N-[5-Chloro-1H-pyridin-(2Z)-ylidene]-4-methyl-benzenesulfonamide | 54818-84-7

• 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: N-[5-Chloro-1H-pyridin-(2Z)-ylidene]-4-methyl-benzenesulfonamide
• 英文别名: N-(5-chloropyridin-2-yl)-4-methylbenzenesulfonamide
• CAS: 54818-84-7
• 化学式: C₁₂H₁₁ClN₂O₂S
• mdl: MFCD00754770
• 分子量: 282.751
• InChiKey: YXJGFYBONFESMN-UHFFFAOYSA-N

物化性质

• 溶解度：
  28.3 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  67.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[5-Chloro-1H-pyridin-(2Z)-ylidene]-4-methyl-benzenesulfonamide 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 N-(6-chloroimidazo[1,2-a]pyridin-2-yl)-2,2,2-trifluoroacetamide
  参考文献：
  名称：

  Chemoselective Arylsulfenylation of 2-Aminoimidazol[1,2-a]pyridines by Phenyliodine(III) Bis(trifluoroacetate) (PIFA)

  摘要：

  DOI：

  10.1055/s-1998-2078
• 作为产物：
  描述：

  2-氨基-5-碘吡啶 、 对甲苯磺酰氯 在 吡啶 作用下， 以94%的产率得到N-[5-Chloro-1H-pyridin-(2Z)-ylidene]-4-methyl-benzenesulfonamide
  参考文献：
  名称：

  6-Substituted 2-(N-trifluoroacetylamino)imidazopyridines induce cell cycle arrest and apoptosis in SK-LU-1 human cancer cell line

  摘要：

  A series of 6-substituted 2-(N-trifluoroacetylamino)imidazopyridines have been synthesized and their bioactivities were evaluated. Compounds 6a, 6c, and 11a were the most active Compounds with modest cytotoxic activity against six human cancer cell lines U251 (glioma), PC-3 (prostate), K-562 (leukemia), HCT-15 (colon), MCF7 (breast) and SK-LU-1 (lung). The cell cycle analysis showed that Compounds 6a, 6c, and 11a induce a G2/M phase cell cycle arrest on SK-LU-1 cell line where inhibition of CDK-1 and CDK-2 may be implicated. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.11.049

文献信息

• Chemoselective Deprotection of Sulfonamides Under Acidic Conditions: Scope, Sulfonyl Group Migration, and Synthetic Applications
  作者：Tomas Javorskis、Edvinas Orentas

  DOI：10.1021/acs.joc.7b02507

  日期：2017.12.15

  Chemoselective acidic hydrolysis of sulfonamides with trifluoromethanesulfonic acid has been evaluated as a deprotection method and further extended to more complex synthetic applications. In contrast to conventional troublesome sulfonamide hydrolysis, a near-stoichiometric amount of acid was found to be sufficient to bring about efficient deprotection of various neutral or electron-deficient N-arylsulfonamides

  磺酰胺与三氟甲磺酸的化学选择性酸性水解已被评估为一种脱保护方法，并进一步扩展到更复杂的合成应用中。与常规的麻烦的磺酰胺水解相反，发现接近化学计量的酸足以引起各种中性或电子缺陷的N-芳基磺酰胺的有效脱保护，而富电子的底物提供了磺酰基迁移产物。所开发的脱保护方法对N-芳基磺酰胺具有完全选择性，并且证明了区分各种不同磺酰胺的可能性。
• ——
  作者：K. I. Petko、A. A. Tolmachev、L. M. Yagupol'skii

  DOI：10.1023/a:1020813915169

  日期：——

  Reactions of sulfonamides RSO2NHR' with chlorodifluoromethane and solid alkali give the corresponding derivatives RSO2N(CHF2)R' containing a difluoromethyl group on the nitrogen atom. Sulfonamides derived from 2-aminobenzothiazole and 2- and 4-aminopyridines react with chlorodifluoromethane at the endocyclic nitrogen atom.
• Chemoselective Arylsulfenylation of 2-Aminoimidazol[1,2-a]pyridines by Phenyliodine(III) Bis(trifluoroacetate) (PIFA)
  作者：Chafiq Hamdouchi

  DOI：10.1055/s-1998-2078

  日期：1998.6
• 6-Substituted 2-(N-trifluoroacetylamino)imidazopyridines induce cell cycle arrest and apoptosis in SK-LU-1 human cancer cell line
  作者：Miguel Angel Martínez-Urbina、Alejandro Zentella、Miguel Angel Vilchis-Reyes、Ángel Guzmán、Omar Vargas、María Teresa Ramírez Apan、José Luis Ventura Gallegos、Eduardo Díaz

  DOI：10.1016/j.ejmech.2009.11.049

  日期：2010.3

  A series of 6-substituted 2-(N-trifluoroacetylamino)imidazopyridines have been synthesized and their bioactivities were evaluated. Compounds 6a, 6c, and 11a were the most active Compounds with modest cytotoxic activity against six human cancer cell lines U251 (glioma), PC-3 (prostate), K-562 (leukemia), HCT-15 (colon), MCF7 (breast) and SK-LU-1 (lung). The cell cycle analysis showed that Compounds 6a, 6c, and 11a induce a G2/M phase cell cycle arrest on SK-LU-1 cell line where inhibition of CDK-1 and CDK-2 may be implicated. (C) 2009 Elsevier Masson SAS. All rights reserved.