N'-(2-chlorophenylsulfonyl)quinoline-2-carboximidamide | 1431320-02-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N'-(2-chlorophenylsulfonyl)quinoline-2-carboximidamide
• 英文别名: N'-(2-chlorophenyl)sulfonylquinoline-2-carboximidamide
• CAS: 1431320-02-3
• 化学式: C₁₆H₁₂ClN₃O₂S
• 分子量: 345.809
• InChiKey: SIMJBEGYZGAFJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  93.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N'-(2-chlorophenylsulfonyl)quinoline-2-carboximidamide 在 吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 反应 2.0h， 以40%的产率得到3-(quinolin-2-yl)-2H-benzo[e][1,2,4]thiadiazine-1,1-dioxide
  参考文献：
  名称：

  新型3-杂芳基-2-吡啶[4,3-] [1,2,4]噻二嗪和3-杂芳基-2-苯并[] [1,2,4]噻二嗪1,1-二氧化物的合成及生物活性。

  摘要：

  摘要：通过将2-氯苯磺酰胺和4-氯吡啶-3-磺酰胺与从杂环腈中获得的杂环甲基氨基甲酸酯缩合，合成了一系列新型的1,2,4-噻二嗪1,1-二氧化物。 。分离出取代的am作为与2-氯苯磺酰胺反应的中间体。加入DBU，将这些中间体成功地环化成吡啶中的相应1,2,4-噻二嗪1,1-二氧化物。对新合成的化合物的抗结核和抗癌活性进行了评估。八种化合物能够抑制某些肾脏和非小细胞肺癌细胞系的生长。图形概要：

  DOI：

  10.1007/s00706-013-0988-5
• 作为产物：
  描述：

  2-氰基喹啉 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 反应 3.5h， 生成 N'-(2-chlorophenylsulfonyl)quinoline-2-carboximidamide
  参考文献：
  名称：

  Synthesis, structure, and biological activity of novel heterocyclic sulfonyl-carboximidamides

  摘要：

  A series of novel heterocyclic sulfonyl-carboximidamides were synthesized in satisfactory yields via condensation of heterocyclic methyl carbimidates with 2-chlorobenzenesulfonamide and 4-chloropyridine-3-sulfonamide. New structures were confirmed by IR and NMR spectra as well as elemental analyses. X-ray crystallography of two derivatives was performed. The single-crystal structures confirmed the presence of a primary amine group in the amidine moiety. All the compounds were screened for their tuberculostatic, antibacterial, and anticancer activities. Preliminary results indicated that target compounds exhibited weak tuberculostatic and antibacterial activities. Seven compounds inhibited the growth of some cancer cell lines, whereas one of the 2-quinoline derivatives displayed favorable activity against all tested cancer cells with GI (50) values of 0.92-13 mu M.

  DOI：

  10.1007/s00706-012-0888-0

文献信息

• Synthesis, structure, and biological activity of novel heterocyclic sulfonyl-carboximidamides
  作者：Katarzyna Gobis、Henryk Foks、Jarosław Sławiński、Artur Sikorski、Damian Trzybiński、Ewa Augustynowicz-Kopeć、Agnieszka Napiórkowska、Krzysztof Bojanowski

  DOI：10.1007/s00706-012-0888-0

  日期：2013.5

  A series of novel heterocyclic sulfonyl-carboximidamides were synthesized in satisfactory yields via condensation of heterocyclic methyl carbimidates with 2-chlorobenzenesulfonamide and 4-chloropyridine-3-sulfonamide. New structures were confirmed by IR and NMR spectra as well as elemental analyses. X-ray crystallography of two derivatives was performed. The single-crystal structures confirmed the presence of a primary amine group in the amidine moiety. All the compounds were screened for their tuberculostatic, antibacterial, and anticancer activities. Preliminary results indicated that target compounds exhibited weak tuberculostatic and antibacterial activities. Seven compounds inhibited the growth of some cancer cell lines, whereas one of the 2-quinoline derivatives displayed favorable activity against all tested cancer cells with GI (50) values of 0.92-13 mu M.
• Synthesis and biological activity of novel 3-heteroaryl-2H-pyrido[4,3-e][1,2,4]thiadiazine and 3-heteroaryl-2H-benzo[e][1,2,4]thiadiazine 1,1-dioxides
  作者：Katarzyna Gobis、Henryk Foks、Jarosłw Sławiński、Ewa Augustynowicz-Kopeć、Agnieszka Napiórkowska

  DOI：10.1007/s00706-013-0988-5

  日期：2013.8

  ABSTRACT: A series of novel 1,2,4-thiadiazine 1,1-dioxides were synthesized by condensation of 2-chlorobenzenesulfonamide and 4-chloropyridine-3-sulfonamide with heterocyclic methyl carbimidates obtained from heterocyclic carbonitriles and used at the time of their creation. Substituted amidines were isolated as the intermediates in the reaction with 2-chlorobenzenesulfonamide. Those intermediates

  摘要：通过将2-氯苯磺酰胺和4-氯吡啶-3-磺酰胺与从杂环腈中获得的杂环甲基氨基甲酸酯缩合，合成了一系列新型的1,2,4-噻二嗪1,1-二氧化物。 。分离出取代的am作为与2-氯苯磺酰胺反应的中间体。加入DBU，将这些中间体成功地环化成吡啶中的相应1,2,4-噻二嗪1,1-二氧化物。对新合成的化合物的抗结核和抗癌活性进行了评估。八种化合物能够抑制某些肾脏和非小细胞肺癌细胞系的生长。图形概要：