4-氨基-N-(6-甲基-1,3-苯并噻唑-2-基)苯磺酰胺 | 93431-64-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-氨基-N-(6-甲基-1,3-苯并噻唑-2-基)苯磺酰胺
• 英文名称: 2-<4-Amino-benzolsulfonamino>-6-methyl-benzothaizol
• 英文别名: 2-<4-Amino-benzolsulfonamino>-6-methyl-benzothiazol；4-amino-N-(6-methyl-benzothiazol-2-yl)-benzenesulfonamide；sulfanilic acid-(6-methyl-benzothiazol-2-ylamide)；Sulfanilsaeure-(6-methyl-benzothiazol-2-ylamid)；4-Amino-N-(6-methyl-1,3-benzothiazol-2-yl)benzene-1-sulfonamide；4-amino-N-(6-methyl-1,3-benzothiazol-2-yl)benzenesulfonamide
• CAS: 93431-64-2
• 化学式: C₁₄H₁₃N₃O₂S₂
• 分子量: 319.408
• InChiKey: SORZWLXKQPVBEA-UHFFFAOYSA-N

物化性质

• 熔点：
  282.5-284 °C
• 沸点：
  544.9±52.0 °C(Predicted)
• 密度：
  1.493±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-氯烟酸 、 4-氨基-N-(6-甲基-1,3-苯并噻唑-2-基)苯磺酰胺 在 铜 、 potassium carbonate 作用下， 以 乙二醇乙醚 为溶剂， 反应 5.0h， 以64%的产率得到2-((4-(N-(6-methylbenzo[d]thiazol-2-yl)sulfamoyl)phenyl)amino)nicotinic acid
  参考文献：
  名称：

  Synthesis and antimicrobial studies of new pyridine derivatives

  摘要：

  2-(p-Acetylaminobenzenesulfonylamido)-substituted benzothiazoles were prepared from 2-amino-substituted benzothiazoles and p-acetamidobenzenesulfonyl chloride using a mixture of pyridine and Ac2O, which formed an electrophilic N-acetyl-pyridinium complex facilitating condensation to give the desired products by removal of HCl. 2-[4-(Substituted benzothiazol-2-yl)aminosulfonylanilino]pyridine-3-carboxylic acids (synthesized from 2-chloropyridine-3-carboxylic acid and the corresponding substituted 2-(p-aminobenzenesulfonylamido)benzothiazole in 2-ethoxyethanol using Cu-powder and K2CO3)were then converted to acid chlorides, which on further reaction with piperazine and 4-methoxyphenylpiperazine yielded the corresponding 2-[4-(substituted benzothiazol-2-yl)aminosulfonyl]anilino-3-(piperazinocarbonyl)pyridine and 2-[4-(substituted benzothiazol-2-yl)aminosulfonyl]anilino-3-[(4-methoxyphenyl)piperazin-1-yl-carbonyl]pyridine. The structures of the new compounds have been established on the basis of their elemental analyses as well as IR, H-1 NMR, and mass-spectral data. All the compounds have been screened for antimicrobial activity and found to possess considerable antibacterial activity.

  DOI：

  10.1007/s10593-010-0432-2
• 作为产物：
  描述：

  对乙酰胺基苯磺酰氯 在 吡啶 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 2.0h， 生成 4-氨基-N-(6-甲基-1,3-苯并噻唑-2-基)苯磺酰胺
  参考文献：
  名称：

  稠合杂环MLKL抑制剂的设计、合成及其抗坏死性凋亡活性

  摘要：

  坏死性凋亡是程序性细胞死亡 (PCD) 的一种重要形式，由死亡受体介导且独立于 caspase 蛋白水解酶。混合谱系激酶结构域样（MLKL）是坏死性凋亡的最终效应器，在坏死性凋亡的执行中发挥着不可替代的作用。然而，MLKL抑制剂的研究还处于起步阶段。 Necrosulfonamide (NSA) 是一种早期发现的共价 MLKL 抑制剂，具有中等抗坏死性凋亡活性和尚未广泛披露的构效关系 (SAR)。在本研究中，在保留共价基序的情况下，我们旨在通过引入末端稠合杂环并同时揭示部分的SAR来提高活性。结果，化合物 和 通过与 MLKL 共价结合而在类似物中表现出最佳的抗坏死性凋亡活性（EC = 148.4 和 595.9 nM）。特区政府的成立也是为了指导该领域的进一步结构优化。

  DOI：

  10.1016/j.bmc.2024.117659

文献信息

• Takatori; Nishida, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1950, vol. 70, p. 271,276
  作者：Takatori、Nishida

  DOI：——

  日期：——
• Studies on Sulfabenzothiazoles
  作者：Prithwi Nath Bhargava、Suresh Chandra Sharma

  DOI：10.1246/bcsj.35.942

  日期：1962.6
• Sulfonamido Derivatives of Thiazoles
  作者：James M. Sprague、L. W. Kissinger

  DOI：10.1021/ja01847a063

  日期：1941.2
• 2-(benzene sulfonamido)-tetra-hydrobenzothiazoles
  申请人：SHARP & DOHME INC

  公开号：US02494524A1

  公开（公告）日：1950-01-10
• Synthesis and antimicrobial studies of new pyridine derivatives
  作者：N. B. Patel、S. N. Agravat

  DOI：10.1007/s10593-010-0432-2

  日期：2009.11

  2-(p-Acetylaminobenzenesulfonylamido)-substituted benzothiazoles were prepared from 2-amino-substituted benzothiazoles and p-acetamidobenzenesulfonyl chloride using a mixture of pyridine and Ac2O, which formed an electrophilic N-acetyl-pyridinium complex facilitating condensation to give the desired products by removal of HCl. 2-[4-(Substituted benzothiazol-2-yl)aminosulfonylanilino]pyridine-3-carboxylic acids (synthesized from 2-chloropyridine-3-carboxylic acid and the corresponding substituted 2-(p-aminobenzenesulfonylamido)benzothiazole in 2-ethoxyethanol using Cu-powder and K2CO3)were then converted to acid chlorides, which on further reaction with piperazine and 4-methoxyphenylpiperazine yielded the corresponding 2-[4-(substituted benzothiazol-2-yl)aminosulfonyl]anilino-3-(piperazinocarbonyl)pyridine and 2-[4-(substituted benzothiazol-2-yl)aminosulfonyl]anilino-3-[(4-methoxyphenyl)piperazin-1-yl-carbonyl]pyridine. The structures of the new compounds have been established on the basis of their elemental analyses as well as IR, H-1 NMR, and mass-spectral data. All the compounds have been screened for antimicrobial activity and found to possess considerable antibacterial activity.