N-((4-chlorophenyl)sulfonyl)-2-methylbenzamide

• 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-((4-chlorophenyl)sulfonyl)-2-methylbenzamide
• 英文别名: N-(4-chlorobenzenesulfonyl)-2-methylbenzamide；N-(4-chlorophenyl)sulfonyl-2-methylbenzamide
• 化学式: C₁₄H₁₂ClNO₃S
• 分子量: 309.773
• InChiKey: JQSONZDJELNSLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3,5-bis(trifluoromethyl)benzylidene)-4-methylbenzenesulfonamide 、 N-((4-chlorophenyl)sulfonyl)-2-methylbenzamide 在 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 碳酸氢钠 作用下， 以 均三甲苯 为溶剂， 反应 3.0h， 以17%的产率得到3-(3,5-bis(trifluoromethyl)phenyl)-7-methyl-2-tosylisoindolin-1-one
  参考文献：
  名称：

  钌催化的酰胺CH键与醛亚胺直接加成合成异吲哚啉酮

  摘要：

  直截了当的路线！[RuCl 2（p- cymene）] 2在催化量的碱存在下促进了醛胺的酰胺基加氢芳基化反应，得到了相应的异吲哚啉酮衍生物。多种酰胺和沙丁胺类药物参与了Ru催化的当前反应，以中等至高收率提供了相应的异吲哚啉酮。多种酰胺和醛亚胺参与了目前的Ru催化反应，以高至高收率提供了相应的异吲哚啉酮。

  DOI：

  10.1002/ejoc.201801755
• 作为产物：
  描述：

  对甲苯甲酸 、 4-氯苯磺酰胺 在 4-二甲氨基吡啶 、 N'-methyl polystyrene HL 、 N-cyclohexylcarbodiimide 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以47%的产率得到N-((4-chlorophenyl)sulfonyl)-2-methylbenzamide
  参考文献：
  名称：

  Acyl Sulfonamide Anti-Proliferatives:  Benzene Substituent Structure−Activity Relationships for a Novel Class of Antitumor Agents

  摘要：

  Two closely related diaryl acylsulfonamides were recently reported as potent antitumor agents against a broad spectrum of human tumor xenografts (colon, lung, breast, ovary, and prostate) in nude mice. Especially intriguing was their activity against colorectal cancer xenografts. In this paper, rapid parallel synthesis along with traditional medicinal chemistry techniques were used to quickly delineate the structure-activity relationships of the substitution patterns in both phenyl rings of the acylsufonamide anti-proliferative scaffold. Although the molecular target of the compounds remains unclear, we determined that the vascular endothelial growth factor-dependent human umbilical vein endothelial cells assay in combination with a soft agar disk diffusion assay allowed for optimization of potency in the series. The pharmacokinetic properties and in vivo activity in an HCT116 xenograft model are reported for representative compounds.

  DOI：

  10.1021/jm030594r

文献信息

• Ruthenium-Catalyzed Addition of Aromatic Amides to Internal Alkynes and Subsequent Intramolecular Cyclization for the Atom-Economical Synthesis of Isoindolinones
  作者：Hiroki Miura、Sachie Terajima、Kentaro Tsutsui、Tetsuya Shishido

  DOI：10.1021/acs.joc.6b02552

  日期：2017.1.20

  isoindolinones is described. This novel synthetic strategy involves two catalytic reactions: the ruthenium-catalyzed regioselective alkenylation of aromatic C–H bond of aromatic amides with internal alkynes, and subsequent intramolecular cyclization of the resulting alkene with amide functionalities. The addition of only a catalytic amount of bases is required for efficient construction of the desired

  描述了异吲哚啉酮的选择性和原子经济的合成。这种新颖的合成策略涉及两个催化反应：钌催化的芳香酰胺与内部炔烃的芳香C–H键的区域选择性烯基化，以及随后的具有酰胺官能团的烯烃的分子内环化。为了有效地构建所需的异吲哚啉酮，仅需要添加催化量的碱，并且在串联催化反应中不会形成副产物。在本反应中可以使用各种芳族酰胺和内部炔烃，并且以良好或高收率获得了在C3位带有季碳的相应的异吲哚满酮。
• Acyl Sulfonamide Anti-Proliferatives:  Benzene Substituent Structure−Activity Relationships for a Novel Class of Antitumor Agents
  作者：Karen L. Lobb、Philip A. Hipskind、James A. Aikins、Enrique Alvarez、Yiu-Yin Cheung、Eileen L. Considine、Alfonso De Dios、Gregory L. Durst、Rafael Ferritto、Cora Sue Grossman、Deborah D. Giera、Beth A. Hollister、Zhongping Huang、Philip W. Iversen、Kevin L. Law、Tiechao Li、Ho-Shen Lin、Beatriz Lopez、Jose E. Lopez、Luisa M. Martin Cabrejas、Denis J. McCann、Victoriano Molero、John E. Reilly、Michael E. Richett、Chuan Shih、Beverly Teicher、James H. Wikel、Wesley T. White、Mary M. Mader

  DOI：10.1021/jm030594r

  日期：2004.10.1

  Two closely related diaryl acylsulfonamides were recently reported as potent antitumor agents against a broad spectrum of human tumor xenografts (colon, lung, breast, ovary, and prostate) in nude mice. Especially intriguing was their activity against colorectal cancer xenografts. In this paper, rapid parallel synthesis along with traditional medicinal chemistry techniques were used to quickly delineate the structure-activity relationships of the substitution patterns in both phenyl rings of the acylsufonamide anti-proliferative scaffold. Although the molecular target of the compounds remains unclear, we determined that the vascular endothelial growth factor-dependent human umbilical vein endothelial cells assay in combination with a soft agar disk diffusion assay allowed for optimization of potency in the series. The pharmacokinetic properties and in vivo activity in an HCT116 xenograft model are reported for representative compounds.
• Ruthenium-Catalyzed Synthesis of Isoindolinones via Amide-Directed Addition of Aromatic C-H Bonds to Aldimines
  作者：Hiroki Miura、Yuriko Kimura、Sachie Terajima、Tetsuya Shishido

  DOI：10.1002/ejoc.201801755

  日期：2019.5.8

  Straightforward Route! [RuCl2(p‐cymene)]2 promoted amide‐directed hydroarylation of aldimines in the presence of a catalytic amount of base gives the corresponding isoindolinone derivatives. A variety of amides and saldimines participated in the present Ru‐catalyzed reaction to furnish the corresponding isoindolinones in moderate to high yield. A variety of amides and aldimines participated in the

  直截了当的路线！[RuCl 2（p- cymene）] 2在催化量的碱存在下促进了醛胺的酰胺基加氢芳基化反应，得到了相应的异吲哚啉酮衍生物。多种酰胺和沙丁胺类药物参与了Ru催化的当前反应，以中等至高收率提供了相应的异吲哚啉酮。多种酰胺和醛亚胺参与了目前的Ru催化反应，以高至高收率提供了相应的异吲哚啉酮。