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2001 Fiscal Year Final Research Report Summary

Synthesis of biologically compounds to control of the signal transduction by an application of phophorus functional group

Research Project

Project/Area Number 12672067
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionTokyo Univ. Pharm. & Life Science

Principal Investigator

SHIBUYA Shiroshi  TokyoUniv. Pharm. & LifeScience, School ofPharm., Professor, 薬学部, 教授 (10057325)

Project Period (FY) 2000 – 2001
Keywordsstereoselective synthesis / punne nucleoside phosphorylase / radical cyclization / Diels-Alder reaction / β-amino acid / chiral catalyst / lipase / hydrophosphinylation
Research Abstract

A variety of biologically active compounds to control of the signal transduction were synthesized. The results can be classified into following items
1.A variety of nucleotide analogues having a were cynthesized by condensation of cyclic and acyclic alkyl spacer containing difluoromethylenephosphonic acid moiety were synthesized and condensed with nucleic acid base to get high inhibitory activity to purine nucleoside phosphorylase.
2.Sphingomyelin analogous compounds containing difluoromethylenephosphonic acid moiety were synthesized starting with L-serine and D-serine for the evaluation of their inhibitory potency to sphingomyelinase.
3.Cyclopropyl carbinols possessing a difluoromethylenephosphonate group were synthesized by reduction of the corresponding ketones.
4.Cyclohexane derivative possessing a (diethoxyphosphinyl)difluoromethyl unit were synthesized by the Diels-Alder rection of the 1, 3-butadinene possessing a (diethoxyphosphinyl)difluoromethyl group with dienophiles.
5.β-Amino acid derivatives possessing a nucleic acid base were prepared by an application of kinetic resolution of 3-subsituted 1, 3-propane diol as the key reaction.
6.Diastereoselective synthesis of chiral β-amino-α-hydroxy-H-phosphinates by hydrophosphinylation of a-amino acids in the prsence of chiral catalyst.

  • Research Products

    (16 results)

All Other

All Publications (16 results)

  • [Publications] Tsutomu Yokomatsu: "Stereoselective Reduction of Cyclopropylalkanones Possessing a Difluoro-methylenephosphonate Group at the Ring : Application to Stereoselective Synthesis of Novel Cyclopropane Nucleotide Analogues"Tetrahedron. 56. 7099-7108 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Tsutomu Yokomatsu: "Synthesis of allenic (α,α-Difluoromethylene) phosphosnates from Propar gylic Tosylates and Acetates Synthesis of allenic (α,α-Difluoromethylene )phosphonates from Propargylic Tosylates and Acetates"Synlett. 287-289 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Tsutomu Yokomatsu: "Synthesis and Evaluation of Difluoromethylene Analogue of Sphigomyelin as an Inhibitors of Sphingomyelinase"Bioorg. Med. Chem. Lett.. 11. 1277-1280 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Tsutomu Yokomatsu: "Diels-Alder Cycloaddition of Novel Buta-1,3-dieneDerivatives Possessing a (Diethoxyphosphinoyl)-difluoromethyl Unit"Chem. Commun.. 2001. 1878-1879 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Tsutomu Yokomatsu: "1, 3-Dipolar Cycloadition of Diazomethane to, 1, 1-Difluoro-allylphosphonates : Application to Synthesis of Cyclo Propane Derivatives Having a Diethoxyphosphoryldifluoromethylene Unit"Heterocycles. 56. 273-282 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Takehiro Yamagishi: "Asymmetric Synthesis of β-Amino-α-hydroxy-phosphinic Acid Derivatives hrough Hydrophosphinylation of α-Amino Aldehydes"Tetrahedron. 58. 2577-2583 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Tsutomu Yokomatsu: "Synthesis of Aryldifluorophosphonothioic Acids from 0, 0-Diethyl Aryldifluoromethylphos phonothioates"J.Org.Chemistry. Vol.65. 5858-5861 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Tsutomu Yokomatsu: "Synthesis and Evaluation of Multisubstrate Analogue Inhibitors of Purine Nucleoside Phosphorylases"Bioorganic & Medicinal.Chem.. Vol.8. 2571-2579 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Tsutomu Yokomatsu: "Stereoselective Reduction of Cyclopropylalka nones Possessing a Difluoromethylene phosphonate Group at the Ring : Application to Stereoselective Synthesis of Novel Cyclopropane Nucleotide Analogues"Tetrahedron. Vol.56. 7099-7108 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Tsutomu Yokomatsu: "Synthesis of ailenic (a,a-Difluoromethylene)- phosphosnates from Propargylic Tosylates and Acetates"Synlett. 287-289 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Tsutomu Yokomatsu: "Synthesis and Evaluation of Difluoromethylene Analogue of Sphigomyelin as an Inhibitors of Sphingomyelinase"Bioorganic & Medicinal.Chem.Lett.. Vol.11. 1277-1280 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Takehiro Yamagishi: "Diastereoselective Synthesis of Chifal β-Amino-αhydroxy-H-phosphinates though Hydrophos phinylation of α-Amino Aldehydes"Tetrahedron Lett.. Vol.42. 5033-5036 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Tsutomu Yokomatsu: "Diels-Alder Cycloadition of Novel Buta-1,3-dieneDerivatives Prossessing a (Diethoxy-phosphinoyl)-difluoronethyl Unite"Chemical Commun.. 1878-1879 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Tsutomu Yokomatsu: "1,3-Dipolar Cycloadition of Difluoro-alylphosphonates : Application to Synthesis of Cyclopropane Derivatives Having a Diethoxyphosphoryldifluoromethylene Unit"Heterocycles. Vol.56. 273-282 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Tsutomu Yokomatsu: "Chemo-enzymatic Synthesis of Novel β-Amino Acids Substituted by (Thymin- 1-yl)methyl Functional Group at the α-Positon"Heterocycles. Vol.56. 545-552 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Takehiro Yamagishi: "Asymmetric Synthesis of β-Amino-α-hydroxy r phosphinic Acid Derivatives through Hydrophos phinylation of α-Amino Aldehydes"Tetrahedron. Vol.58. 2577-2583 (2002)

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 2003-09-17  

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