2-((S)-1-((S)-2-((S)-1-(2-(2-((S)-1-(L-leucyl)pyrrolidin-2-yl)thiazol-4-yl)oxazole-4-carbonyl)-N-methylpyrrolidine-2-carboxamido)-3-methylbutanamido)ethyl)thiazole-4-carboxylic acid | 1588428-13-0

• 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: 2-((S)-1-((S)-2-((S)-1-(2-(2-((S)-1-(L-leucyl)pyrrolidin-2-yl)thiazol-4-yl)oxazole-4-carbonyl)-N-methylpyrrolidine-2-carboxamido)-3-methylbutanamido)ethyl)thiazole-4-carboxylic acid
• CAS: 1588428-13-0
• 化学式: C₃₄H₄₆N₈O₇S₂
• 分子量: 742.921
• InChiKey: WMBCMQHEOBOHDK-RAAUGIHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  51.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  205.16
• 氢给体数：
  3.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2-((S)-1-((S)-2-((S)-1-(2-(2-((S)-1-(L-leucyl)pyrrolidin-2-yl)thiazol-4-yl)oxazole-4-carbonyl)-N-methylpyrrolidine-2-carboxamido)-3-methylbutanamido)ethyl)thiazole-4-carboxylic acid 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 4-(4,6-二甲氧基三嗪-2-基)-4-甲基吗啉盐酸盐 作用下， 以 二氯甲烷 为溶剂， 生成 (6S,12S,19S,22S,25S)-19,23-dimethyl-12-(2-methylpropyl)-22-propan-2-yl-33-oxa-4,17-dithia-10,13,20,23,29,34,35,36-octazahexacyclo[29.2.1.12,5.115,18.06,10.025,29]hexatriaconta-1(34),2,5(36),15,18(35),31-hexaene-11,14,21,24,30-pentone
  参考文献：
  名称：

  Sanguinamide B analogs: identification of active macrocyclic structures

  摘要：

  We report the synthesis of three new sanguinamide B (San B) analogs. We substituted in amino acids along the San B backbone with an N-Me, glycine, or an aromatic moiety (Phe or D-Phe) generating twelve derivatives in total. Testing in HCT-116 colon cancer cell lines resulted in establishing a structure-activity relationship. Our data show that the substitution of L- or D-Phe adjacent to the thiazole in the San B backbone locks the macrocycle into a single conformer, but only D-Phe analogs are cytotoxic. We demonstrate that the conformation of the macrocycle is extremely sensitive to stereochemistry and amino acid placement. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.02.106
• 作为产物：
  描述：

  乙基2-[(1S)-1-氨基乙基]-1,3-噻唑-4-羧酸酯 在 双氧水 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 苯甲醚 、 N,N-二异丙基乙胺 、 三氟乙酸 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 lithium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 2-((S)-1-((S)-2-((S)-1-(2-(2-((S)-1-(L-leucyl)pyrrolidin-2-yl)thiazol-4-yl)oxazole-4-carbonyl)-N-methylpyrrolidine-2-carboxamido)-3-methylbutanamido)ethyl)thiazole-4-carboxylic acid
  参考文献：
  名称：

  Sanguinamide B analogs: identification of active macrocyclic structures

  摘要：

  We report the synthesis of three new sanguinamide B (San B) analogs. We substituted in amino acids along the San B backbone with an N-Me, glycine, or an aromatic moiety (Phe or D-Phe) generating twelve derivatives in total. Testing in HCT-116 colon cancer cell lines resulted in establishing a structure-activity relationship. Our data show that the substitution of L- or D-Phe adjacent to the thiazole in the San B backbone locks the macrocycle into a single conformer, but only D-Phe analogs are cytotoxic. We demonstrate that the conformation of the macrocycle is extremely sensitive to stereochemistry and amino acid placement. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.02.106