H-His-OBzl*2HCl | 31321-62-7

• 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-His-OBzl*2HCl
• 英文别名: H-L-His-OBzl*2HCl；Benzyl L-histidinate hydrochloride；benzyl (2S)-2-amino-3-(1H-imidazol-5-yl)propanoate;hydrochloride
• CAS: 31321-62-7
• 化学式: C₁₃H₁₅N₃O₂*2ClH
• 分子量: 318.203
• InChiKey: FRJRDAPZBUIVLH-YDALLXLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.44
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  81
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-benzyloxycarbonyl-glycyl-L-2-methylproline 、 H-His-OBzl*2HCl 在 三乙胺 、 双(2-氧代-3-恶唑烷基)次磷酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以69%的产率得到
  参考文献：
  名称：

  Development of glycine-α-methyl-proline-containing tripeptides with neuroprotective properties

  摘要：

  Herein is described the synthesis of novel glycine-alpha-methyl-proline-containing tripeptides (GP(Me)X tripeptides namely GP(Me)R, GP(Me)K, and GP(Me)H) with the aim of obtaining derivatives highly stable in human plasma and able to counteract neuroinflammatory processes that are distinctive of neurodegenerative pathologies. The syntheses of GP(Me)R, GP(Me)K, and GP(Me)H were all achieved both by introducing the Pro(Me) residue into the Gly-Pro-Arg (GPR) sequence in place of the native Pro in P2 position and replacing the basic amino acid Arg in P3 position by Lys or His.Results showed that all novel GP(Me)X tripeptides are stable in human plasma (t(1/2) > 51 h) and that GP(Me)H generating stable intramolecular H-bond in a C-11-turn by interaction of His imidazole ring and Gly carbonyl group restored physiological levels of nitric oxide deriving from neuronal NOS (nNOS) activity, thus preventing the inflammatory response by suppression of the NF-kB activity and, consequently, the expression of inflammatory genes such as inducibile NOS (iNOS). Therefore, GP(Me)H could be a lead compound for further development of peptidomimetics able to contrast neuroinflammatory processes. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.12.003
• 作为产物：
  描述：

  tert-butyl 5-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxo-3-phenylmethoxypropyl]imidazole-1-carboxylate 生成 H-His-OBzl*2HCl
  参考文献：
  名称：

  HOOVER, DENNIS J.;ROSATI, ROBERT L.

  摘要：

  DOI：

文献信息

• A new class of anti-thrombosis hexahydropyrazino-[1′,2′:1,6]pyrido-[3,4-b]-indole-1,4-dions: Design, synthesis, logK determination, and QSAR analysis
  作者：Jiawang Liu、Guofeng Wu、Guohui Cui、Wei-Xuan Wang、Ming Zhao、Chao Wang、Ziding Zhang、Shiqi Peng

  DOI：10.1016/j.bmc.2007.06.012

  日期：2007.9.1

  (tetrahydro-beta-carboline-3-carboxy-l-amino acid benzylesters, 2-aminoacyltetrahydro-beta-carboline-3-carboxylic acid benzylesters) were prepared and used for the cyclization to form 5a-t. Coupling hydrochloric acid salt of tetrahydro-beta-carboline-3-carboxylic acid esters and Boc-amino acids in the reported literature usually generates very low yield products accompanied by racemization. However, in our case, the

  基于N-[（3S）]-1,2,3,4-四氢-β-咔啉-3-羧基] -1-赖氨酸在乙酸水溶液（5％）和大鼠中的环化血浆给出了相同的产物，并假设环化产物具有抗血栓活性，我们报道了20种六氢吡嗪并[1'，2'：1,6]吡啶并[ 3,4-b]吲哚-1,4-dion（5a-t）作为潜在的抗血栓形成剂。制备了两种中间体（四氢-β-咔啉-3-羧基-1-氨基酸苄酯，2-氨基酰基四氢-β-咔啉-3-羧酸苄酯），并用于环化形成5a-t。在已报道的文献中，四氢-β-咔啉-3-羧酸酯的盐酸盐与Boc-氨基酸的偶联通常产生非常低的收率产物，并伴随着消旋作用。然而，在我们的情况下，四氢-β-咔啉-3-羧酸苄酯的游离碱以高收率且没有外消旋作用产生了所需的产物。来自体外和体内研究的抗血栓形成结果表明，5a-t可能是一类新型的抗血栓形成剂，口服有效有效浓度为0.5μmol/ kg。此外，使用e-dragon服务器生成的分子
• Carvacrol prodrugs as novel antimicrobial agents
  作者：Lisa Marinelli、Erika Fornasari、Piera Eusepi、Michele Ciulla、Salvatore Genovese、Francesco Epifano、Serena Fiorito、Hasan Turkez、Serkan Örtücü、Marina Mingoia、Serena Simoni、Armanda Pugnaloni、Antonio Di Stefano、Ivana Cacciatore

  DOI：10.1016/j.ejmech.2019.05.093

  日期：2019.9

  solubility was increased by using polar neutral groups (such as natural amino acids) with the aim of improving oral drug delivery. On the other hand, CAR lipophilic prodrugs, obtained by prenylation of CAR hydroxyl group, were designed to promote membrane permeation and oral absorption. Our results revealed that WSCP1-3, showing the highest water solubility (>1700-fold compared to that of CAR), possessed good

  香芹酚（CAR）是一种天然的单萜，在唇形科的植物中特别丰富，最近因其许多生物学特性（抗氧化剂，抗炎剂，神经保护剂，抗肿瘤剂，抗菌剂等）而备受关注。但是，CAR具有较差的化学物理性质（低水溶性和高挥发性），从而妨碍了其潜在的药理用途。 本文报道了23种香芹酚衍生物（WSCP1-23）对一组选定的革兰氏阳性和革兰氏阴性细菌的合成和抗菌评估。采用前药的方法，CAR亲水性（WSCP1-17）和亲脂性药物前体（WSCP18 - 23）制备。值得注意的是，通过使用极性中性基团（例如天然氨基酸）来提高CAR的水溶性，以改善口服药物的递送。另一方面，通过CAR羟基的烯丙基化获得的CAR亲脂性前药被设计用于促进膜渗透和口服吸收。 我们的结果表明，WSCP1-3具有最高的水溶性（是CAR的1700倍），对革兰氏阴性菌具有良好的抗菌活性，MIC值与CAR相当，并且对不同种类的念珠菌具有抗真菌特性。WSCP18 -
• Homocyclostatine and cyclostatine containing polypeptides as antihypertensive agents
  申请人：PFIZER INC.

  公开号：EP0297816A2

  公开（公告）日：1989-01-04

  Polypeptides and derivatives thereof containing homocyclostatine and cyclostatine are useful for inhibiting the angiotensinogen-cleaving action of the enzyme renin.

  含有同型环丝氨酸和环丝氨酸的多肽及其衍生物可用于抑制肾素酶的血管紧张素原分解作用。
• A class of novel carboline intercalators: Their synthesis, in vitro anti-proliferation, in vivo anti-tumor action, and 3D QSAR analysis
  作者：Jianhui Wu、Chunyu Li、Ming Zhao、Wenjing Wang、Yuji Wang、Shiqi Peng

  DOI：10.1016/j.bmc.2010.07.043

  日期：2010.9

  Based on DOCK scores 18 N-(3-benzyloxycarbonylcarboline-1-yl) ethylamino acid benzylesters (6a-r) were synthesized as anti-tumor agents. Their IC50 values against five human carcinoma cell lines ranged from 11.1 mu M to more than 100 mu M. The in vivo assay identified five derivatives of them had no antitumor action, the anti-tumor activity of nine derivatives of them equaled that of cytarabine, and the anti-tumor activity of three derivatives of them was higher than that of cytarabine. The UV and fluorescence spectra, as well as the relative viscosity and melting temperature measurements of calf thymus DNA (CT DNA) with and without the representative compound suggested that DNA intercalation could be their action mechanism. The 3D QSAR analysis of N-(3-benzyloxycarbonylcarboline-1-yl) ethylamino acid benzylesters (6a-r) revealed that their in vivo anti-tumor activity significantly depends on the molecular electrostatic and steric fields of the side chain of the amino acid residue. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.
• Indole-TEMPO conjugates alleviate ischemia-reperfusion injury via attenuation of oxidative stress and preservation of mitochondrial function
  作者：Wei Bi、Yue Bi、Xiang Gao、Pengfei Li、Shanshan Hou、Yanrong Zhang、Cathy Bammert、Steffen Jockusch、Thomas D. Legalley、K. Michael Gibson、Lanrong Bi

  DOI：10.1016/j.bmc.2017.03.033

  日期：2017.5

  Mitochondrial oxidative damage contributes to a wide range of pathologies including ischemia/reperfusion injury. Accordingly, protecting mitochondria from oxidative damage should possess therapeutic relevance. In the present study, we have designed and synthesized a series of novel indole-TEMPO conjugates that manifested good anti-inflammatory properties in a murine model of xylene-induced ear edema. We have demonstrated that these compounds can protect cells from simulated ischemia/reperfusion (s-I/R)-induced reactive oxygen species (ROS) overproduction and mitochondrial dysfunction. Furthermore, we have demonstrated that indole-TEMPO conjugates can attenuate organ damage induced in rodents via intestinal I/R injury. We therefore propose that the pharmacological profile and mechanism of action of these indole-TEMPO conjugates involve convergent roles, including the ability to decrease free radical production via lipid peroxidation which couples to an associated decrease in ROS-mediated activation of the inflammatory process. We further hypothesize that the protective effects of indole-TEMPO conjugates partially reside in maintaining optimal mitochondrial function. (C) 2017 Published by Elsevier Ltd.