L-valyl-L-proline phenylmethyl ester | 106665-76-3

• 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: L-valyl-L-proline phenylmethyl ester
• 英文别名: H-Val-Pro-OBzl；Val-Pro-OBzl；VP-OBzl；benzyl (2S)-1-[(2S)-2-amino-3-methylbutanoyl]pyrrolidine-2-carboxylate
• CAS: 106665-76-3
• 化学式: C₁₇H₂₄N₂O₃
• 分子量: 304.389
• InChiKey: ONPMQVDELWBJTG-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  72.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  L-valyl-L-proline phenylmethyl ester 在 palladium on activated charcoal ammonium formate 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.33h， 生成 (S)-1-((S)-2-{2-[(2S,3S)-2-(2-tert-Butoxycarbonylamino-acetylamino)-3-methyl-pentanoylamino]-acetylamino}-3-methyl-butyryl)-pyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  Gowda, D. Channe; Baba, A. Ramesha; Luan, Chi-Hao, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002, vol. 41, # 12, p. 2606 - 2613

  摘要：

  DOI：
• 作为产物：
  描述：

  Boc-Val-Pro-OBzl 在 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 L-valyl-L-proline phenylmethyl ester
  参考文献：
  名称：

  设计和合成含色氨酸的肽作为潜在的止痛药和消炎药。

  摘要：

  通过分析和光谱技术设计，合成和表征了一系列新的较小肽，这些肽在C端具有色氨酸，并且具有不同的N保护的氨基酸/肽。这些肽的镇痛和抗炎特性在体内进行分别以不同剂量和不同时间间隔使用甩尾法和角叉菜胶诱发的爪水肿法。合成的大多数肽都显示出增强的活性，特别是四肽和六肽29-31被发现比使用的参考标准品更有效。此外，某些肽甚至在给药24小时后仍显示出有希望的活性，而参考标准仅在3 h内才有活性。此外，这些化合物不具有任何致溃疡性。版权所有©2012欧洲肽协会和John Wiley＆Sons，Ltd.

  DOI：

  10.1002/psc.2431

文献信息

• Synthesis and structure-activity relationships of amastatin analogues, inhibitors of aminopeptidase A.
  作者：Hiroyasu TOBE、Hajime MORISHIMA、Takaaki AOYAGI、Hamao UMEZAWA、Kunio ISHIKI、Kenji NAKAMURA、Takeo YOSHIOKA、Yasutaka SHIMAUCHI、Taiji INUI

  DOI：10.1271/bbb1961.46.1865

  日期：——

  Stereoisomers and analogues of amastatin, [(2S, 3R)-3-amino-2-hydroxy-5-methylhexanoyl]-L-Val-L-Val-L-Asp, were synthesized and their inhibitory activities towards aminopeptidase A (AP-A) and other arylamidases tested. Among the four stereoisomers of a new amino acid residue in amastatin, the 2S stereoisomers exhibited strong activity. In a series of compounds in which the C-terminal amino acid of amastatin was substituted by other amino acids, the one containing Asp or Glu showed the strongest activity towards AP-A. In a series of compounds in which the second or third residue from the amino terminal of amastatin was substituted by other amino acids, the one containing hydrophobic amino acids showed strong activity. In the study of the relationship of the length of the peptide chain and inhibitory activity, the activity towards AP-A was seen to increase until the length of the peptide reached that of a tetrapeptide.

  阿马司他（(2S,3R)-3-氨基-2-羟基-5-甲基己酰基-L-缬氨酰-L-缬氨酰-L-天冬氨酸）的立体异构体和类似物被合成，并测试了它们对氨基肽酶A（AP-A）和其他芳基酰胺酶的抑制活性。在阿马司他中一个新的氨基酸残基的四种立体异构体中，2S立体异构体表现出强烈的活性。在一系列将阿马司他C端氨基酸替换为其他氨基酸的化合物中，含有Asp或Glu的化合物对AP-A显示出最强的活性。在一系列将阿马司他从氨基端开始的第二个或第三个残基替换为其他氨基酸的化合物中，含有疏水氨基酸的化合物表现出强烈的活性。在研究肽链长度与抑制活性关系的研究中，随着肽链长度达到四肽水平，对AP-A的活性逐渐增加。
• Synthesis and Antimicrobial Activity of Quinazolinone Conjugated Peptides
  作者：G. P. Suresha、K. C. Prakasha、Wethroe Kapfo、D. Channe Gowda

  DOI：10.1155/2010/979675

  日期：——

  Antimicrobial compounds were synthesized by coupling 4-(4-oxo-3,4-dihydroquinazolin-2-yl) butanoic acid with VP, GVP, VGVP and GVGVP peptides. Antimicrobial activities of the synthesized compounds were performed against various bacterial strains by disc diffusion method. The structure activity relationship was evaluated with respect to hydrophobicity, polarity, chain length of peptides and alkyl chain length of quinazolinone. Correlations of analogs with respect to their antimicrobial activity in comparison with conventional drugs and probable mechanism for the activity were discussed.

  抗微生物化合物是通过将4-(4-氧代-3,4-二氢喹唑啉-2-基)丁酸与VP、GVP、VGVP和GVGVP肽偶联而合成的。合成化合物的抗微生物活性通过圆片扩散法对各种细菌菌株进行了测试。针对亲疏水性、肽链长度和喹唑啉酮烷基链长度，评估了结构活性关系。讨论了类似物与传统药物相比的抗微生物活性相关性和可能的活性机制。
• Imidazolidinones and their related derivatives as hepatitis C virus NS3 protease inhibitors
  申请人：——

  公开号：US20030100768A1

  公开（公告）日：2003-05-29

  The present invention relates generally to a novel class of imidazolidinones of Formula (I): 1 that are useful as serine protease inhibitors, and more particularly as Hepatitis C virus NS3 protease inhibitors. This invention also relates to pharmaceutical compositions comprising these compounds and methods of using the same.

  本发明涉及一种新型咪唑啉酮类化合物，通式为（I）：1，它们可用作丝氨酸蛋白酶抑制剂，更具体地用作丙型肝炎病毒NS3蛋白酶抑制剂。本发明还涉及包含这些化合物的药物组合物和使用它们的方法。
• Design, synthesis and evaluation of monovalent Smac mimetics that bind to the BIR2 domain of the anti-apoptotic protein XIAP
  作者：Marcos González-Lόpez、Kate Welsh、Darren Finlay、Robert J. Ardecky、Santhi Reddy Ganji、Ying Su、Hongbin yuan、Peter Teriete、Peter D. Mace、Stefan J. Riedl、Kristiina Vuori、John C. Reed、Nicholas D.P. Cosford

  DOI：10.1016/j.bmcl.2011.05.049

  日期：2011.7

  We report the systematic rational design and synthesis of new monovalent Smac mimetics that bind preferentially to the BIR2 domain of the anti-apoptotic protein XIAP. Characterization of compounds in vitro (including 9i; ML101) led to the determination of key structural requirements for BIR2 binding affinity. Compounds 9h and 9j sensitized TRAIL-resistant breast cancer cells to apoptotic cell death, highlighting the value of these probe compounds as tools to investigate the biology of XIAP. (C) 2011 Elsevier Ltd. All rights reserved.
• MARUYAMA, CYCYMY;TAHAKA, XIDEHOKI;TOMITSUKA, NOBORU;SUDZUKI, XIDEHO;SUGAI+
  作者：MARUYAMA, CYCYMY、TAHAKA, XIDEHOKI、TOMITSUKA, NOBORU、SUDZUKI, XIDEHO、SUGAI+

  DOI：——

  日期：——