反式-4-苯基-L-脯氨酸盐酸盐 | 90657-53-7

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 脯氨酸类衍生物
• 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
• 中文名称: 反式-4-苯基-L-脯氨酸盐酸盐
• 英文名称: trans-4-phenyl-l-proline hydrochloride
• 英文别名: (2S,4S)-4-phenylpyrrolidine-2-carboxylic acid；(2S,4S)-4-phenylpyrrolidine-2-carboxylic acid;hydrochloride
• CAS: 90657-53-7
• 化学式: C₁₁H₁₃NO₂*ClH
• 分子量: 227.691
• InChiKey: LWFBRHSTNWMMGN-UXQCFNEQSA-N

物化性质

• 熔点：
  134-140°C

计算性质

• 辛醇/水分配系数(LogP)：
  1.64
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  49.3
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335

反应信息

• 作为反应物：
  描述：

  反式-4-苯基-L-脯氨酸盐酸盐 在 platinum(IV) oxide 氢气 作用下， 以 乙醇 为溶剂， 以91%的产率得到反-4-环己基-L-脯氨酸盐酸盐
  参考文献：
  名称：

  Angiotensin-converting enzyme inhibitors. Mercaptan, carboxyalkyl dipeptide, and phosphinic acid inhibitors incorporating 4-substituted prolines

  摘要：

  Analogues of captopril, enalaprilat, and the phosphinic acid [hydroxy(4-phenylbutyl)phosphinyl]acetyl]-L-proline incorporating 4-substituted proline derivatives have been synthesized and evaluated as inhibitors of angiotensin-converting enzyme (ACE) in vitro and in vivo. The 4-substituted prolines, incorporating alkyl, aryl, alkoxy, aryloxy, alkylthio, and arylthio substituents were prepared from derivatives of 4-hydroxy- and 4-ketoproline. In general, analogues of all three classes of inhibitors with hydrophobic substituents on proline were more potent in vitro than the corresponding unsubstituted proline compounds. 4-Substituted analogues of captopril showed greater potency and duration of action than the parent compound as inhibitors of the angiotensin I induced pressor response in normotensive rats. The S-benzoyl derivative of cis-4-(phenylthio)captopril, zofenopril, was found to be one of the most potent compounds of this class and is now being evaluated clinically as an antihypertensive agent. In the phosphinic acid series, the 4-ethylenethioketal and trans-4-cyclohexyl derivatives were found to be the most potent compounds in vitro and in vivo. A prodrug of the latter compound, fosinopril, is also being evaluated in clinical trials.

  DOI：

  10.1021/jm00401a014
• 作为产物：
  描述：

  N-叔丁氧羰基-(2S,4S)-4-苯基吡咯烷-2-羧酸 在 盐酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 反式-4-苯基-L-脯氨酸盐酸盐
  参考文献：
  名称：

  Labeled molecular imaging agents and methods of use

  摘要：

  描述了一种成像剂，它包括标记的底物，能够通过半胱氨酸/谷氨酸抗转运体引入到细胞内。这些底物可以通过通过半胱氨酸/谷氨酸抗转运体将标记的剂量引入到细胞中，然后进行检测，用于成像或检测细胞中的氧化应激。

  公开号：

  US09468693B2

文献信息

• Design, synthesis and biological evaluation of P2-modified proline analogues targeting the HtrA serine protease in Chlamydia
  作者：Jimin Hwang、Natalie Strange、Rami Mazraani、Matthew J. Phillips、Allan B. Gamble、Wilhelmina M. Huston、Joel D.A. Tyndall

  DOI：10.1016/j.ejmech.2021.114064

  日期：2022.2

  requirement A (HtrA) serine proteases have emerged as a novel class of antibacterial target, which are crucial in protein quality control and are involved in the pathogenesis of a wide array of bacterial infections. Previously, we demonstrated that HtrA in Chlamydia is essential for bacterial survival, replication and virulence. Here, we report a new series of proline (P2)-modified inhibitors of Chlamydia

  高温要求 A (HtrA) 丝氨酸蛋白酶已成为一类新的抗菌靶标，在蛋白质质量控​​制中至关重要，并参与多种细菌感染的发病机制。以前，我们证明衣原体中的 HtrA对于细菌存活、复制和毒力至关重要。在这里，我们报告了一系列新的脯氨酸 (P2) 修饰的沙眼衣原体HtrA (CtHtrA) 抑制剂，通过脯氨酸环扩展和 Cγ-取代开发。基于结构的药物优化过程以分子建模和抑制效力、选择性和细胞毒性的体外药理学评价为指导。化合物25相对于肽先导化合物1，第一代 4 取代脯氨酸类似物的抗 CtHtrA 效力和对人中性粒细胞弹性蛋白酶 (HNE) 的选择性分别提高了约 6 倍和 12 倍。基于该化合物，通过区域选择性叠氮化物-炔烃点击化学合成了含有1,2,3-三唑部分的第二代取代脯氨酸残基。化合物49在全细胞试验中显示出显着提高的抗衣原体活性，在最低测试剂量下将细菌感染后代减少到检测限以下。相对于1 ，化合物49导致抑制效力和选择性提高约
• LABELED MOLECULAR IMAGING AGENTS AND METHODS OF USE
  申请人：General Electric Company

  公开号：US20150202333A1

  公开（公告）日：2015-07-23

  Imaging agents are described that comprise labeled substrates capable of being introduced into cells via the cystine/glutamate antiporter. The substrates may be used for imaging or detecting oxidative stress in cells by introducing the labeled agents into cells via the cystine/glutamate antiporter and subsequent detection.

  描述了包含标记底物的成像剂，这些底物能够通过半胱氨酸/谷氨酸抗转运体引入细胞中。这些底物可用于通过通过半胱氨酸/谷氨酸抗转运体将标记的剂量引入细胞并进行后续检测，从而成像或检测细胞中的氧化应激。
• Angiotensin-converting enzyme inhibitors. Mercaptan, carboxyalkyl dipeptide, and phosphinic acid inhibitors incorporating 4-substituted prolines
  作者：John Krapcho、Chester Turk、David W. Cushman、James R. Powell、Jack M. DeForrest、Ervin R. Spitzmiller、Donald S. Karanewsky、Mark Duggan、George Rovnyak

  DOI：10.1021/jm00401a014

  日期：1988.6

  Analogues of captopril, enalaprilat, and the phosphinic acid [hydroxy(4-phenylbutyl)phosphinyl]acetyl]-L-proline incorporating 4-substituted proline derivatives have been synthesized and evaluated as inhibitors of angiotensin-converting enzyme (ACE) in vitro and in vivo. The 4-substituted prolines, incorporating alkyl, aryl, alkoxy, aryloxy, alkylthio, and arylthio substituents were prepared from derivatives of 4-hydroxy- and 4-ketoproline. In general, analogues of all three classes of inhibitors with hydrophobic substituents on proline were more potent in vitro than the corresponding unsubstituted proline compounds. 4-Substituted analogues of captopril showed greater potency and duration of action than the parent compound as inhibitors of the angiotensin I induced pressor response in normotensive rats. The S-benzoyl derivative of cis-4-(phenylthio)captopril, zofenopril, was found to be one of the most potent compounds of this class and is now being evaluated clinically as an antihypertensive agent. In the phosphinic acid series, the 4-ethylenethioketal and trans-4-cyclohexyl derivatives were found to be the most potent compounds in vitro and in vivo. A prodrug of the latter compound, fosinopril, is also being evaluated in clinical trials.
• Labeled molecular imaging agents and methods of use
  申请人：GENERAL ELECTRIC COMPANY

  公开号：US09468693B2

  公开（公告）日：2016-10-18

  Imaging agents are described that comprise labeled substrates capable of being introduced into cells via the cystine/glutamate antiporter. The substrates may be used for imaging or detecting oxidative stress in cells by introducing the labeled agents into cells via the cystine/glutamate antiporter and subsequent detection.

  描述了一种成像剂，它包括标记的底物，能够通过半胱氨酸/谷氨酸抗转运体引入到细胞内。这些底物可以通过通过半胱氨酸/谷氨酸抗转运体将标记的剂量引入到细胞中，然后进行检测，用于成像或检测细胞中的氧化应激。