3,5-diamino-4-chlorobiphenyl | 58495-18-4

• 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: 3,5-diamino-4-chlorobiphenyl
• 英文别名: 2-Chloro-5-phenyl-m-phenylenediamine；2-Chlor-5-phenyl-m-phenylendiamin；2-chloro-5-phenylbenzene-1,3-diamine
• CAS: 58495-18-4
• 化学式: C₁₂H₁₁ClN₂
• 分子量: 218.686
• InChiKey: OKICDJDUMRLDED-UHFFFAOYSA-N

物化性质

• 沸点：
  415.2±45.0 °C(Predicted)
• 密度：
  1.277±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5-diamino-4-chlorobiphenyl 在 甲醇 、 溴 、 sodium ethanolate 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 1.0h， 生成 2,6-bis-(diethylamino-acetylamino)-4-chloro-8-phenyl-benzo[1,2-d:5,4-d']bisthiazole
  参考文献：
  名称：

  双碱性取代的二氨基苯并双噻唑类作为潜在的抗关节炎药。

  摘要：

  筛选了一系列苯并双噻唑类在角叉菜胶足肿胀和辅助性关节炎试验中的抗炎活性。在预防性佐剂关节炎模型中，发现化合物26，2,6-双（N，N-二乙氨基）苯并[1,2-d：5,4-d']双噻唑可抑制未注射的爪肿胀。口服ED50为2.3 mg / kg。与该系列的大多数化合物一样，在急性炎症模型（如爪水肿）中，有26种没有活性。像类固醇一样，它在肉芽肿袋试验中显示出活性，但没有抑制环氧合酶，表明其作用方式不同于经典的非甾体类抗炎药（NSAID's）。在高于产生抗炎活性的剂量时，26具有一定的免疫调节特性。

  DOI：

  10.1021/jm00080a022
• 作为产物：
  描述：

  2-氯-1,3-二硝基-5-苯基苯 在 镍 氢气 作用下， 以 1,4-二氧六环 为溶剂， 生成 3,5-diamino-4-chlorobiphenyl
  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。
• Compounds, compositions and methods of use
  申请人：The Upjohn Company

  公开号：US04044148A1

  公开（公告）日：1977-08-23

  It has now been discovered that novel compounds of Formula 1 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, the compounds are formulated with pharmaceutical carriers for oral, parenteral, inhalation, or rectal means of administration.

  现在已经发现，公式1的新化合物在预防治疗敏感人和动物对过敏和所有抗原或非抗原介导的过敏反应中是有用的。此外，这些化合物与药物载体配制，可通过口服、注射、吸入或直肠途径进行给药。
• 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
• Bis basic substituted diaminobenzobisthiazoles as potential antiarthritic agents
  作者：Ernest Cullen、Reinhold Becker、Kurt Freter、Thelma LeClerq、Genus Possanza、Hin Chor Wong

  DOI：10.1021/jm00080a022

  日期：1992.1

  A series of benzobisthiazoles were screened for antiinflammatory activity in the carrageenan paw edema and adjuvant arthritis tests. Compound 26, 2,6-bis(N,N-diethylamino)benzo[1,2-d:5,4-d']bisthiazole, was found to inhibit the swelling of the uninjected paw in the prophylactic adjuvant arthritis model with an ED50 of 2.3 mg/kg orally. As with most compounds of this series, 26 was inactive in acute

  筛选了一系列苯并双噻唑类在角叉菜胶足肿胀和辅助性关节炎试验中的抗炎活性。在预防性佐剂关节炎模型中，发现化合物26，2,6-双（N，N-二乙氨基）苯并[1,2-d：5,4-d']双噻唑可抑制未注射的爪肿胀。口服ED50为2.3 mg / kg。与该系列的大多数化合物一样，在急性炎症模型（如爪水肿）中，有26种没有活性。像类固醇一样，它在肉芽肿袋试验中显示出活性，但没有抑制环氧合酶，表明其作用方式不同于经典的非甾体类抗炎药（NSAID's）。在高于产生抗炎活性的剂量时，26具有一定的免疫调节特性。