methyl (2E)-3-[3-(methylsulfanyl)phenyl]acrylate | 874899-34-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl (2E)-3-[3-(methylsulfanyl)phenyl]acrylate
• 英文别名: methyl (2E)-3-[3-(methylthio)phenyl]acrylate；Methyl(2E)-3-[3-(methylthio)phenyl]acrylate；methyl (E)-3-(3-methylsulfanylphenyl)prop-2-enoate
• CAS: 874899-34-0
• 化学式: C₁₁H₁₂O₂S
• 分子量: 208.281
• InChiKey: UMUDJBDRRIBERP-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (2E)-3-[3-(methylsulfanyl)phenyl]acrylate 在 吡啶 、 palladium 10% on activated carbon 、 氢气 、 sodium methylate 、 溶剂黄146 、 copper(ll) bromide 作用下， 以 甲醇 、 乙醇 、 氯仿 、 乙酸乙酯 为溶剂， 65.0 ℃ 、405.33 kPa 条件下， 反应 41.0h， 生成 ethyl 2-(acetylamino)-5-[3-(methylthio)benzyl]-1,3-thiazole-4-carboxylate
  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：

  甲氧羰基亚甲基三苯基正膦 在 二异丁基氢化铝 、 甲醇 作用下， 以 四氢呋喃 为溶剂， 反应 5.17h， 生成 methyl (2E)-3-[3-(methylsulfanyl)phenyl]acrylate
  参考文献：
  名称：

  [EN] THIAZOLE DERIVATIVES HAVING VAP-1 INHIBITORY ACTIVITY
  [FR] DERIVES DE THIAZOLE PRESENTANT UNE ACTIVITE D'INHIBITION DE LA VAP-1

  摘要：

  公开号：

  WO2006011631A3

文献信息

• Thiazole Derivatives Having Vap-1 Inhibitory Activity
  申请人：Inoue Takayuki

  公开号：US20070254931A1

  公开（公告）日：2007-11-01

  A compound of the formula (I), (II), (III) or (IV): wherein each symbol is as defined in the specification, or a pharmaceutically acceptable salt thereof useful as a vascular adhesion protein-1 (VAP-1) inhibitor, a pharmaceutical composition, a method for preventing or treating a VAP-1 associated disease, especially macular edema, which method includes administering an effective amount of the compound or a pharmaceutically acceptable salt thereof to a subject, and the like.

  公式（I），（II），（III）或（IV）的化合物：其中每个符号如规范中所定义，或其药学上可接受的盐，可用作血管黏附蛋白-1（VAP-1）抑制剂，制药组合物，预防或治疗VAP-1相关疾病，特别是黄斑水肿的方法，该方法包括向受试者投予化合物或其药学上可接受的盐的有效量等。
• [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.