3-Bromo-2-methylbenzenesulfonamide | 1032507-35-9

• 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: 3-Bromo-2-methylbenzenesulfonamide
• CAS: 1032507-35-9
• 化学式: C₇H₈BrNO₂S
• 分子量: 250.116
• InChiKey: OJPKVYUOZLYJSY-UHFFFAOYSA-N

物化性质

• 沸点：
  386.8±52.0 °C(Predicted)
• 密度：
  1.658±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  68.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Bromo-2-methylbenzenesulfonamide 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 potassium acetate 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 四氯化碳 为溶剂， 生成 2-sulfamoyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate
  参考文献：
  名称：

  Synthesis of new acylsulfamoyl benzoxaboroles as potent inhibitors of HCV NS3 protease

  摘要：

  HCV NS3/4A serine protease is essential for the replication of the HCV virus and has been a clinically validated target. A series of HCV NS3/4A protease inhibitors containing a novel acylsulfamoyl benzoxaborole moiety at the P1 ' region was synthesized and evaluated. The resulting P1-P3 and P2-P4 macrocyclic inhibitors exhibited sub-nanomolar potency in the enzymatic assay and low nanomolar activity in the cell-based replicon assay. The in vivo PK evaluations of selected compounds are also described. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.10.007
• 作为产物：
  描述：

  3-溴-2-甲基苯磺酰氯 在 ammonium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 以100%的产率得到3-Bromo-2-methylbenzenesulfonamide
  参考文献：
  名称：

  Synthesis of new acylsulfamoyl benzoxaboroles as potent inhibitors of HCV NS3 protease

  摘要：

  HCV NS3/4A serine protease is essential for the replication of the HCV virus and has been a clinically validated target. A series of HCV NS3/4A protease inhibitors containing a novel acylsulfamoyl benzoxaborole moiety at the P1 ' region was synthesized and evaluated. The resulting P1-P3 and P2-P4 macrocyclic inhibitors exhibited sub-nanomolar potency in the enzymatic assay and low nanomolar activity in the cell-based replicon assay. The in vivo PK evaluations of selected compounds are also described. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.10.007

文献信息

• [EN] COVALENT CDK2-BINDING COMPOUNDS FOR THERAPEUTIC PURPOSES<br/>[FR] COMPOSÉS DE LIAISON À CDK2 COVALENTS UTILISÉS À DES FINS THÉRAPEUTIQUES
  申请人：UMBRA THERAPEUTICS INC

  公开号：WO2022187693A1

  公开（公告）日：2022-09-09

  Heteroaryl sulfonyl compounds and compositions that have a CDK2 Recognition Moiety bound to an electrophile for the selective covalent modification of CDK2 to treat CDK2-mediated disorders are described.

  本文描述了具有CDK2识别基团结合到亲电体的杂环磺酰化合物和组合物，用于选择性共价修饰CDK2以治疗CDK2介导的疾病。
• COMPOUNDS
  申请人：Astra Pharmaceuticals Limited

  公开号：EP0865431A2

  公开（公告）日：1998-09-23
• US5977105A
  申请人：——

  公开号：US5977105A

  公开（公告）日：1999-11-02
• [EN] COMPOUNDS<br/>[FR] COMPOSES
  申请人：——

  公开号：WO1997020815A1

  公开（公告）日：1997-06-12

  [EN] A compound of formula (I), wherein X represents (CH2)nO, (CH2)nS or C2 alkylene; n represents 1 or 2; Ar<1> represents indanyl, tetrahydronaphthyl, naphthyl or phenyl, which latter two groups may be substituted by one or more substituents selected from chloro, fluoro, OR<1>, O(CH2)mCONR<2O>R<21>, C(O)R<2>, C1-6 alkyl (optionally substituted by one or more fluorine atoms), pyridyl, thiazinyl, phenyl or C7-9 alkylphenyl which latter two groups are optionally substituted by one or more substituent selected from halo, nitro, OR<3>, C1-6alkyl (optionally substituted by one or more fluorine atoms), C(O)R<4>, C(O)OR<5>, C(O)N(R<6>)R<7>, CN, CH2OR<14>, CH2NR<15>R<16>, N(R<8>)R<9>, N(R<10>)SO2R<11>, N(R<12>)C(O)R<13>, OC(O)R<19> and SO2NR<17>R<18>; m represents an integer 1 to 3; R<1>, R<2> and R<3> independently represent H, C1-10 alkyl (optionally substituted by one or more fluorine atoms), C7-9 alkylphenyl or phenyl, which latter group is optionally substituted by hydroxy; and R<4>, R<5>, R<6>, R<7>, R<8>, R<9>, R<10>, R<11>, R<12>, R<13>, R<14>, R<15>, R<16>, R<17>, R<18>, R<19>, R<20> and R<21> independently represent H, C1-6 alkyl (optionally substituted by one or more fluorine atoms) or phenyl; in which any alkyl group represent may be interrupted by one or more oxygen atoms; provided that when X represents CH2CH2, Ar<1> may not represent phenyl or phenyl substituted with one or more substituents OR<1>, in which R<1> represents C1-10 alkyl; or a pharmaceutically acceptable derivative thereof, may be used for the treatment of reversible obstructive airways disease or allergic conditions of the skin, nose and eye.
  [FR] La présente invention concerne un composé représenté par la formule générale (I). dans cette formule, X représente (CH2)nO,(CH2)nS ou C2 alkylène; n représente 1 ou 2; Ar<1> représente indanyle, tétrahydronaphthyle, naphthyle ou phényle, ces deux derniers groupes pouvant être substitués par un ou plusieurs substituants sélectionnés parmi chloro, fluoro, OR<1>, O(CH2)mCONR<20>R<21>, C(O)R<2>, alkyleC1-6 (éventuellement substitué par un ou plusieurs atomes de fluor), pyridyle, tiazinyle, phényle ou alkylphényleC7-9, ces deux derniers groupes étant éventuellement substitués par un ou plusieurs substituants sélectionnés parmi les halo, nitro, OR<3>, alkyleC1-6 (éventuellement substitué par un ou plusieurs atomes de fluor), C(O)R<4>, C(O)OR<5>, C(O)N(R<6>)R<7>, CN, CH2OR<14>, CH2NR<15>R<16>, N(R<8>)R<9>, N(R<10>)SO2R<11>, N(R<12>)C(O)R<13>, OC(O)R<19> et SO2NR<17>R<18>; m représente un entier de 1 à 3; R<1>, R<2> et R<3> représentent indépendamment H, alkyleC1-10, éventuellement substitué par un ou plusieurs atomes fluor, alkylphényleC7-9 ou phényle, ce dernier groupe étant éventuellement substitué par hydroxy; et R<4>, R<5>, R<6>, R<7>, R<8>, R<9>, R<10>, R<11>, R<12>, R<13>, R<14>, R<15>, R<16>, R<17>, R<18>, R<19>, R<20> et R<21> représentent indépendamment H, alkyleC1-6 (éventuellement substitué par un ou plusieurs atomes fluor) ou phényle. Dans cette formule tout groupe alkyle présent peut être interrompu par un ou plusieurs atomes d'oxygène. Dans le cas où X représente CH2CH2, Ar<1> ne peut par représenter phényle ou phényle substitué par un ou plusieurs substituants OR<1> R<1> représentant alkyleC1-10. L'invention concerne également un dérivé pharmaceutiquement acceptable de ce composés, lesquels composés conviennent au traitement des affections obstructives réversibles des voies aériennes supérieures ou d'états allergiques de la peau, du nez et de l'oeil.
• Design and Synthesis of Benzenesulfonamide Derivatives as Potent Anti-Influenza Hemagglutinin Inhibitors
  作者：Guozhi Tang、Xianfeng Lin、Zongxing Qiu、Wentao Li、Lei Zhu、Lisha Wang、Shaohua Li、Haodong Li、Wenbin Lin、Mei Yang、Tao Guo、Li Chen、Daniel Lee、Jim Z. Wu、Wengang Yang

  DOI：10.1021/ml2000627

  日期：2011.8.11

  Structural optimization of salicylamide-based hemagglutinin (HA) inhibitor 1 resulted in the identification of cis-3-(5-hydroxy-1,3,3-timethylcyclohexylmethylamino)benzenesulfonamide 28 and its derivatives as potent anti-influenza agents. The lead compound 28 and its 2-chloro analogue 40 can effectively prevent cytopathic effects (CPE) caused by infection of influenza A/Weiss/43 strain (H1N1) with EC(50) values of 210 and 86 nM, respectively. Mechanism of action studies indicate that 40 and its analogues inhibit the virus fusion with host endosome membrane by binding to HA and stabilizing the prefusion HA structure. With significantly improved metabolic stability, the reported series represents the first generation of orally bioavailable HA inhibitors that have a good selectivity window and potential for further development as novel anti-influenza agents.