1-[[4-[6-(Azepane-1-carbonyl)-1,3-benzothiazol-2-yl]-3-fluorophenyl]methyl]azetidine-3-carboxylic acid | 1356679-37-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 1-[[4-[6-(Azepane-1-carbonyl)-1,3-benzothiazol-2-yl]-3-fluorophenyl]methyl]azetidine-3-carboxylic acid
• CAS: 1356679-37-2
• 化学式: C₂₅H₂₆FN₃O₃S
• 分子量: 467.564
• InChiKey: KOHIJMVMRQZIAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-溴-2-氟苯基异硫氰酸 在 盐酸 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 正丁基锂 、 水 、 sodium cyanoborohydride 、 sodium carbonate 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 溶剂黄146 、 三乙胺 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， -78.0~110.0 ℃ 、172.37 kPa 条件下， 反应 40.0h， 生成 1-[[4-[6-(Azepane-1-carbonyl)-1,3-benzothiazol-2-yl]-3-fluorophenyl]methyl]azetidine-3-carboxylic acid
  参考文献：
  名称：

  Novel 5- and 6-subtituted benzothiazoles with improved physicochemical properties: Potent S1P1 agonists with in vivo lymphocyte-depleting activity

  摘要：

  An SAR campaign designed to increase polarity in the 'tail' region of benzothiazole 1 resulted in two series of structurally novel 5- and 6-substituted S1P(1) agonists. Structural optimization for potency ultimately delivered carboxamide (+)-11f, which in addition to possessing improved physicochemical properties relative to starting benzothiazole 1, also displayed good S1P(3) selectivity and acceptable in vivo lymphocyte-depleting activity. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2011.10.069

文献信息

• Novel 5- and 6-subtituted benzothiazoles with improved physicochemical properties: Potent S1P1 agonists with in vivo lymphocyte-depleting activity
  作者：Mike Frohn、Victor J. Cee、Brian A. Lanman、Alexander J. Pickrell、Jennifer Golden、Dalia Rivenzon-Segal、Scot Middleton、Mike Fiorino、Han Xu、Michael Schrag、Yang Xu、Michele McElvain、Kristine Muller、Jerry Siu、Roland Bürli

  DOI：10.1016/j.bmcl.2011.10.069

  日期：2012.1

  An SAR campaign designed to increase polarity in the 'tail' region of benzothiazole 1 resulted in two series of structurally novel 5- and 6-substituted S1P(1) agonists. Structural optimization for potency ultimately delivered carboxamide (+)-11f, which in addition to possessing improved physicochemical properties relative to starting benzothiazole 1, also displayed good S1P(3) selectivity and acceptable in vivo lymphocyte-depleting activity. (C) 2011 Published by Elsevier Ltd.