Z-(S)-Val-NMe-(S)-Val-(S)-Pro | 160811-54-1

• 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: Z-(S)-Val-NMe-(S)-Val-(S)-Pro
• 英文别名: Cbz-Val-N(Me)Val-Pro-OH；(2S)-1-[(2S)-3-methyl-2-[methyl-[(2S)-3-methyl-2-(phenylmethoxycarbonylamino)butanoyl]amino]butanoyl]pyrrolidine-2-carboxylic acid
• CAS: 160811-54-1
• 化学式: C₂₄H₃₅N₃O₆
• 分子量: 461.558
• InChiKey: YIPQFMOFMZQLAI-UFYCRDLUSA-N

物化性质

• 沸点：
  672.7±55.0 °C(Predicted)
• 密度：
  1.202±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Z-(S)-Val-NMe-(S)-Val-(S)-Pro 在 palladium on activated charcoal 氰基磷酸二乙酯 、 氢气 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 38.0h， 生成 dolastatin 15
  参考文献：
  名称：

  The Dolastatins 20. A Convenient Synthetic Route to Dolastatin 15

  摘要：

  A segment synthetic strategy was utilized for obtaining the Dolabella auricularia (Indian Ocean sea hare) depsipeptide dolastatin 15. Reaction of protected (S)-Hiva-(S)-Phe 2c with isopropenyl chloroformate followed by Meldrum's ester, cyclization (2c --> 3a) of the product in toluene and finally methylation afforded the key (S)-dolapyrrolidine (Dpy) derivative 3b. Condensation of tripeptide 8 with the three unit Dpy segment 5b followed by deprotection and coupling (diethyl phosphorocyanidate) led to dolastatin 15 in 11% overall yield. The powerful and selective activity of dolastatin 15 against the U.S. National Cancer Institute's panel of human cell lines has been summarized.

  DOI：

  10.1016/s0040-4020(01)89562-4
• 作为产物：
  描述：

  N-苄氧羰基-N-甲基-L-缬氨酸 在 palladium on activated charcoal N-甲基吗啉 、 sodium hydroxide 、 氰基磷酸二乙酯 、 氢气 、 三甲基乙酰氯 、 三乙胺 作用下， 以 甲醇 、 乙二醇二甲醚 、 乙醇 、 水 、 乙酸乙酯 为溶剂， 反应 39.0h， 生成 Z-(S)-Val-NMe-(S)-Val-(S)-Pro
  参考文献：
  名称：

  The Dolastatins 20. A Convenient Synthetic Route to Dolastatin 15

  摘要：

  A segment synthetic strategy was utilized for obtaining the Dolabella auricularia (Indian Ocean sea hare) depsipeptide dolastatin 15. Reaction of protected (S)-Hiva-(S)-Phe 2c with isopropenyl chloroformate followed by Meldrum's ester, cyclization (2c --> 3a) of the product in toluene and finally methylation afforded the key (S)-dolapyrrolidine (Dpy) derivative 3b. Condensation of tripeptide 8 with the three unit Dpy segment 5b followed by deprotection and coupling (diethyl phosphorocyanidate) led to dolastatin 15 in 11% overall yield. The powerful and selective activity of dolastatin 15 against the U.S. National Cancer Institute's panel of human cell lines has been summarized.

  DOI：

  10.1016/s0040-4020(01)89562-4

文献信息

• Synthetic antineoplastic agents derived from dolastatin 15 and methods of making same
  申请人：Arizona Board of Regents, acting for and on behalf of Arizona State University

  公开号：US06686445B1

  公开（公告）日：2004-02-03

  A composition of matter, denominated herein as 12a-r, having the structural formula set forth below: wherein R is selected from the group consisting of: a) R=NHPh; b) R=NHCH2Ph; c) R=NH(CH2)2Ph; d) R=NH(CH2)2‘-4-F-Ph; e) R=NH(CH2)2-4-Cl-Ph; f) R=NH(CH2)2-3-Cl-Ph; g) R=NH(CH2)2-2-Cl-Ph; h) R=NH(CH2)2-4-Br-Ph; i) R=NH(CH2)2-4-NO2-Ph; j) R=NH(CH2)2-3,4-(CH3O)2Ph; k) R=NH(CH2)2-2-pyridine; l) R=NH(CH2)3Ph; m) R=L-Phe-OCH3; n) R=L-Met-OCH3; o) R=L-Pro-OCH3; p) R=NH-2-thiazolyl; q) R=NH-2-benzothiazolyl; r) R=NH-3-quinolyl; and methods of making these compounds 12a-r.

  一种物质组合物，以下简称为12a-r，具有以下结构式：其中R选择自以下组合：a) R=NHPh; b) R=NHCH2Ph; c) R=NH(CH2)2Ph; d) R=NH(CH2)2‘-4-F-Ph; e) R=NH(CH2)2-4-Cl-Ph; f) R=NH(CH2)2-3-Cl-Ph; g) R=NH(CH2)2-2-Cl-Ph; h) R=NH(CH2)2-4-Br-Ph; i) R=NH(CH2)2-4-NO2-Ph; j) R=NH(CH2)2-3,4-(CH3O)2Ph; k) R=NH(CH2)2-2-pyridine; l) R=NH(CH2)3Ph; m) R=L-Phe-OCH3; n) R=L-Met-OCH3; o) R=L-Pro-OCH3; p) R=NH-2-thiazolyl; q) R=NH-2-benzothiazolyl; r) R=NH-3-quinolyl；以及制备这些化合物12a-r的方法。
• The Dolastatins 20. A Convenient Synthetic Route to Dolastatin 15
  作者：George R. Pettit、Timothy J. Thornton、Jeffrey T. Mullaney、Michael R. Boyd、Delbert L. Herald、Sheo-Bux Singh、Erik J. Flahive

  DOI：10.1016/s0040-4020(01)89562-4

  日期：1994.1

  A segment synthetic strategy was utilized for obtaining the Dolabella auricularia (Indian Ocean sea hare) depsipeptide dolastatin 15. Reaction of protected (S)-Hiva-(S)-Phe 2c with isopropenyl chloroformate followed by Meldrum's ester, cyclization (2c --> 3a) of the product in toluene and finally methylation afforded the key (S)-dolapyrrolidine (Dpy) derivative 3b. Condensation of tripeptide 8 with the three unit Dpy segment 5b followed by deprotection and coupling (diethyl phosphorocyanidate) led to dolastatin 15 in 11% overall yield. The powerful and selective activity of dolastatin 15 against the U.S. National Cancer Institute's panel of human cell lines has been summarized.