Thioacetic acid S-[(R)-2-{(R)-3-acetylsulfanyl-2-[(R)-3-acetylsulfanyl-2-methyl-2-(3-phenyl-propionylamino)-propionylamino]-2-methyl-propionylamino}-2-(5-methyl-4-methylcarbamoyl-oxazol-2-yl)-propyl] ester | 171011-91-9

• 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: Thioacetic acid S-[(R)-2-{(R)-3-acetylsulfanyl-2-[(R)-3-acetylsulfanyl-2-methyl-2-(3-phenyl-propionylamino)-propionylamino]-2-methyl-propionylamino}-2-(5-methyl-4-methylcarbamoyl-oxazol-2-yl)-propyl] ester
• 英文别名: S-[(2R)-2-[[(2R)-3-acetylsulfanyl-2-[[(2R)-3-acetylsulfanyl-2-methyl-2-(3-phenylpropanoylamino)propanoyl]amino]-2-methylpropanoyl]amino]-2-[5-methyl-4-(methylcarbamoyl)-1,3-oxazol-2-yl]propyl] ethanethioate
• CAS: 171011-91-9
• 化学式: C₃₂H₄₃N₅O₈S₃
• 分子量: 721.92
• InChiKey: MONWZAOYMGMJPX-CPCREDONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  48
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  270
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  Thioacetic acid S-[(R)-2-{(R)-3-acetylsulfanyl-2-[(R)-3-acetylsulfanyl-2-methyl-2-(3-phenyl-propionylamino)-propionylamino]-2-methyl-propionylamino}-2-(5-methyl-4-methylcarbamoyl-oxazol-2-yl)-propyl] ester 在 氨 、 四氯化钛 作用下， 生成 (4R,4'S,4''S)-5-Methyl-2-<4,4',4''-trimethyl-2''-phenethyl-4,5,4',5',4'',5''-hexahydro<2,4':2',4''>terthiazol-4-yl>oxazole-4-carboxylic acid methylamine
  参考文献：
  名称：

  Total Synthesis of (-)-Thiangazole and Structurally Related Polyazoles

  摘要：

  Thiangazole was reported to be an extremely potent, nontoxic inhibitor of HIV-1 in MT4 cell assays. By employing a strategy of selective oxazoline-thiazoline interconversions, we have accomplished a total synthesis of the natural product in 16 steps and 1.1% overall yield from (S)-alpha-methylserine. This new methodology is especially useful for the preparation of analogs of thiangazole and structure-activity studies. Our preliminary biological testing of (-)-thiangazole revealed a high level of cytotoxicity that was considerably reduced in the oxazoline-containing analogs.

  DOI：

  10.1021/jo00127a030
• 作为产物：
  描述：

  (4'S,4''S,4'''S)-5,4',4'',4''-Tetramethyl-2'''-phenethyl-4',5',4'',5'',4''',5'''-hexahydro<2,4':2',4'':2'',4'''>quateroxazole-4-carboxylic acid methylamine 、 硫代乙酸 生成 Thioacetic acid S-[(R)-2-{(R)-3-acetylsulfanyl-2-[(R)-3-acetylsulfanyl-2-methyl-2-(3-phenyl-propionylamino)-propionylamino]-2-methyl-propionylamino}-2-(5-methyl-4-methylcarbamoyl-oxazol-2-yl)-propyl] ester
  参考文献：
  名称：

  从氮丙啶到恶唑啉和噻唑啉：杂环路线到噻唑啉

  摘要：

  自1991年分离以来，多氮杂环天然产物硫氮唑已成为全合成的热门目标，因其拥有复杂的杂环片段以及报告显示的强效抗病毒活性。本文回顾了针对硫氮唑的合成活动，并提出了一种新颖的方法，该方法利用了在合成硫唑啉过程中使用的氮杂环和噁唑烯中间体。

  DOI：

  10.1055/s-1997-681

文献信息

• Total Synthesis of (-)-Thiangazole and Structurally Related Polyazoles
  作者：Peter Wipf、Srikanth Venkatraman

  DOI：10.1021/jo00127a030

  日期：1995.11

  Thiangazole was reported to be an extremely potent, nontoxic inhibitor of HIV-1 in MT4 cell assays. By employing a strategy of selective oxazoline-thiazoline interconversions, we have accomplished a total synthesis of the natural product in 16 steps and 1.1% overall yield from (S)-alpha-methylserine. This new methodology is especially useful for the preparation of analogs of thiangazole and structure-activity studies. Our preliminary biological testing of (-)-thiangazole revealed a high level of cytotoxicity that was considerably reduced in the oxazoline-containing analogs.
• From Aziridines to Oxazolines and Thiazolines: The Heterocyclic Route to Thiangazole
  作者：Peter Wipf、Srikanth Venkatraman

  DOI：10.1055/s-1997-681

  日期：——

  Since its isolation in 1991, the polyazole natural product thiangazole has become a popular target for total synthesis due to its challenging array of heterocyclic segments and its reported potent antiviral activity. The synthetic activity toward thiangazole is reviewed and a novel approach that takes advantage or aziridine and oxazoline intermediates en route to thiazolines is presented.

  自1991年分离以来，多氮杂环天然产物硫氮唑已成为全合成的热门目标，因其拥有复杂的杂环片段以及报告显示的强效抗病毒活性。本文回顾了针对硫氮唑的合成活动，并提出了一种新颖的方法，该方法利用了在合成硫唑啉过程中使用的氮杂环和噁唑烯中间体。