methyl 3-(4-mercaptophenyl)propanoate | 122483-74-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚类
• 英文名称: methyl 3-(4-mercaptophenyl)propanoate
• 英文别名: methyl-3-(4-mercaptolphenyl)propionate；methyl 3-(4-sulfanylphenyl)propionate；methyl 3-(4-Sulfanylphenyl)propanoate；methyl-3-(4-mercaptophenyl)propionate；Methyl 4-mercaptobenzenepropanoate
• CAS: 122483-74-3
• 化学式: C₁₀H₁₂O₂S
• 分子量: 196.27
• InChiKey: BXMQSECLXFZSSW-UHFFFAOYSA-N

物化性质

• 沸点：
  293.8±15.0 °C(Predicted)
• 密度：
  1.145±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  27.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 3-(4-mercaptophenyl)propanoate 在 N-甲基吲哚酮 、 四丙基高钌酸铵 、 4 A molecular sieve 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 5.0h， 生成 methyl 3-[4-[[2-[5-chloro-1-(diphenylmethyl)-2-methyl-1H-indol-3-yl]ethyl]sulfonyl]phenyl]propanoate
  参考文献：
  名称：

  Inhibition of Cytosolic Phospholipase A₂α: Hit to Lead Optimization

  摘要：

  Compound I was previously reported to be a potent inhibitor of cPLA,(x in both artificial monomeric substrate and cell-based assays. However, I was inactive in whole blood assays previously used to characterize cyclooxygenase and lipoxygenase inhibitors. The IC(50) of 1 increased dramatically with cell number or lipid/detergent concentration. In an attempt to insert an electrophilic ketone between the indole and benzoic acid moieties, we discovered that increasing the distance between the two moieties gave a compound with activity in the GLU (7-hydroxycoumarinyl-gamma-linolenate) micelle assay, which contains lipid and detergent. Extensive structure-activity relationship work around this lead identified a potent pharmacophore for cPLA a inhibition. The IC(50)s between the GLU micelle and rat whole blood assays correlated highly. No correlation was found for other parameters, including lipophilicity or acidity of the required acid functionality. Compounds 25, 39, and 94 emerged as potent, selective inhibitors of cPLA(2)alpha and represent well-validated starting points for further optimization.

  DOI：

  10.1021/jm0507882
• 作为产物：
  描述：

  甲醇 、 4-巯基羟基肉桂酸 在 硫酸 作用下， 以 水 为溶剂， 反应 3.0h， 以86%的产率得到methyl 3-(4-mercaptophenyl)propanoate
  参考文献：
  名称：

  Design, Synthesis, and Biological Activity of Potent and Orally Available G Protein-Coupled Receptor 40 Agonists

  摘要：

  G protein-coupled receptor 40 (GPR40) is being recently considered to be a new potential drug target for the treatment of type 2 diabetes because of its role in the enhancement of free fatty acid-regulated glucose-stimulated insulin secretion in pancreatic beta-cells. We initially identified benzyloxyphenylproparoic acid (1b) (EC50 = 510 nM), which was designed based on the structure of free fatty acids, as a promising lead compound with GPR40 agonist activity. Chemical modification of compound 1b led to the discovery of 3-{4-[(2',6'-dimethylbiphenyl-3-yl)methoxy]-2-fluorophenyl}propanoic acid (4p) as a potent GPR40 agonist (EC50 = 5,7 nM). Compound 4p exhibited acceptable pharmacokinetic profiles and significant glucose-lowering effects during an oral glucose tolerance test in diabetic rat;. Moreover, no hypoglycemic event was observed even after administration of a high dose of compound 4p to normal fasted rats. These pharmacological results suggest that GPR40 agonists might be novel glucose-dependent insulin secretagogues with little or no risk of hypoglycemia.

  DOI：

  10.1021/jm101405t

文献信息

• Inhibitors of cytosolic phospholipase A2
  申请人：Wyeth

  公开号：US20030144282A1

  公开（公告）日：2003-07-31

  This invention provides substituted indole compounds of the general formula: 1 and pharmaceutically acceptable salt forms thereof, and methods for using the compounds as inhibitors of the activity of various phospholipase enzymes, particularly phospholipase A 2 enzymes, and for the medical treatment, prevention and inhibition of pain and inflammation.

  这项发明提供了一般式如下的取代吲哚化合物： 1 及其药用可接受的盐形式，以及将这些化合物用作各种磷脂酶酶的抑制剂的方法，特别是磷脂酶A 2 酶，并用于医疗治疗、预防和抑制疼痛和炎症。
• 3-Arylsulfanyl and 3-heteroarylsulfanyl substituted benzo[b]thiophenes as therapeutic agents
  申请人：——

  公开号：US20040248953A1

  公开（公告）日：2004-12-09

  The present invention provides benzo[b]thiophenes of Formula I: 1 wherein R 1 , R 2 , R 3 , and L have any of the values defined therefor in the specification, and pharmaceutically acceptable salts thereof, that are useful as agents in the treatment of diseases and conditions, including inflammatory diseases, cardiovascular diseases, and cancers. Also provided are pharmaceutical compositions comprising one or more compounds of Formula I.

  本发明提供了公式I:1中的苯并[b]噻吩，其中R1、R2、R3和L具有规范中定义的任何值，以及其药用可接受的盐，可用作治疗疾病和症状的药物，包括炎症性疾病、心血管疾病和癌症。还提供了包含一个或多个公式I化合物的药物组合物。
• Cycloalkylsulfanyl substituted benzo[b]thiophenes as therapeutic agents
  申请人：——

  公开号：US20040248954A1

  公开（公告）日：2004-12-09

  The present invention provides benzo[b]thiophenes of Formula I: 1 wherein R 1 , R 2 , R 3 , and L have any of the values defined therefor in the specification, and pharmaceutically acceptable salts thereof, that are useful as agents in the treatment of diseases and conditions, including inflammatory diseases, cardiovascular diseases, and cancers. Also provided are pharmaceutical compositions comprising one or more compounds of Formula I.

  本发明提供了公式I中的苯并[b]噻吩：其中R1、R2、R3和L具有规范中定义的任何值，以及其药用盐，这些化合物可用作治疗疾病和症状的药剂，包括炎症性疾病、心血管疾病和癌症的药剂。还提供了包括一个或多个公式I化合物的药物组合物。
• [EN] HALO SUBSTITUTED BENZO`B! THIOPHENES WITH PI3K INHIBITORY ACTIVITY AS THERAPEUTIC AGENTS<br/>[FR] BENZO[B]THIOPHENES HALO-SUBSTITUES A ACTIVITE INHIBITRICE DE PI3K UTILES COMME AGENTS THERAPEUTIQUES
  申请人：WARNER LAMBERT CO

  公开号：WO2005023800A1

  公开（公告）日：2005-03-17

  The present invention provides benzo[b]thiophenes of Formula (I), wherein R3, R4, R5, R6, R7, Y, and L have any of the values defined therefor in the specification, and pharmaceutically acceptable salts thereof, that are useful as agents in the treatment of diseases and conditions, including inflammatory diseases, cardiovascular diseases, and cancers. Also provided are pharmaceutical compositions comprising one or more compounds of Formula (I)

  本发明提供了公式（I）中的苯并[b]噻吩，其中R3、R4、R5、R6、R7、Y和L具有规范中定义的任何值，以及其药用盐，这些化合物可用作治疗疾病和病况的药物，包括炎症性疾病、心血管疾病和癌症的药物。还提供了包含一个或多个公式（I）化合物的药物组合物。
• Methods for the use of inhibitors of cytosolic phospholipase A2 in the treatment of thrombosis
  申请人：Clerin Valerie

  公开号：US20080009485A1

  公开（公告）日：2008-01-10

  This invention provides methods for the use of substituted indole compounds of the general formula: and pharmaceutically acceptable salt forms thereof. The invention provides methods for the use of the compounds in the treating or preventing thrombosis in a mammal, or preventing progression of symptoms of thrombosis.

  这项发明提供了一种使用通式所示的取代吲哚化合物及其药用盐形式的方法。该发明提供了一种在哺乳动物中治疗或预防血栓形成，或预防血栓形成症状进展的化合物使用方法。