3,5-diamino-4-chlorobenzamide | 67451-38-1

• 物质功能分类: 有机原料 - 氨基化合物
• 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-chlorobenzamide
• 英文别名: 4-Chloro-3,5-diaminobenzamide
• CAS: 67451-38-1
• 化学式: C₇H₈ClN₃O
• 分子量: 185.613
• InChiKey: ZKBYBYGNWFJHGD-UHFFFAOYSA-N

物化性质

• 沸点：
  325.9±42.0 °C(predicted)
• 密度：
  1.489±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  95.1
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,5-diamino-4-chlorobenzamide 在 sodium hydroxide 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-[5-Carbamoyl-2-chloro-3-(oxaloamino)anilino]-2-oxoacetic 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：

  4-氯-3,5-二硝基苯甲酰胺 在 盐酸 、 tin(ll) chloride 作用下， 生成 3,5-diamino-4-chlorobenzamide
  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

• Novel antiallergic and antiinflammatory agents. Part II: Synthesis and pharmacology of TYB-2285 and its related compounds
  作者：Masakazu Ban、Hiroaki Taguchi、Takeo Katsushima、Mitsuru Takahashi、Kiyotaka Shinoda、Akihiko Watanabe、Takanari Tominaga

  DOI：10.1016/s0968-0896(98)00066-2

  日期：1998.7

  chloride derivatives in pyridine. Hydrolysis of acetyl compounds gave hydroxy derivatives, from which other acyl derivatives could be synthesized. These compounds were tested in the rat PCA (passive cutaneous anaphylaxis) assay by oral administration. Benzonitrile derivatives (4c, 5c, 6c, 4h, 5h) exhibited notable inhibition in this assay. Compounds 5c and 6c also showed remarkable inhibition of eosinophil

  通过在吡啶中用乙醇酰氯衍生物处理相应的间二氨基苯衍生物，合成了一系列间二（糖基氨基）苯衍生物。乙酰基化合物的水解产生羟基衍生物，从中可以合成其他酰基衍生物。这些化合物在口服PCA（被动性皮肤过敏反应）试验中进行了测试。苯甲腈衍生物（4c，5c，6c，4h，5h）在该试验中表现出显着的抑制作用。化合物5c和6c在10（-8）-10（-5）M的范围内也显示出嗜酸性粒细胞对TNF-（肿瘤坏死因子）α处理的HUVEC（人脐静脉内皮细胞）粘附的显着抑制。化合物5c是目前正在日本进行TYB-2285（图1）研究，用于II期临床研究中的哮喘和特应性皮炎。
• Amide compounds
  申请人：Toyo Boseki Kabushiki Kaisha

  公开号：US04912135A1

  公开（公告）日：1990-03-27

  Novel amide compounds of the formula: ##STR1## wherein R.sup.1 is hydrogen, lower alkyl, acetyl, or propionyl; R.sup.2 is hydrogen or chlorine; R.sup.3 is hydrogen or a group of the formula: --CO.sub.2 R.sup.6 (wherein R.sup.6 is hydrogen, lower alkyl or alkali metal); R.sup.4 is hydrogen, trifluoromethyl, cyano, aminocarbonyl, or a group of the formula: --CO.sub.2 R.sup.7 (wherein R.sup.7 is hydrogen, lower alkyl, or alkali metal); R.sup.5 is hydrogen, or a group of the formula: --CO.sub.2 R.sup.8 (wherein R.sup.8 is hydrogen, lower alkyl, or alkali metal), which have excellent anti-allergic activity and are useful for the prophylaxis and treatment of various allergic diseases, and a pharmaceutical composition containing the amide compound as set forth above as an active ingredient.

  化合物的通式为：##STR1## 其中，R.sup.1为氢、较低的烷基、乙酰基或丙酰基；R.sup.2为氢或氯；R.sup.3为氢或公式为--CO.sub.2R.sup.6（其中，R.sup.6为氢、较低的烷基或碱金属）的基团；R.sup.4为氢、三氟甲基、氰基、氨基甲酰基或公式为--CO.sub.2R.sup.7（其中，R.sup.7为氢、较低的烷基或碱金属）的基团；R.sup.5为氢或公式为--CO.sub.2R.sup.8（其中，R.sup.8为氢、较低的烷基或碱金属）的基团。该化合物具有卓越的抗过敏活性，可用于预防和治疗各种过敏性疾病，并且一种含有上述酰胺化合物作为活性成分的药物组合物。
• Novel amide compounds
  申请人：Toyo Boseki Kabushiki Kaisha

  公开号：EP0315112B1

  公开（公告）日：1993-03-17
• US4912135A
  申请人：——

  公开号：US4912135A

  公开（公告）日：1990-03-27
• 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.