N-{5-[4-(methylsulfonyl)benzyl]-4-[2-(4-nitrophenyl)vinyl]-1,3-thiazol-2-yl}acetamide | 737824-53-2

• 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-{5-[4-(methylsulfonyl)benzyl]-4-[2-(4-nitrophenyl)vinyl]-1,3-thiazol-2-yl}acetamide
• 英文别名: N-[5-[(4-methylsulfonylphenyl)methyl]-4-[2-(4-nitrophenyl)ethenyl]-1,3-thiazol-2-yl]acetamide
• CAS: 737824-53-2
• 化学式: C₂₁H₁₉N₃O₅S₂
• 分子量: 457.531
• InChiKey: KQTXPUPEWYNVFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  159
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-{5-[4-(methylsulfonyl)benzyl]-4-[2-(4-nitrophenyl)vinyl]-1,3-thiazol-2-yl}acetamide 在 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 20.0 ℃ 、303.99 kPa 条件下， 反应 3.0h， 以90%的产率得到N-{4-[2-(4-aminophenyl)ethyl]-5-[4-(methylsulfonyl)benzyl]-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: Part 2

  摘要：

  Novel thiazole derivatives were synthesized and evaluated as vascular adhesion protein-1 (VAP-1) inhibitors. Although our previous compound 1 showed potent VAP-1 inhibitory activity, the activity differed between humans and rats. This issue was overcome by a hybrid design using human VAP-1 specific inhibitor 2, which was found by high-throughput screening (HTS), a docking study of a human VAP-1 homology model, and an analysis of sequence information for humans and rats. As a result, we identified compound 35c, which showed strong VAP-1 inhibitory activity (human IC50 of 20 nM; rat IC50 of 72 nM) and significant inhibitory effects in the ex vivo test. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.02.048
• 作为产物：
  描述：

  4-巯基羟基肉桂酸 在 吡啶 、 manganese(IV) oxide 、 Oxone 、 lithium aluminium tetrahydride 、 potassium tert-butylate 、 sodium methylate 、 potassium carbonate 、 copper(ll) bromide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 氯仿 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 46.0h， 生成 N-{5-[4-(methylsulfonyl)benzyl]-4-[2-(4-nitrophenyl)vinyl]-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: Part 2

  摘要：

  Novel thiazole derivatives were synthesized and evaluated as vascular adhesion protein-1 (VAP-1) inhibitors. Although our previous compound 1 showed potent VAP-1 inhibitory activity, the activity differed between humans and rats. This issue was overcome by a hybrid design using human VAP-1 specific inhibitor 2, which was found by high-throughput screening (HTS), a docking study of a human VAP-1 homology model, and an analysis of sequence information for humans and rats. As a result, we identified compound 35c, which showed strong VAP-1 inhibitory activity (human IC50 of 20 nM; rat IC50 of 72 nM) and significant inhibitory effects in the ex vivo test. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.02.048

文献信息

• [EN] THIAZOLE DERIVATIVES HAVING VAP-1 INHIBITORY ACTIVITY<br/>[FR] DERIVES DE THIAZOLE PRESENTANT UNE ACTIVITE D'INHIBITION DE LA VAP-1
  申请人：ASTELLAS PHARMA INC

  公开号：WO2006011631A3

  公开（公告）日：2006-04-20
• Synthesis and SAR study of new thiazole derivatives as vascular adhesion protein-1 (VAP-1) inhibitors for the treatment of diabetic macular edema: Part 2
  作者：Takayuki Inoue、Masataka Morita、Takashi Tojo、Akira Nagashima、Ayako Moritomo、Keisuke Imai、Hiroshi Miyake

  DOI：10.1016/j.bmc.2013.02.048

  日期：2013.5

  Novel thiazole derivatives were synthesized and evaluated as vascular adhesion protein-1 (VAP-1) inhibitors. Although our previous compound 1 showed potent VAP-1 inhibitory activity, the activity differed between humans and rats. This issue was overcome by a hybrid design using human VAP-1 specific inhibitor 2, which was found by high-throughput screening (HTS), a docking study of a human VAP-1 homology model, and an analysis of sequence information for humans and rats. As a result, we identified compound 35c, which showed strong VAP-1 inhibitory activity (human IC50 of 20 nM; rat IC50 of 72 nM) and significant inhibitory effects in the ex vivo test. (C) 2013 Elsevier Ltd. All rights reserved.