1-[[3-Fluoro-4-[5-(pyridin-2-ylmethyl)-1,3-benzothiazol-2-yl]phenyl]methyl]azetidine-3-carboxylic acid | 1356679-15-6

• 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-[[3-Fluoro-4-[5-(pyridin-2-ylmethyl)-1,3-benzothiazol-2-yl]phenyl]methyl]azetidine-3-carboxylic acid
• CAS: 1356679-15-6
• 化学式: C₂₄H₂₀FN₃O₂S
• 分子量: 433.506
• InChiKey: LUKHRLXUFGNPKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  94.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-fluoro-4-(5-(pyridin-2-ylmethyl)benzo[d]thiazol-2-yl)benzaldehyde 在 sodium cyanoborohydride 、 溶剂黄146 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 1-[[3-Fluoro-4-[5-(pyridin-2-ylmethyl)-1,3-benzothiazol-2-yl]phenyl]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.