methyl 3-ethylthiophenylacetate | 139988-05-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: methyl 3-ethylthiophenylacetate
• 英文别名: methyl 2-(3-ethylsulfanylphenyl)acetate
• CAS: 139988-05-9
• 化学式: C₁₁H₁₄O₂S
• 分子量: 210.297
• InChiKey: HOLHLHZHUMWDMS-UHFFFAOYSA-N

物化性质

• 沸点：
  298.8±23.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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 3-ethylthiophenylacetate 、 苯乙酸甲酯 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以49.8 g的产率得到3-ethylthiophenylacetic acid
  参考文献：
  名称：

  Pharmaceutically active benzoquinazoline compounds

  摘要：

  公开号：

  EP1199307B1
• 作为产物：
  描述：

  3-氨基苯乙酸甲酯 、 potassium ethanethiolate 在 盐酸 、 sodium nitrite 作用下， 生成 methyl 3-ethylthiophenylacetate 、 苯乙酸甲酯
  参考文献：
  名称：

  Benzoquinazoline inhibitors of thymidylate synthase: enzyme inhibitory activity and cytotoxicity of some 3-amino- and 3-methylbenzo[f]quinazolin-1(2H)-ones

  摘要：

  The synthesis and thymidylate synthase (TS) inhibitory activity of a series of simple benzo-[f]-quinazolin-1(2H)-ones are described. Fully aromatic 3-amino compounds with compact lipophilic substituents in the 9-position were found to have I50 values as low as 20 nM on the isolated enzyme, and represent the first examples of potent, folate-based TS inhibitors that completely lack any structural feature corresponding to the (p-aminobenzoyl)glutamate moiety of the cofactor. A number of the compounds also showed moderate growth inhibitory activity against a human colon adenocarcinoma cell line (SW480), with IC50 values as low as 2 muM.

  DOI：

  10.1021/jm00068a004

文献信息

• PHARMACEUTICALLY ACTIVE BENZOQUINAZOLINE COMPOUNDS
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0535034A1

  公开（公告）日：1993-04-07
• US6090941A
  申请人：——

  公开号：US6090941A

  公开（公告）日：2000-07-18
• Pharmaceutically active benzoquinazoline compounds
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP1199307B1

  公开（公告）日：2004-02-25
• Benzoquinazoline inhibitors of thymidylate synthase: enzyme inhibitory activity and cytotoxicity of some 3-amino- and 3-methylbenzo[f]quinazolin-1(2H)-ones
  作者：William Pendergast、Jay V. Johnson、Scott H. Dickerson、Inderjit K. Dev、David S. Duch、Robert Ferone、William R. Hall、Joan Humphreys、Joseph M. Kelly、David C. Wilson

  DOI：10.1021/jm00068a004

  日期：1993.8

  The synthesis and thymidylate synthase (TS) inhibitory activity of a series of simple benzo-[f]-quinazolin-1(2H)-ones are described. Fully aromatic 3-amino compounds with compact lipophilic substituents in the 9-position were found to have I50 values as low as 20 nM on the isolated enzyme, and represent the first examples of potent, folate-based TS inhibitors that completely lack any structural feature corresponding to the (p-aminobenzoyl)glutamate moiety of the cofactor. A number of the compounds also showed moderate growth inhibitory activity against a human colon adenocarcinoma cell line (SW480), with IC50 values as low as 2 muM.