6-(4-fluorophenyl)-3-bromoindole-1-carboxylic acid t-butyl ester | 183283-32-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 6-(4-fluorophenyl)-3-bromoindole-1-carboxylic acid t-butyl ester
• 英文别名: tert-butyl 3-bromo-6-(4-fluorophenyl)-1H-indole-1-carboxylate；tert-butyl 3-bromo-6-(4-fluorophenyl)indole-1-carboxylate
• CAS: 183283-32-1
• 化学式: C₁₉H₁₇BrFNO₂
• 分子量: 390.252
• InChiKey: GGSUEZUASRWYPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(4-fluorophenyl)-3-bromoindole-1-carboxylic acid t-butyl ester 在 N-氯代丁二酰亚胺 、 二氧化硫 、 叔丁基锂 作用下， 生成 1-tert-butoxycarbonyl-6-(4-fluorophenyl)indole-3-sulfonyl chloride
  参考文献：
  名称：

  Discovery and Evaluation of a Series of 3-Acylindole Imidazopyridine Platelet-Activating Factor Antagonists

  摘要：

  Studies conducted with the goal of discovering a second-generation platelet-activating factor (PAF) antagonist have identified a novel class of potent and orally active antagonists which have high aqueous solubility and long duration of action in animal models. The compounds arose from the combination of the lipophilic indole portion of Abbott's first-generation PAF antagonist ABT-299 (2) with the methylimidazopyridine heterocycle moiety of British Biotechnology's BB-882 (1) and possess the positive attributes of both of these clinical candidates. Structure-activity relationship (SAR) studies indicated that modification of the indole and benzoyl spacer of lead compound 7b gave analogues that were more potent, longer-lived, and bioavailable and resulted in the identification of 1-(N,N-dimethylcarbamoyl)-4-ethynyl-3-(3-fluoro-4-[(1H-2-methylimidazo[4,5-c]pyrid-1-yl)methyl] benzoyl}indole hydrochloride (ABT-491, 22m.HCl) which has been evaluated extensively and is currently in clinical development.

  DOI：

  10.1021/jm970389+
• 作为产物：
  描述：

  6-(4-氟苯基)吲哚 在 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 为溶剂， 生成 6-(4-fluorophenyl)-3-bromoindole-1-carboxylic acid t-butyl ester
  参考文献：
  名称：

  Discovery and Evaluation of a Series of 3-Acylindole Imidazopyridine Platelet-Activating Factor Antagonists

  摘要：

  Studies conducted with the goal of discovering a second-generation platelet-activating factor (PAF) antagonist have identified a novel class of potent and orally active antagonists which have high aqueous solubility and long duration of action in animal models. The compounds arose from the combination of the lipophilic indole portion of Abbott's first-generation PAF antagonist ABT-299 (2) with the methylimidazopyridine heterocycle moiety of British Biotechnology's BB-882 (1) and possess the positive attributes of both of these clinical candidates. Structure-activity relationship (SAR) studies indicated that modification of the indole and benzoyl spacer of lead compound 7b gave analogues that were more potent, longer-lived, and bioavailable and resulted in the identification of 1-(N,N-dimethylcarbamoyl)-4-ethynyl-3-(3-fluoro-4-[(1H-2-methylimidazo[4,5-c]pyrid-1-yl)methyl] benzoyl}indole hydrochloride (ABT-491, 22m.HCl) which has been evaluated extensively and is currently in clinical development.

  DOI：

  10.1021/jm970389+

文献信息

• CARBAZOLE CARBOXAMIDE COMPOUNDS USEFUL AS KINASE INHIBITORS
  申请人：Liu Qingjie

  公开号：US20100160303A1

  公开（公告）日：2010-06-24

  Compounds having the formula (I), and enantiomers, and diastereomers, pharmaceutically-acceptable salts, thereof, are useful as kinase modulators, including Btk modulation.

  具有化学式(I)的化合物，以及其对映体、非对映异构体、药用可接受的盐，可用作激酶调节剂，包括Btk调节。
• Indole piperazine platelet activating factor antagonists
  申请人：Abbott Laboratories

  公开号：US05654305A1

  公开（公告）日：1997-08-05

  The present invention provides compounds of formula ##STR1## wherein Y is >C.dbd.O or >S(O).sub.t wherein t is 1 or 2 and the pharmaceutically acceptable salts thereof which are potent antagonists of PAF and are useful in the treatment of PAF-related disorders including asthma, rhinitis, shock, respiratory distress syndrome, acute inflammation, transplanted organ rejection, gastrointestinal ulceration, allergic skin diseases, delayed cellular immunity, parturition, fetal lung maturation, and cellular differentiation.

  本发明提供了式子##STR1##中的化合物，其中Y为> C = O或> S（O）.sub.t，其中t为1或2，以及其药学上可接受的盐，这些化合物是PAF的有效拮抗剂，可用于治疗与PAF相关的疾病，包括哮喘，鼻炎，休克，呼吸窘迫综合征，急性炎症，移植器官排斥，胃肠溃疡，过敏性皮肤病，迟发性细胞免疫，分娩，胎肺成熟和细胞分化。
• Indole-3-carbonyl and indole-3-sulfonyl derivatives as platelet
  申请人：Abbott Laboratories

  公开号：US05567711A1

  公开（公告）日：1996-10-22

  The present invention provides compounds of formula ##STR1## and the pharmaceutically acceptable salts thereof which are potent antagonists of PAF and are useful in the treatment of PAF-related disorders including asthma, shock, respiratory distress syndrome, acute inflammation, transplanted organ rejection, gastrointestinal ulceration, allergic skin diseases, delayed cellular immunity, parturition, fetal lung maturation, and cellular differentiation.

  本发明提供了公式##STR1##的化合物及其药学上可接受的盐，它们是PAF的强效拮抗剂，并可用于治疗与PAF相关的疾病，包括哮喘，休克，呼吸窘迫综合症，急性炎症，移植器官排斥，胃肠溃疡，过敏性皮肤病，延迟细胞免疫，分娩，胎儿肺成熟和细胞分化。
• Carbazole carboxamide compounds useful as kinase inhibitors
  申请人：Bristol-Myers Squibb Company

  公开号：US08084620B2

  公开（公告）日：2011-12-27

  Compounds having the formula (I), and enantiomers, and diastereomers, pharmaceutically-acceptable salts, thereof, are useful as kinase modulators, including Btk modulation.

  具有公式（I）的化合物，其对映异构体，顺反异构体，以及其药学上可接受的盐，可用作激酶调节剂，包括Btk调节。
• INDOLE-3-CARBONYL AND INDOLE-3-SULFONYL DERIVATIVES AS PLATELET ACTIVATING FACTOR ANTAGONISTS
  申请人：ABBOTT LABORATORIES

  公开号：EP0821685B1

  公开（公告）日：2001-10-04