| 1588428-10-7

• 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: 1588428-10-7
• 化学式: C₄₄H₅₆N₈O₉S₂
• 分子量: 905.109
• InChiKey: KPPOBUFBNKZNOS-WXMFNODNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.24
• 重原子数：
  63.0
• 可旋转键数：
  16.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  215.26
• 氢给体数：
  3.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  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 、 4-(4,6-二甲氧基三嗪-2-基)-4-甲基吗啉盐酸盐 、 lithium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 (12S,22Z,32Z,52S,122Z,8R,11S,15S)-8-benzyl-15-isobutyl-11-methyl-7,10,14-triaza-3(2,4)-oxazola-2,12(2,4)-dithiazola-1(2,1),5(1,2)-dipyrrolidinacyclohexadecaphane-4,6,9,13,16-pentaone
  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：

  ethyl 2-<(S)-1-(N-t-butoxycarbonyl)aminoethyl>thiazole-4-carboxylate 在 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 作用下， 以 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