N-(3-bromophenyl)-N-methylmethanesulfonamide | 875917-18-3

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物
• 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: N-(3-bromophenyl)-N-methylmethanesulfonamide
• CAS: 875917-18-3
• 化学式: C₈H₁₀BrNO₂S
• 分子量: 264.143
• InChiKey: CPWCZQQEEWJMCV-UHFFFAOYSA-N

物化性质

• 沸点：
  349.6±44.0 °C(Predicted)
• 密度：
  1.604±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3-bromophenyl)-N-methylmethanesulfonamide 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 四丁基氟化铵 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 N-(3-ethynylphenyl)-N-methylmethanesulfonamide
  参考文献：
  名称：

  Triazole-linked reduced amide isosteres: An approach for the fragment-based drug discovery of anti-Alzheimer’s BACE1 inhibitors

  摘要：

  In the course of a beta-site APP-cleaving enzyme 1 (BACE1) inhibitor discovery project an in situ synthesis/screening protocol was employed to prepare 120 triazole-linked reduced amide isostere inhibitors. Among these compounds, four showed modest (single digit micromolar) BACE1 inhibition. Our ligand design was based on a potent reduced amide isostere 1, wherein the P(2) amide moiety was replaced with an anti-1,2,3-triazole unit. Unfortunately, this replacement resulted in a 1000-fold decrease in potency. Docking studies of triazole-linked reduced amide isostere A3Z10 and potent oxadiazole-linked tertiary carbinamine 2a with BACE1 suggests that the docking poses of A3Z10 and 2a in the active sites are quite similar, with one exception. In the docked structures the placement of the protonated amine that engages D228 differs considerably between 2a and A3Z10. This difference could account for the lower BACE1 inhibition potency of A3Z10 and related compounds relative to 2a. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.007
• 作为产物：
  描述：

  间溴苯胺 在 吡啶 、 盐酸 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 N-(3-bromophenyl)-N-methylmethanesulfonamide
  参考文献：
  名称：

  设计，合成，生物学评估和分子对接研究作为有效的FAK抑制剂的新型噻吩并[3,2-d]嘧啶衍生物。

  摘要：

  设计，合成和评价了一系列的2,7-二取代-噻吩并[3,2-d]嘧啶衍生物，作为新型的粘着斑激酶（FAK）抑制剂。新型的2,7-二取代-噻吩并[3,2-d]嘧啶骨架已被设计为一种新的激酶抑制剂平台，可模仿众所周知的二氨基嘧啶基序的生物活性构象。大多数化合物有效抑制FAK的酶活性，并有效抑制U-87MG，A-549和MDA-MB-231癌细胞系的增殖。在这些衍生物中，优化的化合物26f在U-87MG，A-549和MDA-MB-231细胞中均能有效抑制酶（IC50 = 28.2 nM），并显示出比TAE-226更强的效力，IC50值为0.16、0.27，和0.19μM。化合物26f还具有相对较低的细胞毒性（IC50 = 3）。32μM）朝向正常人细胞株HK2。根据流式细胞术结果，化合物26f以剂量依赖性方式诱导MDA-MB-231细胞的凋亡，并有效地将MDA-MB-231细胞阻滞在G0 / G1

  DOI：

  10.1016/j.ejmech.2019.112024

文献信息

• SULFONYL AMIDE DERIVATIVES FOR THE TREATMENT OF ABNORMAL CELL GROWTH
  申请人：Luzzio Michael Joseph

  公开号：US20090054395A1

  公开（公告）日：2009-02-26

  The present invention relates to a compound of the formula I wherein R 1 to R 6 , A, B, n and m are as defined herein. Such novel sulfonyl amide derivatives are useful in the treatment of abnormal cell growth, such as cancer, in mammals. This invention also relates to a method of using such compounds in the treatment of abnormal cell growth in mammals, especially humans, and to pharmaceutical compositions containing such compounds.

  本发明涉及一种具有以下式I的化合物 其中R 1 至R 6 ，A，B，n和m如本文所定义。这种新型磺酰胺衍生物在治疗哺乳动物（如癌症）中的异常细胞生长方面是有用的。本发明还涉及一种在治疗哺乳动物（尤其是人类）中的异常细胞生长中使用这种化合物的方法，以及含有这种化合物的药物组合物。
• NOVEL CEPHALOSPORINS USEFUL AS ANTIBACTERIAL AGENTS
  申请人：Duclos Brian A.

  公开号：US20120283237A1

  公开（公告）日：2012-11-08

  The present invention provides novel cephalosporin derivatives of formula I, their analogues, their use for the treatment of infections in mammals, pharmaceutical composition containing these novel compounds, and methods for the preparation of these compounds.

  本发明提供了式I的新型头孢菌素衍生物，它们的类似物，它们用于治疗哺乳动物感染的用途，含有这些新化合物的药物组合物，以及制备这些化合物的方法。
• [EN] COMPOUNDS WHICH POTENTIATE GLUTAMATE RECEPTOR AND USES THEREOF IN MEDICINE<br/>[FR] COMPOSÉS POTENTIALISATEURS DE RÉCEPTEUR DE GLUTAMATE ET UTILISATIONS DE CEUX-CI EN MÉDECINE
  申请人：GLAXO GROUP LTD

  公开号：WO2006015829A1

  公开（公告）日：2006-02-16

  Compounds of formula (I), a pharmaceutically acceptable salt, solvate or prodrug thereof are disclosed: wherein R1 is C1-6alkyl, haloC1-6alkyl, C2-6alkenyl, amino, monoC1-4alkylamino or diC1 4alkylamino; R2 and R3, which may be the same or different, are hydrogen, halogen, C1-6alkyl, haloC1-6alkyl, C1-4alkoxy, haloC1-4alkoxy, cyano or amino; each R4, which may be the same or different, is C1-6alkyl, halogen, haloC1-6alkyl, C1-4alkoxy, haloC1-4alkoxy, cyano, nitro or amino; p is 0, 1 or 2; each R5, which may be the same or different, is C1-6alkyl, halogen, haloC1-6alkyl, C1-4alkoxy, haloC1-4alkoxy, cyano, nitro or amino; q is 0,1 or 2; R6 is -NR6aSO2R6b, -NR6aC(=O)R6b, -NR6a(C=O)N(R6c)2, -(C=O)R6d, CH2NR6aSO2R6b, -CH2NR6aC(=O)R6b, -CH2NR6a(C=O)N(R6c)2 or CH2(C=O)R6d; where R6a and each R6c, which may be the same or different, is hydrogen or C1-6alkyl; R6b and R6d are C1-6alkyl or haloC1-6alkyl; or R6a and R6b, or R6a and R6c, together with the interconnecting atoms, may form a 5- or 6-membered ring; n is 1 or 2; and R7 and R8, which may be the same or different, are hydrogen, halogen, C1-6alkyl, haloC1-6alkyl, C1-4alkoxy, haloC1-4alkoxy, cyano or amino. Methods of preparation of the compounds, and uses thereof in medicine, for example treatment of schizophrenia, are also disclosed.

  本文披露了公式（I）的化合物，其为药学上可接受的盐、溶剂或前药：其中R1为C1-6烷基、卤代C1-6烷基、C2-6烯基、氨基、单C1-4烷基氨基或双C1-4烷基氨基；R2和R3可以相同也可以不同，为氢、卤素、C1-6烷基、卤代C1-6烷基、C1-4烷氧基、卤代C1-4烷氧基、氰基或氨基；每个R4可以相同也可以不同，为C1-6烷基、卤素、卤代C1-6烷基、C1-4烷氧基、卤代C1-4烷氧基、氰基、硝基或氨基；p为0、1或2；每个R5可以相同也可以不同，为C1-6烷基、卤素、卤代C1-6烷基、C1-4烷氧基、卤代C1-4烷氧基、氰基、硝基或氨基；q为0、1或2；R6为-NR6aSO2R6b、-NR6aC（=O）R6b、-NR6a（C=O）N（R6c）2、-（C=O）R6d、CH2NR6aSO2R6b、-CH2NR6aC（=O）R6b、-CH2NR6a（C=O）N（R6c）2或CH2（C=O）R6d；其中R6a和每个R6c可以相同也可以不同，为氢或C1-6烷基；R6b和R6d为C1-6烷基或卤代C1-6烷基；或者R6a和R6b，或R6a和R6c，连通的原子可以形成5-或6-成员环；n为1或2；R7和R8可以相同也可以不同，为氢、卤素、C1-6烷基、卤代C1-6烷基、C1-4烷氧基、卤代C1-4烷氧基、氰基或氨基。还披露了制备这些化合物的方法以及在医学上的用途，例如治疗精神分裂症。
• Compounds Which Potentiate Glutamate Receptor And Uses Thereof In Medicine
  申请人：Thewlis Michael Kevin

  公开号：US20070203218A1

  公开（公告）日：2007-08-30

  This case discloses compounds of formula (I) wherein R 1 is C 1-6 alkyl, haloC 1-6 alkyl, C 2-6 alkenyl, amino, monoC 1-4 alkylamino or diC 1-4 alkylamino; R 2 and R 3 , which may be the same or different, are hydrogen, halogen, C 1-6 alkyl, haloC 1-6 alkyl, C 1-4 alkoxy, haloC 1-4 alkoxy, cyano or amino; each R 4 , which may be the same or different, is C 1-6 alkyl, halogen, haloC 1-6 alkyl, C 1-4 alkoxy, haloC 1-4 alkoxy, cyano, nitro or amino; p is 0, 1 or 2; each R 5 , which may be the same or different, is C 1-6 alkyl, halogen, haloC 1-6 alkyl, C 1-4 alkoxy, haloC 1-4 alkoxy, cyano, nitro or amino; q is 0,1 or 2; R 6 is −NR 6a SO 2 R 6b , —NR 6a C(═O)R 6b , —NR 6a (C═O)N(R 6c ) 2 , —(C═O)R 6d , —CH 2 NR 6a SO 2 R 6b , —CH 2 NR 6a C(═O)R 6b , CH 2 NR 6a (C═O)N(R 6c ) 2 or —CH 2 (C═O)R 6d ; where R 6a and each R 6c , which may be the same or different, is hydrogen or C 1-6 alkyl; R 6b and R 6d are C 1-6 alkyl or haloC 1-6 alkyl; or R 6a and R 6b , or R 6a and R 6c , together with the interconnecting atoms, may form a 5- or 6-membered ring; n is 1 or 2; and R 7 and R 8 , which may be the same or different, are hydrogen, halogen, C 1-6 alkyl, haloC 1-6 alkyl, C 1-4 alkoxy, haloC 1-4 alkoxy, cyano or amino. It also discloses methods for preparing the compounds and their use in therapy such as treating schizophrenia.

  本案例揭示了式（I）的化合物，其中R1为C1-6烷基，卤代C1-6烷基，C2-6烯基，氨基，单C1-4烷基氨基或双C1-4烷基氨基；R2和R3，可以相同也可以不同，为氢，卤素，C1-6烷基，卤代C1-6烷基，C1-4烷氧基，卤代C1-4烷氧基，氰基或氨基；每个R4，可以相同也可以不同，为C1-6烷基，卤素，卤代C1-6烷基，C1-4烷氧基，卤代C1-4烷氧基，氰基，硝基或氨基；p为0、1或2；每个R5，可以相同也可以不同，为C1-6烷基，卤素，卤代C1-6烷基，C1-4烷氧基，卤代C1-4烷氧基，氰基，硝基或氨基；q为0、1或2；R6为−NR6aSO2R6b、—NR6aC（═O）R6b、—NR6a（C═O）N（R6c）2、—（C═O）R6d、—CH2NR6aSO2R6b、—CH2NR6aC（═O）R6b、CH2NR6a（C═O）N（R6c）2或—CH2（C═O）R6d；其中R6a和每个R6c，可以相同也可以不同，为氢或C1-6烷基；R6b和R6d为C1-6烷基或卤代C1-6烷基；或R6a和R6b，或R6a和R6c，与连接的原子一起可以形成5-或6-成员环；n为1或2；R7和R8，可以相同也可以不同，为氢，卤素，C1-6烷基，卤代C1-6烷基，C1-4烷氧基，卤代C1-4烷氧基，氰基或氨基。本案例还揭示了制备这些化合物的方法以及它们在治疗精神分裂症等疾病方面的用途。
• Compounds which potentiate glutamate receptor and uses thereof in medicine
  申请人：Glaxo Group Limited

  公开号：US07741351B2

  公开（公告）日：2010-06-22

  This case discloses compounds of formula (I) wherein R1 is C1-6alkyl, haloC1-6alkyl, C2-6alkenyl, amino, monoC1-4alkylamino or diC1-4alkylamino; R2 and R3, which may be the same or different, are hydrogen, halogen, C1-6alkyl, haloC1-6alkyl, C1-4alkoxy, haloC1-4alkoxy, cyano or amino; each R4, which may be the same or different, is C1-6alkyl, halogen, haloC1-6alkyl, C1-4alkoxy, haloC1-4alkoxy, cyano, nitro or amino; p is 0, 1 or 2; each R5, which may be the same or different, is C1-6alkyl, halogen, haloC1-6alkyl, C1-4alkoxy, haloC1-4alkoxy, cyano, nitro or amino; q is 0, 1 or 2; R6 is —NR6aSO2R6b, —NR6aC(═O)R6b, —NR6a(C═O)N(R6c)2, —(C═O)R6d, —CH2NR6aSO2R6b, —CH2NR6aC(═O)R6b, CH2NR6a(C═O)N(R6c)2 or —CH2(C═O)R6d; where R6a and each R6c, which may be the same or different, is hydrogen or C1-6alkyl; R6b and R6d are C1-6alkyl or haloC1-6alkyl; or R6a and R6b, or R6a and R6c, together with the interconnecting atoms, may form a 5- or 6-membered ring; n is 1 or 2; and R7 and R8, which may be the same or different, are hydrogen, halogen, C1-6alkyl, haloC1-6alkyl, C1-4alkoxy, haloC1-4alkoxy, cyano or amino. It also discloses methods for preparing the compounds and their use in therapy such as treating schizophrenia.

  该案例揭示了式（I）的化合物，其中R1为C1-6烷基，卤代C1-6烷基，C2-6烯基，氨基，单C1-4烷基氨基或双C1-4烷基氨基；R2和R3，可以相同也可以不同，为氢，卤素，C1-6烷基，卤代C1-6烷基，C1-4烷氧基，卤代C1-4烷氧基，氰基或氨基；每个R4，可以相同也可以不同，为C1-6烷基，卤素，卤代C1-6烷基，C1-4烷氧基，卤代C1-4烷氧基，氰基，硝基或氨基；p为0、1或2；每个R5，可以相同也可以不同，为C1-6烷基，卤素，卤代C1-6烷基，C1-4烷氧基，卤代C1-4烷氧基，氰基，硝基或氨基；q为0、1或2；R6为-NR6aSO2R6b，-NR6aC（═O）R6b，-NR6a（C═O）N（R6c）2，-（C═O）R6d，-CH2NR6aSO2R6b，-CH2NR6aC（═O）R6b，CH2NR6a（C═O）N（R6c）2或-CH2（C═O）R6d；其中R6a和每个R6c，可以相同也可以不同，为氢或C1-6烷基；R6b和R6d为C1-6烷基或卤代C1-6烷基；或者R6a和R6b，或者R6a和R6c，连通原子形成5-或6-环；n为1或2；R7和R8，可以相同也可以不同，为氢，卤素，C1-6烷基，卤代C1-6烷基，C1-4烷氧基，卤代C1-4烷氧基，氰基或氨基。它还揭示了制备这些化合物的方法以及它们在治疗精神分裂症等疾病中的应用。