2-(hydroxymethyl)-N-methylbenzenesulfonamide | 40431-34-3

• 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: 2-(hydroxymethyl)-N-methylbenzenesulfonamide
• CAS: 40431-34-3
• 化学式: C₈H₁₁NO₃S
• 分子量: 201.246
• InChiKey: FPPKCGQRCGKDPX-UHFFFAOYSA-N

物化性质

• 熔点：
  78 °C(Solv: benzene (71-43-2))
• 沸点：
  383.8±44.0 °C(Predicted)
• 密度：
  1.308±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 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：
  74.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(hydroxymethyl)-N-methylbenzenesulfonamide 在 N-溴代丁二酰亚胺(NBS) 、 三溴化磷 、 sodium hydride 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 xylene 为溶剂， 反应 140.0h， 生成 N-[3-(dimethylamino)propyl]-2-methyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide
  参考文献：
  名称：

  A Simple and Efficient Synthesis of Methyl 3,4-Dihydro-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-Dioxide from Saccharin Sodium Salt

  摘要：

  以糖精钠为原料，通过五个步骤直接合成了 3,4-二氢-2-甲基-2H-1,2-苯并噻嗪-3-羧酸甲酯 1,1-二氧化物。3,4-二氢-2-甲基-2H-1,2-苯并噻嗪-3-羧酸甲酯 1,1-二氧化物可用作合成一类新型季铵衍生物的前体，这类衍生物具有抗关节炎的潜力。

  DOI：

  10.1055/s-2006-926289
• 作为产物：
  描述：

  saccharin sodium salt 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-(hydroxymethyl)-N-methylbenzenesulfonamide
  参考文献：
  名称：

  A Simple and Efficient Synthesis of Methyl 3,4-Dihydro-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-Dioxide from Saccharin Sodium Salt

  摘要：

  以糖精钠为原料，通过五个步骤直接合成了 3,4-二氢-2-甲基-2H-1,2-苯并噻嗪-3-羧酸甲酯 1,1-二氧化物。3,4-二氢-2-甲基-2H-1,2-苯并噻嗪-3-羧酸甲酯 1,1-二氧化物可用作合成一类新型季铵衍生物的前体，这类衍生物具有抗关节炎的潜力。

  DOI：

  10.1055/s-2006-926289

文献信息

• [EN] BENZIMIDAZOLE DERIVATIVES, COMPOSITIONS CONTAINING THEM, PREPARATION THEREOF AND USES THEREOF<br/>[FR] DERIVES DE BENZIMIDAZOLE, COMPOSITIONS LES CONTENANT, PREPARATION DE CES COMPOSITIONS ET UTILISATIONS CORRESPONDANTES
  申请人：ASTRAZENECA AB

  公开号：WO2005030761A1

  公开（公告）日：2005-04-07

  Compounds of Formula (I) or pharmaceutically acceptable salts thereof; wherein R1, R2, R3, R4, n and Ar are as defined in the specification as well as salts and pharmaceutical compositions including the compounds are prepared. They are useful in therapy, in particular in the management of pain.

  化合物的分子式（I）或其药用盐；其中R1、R2、R3、R4、n和Ar的定义如规范中所述，以及包括这些化合物的盐和药物组合物已经准备好。它们在治疗中很有用，特别是在疼痛管理方面。
• [EN] BENZIMIDAZOLE DERIVATIVES, COMPOSITIONS CONTAINING THEM, PREPARATION THEREOF AND USES THEREOF<br/>[FR] DERIVES DE BENZIMIDAZOLE, COMPOSITIONS CONTENANT CES DERIVES, PREPARATION ET UTILISATIONS
  申请人：ASTRAZENECA AB

  公开号：WO2005030762A1

  公开（公告）日：2005-04-07

  Compounds of Formula (I) or pharmaceutically acceptable salts thereof; wherein R1, R2, R3 and Ar are as defined in the specification as well as salts and pharmaceutical compositions including the compounds are prepared. They are useful in therapy, in particular in the management of pain.

  化合物的化学式（I）或其药用可接受的盐；其中R1、R2、R3和Ar的定义如规范中所述，以及包括这些化合物的盐和药用组合物已经制备。它们在治疗中有用，特别是在疼痛管理中。
• Zinner et al., Journal fur praktische Chemie (Leipzig 1954), 1959, vol. <4> 8, p. 151,152
  作者：Zinner et al.

  DOI：——

  日期：——
• BENZIMIDAZOLE DERIVATIVES, COMPOSITIONS CONTAINING THEM, PREPARATION THEREOF AND USES THEREOF
  申请人：AstraZeneca AB

  公开号：EP1670790A1

  公开（公告）日：2006-06-21
• 10.1002/anie.202404195
  作者：Wang, Xuan、Sun, Jie、Huang, Huisi、Tang, Guanghui、Chen, Peng、Xiang, Menghua、Li, Lin、Zhang, Zhi-Min、Gao, Liqian、Yao, Shao Q.

  DOI：10.1002/anie.202404195

  日期：——

  AbstractRemarkable 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.