L-valine-L-proline methyl ester | 77390-94-4

• 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-valine-L-proline methyl ester
• 英文别名: methyl L-valyl-L-prolinate；L-Val-L-Pro methyl ester；H-Val-Pro-OMe；methyl (2S)-1-[(2S)-2-amino-3-methylbutanoyl]pyrrolidine-2-carboxylate
• CAS: 77390-94-4
• 化学式: C₁₁H₂₀N₂O₃
• 分子量: 228.291
• InChiKey: IZAPPFQMAUWRCO-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 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-valine-L-proline methyl ester 在 三乙胺 作用下， 以 甲苯 、 仲丁醇 为溶剂， 反应 16.0h， 生成 环(L-脯-L-缬)二肽
  参考文献：
  名称：

  C 2对称手性二胺-铜（II）配合物 催化对映选择性亨利反应†

  摘要：

  事实证明，C 2对称二胺的铜（II）络合物是硝基链烷烃与各种醛之间对映选择性亨利反应的有效催化剂，以高产率（高达97％），中等非对映选择性（高达90％以上）提供β-羟基硝基链烷烃。至71:29）和出色的对映体过量（高达96％）。所获得的手性硝基醛醇加合物在几个步骤中已进一步转化为手性氮丙啶。

  DOI：

  10.1039/b904254g
• 作为产物：
  描述：

  L-脯氨酸甲酯盐酸盐 在 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 26.33h， 生成 L-valine-L-proline methyl ester
  参考文献：
  名称：

  Total synthesis and structure–activity relationships of new echinocandin-like antifungal cyclolipohexapeptides

  摘要：

  A series of new echinocandin-like cyclolipohexapeptides were designed and total synthesized via solution phase [3 + 3]-segment coupling strategy with an attempt to improve antifungal activity. The designed compounds showed potent antifungal activities with broad spectrum. In particular, 11 compounds (i.e. 28a-e, 28g, 28i-j, 29a, 29c and 29e) showed better in vitro antifungal activities against Candida albicans or Aspergillus fumigatus than caspofungin. Moreover, the synthesized compounds provided new SAR information for the echinocandins. The findings in this work suggested that the "left" tripeptide segment of cyclolipohexapeptide scaffold might be a hydrophilic structural motif, whereas the "right" lipopeptide segment was preferred as a hydrophobic core. The amino acid component of the cyclolipohexapeptide scaffold could significantly affect the SAR of the side chains. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.01.054

文献信息

• Dynamic combinatorial libraries of hydrazone-linked pseudo-peptides: dependence of diversity on building block structure and chirality
  作者：Jingyuan Liu、Kevin R. West、Chantelle R. Bondy、Jeremy K. M. Sanders

  DOI：10.1039/b617217b

  日期：——

  Expanding on our earlier building block architecture [(MeO)2CH–Linker–Pro–X–NHNH2 where X = Phe, Cha], we have produced a series of new pseudo-dipeptides [(MeO)2CH–Linker–Pro–X–NHNH2 where X = Val, Leu, Ile, Ala] for use in hydrazone-based dynamic combinatorial libraries (DCLs); reverse order analogues [Phe-Pro and Val-Pro] and two enantio-analogues [Pro-Phe and Pro-Val] were also prepared. The behaviours of these building blocks in DCLs, as single components and in mixtures, were studied systematically using HPLC and mass spectrometry in order to gain insight into the relationship between building block structure and good library diversity. Subtle changes in building block structure lead to significant changes in library distribution and in the ability to produce diverse libraries in mixtures.

  基于我们早期的构建模块架构[(MeO)2CH–Linker–Pro–X–NHNH2，其中X = Phe, Cha]，我们合成了一系列新的伪二肽[(MeO)2CH–Linker–Pro–X–NHNH2，其中X = Val, Leu, Ile, Ala]，用于基于脒的动态组合库（DCLs）；反向顺序类似物[Phe-Pro和Val-Pro]以及两种对映异构类似物[Pro-Phe和Pro-Val]也被制备。我们系统地研究了这些构建模块在DCL中的行为，无论是单独成分还是混合物，都使用了高效液相色谱法和质谱法，以深入了解构建模块结构与良好库多样性之间的关系。构建模块结构的细微变化导致了库分布的显著变化以及在混合物中产生多样性库的能力的变化。
• [EN] MALT1 INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE MALT1 ET LEURS UTILISATIONS
  申请人：UNIV CORNELL

  公开号：WO2017040304A1

  公开（公告）日：2017-03-09

  Provided herein are compounds of Formula (I) and pharmaceutical compositions thereof, which may be useful as MALT1 inhibitors. Also provided are for the treatment of proliferative disorders (e.g., cancer (e.g., non-Hodgkin' s lymphoma, diffuse large B-cell lymphoma, MALT lymphoma), benign neoplasm, a disease associated with angiogenesis,an autoimmune disease, an inflammatory disease, an autoinflammatory disease) by administering a compound of Formula (I).

  本文提供了化合物的化学式(I)及其药物组合物，可用作MALT1抑制剂。还提供了通过给予化合物的化学式(I)来治疗增生性疾病（例如癌症（例如非霍奇金淋巴瘤、弥漫性大B细胞淋巴瘤、MALT淋巴瘤）、良性肿瘤、与血管生成有关的疾病、自身免疫疾病、炎症性疾病、自身炎症性疾病）的方法。
• Dipeptide derivative of fatty acid
  申请人：Suntory Limited

  公开号：US04772587A1

  公开（公告）日：1988-09-20

  A novel compound that exhibits inhibitory activity against prolyl endopeptidase and a method for chemical synthesis of said compound, as well as its use as a prolyl endopeptidase inhibitor and an anti-amnesic agent that contains said compound as the active ingredient are provided.

  本发明提供了一种新的化合物，该化合物具有抑制脯氨酰内切酶活性的作用，以及一种该化合物的化学合成方法，以及将该化合物用作脯氨酰内切酶抑制剂和抗遗忘剂的用途，其中该化合物为活性成分。
• MALT1 inhibitors and uses thereof
  申请人：Cornell University

  公开号：US10711036B2

  公开（公告）日：2020-07-14

  Provided herein are compounds of Formula (I) and pharmaceutical compositions thereof, which may be useful as MALT1 inhibitors. Also provided are for the treatment of proliferative disorders (e.g., cancer (e.g., non-Hodgkin's lymphoma, diffuse large B-cell lymphoma, MALT lymphoma), benign neoplasm, a disease associated with angiogenesis, an autoimmune disease, an inflammatory disease, an autoinflammatory disease) by administering a compound of Formula (I).

  本文提供的式(I)化合物及其药物组合物可用作 MALT1 抑制剂。还提供了通过施用式（I）化合物治疗增殖性疾病（如癌症（如非霍奇金淋巴瘤、弥漫大 B 细胞淋巴瘤、MALT 淋巴瘤）、良性肿瘤、与血管生成相关的疾病、自身免疫性疾病、炎症性疾病、自身炎症性疾病）。
• Structure-based design, synthesis and biochemical testing of novel and potent Smac peptido-mimetics
  作者：Haiying Sun、Zaneta Nikolovska-Coleska、Jianyong Chen、Chao-Yie Yang、York Tomita、Hongguang Pan、Yoshiko Yoshioka、Krzysztof Krajewski、Peter P. Roller、Shaomeng Wang

  DOI：10.1016/j.bmcl.2004.11.008

  日期：2005.2

  Structure-based design, chemical synthesis and biochemical testing of a series of novel Smac peptido-mimetics as inhibitors of XIAP protein are described. The most potent compound, 6j, has a binding affinity (K-i value) of 24 nM to XIAP BIR3 protein and is 24 times more potent than the native Smac AVPI peptide. Further optimization of these potent Smac mimetics may ultimately lead to the development of a novel class of anticancer drugs for the treatment of human cancer by overcoming apoptosis-resistance of cancer cells through targeting the inhibitor of apoptosis proteins. (C) 2004 Elsevier Ltd. All rights reserved.