NMe-(S)-Val-(S)-Pro-OMe | 182573-17-7

• 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: NMe-(S)-Val-(S)-Pro-OMe
• 英文别名: 1-(3-methyl-2-methylamino-butyryl)-pyrrolidine-2-carboxylic acid methyl ester；N-methyl-L-valyl-O-methyl-L-proline；methyl (2S)-1-[(2S)-3-methyl-2-(methylamino)butanoyl]pyrrolidine-2-carboxylate
• CAS: 182573-17-7
• 化学式: C₁₂H₂₂N₂O₃
• 分子量: 242.318
• InChiKey: VMIFQLPBZJFBPK-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  NMe-(S)-Val-(S)-Pro-OMe 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 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 67.0h， 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：

  L-脯氨酸甲酯盐酸盐 在 palladium on activated charcoal 氰基磷酸二乙酯 、 氢气 、 三乙胺 作用下， 以 甲醇 、 乙二醇二甲醚 、 乙酸乙酯 为溶剂， 反应 10.0h， 生成 NMe-(S)-Val-(S)-Pro-OMe
  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
• 作为试剂：
  描述：

  N-Boc-L-缬氨酸 在 N-甲基吗啉 、 三甲基乙酰氯 、 NMe-(S)-Val-(S)-Pro-OMe 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 methyl N-((tert-butoxycarbonyl)-L-valyl)-N-methyl-L-valyl-L-prolinate
  参考文献：
  名称：

  Synthetic antineoplastic agents derived from dolastatin 15 and methods of making same

  摘要：

  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。

  公开号：

  US06686445B1

文献信息

• Compounds for treating tumors
  申请人：Zask Arie

  公开号：US20050037977A1

  公开（公告）日：2005-02-17

  The invention provides compounds of formula (I): wherein E, A, B′, R 6 , R 7 , R 8 , and R 9 are defined in the specification which compounds exhibit anticancer activity and are useful for treating cancer.

  该发明提供了以下式（I）的化合物： 其中E、A、B′、R6、R7、R8和R9在规范中定义，这些化合物表现出抗癌活性，并可用于治疗癌症。
• Dolastatin-15 derivatives in combination with taxanes
  申请人：BASF Aktiengesellschaft

  公开号：US06103698A1

  公开（公告）日：2000-08-15

  The present invention provides compositions and methods for the treatment of cancer in a subject wherein compounds of Formula I as defined herein in combination with paclitaxel, taxotere or modified taxane or taxoid analogs provide enhanced anticancer effects over the effects achieved with the individual compounds.

  本发明提供了一种用于治疗患者癌症的组合物和方法，其中公式I中定义的化合物与紫杉醇、紫杉醇衍生物或类似物结合使用，可以比单独使用这些化合物更有效地产生抗癌效果。
• COMPOUNDS FOR TREATING TUMORS
  申请人：Zask Arie

  公开号：US20080221181A1

  公开（公告）日：2008-09-11

  The invention provides compounds of formula (I): wherein E, A, B′, R 6 , R 7 , R 8 , and R 9 are defined in the specification which compounds exhibit anticancer activity and are useful for treating cancer.

  本发明提供公式（I）的化合物：其中E，A，B'，R6，R7，R8和R9在说明书中定义，这些化合物表现出抗癌活性并可用于治疗癌症。
• Total Synthesis of Depsilairdin
  作者：Dale E. Ward、Sandip G. Pardeshi

  DOI：10.1021/jo1009239

  日期：2010.8.6

  The total synthesis of depsilairdin, a host-selective phytotoxin isolated from Leptosphaeria maculans (the causal agent of blackleg disease of oilseed Brassicas), has been achieved by N-terminal extension of a suitably protected derivative of the hitherto unknown amino acid (2S,3S,4R)-3,4-dihydroxy-3-methyl-proline (Dhmp) followed by esterification with lairdinol A. The latter esterification, complicated by the sterically hindered nature of the carboxyl group, was accomplished by a novel method involving reaction of the 1-hydroxybenzotriazole (HOBt) derived active ester with the bromomagnesium alkoxide of lairdinol A. Three depsilairdin analogues were also prepared by replacing the Dhmp residue with L-proline and cis- and trans-4-hydroxy-L-proline. Phytotoxicity assays showed that the analogues were nontoxic to both blackleg-susceptible (brown mustard) and -resistant (canola) plants, suggesting that the presence of the Dhmp residue in depsilairdin is important for its host-selective toxicity toward brown mustard.
• US6686445B1
  申请人：——

  公开号：US6686445B1

  公开（公告）日：2004-02-03