2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)benzo[d]thiazole-6-carboxylic acid | 1202077-22-2

• 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: 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)benzo[d]thiazole-6-carboxylic acid
• 英文别名: 2-[4-(1,3-dioxan-2-yl)-2-fluorophenyl]-1,3-benzothiazole-6-carboxylic acid
• CAS: 1202077-22-2
• 化学式: C₁₈H₁₄FNO₄S
• 分子量: 359.378
• InChiKey: SQSOSHDCHQYKDE-UHFFFAOYSA-N

物化性质

• 沸点：
  563.5±60.0 °C(Predicted)
• 密度：
  1.428±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  96.9
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)benzo[d]thiazole-6-carboxylic acid 在 盐酸 、 水 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 methyl 1-(4-(6-(2-ethylthiazolidine-3-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
• 作为产物：
  描述：

  4-溴-2-氟苯基异硫氰酸 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 正丁基锂 、 水 、 sodium carbonate 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 、 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 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)benzo[d]thiazole-6-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

• [EN] S1P1 RECEPTOR AGONISTS AND USE THEREOF<br/>[FR] AGONISTES DU RÉCEPTEUR S1P1 ET UTILISATIONS
  申请人：AMGEN INC

  公开号：WO2009154775A1

  公开（公告）日：2009-12-23

  The present invention relates to compounds of Formula (I), that have activity as S1P receptor modulating agents, more specifically to specifically compounds that are S1P1 receptor agonists. The invention also related to the use of such compounds to treat diseases associated with inappropriate S1P1 receptor activity such as autoimmune diseases.

  本发明涉及公式（I）的化合物，该化合物具有作为S1P受体调节剂的活性，更具体地说，是具有S1P1受体激动剂活性的化合物。本发明还涉及使用这种化合物来治疗与不适当的S1P1受体活性相关的疾病，如自身免疫性疾病。
• S1P1 receptor agonists and use thereof
  申请人：Cee Victor J.

  公开号：US20100029611A1

  公开（公告）日：2010-02-04

  The present invention relates to compounds of Formula (I): that are have activity as S1P receptor modulating agents, more specifically to specifically compounds that are S1P1 receptor agonists. The invention also related to the use of such compounds to treat diseases associated with inappropriate S1P1 receptor activity such as autoimmune diseases.

  本发明涉及式（I）的化合物：具有S1P受体调节剂活性，更具体地说是具有S1P1受体激动剂活性的化合物。本发明还涉及使用这些化合物治疗与不适当的S1P1受体活性相关的疾病，如自身免疫性疾病。
• S1P1 RECEPTOR AGONISTS AND USE THEREOF
  申请人：Amgen, Inc

  公开号：EP2306994A1

  公开（公告）日：2011-04-13
• US7842685B2
  申请人：——

  公开号：US7842685B2

  公开（公告）日：2010-11-30
• 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.