-diones and Their Reactions" Chem.Pharm.Bull. 42. 1251-1257 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Nobuya Katagiri: "Explanation for Stereoselectivity of the Cis-Dihydrozylation of Cis-3,5-Disubstituted Cyclopetenes" Chem.Pharm.Bull. 42. 2653-2655 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Nobuya Katagiri: "Selective protection of the hydroxyl groups of oxetanocln A directed towards the Oligonucleotide Synthesis" Nucleic Acids Sympisium Series. 31. 13-14 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Nobuya Katagiri: "A New Synthesis of Highly Functiones Nitrones through a Nltrosoketene Intermediate and Their Use for the Stereoselectivie Synthesis of Amino Acids" J.Org.Chem. 59. 8101-8106 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Akemi Toyota: "Sythesis of 9-(C-5-Hydroxy-C-4-hydroxymethylcyclopent-2-en-r-1-yl)-9H-adenine〔(±)-epinor-BCA〕" Heterocycles. 38. 27-30 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Akemi Toyota: "Additiom of molecular fluorine the bicyclo〔2.2.1〕hept-2-ene derivatives and conversion to fluorine-Containing Carbocyclic nucleosides" Tetrahedron Letters. 35. 5665-5668 (1994)

    • Related Report
      1994 Annual Research Report

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Published: 1994-04-01   Modified: 2016-04-21  

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