2-Amino-5-chloro-N-[3-(1H-imidazol-1-yl)propyl]benzamide | 90259-73-7

• 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-Amino-5-chloro-N-[3-(1H-imidazol-1-yl)propyl]benzamide
• 英文别名: 2-amino-5-chloro-N-(3-imidazol-1-ylpropyl)benzamide
• CAS: 90259-73-7
• 化学式: C₁₃H₁₅ClN₄O
• 分子量: 278.741
• InChiKey: AKSHYZIVQLGDII-UHFFFAOYSA-N

物化性质

• 熔点：
  155-157 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  535.1±50.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  72.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Amino-5-chloro-N-[3-(1H-imidazol-1-yl)propyl]benzamide 在 氢氧化钾 、 乙醇 作用下， 反应 5.0h， 生成 6-chloro-3-(3-imidazol-1-ylpropyl)-1H-quinazoline-2,4-dione
  参考文献：
  名称：

  Thromboxane synthetase inhibitors and antihypertensive agents. 4. N-[(1H-imidazol-1-yl)alkyl] derivatives of quinazoline-2,4(1H,3H)-diones, quinazolin-4(3H)-ones, and 1,2,3-benzotriazin-4(3H)-ones

  摘要：

  The quinazolinedione, quinazolinone, and 1,2,3-benzotriazinone title compounds were prepared as analogues of N-[(1H-imidazol-1-yl)alkyl]-1H-isoindole-1,3(2H)-diones which were the subject of a previous report from our laboratories. These compounds were evaluated as thromboxane (TX) synthetase inhibitors and as antihypertensive agents. While each series of compounds had activity both as TX synthetase inhibitors and as antihypertensives, the best compounds were N-[(1H-imidazol-1-yl)alkyl]quinazoline-2,4(1H,3H]-diones (V). In general these compounds were all selective enzyme inhibitors at least equipotent with the standard dazoxiben. These compounds were also very active antihypertensive agents as determined in SHR. The SAR is discussed for both types of activity. Compound 20a was further evaluated for TX formation inhibiting properties in several other platelet types both in vitro and ex vivo and is between 100 and 1000 times more potent than dazoxiben.

  DOI：

  10.1021/jm00395a016
• 作为产物：
  描述：

  N-(2-氰基乙基)咪唑 在 镍 ammonium hydroxide 、 氢气 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 2-Amino-5-chloro-N-[3-(1H-imidazol-1-yl)propyl]benzamide
  参考文献：
  名称：

  血栓烷合成酶抑制剂和降压药。1. N-[（（1H-咪唑-1-基）烷基]芳基酰胺和N-[（1H-1,2,4-三唑-1-基）烷基]芳基酰胺。

  摘要：

  制备标题化合物以研究其作为血栓烷合成酶抑制剂以及降压药的潜力。制备咪唑VIII和三唑X以检查芳族取代，链长和杂环取代对生物活性的影响。咪唑VIII和三唑X是不抑制前列环素形成的血栓烷合成酶抑制剂。制备的最有趣的血栓烷合成酶抑制剂是（1H-咪唑-1-基）烷基胺的4-氯-，4-（三氟甲基）-和4-溴苯甲酰胺衍生物，其C5-C8烷基链将杂环与酰胺部分分开，而最具活性的降压药是带有C3烷基链的3-或4-氯-，-溴或-（三氟甲基）苯甲酰胺。

  DOI：

  10.1021/jm00154a017

文献信息

• 3-heteroalkyl-2,4.quinzaoline-diones
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0293500A1

  公开（公告）日：1988-12-07

  A compound is described which is selected from the group consisting of those of the formula: wherein A is a divalent moiety of the formula: or and n is an integer from 2-10, inclusive; R is hydrogen, oxygen or alkyl having from one to four carbon atoms; Z is C or N; and when Z is N, --- is ――― and there is no R substituent, when Z is C and R is oxygen, --- is ―――; and when Z is C and R is alkyl, --- is ――― ; R6 is hydrogen or alkyl having from one to four carbon atoms; R1 and R2 may be the same or different and may be selected from the group consisting of hydrogen, halogen, trifluoromethyl, alkoxy having from one to four carbon atoms, alkyl having from one to four carbon atoms, nitro and amino; wherein Heteroaryl is wherein R3 and R4 may be selected from hydrogen, alkyl having from one to four carbon atoms, or phenyl; and X is CH or N, together with the pharmaceutically acceptable salts thereof as well as a process for producing the same and its use for pharmaceutical processes.

  描述了一种化合物，所选自以下组合中的一种，其化学式为：其中A是化学式的二价基团：或者n为2-10之间的整数；R为氢、氧或具有1-4个碳原子的烷基；Z为C或N；当Z为N时，---为―――且没有R取代基，当Z为C且R为氧时，---为―――；当Z为C且R为烷基时，---为―――；R6为氢或具有1-4个碳原子的烷基；R1和R2可以相同也可以不同，可选自氢、卤素、三氟甲基、具有1-4个碳原子的烷氧基、具有1-4个碳原子的烷基、硝基和氨基；其中Heteroaryl为其中R3和R4可以选择自氢、具有1-4个碳原子的烷基或苯基；X为CH或N，以及其药学上可接受的盐，以及用于生产该化合物的过程及其在制药过程中的应用。
• 3-heteroarylalkyl-4-quinazolinones
  申请人：American Cyanamid Company

  公开号：US04710502A1

  公开（公告）日：1987-12-01

  Novel 3-heteroarylalkyl-4-quinazolinones which are useful as inhibitors of thromboxane synthetase and/or as antihypertensive agents in the treatment of hypertension and myocardial ischemia.

  新型3-杂环芳基烷基-4-喹唑啉酮，可用作血栓素合酶抑制剂和/或抗高血压药物，用于治疗高血压和心肌缺血。
• 3-imidazolylalkyl-, triazolylalkyl-,
  申请人：American Cyanamid Company

  公开号：US04680293A1

  公开（公告）日：1987-07-14

  Novel 3-heteroarylalkyl-1,2,3-benzotriazin-4(3H)-ones, having the structural formula: ##STR1## wherein A is a divalent moiety of the formula: ##STR2## wherein n is an integer from 3 to 10, inclusive; R.sub.1 and R.sub.2 may be the same or different and may be selected from the group consisting of hydrogen, halogen, trifluoromethyl, alkoxy having from one to four carbon atoms, alkyl having from one to four carbon atoms, nitro and amino; wherein Heteroaryl is ##STR3## wherein R.sub.3 and R.sub.4 may be hydrogen, alkyl having from one to four carbon atoms or phenyl and X is CH or N; together with the pharmaceutically acceptable salts thereof; processes for their preparation and their use in treating prostaglandin-related vascular disorders including ischemic heart disease, transient ischemic attack, thrombosis, migraine and hypertension.

  3-杂环芳基烷基-1,2,3-苯并三唑啉-4(3H)-酮的结构式为：##STR1##其中A是结构式的二价基团：##STR2##其中n是3到10的整数；R.sub.1和R.sub.2可以相同也可以不同，可以选择自氢、卤素、三氟甲基、含有一至四个碳原子的烷氧基、含有一至四个碳原子的烷基、硝基和氨基的基团；其中Heteroaryl是##STR3##其中R.sub.3和R.sub.4可以是氢、含有一至四个碳原子的烷基或苯基，X是CH或N；以及其药用盐；其制备方法及其在治疗前列腺素相关的血管疾病中的用途，包括缺血性心脏病、短暂性缺血性发作、血栓形成、偏头痛和高血压。
• Pharmaceutical methods of using 3-heteroarylalkyl-4-quinazolinones
  申请人：American Cyanamid Company

  公开号：US04753944A1

  公开（公告）日：1988-06-28

  Novel 3-heteroarylalkyl-4-quinazolinones which are useful as inhibitors of thromboxane synthetase and/or as antihypertensive agents in the treatment of hypertension and myocardial ischemia.

  这是一种新型的3-杂环芳基烷基-4-喹唑啉酮，可用作抑制血栓素合成酶和/或治疗高血压和心肌缺血的降压药物。
• Hypoglycaemic and hypolipidaemic benzamide substituted (1H-) imidazole
  申请人：May & Baker Limited

  公开号：US04507315A1

  公开（公告）日：1985-03-26

  Benzamide derivatives of the general formula: ##STR1## wherein A represents a divalent straight- or branched-chain alkylene group containing from 1 to 6 carbon atoms and R.sup.1 represents a halogen atom or a hydroxy, mercapto, amino, nitro, cyano, carboxy or carbamoyl group or an alkyl, fluorine-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkoxycarbonyl, alkylamino, dialkylamino, alkylcarbamoyl, dialkylcarbamoyl, alkanoyl, alkanoyloxy or alkanoylamino group and m represents zero or the integer 1, 2 or 3, R.sup.2 represents a hydrogen atom or an alkyl group, R.sup.3 represents a halogen atom or a hydroxy, amino, nitro, cyano, carboxy or carbamoyl group or an alkyl, fluorine-substituted alkyl, alkoxy, alkoxycarbonyl, dialkylamino, alkylcarbamoyl or alkanoylamino group and n represents zero or the integer 1 or 2, R.sup.4 represents and alkyl radical and p represents zero or the integer 1 or 2, or a pharmaceutically acceptable salt thereof, possess useful pharmacological properties.

  一般式为：##STR1## 的苯甲酰胺衍生物，其中A代表含有1至6个碳原子的直链或支链烷基，R.sup.1代表卤素原子或羟基、巯基、氨基、硝基、氰基、羧基或氨基甲酰基或烷基、氟代烷基、烷氧基、烷硫基、烷基磺酰基、烷氧羰基、烷基氨基、二烷基氨基、烷基甲酰胺基、二烷基甲酰胺基、烷酰基、烷酰氧基或烷酰氨基基团，m代表零或整数1、2或3，R.sup.2代表氢原子或烷基，R.sup.3代表卤素原子或羟基、氨基、硝基、氰基、羧基或氨基甲酰基或烷基、氟代烷基、烷氧基、烷氧羰基、二烷基氨基、烷基甲酰胺基或烷酰氨基基团，n代表零或整数1或2，R.sup.4代表烷基基团，p代表零或整数1或2，或其药学上可接受的盐具有有用的药理学性质。