H-Val-His-OCH3 | 41839-88-7

• 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: H-Val-His-OCH3
• 英文别名: Val-His-OMe；L-Val-L-His-OMe；methyl (2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-3-(1H-imidazol-5-yl)propanoate
• CAS: 41839-88-7
• 化学式: C₁₂H₂₀N₄O₃
• 分子量: 268.316
• InChiKey: SOTMNTBAGUGOAS-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  H-Val-His-OCH3 以 甲醇 为溶剂， 生成 cyclo-(L-valyl-L-histidyl)
  参考文献：
  名称：

  用由 L-组氨酸和不同脂肪族 α-氨基酸组成的环二肽催化剂水解脂肪族羧酸的活性酯

  摘要：

  使用由 L-组氨酸 (L-His) 组成的环二肽 [环（–L- 或 D-Xyz–His–），在 25 °C、pH 7.8 下研究了一系列具有不同酰基链的对硝基苯基羧酸盐的水解和具有不同脂肪族侧链的α-氨基酸（Xyz）]作为催化剂。因此，发现环（-D-Leu-L-His-）和环（-D-Val-L-His-）是月桂酸对硝基苯酯水解的特别有效的催化剂。这些反式（DL 型）环状二肽是比它们的非对映异构体更有效的催化剂，并且比咪唑更具反应性，尽管前者的碱性不如后者。使用质子磁共振波谱研究了溶液中环肽的构象，并研究了构象与催化活性之间的关系。最后，

  DOI：

  10.1246/bcsj.58.497
• 作为产物：
  描述：

  S-(+)-7-Methoxycarbonyl-5,6,7,8-tetrahydroimidazo<1,5-c>pyrimidin-5-on 在 盐酸 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 H-Val-His-OCH3
  参考文献：
  名称：

  Design, synthesis and evaluation of XZH-5 analogues as STAT3 inhibitors

  摘要：

  Inhibition of the signaling pathways of signal transducer and activator of transcription 3 (STAT 3) has shown to be a promising strategy to combat cancer. In this paper we report the design, synthesis and evaluation of a novel class of small molecule inhibitors, that is, XZH-5 and its analogues, as promising leads for further development of STAT3 inhibitors. Preliminary SARs was established for XZH-5 and its derivatives; and the binding modes were predicted by molecular docking. Lead compounds with IC50 as low as 6.5 mu M in breast cancer cell lines and 7.6 mu M in pancreatic cancer cell lines were identified. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.01.025

文献信息

• Giori; Mazzotta; Vertuani, Farmaco, Edizione Scientifica, 1981, vol. 36, # 12, p. 1019 - 1028
  作者：Giori、Mazzotta、Vertuani、Guarneri、Pancaldi、Brunelli

  DOI：——

  日期：——
• Arena, Giuseppe; Impellizzeri, Giuseppe; Maccarrone, Giuseppe, Journal of the Chemical Society. Perkin transactions II, 1992, # 3, p. 371 - 376
  作者：Arena, Giuseppe、Impellizzeri, Giuseppe、Maccarrone, Giuseppe、Pappalardo, Giuseppe、Sciotto, Domenico、Rizzarelli, Enrico

  DOI：——

  日期：——
• Design, synthesis and evaluation of XZH-5 analogues as STAT3 inhibitors
  作者：Philias Daka、Aiguo Liu、Chamini Karunaratne、Erika Csatary、Cameron Williams、Hui Xiao、Jiayuh Lin、Zhenghu Xu、Richard C. Page、Hong Wang

  DOI：10.1016/j.bmc.2015.01.025

  日期：2015.3

  Inhibition of the signaling pathways of signal transducer and activator of transcription 3 (STAT 3) has shown to be a promising strategy to combat cancer. In this paper we report the design, synthesis and evaluation of a novel class of small molecule inhibitors, that is, XZH-5 and its analogues, as promising leads for further development of STAT3 inhibitors. Preliminary SARs was established for XZH-5 and its derivatives; and the binding modes were predicted by molecular docking. Lead compounds with IC50 as low as 6.5 mu M in breast cancer cell lines and 7.6 mu M in pancreatic cancer cell lines were identified. (C) 2015 Elsevier Ltd. All rights reserved.
• Hydrolysis of Active Esters of Aliphatic Carboxylic Acids with Cyclic Dipeptide Catalysts Consisting of L-Histidine and Different Aliphatic α-Amino Acids
  作者：Yoshihiko Masuda、Masao Tanihara、Yukio Imanishi、Toshinobu Higashimura

  DOI：10.1246/bcsj.58.497

  日期：1985.2

  at 25 °C, pH 7.8 using cyclic dipeptides[cyclo(–L- or D-Xyz–His–) consisting of L-histidine (L-His) and an α-amino acid (Xyz) with different aliphatic side chains] as catalysts. Consequently, cyclo(–D-Leu–L-His–) and cyclo(–D-Val–L-His–) were found to be specifically effective catalysts for the hydrolysis of p-nitrophenyl laurate. These trans (D-L-type) cyclic dipeptides were much more efficient catalysts

  使用由 L-组氨酸 (L-His) 组成的环二肽 [环（–L- 或 D-Xyz–His–），在 25 °C、pH 7.8 下研究了一系列具有不同酰基链的对硝基苯基羧酸盐的水解和具有不同脂肪族侧链的α-氨基酸（Xyz）]作为催化剂。因此，发现环（-D-Leu-L-His-）和环（-D-Val-L-His-）是月桂酸对硝基苯酯水解的特别有效的催化剂。这些反式（DL 型）环状二肽是比它们的非对映异构体更有效的催化剂，并且比咪唑更具反应性，尽管前者的碱性不如后者。使用质子磁共振波谱研究了溶液中环肽的构象，并研究了构象与催化活性之间的关系。最后，