(3R,5'aS,10'aR)-5-methyl-spiro(indol-2-one[3,3']-hexahydro-5,10H-pyrrolo[1,2-a][1,3]thiazolo[3,4-d]pyrazine)-5,10-dione | 1236853-57-8

• 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: (3R,5'aS,10'aR)-5-methyl-spiro(indol-2-one[3,3']-hexahydro-5,10H-pyrrolo[1,2-a][1,3]thiazolo[3,4-d]pyrazine)-5,10-dione
• 英文别名: (3R,3'R,9'S)-5-methylspiro[1H-indole-3,6'-5-thia-1,7-diazatricyclo[7.3.0.03,7]dodecane]-2,2',8'-trione
• CAS: 1236853-57-8
• 化学式: C₁₇H₁₇N₃O₃S
• 分子量: 343.406
• InChiKey: MFOFQOZWYJGNPU-GDZNZVCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  95
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (3R,5aS,10aR)-3-ethyloxycarbonyl-3-(2'-amino-5'-methyl)-phenyl-5,10-dioxooctahydro-5H-pyrrolo[1,2-a][1,3]thiazolo[3,4-d]pyrazine 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 生成 (3R,5'aS,10'aR)-5-methyl-spiro(indol-2-one[3,3']-hexahydro-5,10H-pyrrolo[1,2-a][1,3]thiazolo[3,4-d]pyrazine)-5,10-dione
  参考文献：
  名称：

  Design and synthesis of spirotryprostatin-inspired diketopiperazine systems from prolyl spirooxoindolethiazolidine derivatives

  摘要：

  Based on the spirotryprostatin-A structure, we designed, synthesized, and evaluated different series of compounds belonging to the diketopiperazine structural class as potential cell cycle modulators and cytotoxic agents. Starting from the spirooxoindolthiazolidine scaffold, amide coupling with Pro derivatives and intramolecular cyclization reactions are suitable synthetic methods to generate chemically diverse diketopiperazine system, such as hexahydropyrrolo[1,2-a][1,3]thiazolo[3,2-d]pyrazine-5,10-dione (structure I), hexahydropyrrolo[1,2-a] [1,3]thiazolo[3,4-d]pyrazine-5,10-dione (structure II) and spiroindol-2-one[3,3']hexahydro-5,10H-pyrrolo[1,2-a][1,3]thiazolo[3,4-d]pyrazine-5,10-dione (structure III). Some of these compounds, especially those who belong to the series I and II, showed interesting cytotoxic activity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.04.079

文献信息

• Design and synthesis of spirotryprostatin-inspired diketopiperazine systems from prolyl spirooxoindolethiazolidine derivatives
  作者：Alessia Bertamino、Claudio Aquino、Marina Sala、Nicoletta de Simone、Carlo Andrea Mattia、Loredana Erra、Simona Musella、Pio Iannelli、Alfonso Carotenuto、Paolo Grieco

  DOI：10.1016/j.bmc.2010.04.079

  日期：2010.6.15

  Based on the spirotryprostatin-A structure, we designed, synthesized, and evaluated different series of compounds belonging to the diketopiperazine structural class as potential cell cycle modulators and cytotoxic agents. Starting from the spirooxoindolthiazolidine scaffold, amide coupling with Pro derivatives and intramolecular cyclization reactions are suitable synthetic methods to generate chemically diverse diketopiperazine system, such as hexahydropyrrolo[1,2-a][1,3]thiazolo[3,2-d]pyrazine-5,10-dione (structure I), hexahydropyrrolo[1,2-a] [1,3]thiazolo[3,4-d]pyrazine-5,10-dione (structure II) and spiroindol-2-one[3,3']hexahydro-5,10H-pyrrolo[1,2-a][1,3]thiazolo[3,4-d]pyrazine-5,10-dione (structure III). Some of these compounds, especially those who belong to the series I and II, showed interesting cytotoxic activity. (C) 2010 Elsevier Ltd. All rights reserved.