6-(2-(methylthio)phenyl)-2,3-dihydroquinolin-4(1H)-one | 1001004-06-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6-(2-(methylthio)phenyl)-2,3-dihydroquinolin-4(1H)-one
• CAS: 1001004-06-3
• 化学式: C₁₆H₁₅NOS
• 分子量: 269.367
• InChiKey: QWAMCHQHQNBSJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  6-(2-(methylthio)phenyl)-2,3-dihydroquinolin-4(1H)-one 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Design, structure–activity relationship, and pharmacokinetic profile of pyrazole-based indoline factor Xa inhibitors

  摘要：

  A new series of pyrazole-based factor Xa inhibitors have been identified as part of our ongoing efforts to optimize previously reported clinical candidate razaxaban. Concern over the possible formation of primary aniline metabolites via amide hydrolysis led to the replacement of the primary amide linker between the pyrazole and phenyl moieties with secondary amides. This was accomplished by replacing the aniline with a variety of heterobicycles, of which indolines were the most potent. The indoline series demonstrated subnanomolar factor Xa binding K(i)s, modest to high selectivity versus other serine proteases, and good in vitro clotting activity. A small number of indoline fXa inhibitors were pro. led in a dog pharmacokinetic model, one of which demonstrated pharmacokinetic parameters similar to that of clinical candidate razaxaban. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.09.091
• 作为产物：
  描述：

  6-溴-2,3-二氢喹啉-4(1H)-酮 、 2-甲硫基苯硼酸 在 四(三苯基膦)钯 碳酸氢钠 作用下， 以 甲苯 为溶剂， 以65%的产率得到6-(2-(methylthio)phenyl)-2,3-dihydroquinolin-4(1H)-one
  参考文献：
  名称：

  Design, structure–activity relationship, and pharmacokinetic profile of pyrazole-based indoline factor Xa inhibitors

  摘要：

  A new series of pyrazole-based factor Xa inhibitors have been identified as part of our ongoing efforts to optimize previously reported clinical candidate razaxaban. Concern over the possible formation of primary aniline metabolites via amide hydrolysis led to the replacement of the primary amide linker between the pyrazole and phenyl moieties with secondary amides. This was accomplished by replacing the aniline with a variety of heterobicycles, of which indolines were the most potent. The indoline series demonstrated subnanomolar factor Xa binding K(i)s, modest to high selectivity versus other serine proteases, and good in vitro clotting activity. A small number of indoline fXa inhibitors were pro. led in a dog pharmacokinetic model, one of which demonstrated pharmacokinetic parameters similar to that of clinical candidate razaxaban. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.09.091