N-[4-(1H-imidazol-5-yl)phenyl]-N'-methylmethanimidamide | 83184-12-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-[4-(1H-imidazol-5-yl)phenyl]-N'-methylmethanimidamide
• CAS: 83184-12-7
• 化学式: C₁₁H₁₂N₄
• 分子量: 200.243
• InChiKey: ATPATFRGZLKLMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  53.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-(1H-咪唑-4-基)苯胺盐酸盐 以 乙醇 、 水 为溶剂， 生成 N-[4-(1H-imidazol-5-yl)phenyl]-N'-methylmethanimidamide
  参考文献：
  名称：

  (Imidazolylphenyl)formamidines. A structurally novel class of potent histamine H2 receptor antagonists

  摘要：

  Structure-activity considerations of N alpha-guanylhistamine, the first compound found with detectable H2-antagonist activity, led to the synthesis of a series of conformationally rigid guanylhistamine analogues, namely, (imidazolylphenyl)guanidines, imidazolylbenzamidines, and (imidazolylphenyl)formamidines. It was found that in the guanidine and benzamidine classes, the meta-substituted derivatives (3, 4, 7, and 8) possessed H2-antagonist activity, whereas in the class of formamidines, only the para-substituted derivative 10 was found active. A subsequent increase in the size of the substituent at the formamidino group of 10 led to compounds (15-20) of high H2-antagonist affinity, which was related to the gastric antisecretory effect. Members of this structurally novel class of H2 antagonists were 20- to 50-fold more potent than cimetidine both "in vitro" and "in vivo". Structure-activity relationships are discussed in terms of ionization properties, partitioning behavior, conformational aspects of the selected compound 17, and of possible modes of interaction with the histamine H2 receptor. It was found that the formamidine moiety was an important structural feature and that H2-antagonist activity requires correct steric and electronic properties. Compound 17 (DA 4577), owing to its pharmacological profile and demonstrated safety in animals, was selected to be clinically investigated.

  DOI：

  10.1021/jm00369a025
• 作为试剂：
  描述：

  N-cyano-N'-[4-(imidazol-4-yl)-phenyl]-formamidine 、 甲胺 在 N-[4-(1H-imidazol-5-yl)phenyl]-N'-methylmethanimidamide 、 水 作用下， 以 水 为溶剂， 以to yield 13.45 gm of the desired product, which的产率得到N-[4-(1H-imidazol-5-yl)phenyl]-N'-methylmethanimidamide
  参考文献：
  名称：

  Imidazolylphenyl amidines, pharmaceutical compositions containing same

  摘要：

  本发明涉及咪唑基苯基脲，其制备方法以及含有它们的药物组成物。更具体地说，本发明涉及一般式为##STR1##中的化合物，其中R、R.sub.1、R.sub.3可以相同也可以不同，分别代表氢原子或较低的烷基基团，而R.sub.2则代表线性或支链烷基、烯基或炔基基团、氰基、羟基、取代或未取代的环烷基或环脂肪基烷基团、双环基团、取代或未取代的杂环烷基或杂环基团，其中还可以含有进一步的杂原子，或其无毒、药理学上可接受的酸加成盐。这些化合物在治疗胃肠道疾病方面是有用的。

  公开号：

  US04386099A1

文献信息

• Imidazolylphenyl amidines
  申请人：Instituto de Angeli S.p.A.

  公开号：US04465841A1

  公开（公告）日：1984-08-14

  This invention relates to imidazolylphenyl amidines, the preparation thereof, and pharmaceutical compositions containing them. More particularly, this invention relates to compounds of the general formula ##STR1## in which R, R.sub.1, and R.sub.3, which may be the same or different, each represent a hydrogen atom or a lower alkyl group, and R.sub.2 represents a linear or branched alkyl, alkenyl, or alkynyl group, a cyano group, a hydroxyl group, a substituted or unsubstituted cycloalkyl or cycloaliphatic alkyl group, a bicyclic group, an aralkyl or aryl group optionally substituted by halogen, methyl, methoxy, or methylenedioxy groups, or a substituted or unsubstituted heterocyclylalkyl or heterocyclic group which may also contain a further hetero atom, or a non-toxic, pharmacologically acceptable acid addition salt thereof. These compounds are useful in treating disorders of the gastrointestinal tract.

  本发明涉及咪唑苯基脲类化合物及其制备方法和含有它们的药物组合物。更具体地说，本发明涉及一般式为##STR1##其中，R、R.sub.1和R.sub.3可以相同也可以不同，分别代表氢原子或低碳基；R.sub.2代表线性或支链烷基、烯基或炔基、氰基、羟基、取代或未取代的环烷基或环烷基烷基、双环基、芳基或芳基烷基（可选取代卤素、甲基、甲氧基或亚甲二氧基基团）、取代或未取代的杂环基烷基或杂环基团（也可以含有另一个杂原子）或其非毒性、药理学上可接受的酸盐。这些化合物在治疗胃肠道疾病方面有用。
• New imidazolylphenyl amidines, processes for their preparation and their pharmaceutical use, and intermediates of preparation
  申请人：ISTITUTO DE ANGELI S.p.A.

  公开号：EP0053407B1

  公开（公告）日：1986-12-30
• US4386099A
  申请人：——

  公开号：US4386099A

  公开（公告）日：1983-05-31
• US4465841A
  申请人：——

  公开号：US4465841A

  公开（公告）日：1984-08-14
• (Imidazolylphenyl)formamidines. A structurally novel class of potent histamine H2 receptor antagonists
  作者：Arturo Donetti、Enzo Cereda、Elio Bellora、Alberto Gallazzi、Cesare Bazzano、Piercarlo Vanoni、Piero Del Soldato、Rosamaria Micheletti、Ferdinando Pagani、Antonio Giachetti

  DOI：10.1021/jm00369a025

  日期：1984.3

  Structure-activity considerations of N alpha-guanylhistamine, the first compound found with detectable H2-antagonist activity, led to the synthesis of a series of conformationally rigid guanylhistamine analogues, namely, (imidazolylphenyl)guanidines, imidazolylbenzamidines, and (imidazolylphenyl)formamidines. It was found that in the guanidine and benzamidine classes, the meta-substituted derivatives (3, 4, 7, and 8) possessed H2-antagonist activity, whereas in the class of formamidines, only the para-substituted derivative 10 was found active. A subsequent increase in the size of the substituent at the formamidino group of 10 led to compounds (15-20) of high H2-antagonist affinity, which was related to the gastric antisecretory effect. Members of this structurally novel class of H2 antagonists were 20- to 50-fold more potent than cimetidine both "in vitro" and "in vivo". Structure-activity relationships are discussed in terms of ionization properties, partitioning behavior, conformational aspects of the selected compound 17, and of possible modes of interaction with the histamine H2 receptor. It was found that the formamidine moiety was an important structural feature and that H2-antagonist activity requires correct steric and electronic properties. Compound 17 (DA 4577), owing to its pharmacological profile and demonstrated safety in animals, was selected to be clinically investigated.