2,4-dichloro-N-(benzenesulfonyl)benzenecarboxamide | 1026665-64-4

• 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: 2,4-dichloro-N-(benzenesulfonyl)benzenecarboxamide
• 英文别名: LY 32262；N-[2,4-dichlorobenzoyl]phenylsulfonamide；N-(benzenesulfonyl)-2,4-dichlorobenzamide
• CAS: 1026665-64-4
• 化学式: C₁₃H₉Cl₂NO₃S
• 分子量: 330.191
• InChiKey: TXHQSKPOVJIXCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  2,4-dichloro-N-(benzenesulfonyl)benzenecarboxamide 在 1-(125I)iodanylpyrrolidine-2,5-dione 、 palladium diacetate 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以37%的产率得到[¹²⁵I]-2,4-dichloro-6-iodo-N-(benzenesulfonyl)benzenecarboxamide
  参考文献：
  名称：

  Improvements of C–H Radio-Iodination of N-Acylsulfonamides toward Implementation in Clinics

  摘要：

  描述了一种改进的C-H放射性碘化协议。这些新条件允许使用[125I]NIS和少量钯醋酸盐和对甲苯磺酸催化快速干净地形成放射性碘化N-酰基磺酰胺。不需要预功能化的前体，产物以27-84%的放射化学转化率（RCC）获得。

  DOI：

  10.1055/s-0037-1611884
• 作为产物：
  描述：

  苯磺酰胺 、 2,4-二氯苯甲酰氯 在 potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 以80%的产率得到2,4-dichloro-N-(benzenesulfonyl)benzenecarboxamide
  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

• An expeditious and convenient synthesis of acylsulfonamides utilizing polymer-supported reagents
  作者：Ying Wang、Kathy Sarris、Daryl R. Sauer、Stevan W. Djuric

  DOI：10.1016/j.tetlet.2007.05.158

  日期：2007.7

  Acylsulfonamides can be rapidly and conveniently synthesized from a variety of carboxylic acids and sulfonamides utilizing the commercially available reagents, PS-DCC and DMAP under mild reaction conditions. DMAP can be efficiently scavenged by utilization of a silica-supported tosic acid cartridge (Si-SCX). In most of the cases studied, products with high purities and yields were obtained without

  使用市售试剂PS-DCC和DMAP，可以在温和的反应条件下，从各种羧酸和磺酰胺快速方便地合成酰基磺酰胺。通过使用二氧化硅支撑的甲苯磺酸盒（Si-SCX），可以有效地清除DMAP。在大多数研究案例中，无需进一步纯化即可获得高纯度和高收率的产品。
• [EN] BENZOYLSULFONAMIDES AND SULFONYLBENZAMIDINES FOR USE AS ANTITUMOUR AGENTS<br/>[FR] BENZOYLSULFONAMIDES ET SULFONYLBENZAMIDINES EN TANT QU'AGENTS ANTITUMORAUX
  申请人：LILLY CO ELI

  公开号：WO2002098848A1

  公开（公告）日：2002-12-12

  The present invention provides antitumor compounds of the formula(I), and antitumor methods.

  本发明提供了公式(I)的抗肿瘤化合物，以及抗肿瘤方法。
• Benzoylsulfonamides and sulfonylbenzamidines for use as antitumour agents
  申请人：——

  公开号：US20040157741A1

  公开（公告）日：2004-08-12

  The present invention provides antitumor compounds of the formula (I), and antitumor methods. 1

  本发明提供了式(I)的抗肿瘤化合物和抗肿瘤方法。
• Palladium-Mediated Site-Selective C–H Radio-iodination
  作者：Emmanuelle Dubost、Victor Babin、Florian Benoist、Alexandra Hébert、Pierre Barbey、Céline Chollet、Jean-Philippe Bouillon、Alain Manrique、Grégory Pieters、Frédéric Fabis、Thomas Cailly

  DOI：10.1021/acs.orglett.8b02819

  日期：2018.10.5

  The palladium-mediated C-H radio-iodination of arenes using sodium iodide as the primary isotopic source is reported and performed without chemical know-how in 30 min and applied to the synthesis of complex radio-iodinated compounds of biological interest.
• DE2744137
  申请人：——

  公开号：——

  公开（公告）日：——