diethyl N,N'-(5-cyano-m-phenylene)dioxamate | 53882-11-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: diethyl N,N'-(5-cyano-m-phenylene)dioxamate
• 英文别名: ethyl 2-[3-cyano-5-[(2-ethoxy-2-oxoacetyl)amino]anilino]-2-oxoacetate
• CAS: 53882-11-4
• 化学式: C₁₅H₁₅N₃O₆
• 分子量: 333.301
• InChiKey: XLLVGCSYPFWYFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.56
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  134.59
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  diethyl N,N'-(5-cyano-m-phenylene)dioxamate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 以77 %的产率得到N,n'-(5-cyano-m-phenylene)dioxamic acid
  参考文献：
  名称：

  Discovery of a novel GPR35 agonist with high and equipotent species potency for oral treatment of IBD

  摘要：

  DOI：

  10.1016/j.bmc.2023.117511
• 作为产物：
  描述：

  3,5-二硝基苯甲腈 在 盐酸 、 三乙胺 、 tin(ll) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 diethyl N,N'-(5-cyano-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

• Cyano phenylene dioxamic molecules
  申请人：The Upjohn Company

  公开号：US03993679A1

  公开（公告）日：1976-11-23

  Compounds represented below ##SPC1## And pharmaceutical compositions thereof, the compositions including the non-substituted phenylene dioxamates are useful in the prophylactic treatment of sensitized mammals for allergy and all anaphylactic reactions of a reagin or non-reagin mediated nature.

  下面代表的化合物##SPC1##及其制药组合物，其中包括非取代苯二酰氧胺，在对过敏反应和变态反应进行预防性治疗的敏感哺乳动物中是有用的，无论是由抗原或非抗原介导的自然。
• Dioxamic acids and salts
  申请人：The Upjohn Company

  公开号：US04159278A1

  公开（公告）日：1979-06-26

  Compounds represented below ##STR1## and pharmaceutical compositions thereof, the compositions including the non-substituted phenylene dioxamates are useful in the prophylactic treatment of sensitized mammals for allergy and all anaphylactic reactions of a reagin or non-reagin mediated nature.

  下面所代表的化合物##STR1##及其药物组成物，其中包括非取代苯二酰肟，可用于对致敏哺乳动物的预防性治疗，用于对抗抗原或非抗原介导的过敏反应。
• N-Hetero substituted dioxamic acid compounds
  申请人：The Upjohn Company

  公开号：US04186127A1

  公开（公告）日：1980-01-29

  Compounds represented below ##STR1## and pharmaceutical compositions thereof, the compositions including the non-substituted phenylene dioxamates are useful in the prophylactic treatment of sensitized mammals for allergy and all anaphylactic reactions of a reagin or non-reagin mediated nature.

  下面所代表的化合物##STR1##及其制药组合物，其中包括非取代的苯二酰胺，可用于预防治疗对变态反应或非变态反应介导的过敏反应敏感的哺乳动物。
• Phenylene dioxamate esters
  申请人：The Upjohn Company

  公开号：US04281151A1

  公开（公告）日：1981-07-28

  Compounds represented below ##STR1## and pharmaceutical compositions thereof, the compositions including the non-substituted phenylene dioxamates are useful in the prophylactic treatment of sensitized mammals for allergy and all anaphylactic reactions of a reagin or non-reagin mediated nature.

  下面所代表的化合物 ##STR1## 及其制药组合物，其中包括非取代的苯基二氧甲酸酯，可用于对敏感哺乳动物进行预防性治疗，以治疗由免疫球蛋白E介导或非介导的过敏和全身性过敏反应。
• Substituted dioxamic acid esters
  申请人：The Upjohn Company

  公开号：US04095028A1

  公开（公告）日：1978-06-13

  Compounds represented below ##STR1## and pharmaceutical compositions thereof, the compositions including the non-substituted phenylene dioxamates are useful in the prophylactic treatment of sensitized mammals for allergy and all anaphylactic reactions of a reagin or non-reagin mediated nature.

  以下化合物##STR1##及其制药组合物，其中包括非取代苯基二氧甲酸酯，可用于对过敏和变态反应的预防性治疗，这些变态反应具有变态反应素或非变态反应素介导的性质。