N-[4-(4-nitrobenzyl)-1,3-thiazol-2-yl]acetamide | 91397-47-6

• 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: N-[4-(4-nitrobenzyl)-1,3-thiazol-2-yl]acetamide
• 英文别名: 2-Acetamino-4-<4-nitro-benzyl>-thiazol；N-[4-(4-nitro-benzyl)-thiazol-2-yl]-acetamide；N-(4-(4-nitrobenzyl)thiazol-2-yl)acetamide；N-[4-[(4-nitrophenyl)methyl]-1,3-thiazol-2-yl]acetamide
• CAS: 91397-47-6
• 化学式: C₁₂H₁₁N₃O₃S
• 分子量: 277.304
• InChiKey: DSADQVUEXXONIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[4-(4-nitrobenzyl)-1,3-thiazol-2-yl]acetamide 在 盐酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 乙醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 20.0~100.0 ℃ 、303.99 kPa 条件下， 反应 74.0h， 生成 N-[4-(4-carbamimidamidobenzyl)-1,3-thiazol-2-yl]acetamide
  参考文献：
  名称：

  Synthesis and SAR study of new thiazole derivatives as vascular adhesion protein-1 (VAP-1) inhibitors for the treatment of diabetic macular edema

  摘要：

  Vascular adhesion protein-1 (VAP-1), an amine oxidase that is also known as a semicarbazide-sensitive amine oxidase (SSAO), is present in particularly high levels in human plasma, and is considered a potential therapeutic target for various inflammatory diseases, including diabetes complications such as macular edema.In our VAP-1 inhibitor program, structural modifications following high-throughput screening (HTS) of our compound library resulted in the discovery that thiazole derivative 10, which includes a guanidine group, shows potent human VAP-1 inhibitory activity (IC50 of 230 nM; rat IC50 of 14 nM). Moreover, compound 10 exhibited significant inhibitory effects on ocular permeability in STZ-induced diabetic rats. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.12.025
• 作为产物：
  描述：

  4-硝基苯丙酮 在 吡啶 、 氢溴酸 、 溴 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 39.0h， 生成 N-[4-(4-nitrobenzyl)-1,3-thiazol-2-yl]acetamide
  参考文献：
  名称：

  Synthesis and SAR study of new thiazole derivatives as vascular adhesion protein-1 (VAP-1) inhibitors for the treatment of diabetic macular edema

  摘要：

  Vascular adhesion protein-1 (VAP-1), an amine oxidase that is also known as a semicarbazide-sensitive amine oxidase (SSAO), is present in particularly high levels in human plasma, and is considered a potential therapeutic target for various inflammatory diseases, including diabetes complications such as macular edema.In our VAP-1 inhibitor program, structural modifications following high-throughput screening (HTS) of our compound library resulted in the discovery that thiazole derivative 10, which includes a guanidine group, shows potent human VAP-1 inhibitory activity (IC50 of 230 nM; rat IC50 of 14 nM). Moreover, compound 10 exhibited significant inhibitory effects on ocular permeability in STZ-induced diabetic rats. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.12.025

文献信息

• Aryl or heteroaryl triazolone derivatives or salts thereof, or pharmaceutical compositions comprising the same
  申请人：YUHAN CORPORATION

  公开号：US10562865B2

  公开（公告）日：2020-02-18

  The present technology provides aryl or heteroaryl triazolone derivatives or pharmaceutically acceptable salts thereof, preparation processes thereof, pharmaceutical compositions comprising the same, and the use thereof. The aryl or heteroaryl triazolone derivatives or their pharmaceutically acceptable salts exhibit selective inhibitory activity on VAP-1 and therefore can be usefully applied, e.g., for the treatment and prophylaxis of nonalcoholic hepatosteatosis (NASH).

  本技术提供了芳基或杂芳基三唑酮衍生物或其药学上可接受的盐、其制备工艺、包含这些衍生物的药物组合物及其用途。芳基或杂芳基三唑酮衍生物或其药学上可接受的盐类对 VAP-1 具有选择性抑制活性，因此可用于治疗和预防非酒精性肝病（NASH）等。
• Mahajanshetti,C.S.; Nargund,K.S., Journal of the Indian Chemical Society, 1962, vol. 39, p. 420 - 426
  作者：Mahajanshetti,C.S.、Nargund,K.S.

  DOI：——

  日期：——
• NOVEL ARYL OR HETEROARYL TRIAZOLONE DERIVATIVES OR SALTS THEREOF, OR PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME
  申请人：Yuhan Corporation

  公开号：EP3768663A1

  公开（公告）日：2021-01-27
• ARYL OR HETEROARYL TRIAZOLONE DERIVATIVES OR SALTS THEREOF, OR PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME
  申请人：YUHAN CORPORATION

  公开号：US20210147368A1

  公开（公告）日：2021-05-20

  The present technology provides aryl or heteroaryl triazolone derivatives or pharmaceutically acceptable salts thereof, preparation processes thereof, pharmaceutical compositions comprising the same, and the use thereof. The aryl or heteroaryl triazolone derivatives or their pharmaceutically acceptable salts exhibit selective inhibitory activity on VAP-1 and therefore can be usefully applied, e.g., for the treatment and prophylaxis of nonalcoholic hepatosteatosis (NASH).
• [EN] NOVEL ARYL OR HETEROARYL TRIAZOLONE DERIVATIVES OR SALTS THEREOF, OR PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME<br/>[FR] NOUVEAUX DÉRIVÉS D'ARYL OU HÉTÉROARYL TRIAZOLONE OU LEURS SELS ET COMPOSITIONS PHARMACEUTIQUES LES COMPRENANT
  申请人：YUHAN CORP

  公开号：WO2019180644A1

  公开（公告）日：2019-09-26

  The present technology provides aryl or heteroaryl triazolone derivatives or pharmaceutically acceptable salts thereof, preparation processes thereof, pharmaceutical compositions comprising the same, and the use thereof. The aryl or heteroaryl triazolone derivatives or their pharmaceutically acceptable salts exhibit selective inhibitory activity on VAP-1 and therefore can be usefully applied, e.g., for the treatment and prophylaxis of nonalcoholic hepatosteatosis (NASH).