Diethyl N,N'-(2-chloro-5-phenyl-m-phenylene)dioxamate | 58495-19-5

• 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: Diethyl N,N'-(2-chloro-5-phenyl-m-phenylene)dioxamate
• 英文别名: Ethyl 2-[2-chloro-3-[(2-ethoxy-2-oxoacetyl)amino]-5-phenylanilino]-2-oxoacetate
• CAS: 58495-19-5
• 化学式: C₂₀H₁₉ClN₂O₆
• 分子量: 418.834
• InChiKey: MDDCGNNWRJQKLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Diethyl N,N'-(2-chloro-5-phenyl-m-phenylene)dioxamate 在 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 生成 N,n'-(2-chloro-5-phenyl-m-phenylene)dioxamic acid
  参考文献：
  名称：

  N,N'-(phenylene)dioxamic acids and their esters as antiallergy agents

  摘要：

  A series of dialkyl N,N'-(m-phenylene)dioxamates was synthesized by treatment of the requisite m-phenylenediamines with an alkyloxalyl chloride in the presence of triethylamine. Hydrolysis with sodium hydroxide solution gave the corresponding N,N'-(m-phenylene)dioxamic acids. Several N,N'-(p-phenylene)dioxamic acids were synthesized also in the same manner starting with the requisite p-phenylenediamines. These compounds were tested in the rat passive cutaneous anaphylaxis (PCA) assay. When tested iv, activity was found in the N,N'-(m-phenylene) dioxamic acids up to 2500 times that shown by disodium cromoglycate [50% inhibition at 0.001 mg/kg for N,N'-(2-chloro-5-cyano-m-phenylene)dioxamic acid (compound 61)]. Oral activity was seen in this series of compounds with duration of activity up to 120 min. Oral activity was detected in diethyl N,N'-(2-chloro-5-cyano-m-phenylene)dioxamate (compound 38) at levels of drug as low as 0.1 mg/kg.

  DOI：

  10.1021/jm00207a016
• 作为产物：
  描述：

  2-氯-1,3-二硝基-5-苯基苯 在 镍 氢气 、 三乙胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 生成 Diethyl N,N'-(2-chloro-5-phenyl-m-phenylene)dioxamate
  参考文献：
  名称：

  N,N'-(phenylene)dioxamic acids and their esters as antiallergy agents

  摘要：

  A series of dialkyl N,N'-(m-phenylene)dioxamates was synthesized by treatment of the requisite m-phenylenediamines with an alkyloxalyl chloride in the presence of triethylamine. Hydrolysis with sodium hydroxide solution gave the corresponding N,N'-(m-phenylene)dioxamic acids. Several N,N'-(p-phenylene)dioxamic acids were synthesized also in the same manner starting with the requisite p-phenylenediamines. These compounds were tested in the rat passive cutaneous anaphylaxis (PCA) assay. When tested iv, activity was found in the N,N'-(m-phenylene) dioxamic acids up to 2500 times that shown by disodium cromoglycate [50% inhibition at 0.001 mg/kg for N,N'-(2-chloro-5-cyano-m-phenylene)dioxamic acid (compound 61)]. Oral activity was seen in this series of compounds with duration of activity up to 120 min. Oral activity was detected in diethyl N,N'-(2-chloro-5-cyano-m-phenylene)dioxamate (compound 38) at levels of drug as low as 0.1 mg/kg.

  DOI：

  10.1021/jm00207a016

文献信息

• N,N'(Cyano-phenylene)dioxamic acids and esters
  申请人：The Upjohn Company

  公开号：US03972911A1

  公开（公告）日：1976-08-03

  It has now been discovered that novel compounds of FIG. 1 ##SPC1## are useful in the prophylactic treatment of sensitized humans and animals for allergy and all anaphylactic reactions of a reagin or non-reagin mediated nature. Additionally, these compounds are intermediates to the acids and physiologically acceptable salts which also have the same biological utility. The compounds of the invention are formulated with pharmaceutical carriers for oral, parenteral, inhalation or rectal means of administration.

  现已发现，FIG.1的新化合物##SPC1##可用于预防治疗对变态反应原或非变态反应原介导的过敏和全身过敏反应的敏感人类和动物。此外，这些化合物是酸和生理上可接受的盐的中间体，这些酸和盐也具有相同的生物效用。本发明的化合物与制药载体配制，用于口服、注射、吸入或直肠给药方式。
• US3972911A
  申请人：——

  公开号：US3972911A

  公开（公告）日：1976-08-03
• US4044148A
  申请人：——

  公开号：US4044148A

  公开（公告）日：1977-08-23
• N,N'-(phenylene)dioxamic acids and their esters as antiallergy agents
  作者：John B. Wright、Charles M. Hall、Herbert G. Johnson

  DOI：10.1021/jm00207a016

  日期：1978.9

  A series of dialkyl N,N'-(m-phenylene)dioxamates was synthesized by treatment of the requisite m-phenylenediamines with an alkyloxalyl chloride in the presence of triethylamine. Hydrolysis with sodium hydroxide solution gave the corresponding N,N'-(m-phenylene)dioxamic acids. Several N,N'-(p-phenylene)dioxamic acids were synthesized also in the same manner starting with the requisite p-phenylenediamines. These compounds were tested in the rat passive cutaneous anaphylaxis (PCA) assay. When tested iv, activity was found in the N,N'-(m-phenylene) dioxamic acids up to 2500 times that shown by disodium cromoglycate [50% inhibition at 0.001 mg/kg for N,N'-(2-chloro-5-cyano-m-phenylene)dioxamic acid (compound 61)]. Oral activity was seen in this series of compounds with duration of activity up to 120 min. Oral activity was detected in diethyl N,N'-(2-chloro-5-cyano-m-phenylene)dioxamate (compound 38) at levels of drug as low as 0.1 mg/kg.