| 1588428-05-0

• 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
• CAS: 1588428-05-0
• 化学式: C₄₁H₅₈N₈O₉S₂
• 分子量: 871.092
• InChiKey: OTNKORAVVXWCCW-YUFMXMPISA-N

物化性质

• 密度：
  1.266±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.0
• 重原子数：
  60.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  206.47
• 氢给体数：
  2.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  在 双氧水 、 lithium hydroxide 、 盐酸 作用下， 以 乙醇 、 甲醇 、 水 为溶剂， 生成 2-((S)-1-((S)-2-((S)-1-(2-(2-((S)-1-((tert-butoxycarbonyl)-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
• 作为产物：
  描述：

  methyl 2-(2-((S)-1-((tert-butoxycarbonyl)-L-leucyl)pyrrolidin-2-yl)thiazol-4-yl)oxazole-4-carboxylate 在 双氧水 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 、 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 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成
  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