DL-ethionine (SR)-sulfoximine | 5072-23-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: DL-ethionine (SR)-sulfoximine
• 英文别名: (+/-)-Ethionin-sulfoxim；ethionine sulfoximine；2-Amino-4-(ethylsulfonimidoyl)butanoic acid
• CAS: 5072-23-1
• 化学式: C₆H₁₄N₂O₃S
• 分子量: 194.255
• InChiKey: QALBWPROXXYJKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  DL-ethionine (SR)-sulfoximine 在 盐酸 、 三乙胺 、 氯甲酸异丁酯 作用下， 以 甲醇 为溶剂， 反应 72.75h， 生成 pteroyl-S-ethylhomocysteine sulfoximine
  参考文献：
  名称：

  Synthesis and biological activity of novel folic acid analogs: pteroyl-S-alkylhomocysteine sulfoximines

  摘要：

  The synthesis of a novel series of gamma-substituted folic acid analogues, pteroyl-S-alkyl-DL-homocysteine (RS)-sulfoximines, and the corresponding S-methylhomocysteine sulfone is described. Side reactions of the sulfoximine groups of the amino acid ester reactants were considered. The correct structures of the isolated target compounds were confirmed by NMR and FAB/MS excluding other alternatives. The replacement of the gamma-COOH of the glutamate moiety of folic acid with S-alkylsulfoximine groups or S-methylsulfone did not affect the substrate activity of the vitamin for dihydrofolate reductase. The resulting tetrahydrofolate analogues could serve as cofactors for the thymidylate synthase cycle of murine leukemia L1210 cells in situ. The analogues inhibited the growth of these cells in culture with 2 orders of magnitude lower IC50 values [(2-4) x 10(-4) M] than the parent folic acid.

  DOI：

  10.1021/jm00085a010
• 作为产物：
  描述：

  DL-乙硫氨酸 生成 DL-ethionine (SR)-sulfoximine
  参考文献：
  名称：

  Hayashi,K., Chemical and pharmaceutical bulletin, 1960, vol. 8, p. 177 - 182

  摘要：

  DOI：

文献信息

• NOVEL USES FOR DRUGS TARGETING GLUTAMINE SYNTHETASE
  申请人：Roegel Jean-Christophe

  公开号：US20090209474A1

  公开（公告）日：2009-08-20

  The present invention relates to novel therapeutic uses of tianeptine, salts, isomers, pro-drugs, metabolites and structural analogs thereof. Furthermore, the present invention relates to the use of tianeptine, salts, isomers, pro-drugs, metabolites and structural analogs thereof, in obtaining methods of screening and of developing drugs. Finally, the present invention relates to the novel therapeutic use of other glutamine synthetase (GS) ligands and to the use of these ligands in obtaining methods for screening and developing drugs.
• Hayashi,K., Chemical and pharmaceutical bulletin, 1960, vol. 8, p. 177 - 182
  作者：Hayashi,K.

  DOI：——

  日期：——
• Synthesis and biological activity of novel folic acid analogs: pteroyl-S-alkylhomocysteine sulfoximines
  作者：Peter J. Harvison、Thomas I. Kalman

  DOI：10.1021/jm00085a010

  日期：1992.4

  The synthesis of a novel series of gamma-substituted folic acid analogues, pteroyl-S-alkyl-DL-homocysteine (RS)-sulfoximines, and the corresponding S-methylhomocysteine sulfone is described. Side reactions of the sulfoximine groups of the amino acid ester reactants were considered. The correct structures of the isolated target compounds were confirmed by NMR and FAB/MS excluding other alternatives. The replacement of the gamma-COOH of the glutamate moiety of folic acid with S-alkylsulfoximine groups or S-methylsulfone did not affect the substrate activity of the vitamin for dihydrofolate reductase. The resulting tetrahydrofolate analogues could serve as cofactors for the thymidylate synthase cycle of murine leukemia L1210 cells in situ. The analogues inhibited the growth of these cells in culture with 2 orders of magnitude lower IC50 values [(2-4) x 10(-4) M] than the parent folic acid.