1-benzenesulfonyl-3-bromo-7-fluoroindole | 865712-97-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-benzenesulfonyl-3-bromo-7-fluoroindole
• 英文别名: 1-benzenesulfonyl-3-bromo-7-fluoro-1H-indole；1-(benzenesulfonyl)-3-bromo-7-fluoroindole
• CAS: 865712-97-6
• 化学式: C₁₄H₉BrFNO₂S
• 分子量: 354.199
• InChiKey: PZMPHHJABUIDTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-benzenesulfonyl-3-bromo-7-fluoroindole 、 dimethyl-[1-(4-morpholin-4-yl-2-tri-butylstannanyl-thieno[3,2-d]pyrimidin-6-methyl)-piperidin-4-yl]-amine 在 四(三苯基膦)钯 噻吩-2-甲酸亚铜(I) 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  [EN] BICYCLIC INDOLE-PYRIMIDINE PI3K INHIBITOR COMPOUNDS SELECTIVE FOR P110 DELTA, AND METHODS OF USE
  [FR] COMPOSÉS BICYCLIQUES INDOLE-PYRIMIDINE INHIBITEURS DE PI3K SÉLECTIFS POUR P110 DELTA ET LEURS PROCÉDÉS D'UTILISATION

  摘要：

  Formula I（Ia和Ib）化合物，其中（i）X1为N且X2为S，（ii）X1为CR7且X2为S，（iii）X1为N且X2为NR2，（iv）X1为CR7且X2为O，或（v）X1为CR7且X2为NR2，包括立体异构体、互变异构体、代谢物及其药学上可接受的盐，用于抑制PBK的δ同工酶，并用于治疗由脂质激酶介导的疾病，如炎症、免疫和癌症。公开了使用Formula I化合物进行体外、体内和体内诊断、预防或治疗哺乳动物细胞中的这些疾病，或相关病理条件的方法。

  公开号：

  WO2010136491A1
• 作为产物：
  描述：

  7-fluoro-1-phenylsulfonyl-1H-indole 在 溴 、 碳酸氢钠 作用下， 以 四氯化碳 为溶剂， 反应 16.0h， 以95%的产率得到1-benzenesulfonyl-3-bromo-7-fluoroindole
  参考文献：
  名称：

  [EN] BICYCLIC INDOLE-PYRIMIDINE PI3K INHIBITOR COMPOUNDS SELECTIVE FOR P110 DELTA, AND METHODS OF USE
  [FR] COMPOSÉS BICYCLIQUES INDOLE-PYRIMIDINE INHIBITEURS DE PI3K SÉLECTIFS POUR P110 DELTA ET LEURS PROCÉDÉS D'UTILISATION

  摘要：

  Formula I（Ia和Ib）化合物，其中（i）X1为N且X2为S，（ii）X1为CR7且X2为S，（iii）X1为N且X2为NR2，（iv）X1为CR7且X2为O，或（v）X1为CR7且X2为NR2，包括立体异构体、互变异构体、代谢物及其药学上可接受的盐，用于抑制PBK的δ同工酶，并用于治疗由脂质激酶介导的疾病，如炎症、免疫和癌症。公开了使用Formula I化合物进行体外、体内和体内诊断、预防或治疗哺乳动物细胞中的这些疾病，或相关病理条件的方法。

  公开号：

  WO2010136491A1

文献信息

• [EN] (INDOL-3-YL)-HETEROCYCLE DERIVATIVES AS AGONISTS OF THE CANNABINOID CB1 RECEPTOR<br/>[FR] DERIVES HETEROCYCLIQUES-(INDOL-3-YL) COMME AGONISTES DU RECEPTEUR DU CANNABINOIDE CB1
  申请人：AKZO NOBEL NV

  公开号：WO2005089754A1

  公开（公告）日：2005-09-29

  The invention relates to (indol-3-yl)-heterocycle derivatives having general Formula (I) wherein A represents a 5-membered aromatic heterocyclic ring, wherein X1, X2 and X3 are independently selected from N, O, S and CR; R is H or (C1-4)alkyl; or R, when present in X2 or X3, may form together with R3 a 5-8 membered ring; R1 is a 5-8 mem­bered saturated carbocyclic ring, optionally containing a heteroatom selected from O and S; R2 is H, CH3 or CH2-CH3; or R2 is joined together with R7 to form a 6-mem­bered ring, optionally containing a heteroatom selected from O and S, and which heteroatom is bonded to the 7-position of the indole ring; R3 and R4 are independent­ly H, (C1-6)alkyl or (C3-7)cycloalkyl, the alkyl groups being optionally substituted with OH, (C1-4)alkyloxy, (C1-4)alkylthio, (C1-4)alkylsulfonyl, CN or halogen; or R3 together with R4 and the N to which they are bonded form a 4-8 membered ring optionally containing a further heteroatom selected from O and S, and which is optionally sub­stituted with OH, (C1-4)alkyl, (C1-4)alkyloxy, (C1-4)alkyloxy- (C1-4)alkyl, or halogen; or R3 together with R5 forms a 4-8 membered ring optionally containing a further hetero­atom selected from O and S, and which is optionally substituted with OH, (C1-4)alkyl, (C1-4)alkyloxy, (C1-4)alkyloxy- (C1-4)alkyl, or halogen; or R3 together with R, when present in X2 or X3, forms a 5-8 membered ring; R5 is H or (C1-4)alkyl; or R5 together with R3 forms a 4-8 membered ring optionally containing a further heteroatom select­ed from O and S, and which is optionally substituted with OH, (C1-4)alkyl, (C1-4)alkyl­oxy, (C1-4) alkyloxy- (C1-4)alkyl, or halogen; R5' is H or (C1-4)alkyl; R6 represents 1-3 substituents independently selected from H, (C1-4 alkyl, (C1-4) alkyloxy, CN and halogen; R7 is H, (C1-4)alkyl, (C1-4)alkyloxy, CN or halogen; or R7 is joined together with R2 to form a 6-membered ring, optionally containing a further heteroatom selected from O and S, and which heteroatom is bonded to the 7-position of the indole ring; or a pharmaceutically acceptable salt thereof, as agonists of the cannabinoid CB1 receptor, which can be used in the treatment of pain such as for example peri-operative pain, chronic pain, neuropathic pain, cancer pain and pain and spasticity associated with multiple sclerosis.

  该发明涉及具有一般式（I）的（吲哚-3-基）-杂环衍生物，其中A代表一个5-成员芳香杂环环，其中X1、X2和X3分别选自N、O、S和CR；R为H或（C1-4）烷基；或者R，在X2或X3中时，可以与R3一起形成一个5-8成员环；R1是一个5-8成员饱和碳环，可选地含有从O和S中选取的杂原子；R2为H、CH3或CH2-CH3；或者R2与R7结合形成一个6-成员环，可选地含有从O和S中选取的杂原子，并且该杂原子与吲哚环的7-位置相结合；R3和R4独立地为H、（C1-6）烷基或（C3-7）环烷基，烷基基团可选地用OH、（C1-4）烷氧基、（C1-4）烷基硫醚、（C1-4）烷基磺酰基、CN或卤素取代；或者R3与R4和它们结合的N形成一个4-8成员环，可选地含有从O和S中选取的进一步杂原子，并且可选地用OH、（C1-4）烷基、（C1-4）烷氧基、（C1-4）烷氧基-（C1-4）烷基或卤素取代；或者R3与R5形成一个4-8成员环，可选地含有从O和S中选取的进一步杂原子，并且可选地用OH、（C1-4）烷基、（C1-4）烷氧基、（C1-4）烷氧基-（C1-4）烷基或卤素取代；或者R3与R，在X2或X3中时，形成一个5-8成员环；R5为H或（C1-4）烷基；或者R5与R3一起形成一个4-8成员环，可选地含有从O和S中选取的进一步杂原子，并且可选地用OH、（C1-4）烷基、（C1-4）烷氧基、（C1-4）烷氧基-（C1-4）烷基或卤素取代；R5'为H或（C1-4）烷基；R6代表独立选择的1-3个取代基，选自H、（C1-4）烷基、（C1-4）烷氧基、CN和卤素；R7为H、（C1-4）烷基、（C1-4）烷氧基、CN或卤素；或者R7与R2结合形成一个6-成员环，可选地含有从O和S中选取的进一步杂原子，并且该杂原子与吲哚环的7-位置相结合；或其药学上可接受的盐，作为大麻素CB1受体的激动剂，可用于治疗疼痛，例如围手术期疼痛、慢性疼痛、神经痛、癌症疼痛以及与多发性硬化相关的疼痛和痉挛。
• (Indol-3-yl) heterocycle derivatives as a agonists of the cannabinoid cb1 receptor
  申请人：Adam-Worrall Julia

  公开号：US20070142446A1

  公开（公告）日：2007-06-21

  Disclosed herein are indole derivatives of the formula (I) wherein each of the substitutents is given the definition as set forth in the specification and claims. Also disclosed are pharmaceutical compositions containing the indole derivatives and use of the derivatives for the treatment of pain.

  本文揭示了公式(I)的吲哚衍生物，其中每个取代基的定义如规范和要求所述。还揭示了含有这些吲哚衍生物的药物组合物，并且这些衍生物可用于治疗疼痛。
• Bicyclic indole-pyrimidine PI3K inhibitor compounds selective for P110 delta, and methods of use
  申请人：Genentech, Inc.

  公开号：US08158625B2

  公开（公告）日：2012-04-17

  Formula I (Ia and Ib) compounds wherein (i) X1 is N and X2 is S, (ii) X1 is CR7 and X2 is S, (iii) X1 is N and X2 is NR2, (iv) X1 is CR7 and X2 is O, or (v) X1 is CR7 and X2 is NR2, including stereoisomers, tautomers, metabolites and pharmaceutically acceptable salts thereof, are useful for inhibiting the delta isoform of PI3K, and for treating disorders mediated by lipid kinases such as inflammation, immunological, and cancer. Methods of using compounds of Formula I for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions, are disclosed.

  公式I（Ia和Ib）化合物，其中（i）X1为N且X2为S，（ii）X1为CR7且X2为S，（iii）X1为N且X2为NR2，（iv）X1为CR7且X2为O，或（v）X1为CR7且X2为NR2，包括立体异构体，互变异构体，代谢物和药学上可接受的盐，可用于抑制PI3K的δ亚型，并用于治疗由脂质激酶介导的疾病，例如炎症，免疫和癌症。公开了使用公式I化合物的方法，用于哺乳动物细胞中的体外，体内诊断，预防或治疗这种疾病或相关病理条件。
• BICYCLIC INDOLE-PYRIMIDINE PI3K INHIBITOR COMPOUNDS SELECTIVE FOR P110 DELTA, AND METHODS OF USE
  申请人：Castanedo Georgette

  公开号：US20100305084A1

  公开（公告）日：2010-12-02

  Formula I (Ia and Ib) compounds wherein (i) X 1 is N and X 2 is S, (ii) X 1 is CR 7 and X 2 is S, (iii) X 1 is N and X 2 is NR 2 , (iv) X 1 is CR 7 and X 2 is O, or (v) X 1 is CR 7 and X 2 is NR 2 , including stereoisomers, tautomers, metabolites and pharmaceutically acceptable salts thereof, are useful for inhibiting the delta isoform of PI3K, and for treating disorders mediated by lipid kinases such as inflammation, immunological, and cancer. Methods of using compounds of Formula I for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions, are disclosed.

  公式I（Ia和Ib）化合物，其中（i）X1为N且X2为S，（ii）X1为CR7且X2为S，（iii）X1为N且X2为NR2，（iv）X1为CR7且X2为O，或（v）X1为CR7且X2为NR2，包括立体异构体，互变异构体，代谢物和药学上可接受的盐，对于抑制PI3K的δ亚型以及治疗由脂质激酶介导的疾病（如炎症，免疫和癌症）有用。公开了使用公式I化合物的方法，用于哺乳动物细胞中的体外，体内和原位诊断，预防或治疗此类疾病或相关病理条件。
• (Indol-3-yl) heterocycle derivatives as agonists of the cannabinoid CB1 receptor
  申请人：N.V. Organon

  公开号：US07700634B2

  公开（公告）日：2010-04-20

  Disclosed herein are indole derivatives of the formula (I) wherein each of the substitutents is given the definition as set forth in the specification and claims. Also disclosed are pharmaceutical compositions containing the indole derivatives and use of the derivatives for the treatment of pain.

  本文揭示了式(I)的吲哚衍生物，其中每个取代基的定义如规范和权利要求所述。还揭示了含有吲哚衍生物的药物组合物以及利用这些衍生物治疗疼痛的用途。