(S)-2-amino-3-(3-chlorophenyl)propan-1-ol | 938462-28-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-2-amino-3-(3-chlorophenyl)propan-1-ol
• 英文别名: (2S)-2-amino-3-(3-chlorophenyl)propan-1-ol
• CAS: 938462-28-3
• 化学式: C₉H₁₂ClNO
• 分子量: 185.653
• InChiKey: DDOXQIODUSXROP-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(6-imidazol-1-yl-4-methyl-1H-benzimidazol-2-yl)-4-iodo-1H-pyridin-2-one 、 (S)-2-amino-3-(3-chlorophenyl)propan-1-ol 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-4-[2-(3-Chloro-phenyl)-1-hydroxymethyl-ethylamino]-3-(6-imidazol-1-yl-4-methyl-1H-benzimidazol-2-yl)-1H-pyridin-2-one
  参考文献：
  名称：

  Discovery and initial SAR of 3-(1H-benzo[d]imidazol-2-yl)pyridin-2(1H)-ones as inhibitors of insulin-like growth factor 1-receptor (IGF-1R)

  摘要：

  The discovery and synthesis of 3-(1H-benzo[d]imidazol-2-yl)pyridin-2(1H)-one inhibitors of insulin-like growth factor I receptor (IGF-1R) are presented. Installing amine containing side chains at the 4-position of pyridone ring significantly improved the enzyme potency. SAR and biological activity of these compounds is presented. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.102

文献信息

• Rational Design of Selective and Bioactive Inhibitors of the <i>Mycobacterium tuberculosis</i> Proteasome
  作者：Kyle A. Totaro、Dominik Barthelme、Peter T. Simpson、Xiuju Jiang、Gang Lin、Carl F. Nathan、Robert T. Sauer、Jason K. Sello

  DOI：10.1021/acsinfecdis.6b00172

  日期：2017.2.10

  The 20S core particle of the proteasome in Mycobacterium tuberculosis (Mtb) is a promising, yet unconventional, drug target. This multimeric peptidase is not essential, yet degrades proteins that have become damaged and toxic via reactions with nitric oxide (and/or the associated reactive nitrogen intermediates) produced during the host immune response. Proteasome inhibitors could render Mtb susceptible

  结核分枝杆菌（Mtb）中蛋白酶体的20S核心颗粒是有前途的但非常规的药物靶标。该多聚体肽酶不是必需的，而是通过与宿主免疫应答过程中产生的一氧化氮（和/或相关的反应性氮中间体）反应，降解已受损且有毒的蛋白质。蛋白酶体抑制剂可以使Mtb对免疫系统敏感，但只有在不抑制人类必需的20S对应物的情况下，它们才在治疗上可行。Mtb的选择性抑制剂设计和合成20S是基于其独特的底物偏好和模仿丁香脂素的真核蛋白酶体的模拟底物的共价抑制剂的结构。与亲本丁香脂素不同，设计的类似物弱抑制人类20S（Hs 20S）蛋白酶体，比人类对应物优先抑制Mtb 20S多达74倍。此外，它们可以穿透分枝杆菌的细胞包膜并使Mtb易受一氧化氮介导的压力的影响。重要的是，它们不会在体外抑制人细胞系的生长，因此可能是结核药物开发的起点。
• REMEDIES FOR DIABETES
  申请人：KYOWA HAKKO KOGYO CO., LTD.

  公开号：EP1092435A1

  公开（公告）日：2001-04-18

  A medicament for the therapeutic treatment of diabetes which comprises as an active ingredient a compound represented by the general formula (I): wherein R1 represents a hydrogen atom, a lower alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aromatic heterocyclic group, R2 represents a hydrogen atom, a lower alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aromatic heterocyclic group, R3 represents a hydrogen atom, a lower alkyl group or a substituted or unsubstituted aralkyl group, X1 and X2 independently represent a hydrogen atom, a lower alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group, and the symbol "n" represents an integer of from 0 to 3, or a physiologically acceptable salt thereof.

  一种治疗糖尿病的药物，其活性成分包括通式(I)所代表的化合物： 其中 R1 代表氢原子、低级烷基、取代或未取代的芳基或取代或未取代的芳香杂环基团， R2 代表氢原子、低级烷基、取代或未取代的芳基、取代或未取代的芳香杂环基团、R3 代表氢原子、低级烷基或取代或未取代的芳基，X1 和 X2 独立地代表氢原子、低级烷基、取代或未取代的芳基或取代或未取代的芳基，符号 "n "代表 0 至 3 的整数，或其生理上可接受的盐。
• Substrate-guided optimization of the syringolins yields potent proteasome inhibitors with activity against leukemia cell lines
  作者：Kyle A. Totaro、Dominik Barthelme、Peter T. Simpson、Robert T. Sauer、Jason K. Sello

  DOI：10.1016/j.bmc.2015.07.041

  日期：2015.9

  Natural products that inhibit the proteasome have been fruitful starting points for the development of drug candidates. Those of the syringolin family have been underexploited in this context. Using the published model for substrate mimicry by the syringolins and knowledge about the substrate preferences of the proteolytic subunits of the human proteasome, we have designed, synthesized, and evaluated syringolin analogs. As some of our analogs inhibit the activity of the proteasome with second-order rate constants 5-fold greater than that of the methyl ester of syringolin B, we conclude that the substrate mimicry model for the syringolins is valid. The improvements in in vitro potency and the activities of particular analogs against leukemia cell lines are strong bases for further development of the syringolins as anti-cancer drugs. (c) 2015 Elsevier Ltd. All rights reserved.
• US6489331B1
  申请人：——

  公开号：US6489331B1

  公开（公告）日：2002-12-03
• Discovery and initial SAR of 3-(1H-benzo[d]imidazol-2-yl)pyridin-2(1H)-ones as inhibitors of insulin-like growth factor 1-receptor (IGF-1R)
  作者：Upender Velaparthi、Mark Wittman、Peiying Liu、Karen Stoffan、Kurt Zimmermann、Xiaopeng Sang、Joan Carboni、Aixin Li、Ricardo Attar、Marco Gottardis、Ann Greer、ChiehYing Y. Chang、Bruce L. Jacobsen、John S. Sack、Yax Sun、David R. Langley、Balu Balasubramanian、Dolatrai Vyas

  DOI：10.1016/j.bmcl.2007.01.102

  日期：2007.4

  The discovery and synthesis of 3-(1H-benzo[d]imidazol-2-yl)pyridin-2(1H)-one inhibitors of insulin-like growth factor I receptor (IGF-1R) are presented. Installing amine containing side chains at the 4-position of pyridone ring significantly improved the enzyme potency. SAR and biological activity of these compounds is presented. (c) 2007 Elsevier Ltd. All rights reserved.