methyl 1-(4-(6-(azepane-1-carbonyl)benzo[d]thiazol-2-yl)-3-fluorobenzyl)azetidine-3-carboxylate | 1365916-84-2

• 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: methyl 1-(4-(6-(azepane-1-carbonyl)benzo[d]thiazol-2-yl)-3-fluorobenzyl)azetidine-3-carboxylate
• CAS: 1365916-84-2
• 化学式: C₂₆H₂₈FN₃O₃S
• 分子量: 481.591
• InChiKey: AQPDBJPHKQPPMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.72
• 重原子数：
  34.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  62.74
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 1-(4-(6-(azepane-1-carbonyl)benzo[d]thiazol-2-yl)-3-fluorobenzyl)azetidine-3-carboxylate 在 水 、 sodium hydroxide 、 盐酸 作用下， 以 四氢呋喃 为溶剂， 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
• 作为产物：
  描述：

  ethyl 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)benzo[d]thiazole-6-carboxylate 在 盐酸 、 水 、 sodium cyanoborohydride 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 溶剂黄146 、 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 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 methyl 1-(4-(6-(azepane-1-carbonyl)benzo[d]thiazol-2-yl)-3-fluorobenzyl)azetidine-3-carboxylate
  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