[(1E,3R,4S,6E)-8-[[(2R)-3-(3-chloro-4-methoxyphenyl)-1-oxo-1-(2,2,2-trichloroethoxy)propan-2-yl]amino]-3-methyl-8-oxo-1-phenylocta-1,6-dien-4-yl] (2S)-4-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate | 186193-23-7

• 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
• 英文名称: [(1E,3R,4S,6E)-8-[[(2R)-3-(3-chloro-4-methoxyphenyl)-1-oxo-1-(2,2,2-trichloroethoxy)propan-2-yl]amino]-3-methyl-8-oxo-1-phenylocta-1,6-dien-4-yl] (2S)-4-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate
• CAS: 186193-23-7
• 化学式: C₃₈H₄₈Cl₄N₂O₈
• 分子量: 802.62
• InChiKey: DROLEMGNTWLKFU-CICNEMSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  52
• 可旋转键数：
  21
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(1E,3R,4S,6E)-8-[[(2R)-3-(3-chloro-4-methoxyphenyl)-1-oxo-1-(2,2,2-trichloroethoxy)propan-2-yl]amino]-3-methyl-8-oxo-1-phenylocta-1,6-dien-4-yl] (2S)-4-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate 在 1-羟基苯并三唑 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 、 锌 作用下， 生成
  参考文献：
  名称：

  Synthesis and biological evaluation of cryptophycin analogs with substitution at C-6 (fragment C region)

  摘要：

  Analogs of the antitumor agents cryptophycins 1 and 8 with dialkyl substitution at C-6 (fragment C) were synthesized and evaluated for in vitro cytotoxicity against human leukemia cells (CCRF-CEM). The activity of these analogs decreased as the size of the substituents at C-6 increased. The C-6 spirocylopropyl compound (2g) was highly potent in vitro and showed excellent antitumor activity in animal models. (C) 1999 Elsevier Science Ltd. ALI rights reserved.

  DOI：

  10.1016/s0960-894x(98)00748-3
• 作为产物：
  描述：

  BOC-L-亮氨酸 、 2,2,2-trichloroethyl (2R)-3-(3-chloro-4-methoxyphenyl)-2-[[(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-phenylocta-2,7-dienoyl]amino]propanoate 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以62%的产率得到[(1E,3R,4S,6E)-8-[[(2R)-3-(3-chloro-4-methoxyphenyl)-1-oxo-1-(2,2,2-trichloroethoxy)propan-2-yl]amino]-3-methyl-8-oxo-1-phenylocta-1,6-dien-4-yl] (2S)-4-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate
  参考文献：
  名称：

  Total Synthesis of Cryptophycin Analogues. Isosteric Replacement of the C−D Ester

  摘要：

  DOI：

  10.1021/jo980536r

文献信息

• Total Synthesis of Cryptophycin Analogues. Isosteric Replacement of the C−D Ester
  作者：Bryan H. Norman、Thomas Hemscheidt、Richard M. Schultz、Sherri L. Andis

  DOI：10.1021/jo980536r

  日期：1998.7.1
• Synthesis and biological evaluation of cryptophycin analogs with substitution at C-6 (fragment C region)
  作者：David L. Varie、Chuan Shih、David A. Hay、Sherri L. Andis、Tom H. Corbett、Lynn S. Gossett、Samantha K. Janisse、Michael J. Martinelli、Eric D. Moher、Richard M. Schultz、John E. Toth

  DOI：10.1016/s0960-894x(98)00748-3

  日期：1999.2

  Analogs of the antitumor agents cryptophycins 1 and 8 with dialkyl substitution at C-6 (fragment C) were synthesized and evaluated for in vitro cytotoxicity against human leukemia cells (CCRF-CEM). The activity of these analogs decreased as the size of the substituents at C-6 increased. The C-6 spirocylopropyl compound (2g) was highly potent in vitro and showed excellent antitumor activity in animal models. (C) 1999 Elsevier Science Ltd. ALI rights reserved.