3-(bromomethyl)-N-methylbenzenesulfonamide | 914094-74-9

• 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-(bromomethyl)-N-methylbenzenesulfonamide
• CAS: 914094-74-9
• 化学式: C₈H₁₀BrNO₂S
• 分子量: 264.143
• InChiKey: DGCRGKVPWCSRKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(bromomethyl)-N-methylbenzenesulfonamide 在 水 作用下， 以84.5 %的产率得到3-(hydroxymethyl)-N-methylbenzene-1-sulfonamide
  参考文献：
  名称：

  Kinase Inhibition via Small Molecule‐Induced Intramolecular Protein Cross‐Linking

  摘要：

  Remarkable progress has been made in the development of cysteine‐targeted covalent inhibitors. In kinase drug discovery, covalent inhibitors capable of targeting other nucleophilic residues (i.e. lysine, or K) have emerged in recent years. Besides a highly conserved catalytic lysine, almost all human protein kinases possess an equally conserved glutamate/aspartate (e.g. E/D) that forms a K–E/D salt bridge within the enzyme's active site. Electrophilic ynamides were previously used as effective peptide coupling reagents and to develop E/D‐targeting covalent protein inhibitors/probes. In the present study, we report the first ynamide‐based small‐molecule inhibitors capable of inducing intramolecular cross‐linking of various protein kinases, leading to subsequent irreversible inhibition of kinase activity. Our strategy took advantage of the close distance between the highly conserved catalytic K and E/D residues in a targeted kinase, thus providing a conceptually general approach to achieve irreversible kinase inhibition with high specificity and desirable cellular potency. Finally, this ynamide‐facilitated, ligand‐induced mechanism leading to intramolecular kinase cross‐linking and inhibition was unequivocally established by using recombinant ABL kinase as a representative.

  DOI：

  10.1002/anie.202404195
• 作为产物：
  描述：

  间甲苯磺酰氯 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 乙腈 为溶剂， 反应 6.33h， 生成 3-(bromomethyl)-N-methylbenzenesulfonamide
  参考文献：
  名称：

  3-（腺苷硫基）苯甲酸衍生物作为 SARS-CoV-2 Nsp14 甲基转移酶抑制剂。

  摘要：

  SARS-CoV-2 nsp14 鸟嘌呤-N7-甲基转移酶通过催化甲基从 S-腺苷甲硫氨酸 (SAM) 转移到病毒 mRNA 帽，在病毒 RNA 翻译过程中发挥重要作用。我们报告了 3-（腺苷硫基）苯甲酸衍生物的结构导向设计和合成作为 nsp14 甲基转移酶抑制剂，与母体抑制剂相比，化合物 5p 具有亚纳摩尔抑制活性和改善的细胞膜通透性。化合物 5p 作为双底物抑制剂，靶向 nsp14 的 SAM 和 mRNA 结合口袋。虽然 3-（腺苷硫基）苯甲酸衍生物对人甘氨酸 N-甲基转移酶的选择性没有提高，但苯基取代类似物 5p,t 的发现可能有助于进一步开发 SARS-CoV-2 nsp14 双底物抑制剂。

  DOI：

  10.3390/molecules28020768

文献信息

• 4-Phenyl-5-Oxo-1,4,5,6,7,8-Hexahydroquinoline Derivatives for the Treatment of Infertility
  申请人：Grima Poveda Pedro Manuel

  公开号：US20080275042A1

  公开（公告）日：2008-11-06

  The present invention relates to 4-phenyl-5-oxo-1,4)5,6,7,8-hexahydroquinoline derivatives according to Formula I, Formula I or a pharmaceutically acceptable salt thereof, wherein R 1 is (1-6C)alkyl, (2-6C)alkenyl or (2-6C)aDcynyl; R 2 , R 3 are independently halogen, (1-4C)allyl, (2-4C)alkenyl, (2-4C)-alkynyl, (1-4C)aBcoxy, (3-4C)alkenyloxy or (3-4C)alkynyloxy; R 4 is phenyl or (2-5C)-heteroaryl, both substituted with R 7 and optionally substituted on the (hetero)aromatic ring with one or more substituents selected from hydroxy, amino, halogen, nitro, trifluoromethyl, cyano, (1-4C)alkyl, (1-4C)alkoxy, (1-4C)alkylthio and (di)(1-4C)-alkylamino. The invention also relates to pharmaceutical compositions comprising said derivatives, as well as to the use of these 4-phenyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline derivatives in therapy, more specifically for the treatment of infertility

  本发明涉及公式I、公式II或其药学上可接受的盐的4-苯基-5-氧代-1,4,5,6,7,8-六氢喹啉衍生物，其中R1是(1-6C)烷基、(2-6C)烯基或(2-6C)炔基；R2、R3独立地为卤素、(1-4C)烯丙基、(2-4C)烯基、(2-4C)炔基、(1-4C)氧代丙基、(3-4C)烯氧基或(3-4C)炔氧基；R4是苯基或(2-5C)杂环芳基，均用R7取代，并且在(杂)芳香环上可选择地用一个或多个取代基取代，所述取代基选自羟基、氨基、卤素、硝基、三氟甲基、氰基、(1-4C)烷基、(1-4C)氧基、(1-4C)硫代烷基和(二)(1-4C)-烷基氨基。本发明还涉及包含上述衍生物的制药组合物，以及这些4-苯基-5-氧代-1,4,5,6,7,8-六氢喹啉衍生物在治疗中的应用，更具体地用于不孕症的治疗。
• Novel Covalent Probe Selectively Targeting Glutathione Peroxidase 4 In Vivo: Potential Applications in Pancreatic Cancer Therapy
  作者：Zifeng Tang、Jie Li、Lijie Peng、Fang Xu、Yi Tan、Xiaoqiang He、Chengjun Zhu、Zhi-Min Zhang、Zhang Zhang、Pinghua Sun、Ke Ding、Zhengqiu Li

  DOI：10.1021/acs.jmedchem.3c01608

  日期：2024.2.8
• 4-PHENYL-5-OXO-1,4,5,6,7,8-HEXAHYDROQUINOLINE DERIVATIVES THE TREATMENT OF INFERTILITY
  申请人：N.V. Organon

  公开号：EP1881830B1

  公开（公告）日：2008-10-08
• US8022218B2
  申请人：——

  公开号：US8022218B2

  公开（公告）日：2011-09-20