6-<4-(1H-imidazole-1-yl)phenyl>-3(2H)-pyridazinone | 84243-59-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 6-<4-(1H-imidazole-1-yl)phenyl>-3(2H)-pyridazinone
• 英文别名: 6-<4-(1H-imidazol-1-yl)phenyl>-3(2H)-pyridazinone；6-[4-(1H-imidazol-1-yl)phenyl]-3(2H)-pyridazinone；6-(4-(1H-Imidazol-1-yl)phenyl)pyridazin-3-ol；3-(4-imidazol-1-ylphenyl)-1H-pyridazin-6-one
• CAS: 84243-59-4
• 化学式: C₁₃H₁₀N₄O
• 分子量: 238.249
• InChiKey: NCNPWWDCUPUDBU-UHFFFAOYSA-N

物化性质

• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-<4-(1H-imidazole-1-yl)phenyl>-3(2H)-pyridazinone 在 一水合肼 作用下， 反应 19.0h， 以78%的产率得到4-amino-6-<4-(1H-imidazol-1-yl)phenyl>-3(2H)pyridazinone
  参考文献：
  名称：

  哒嗪酮与亲核试剂的反应。与氰化物发生异常反应

  摘要：

  报道了吡啶酮强心药的哒嗪酮类似物的合成研究。合成方案涉及哒嗪酮和氯哒嗪酮与亲核试剂的反应。以氰化物为亲核试剂进行了两次加成反应，从而提供了一种新型的双氰基吡啶并嗪酮。

  DOI：

  10.1002/jhet.5570230551
• 作为产物：
  描述：

  伊马咪啶 在 溴 、 溶剂黄146 作用下， 反应 3.5h， 以75%的产率得到6-<4-(1H-imidazole-1-yl)phenyl>-3(2H)-pyridazinone
  参考文献：
  名称：

  强心剂。2. 4,5-二氢-6- [4-（1H-咪唑-1-基）苯基] -3（2H）-哒嗪酮的合成及其构效关系：一类新型的正性变力剂。

  摘要：

  合成了一系列的4,5-二氢-6- [4-（1H-咪唑-1-基）苯基] -3（2H）-哒嗪酮和相关化合物，并评价其正性肌力活性。该系列的大多数成员产生剂量相关的心肌收缩力增加，这与心率相对较小的升高和全身动脉血压的降低有关。在1的5位上引入甲基取代基（CI-914）产生了该系列中最有效的化合物（11，CI-930）。化合物1比氨力农更有效，而化合物11比米力农更有效。1和11的正性肌力作用不是通过刺激β-肾上腺素受体介导的。心脏磷酸二酯酶组分III的选择性抑制代表1和11的正性肌力作用的主要成分。

  DOI：

  10.1021/jm00148a006

文献信息

• One-Pot Preparation of 6-Substituted 3(2<i>H</i>)-Pyridazinones from Ketones
  作者：W. J. Coates、A. Mckillop

  DOI：10.1055/s-1993-25861

  日期：——

  A one-pot process for the preparation of 6-phenyl-3(2H)-pyridazinone from acetophenone and glyoxylic acid has been investigated and shown to have wide utility in the preparation of 6- and 5,6-substituted 3(2H)-pyridazinones. Limitations to the process encountered with 2′-hydroxyacetophenone and with basic heteroaromatic ketones have been overcome, and the processes described offer the rapid and efficient synthesis of many 6-substituted pyridazinones from readily available ketones.

  一种利用乙酰苯和乙醛酸制备6-苯基-3(2H)-吡哒嗪酮的一锅法工艺已被研究，并证明在制备6-和5,6-取代的3(2H)-吡哒嗪酮方面具有广泛应用。该工艺解决了遇到2′-羟基乙酰苯和基本杂芳香酮时的局限性问题，并提供了一种快速高效合成多种6-取代吡哒嗪酮的方法，原料为易得的酮类。
• Substituted
  申请人：Warner-Lambert Company

  公开号：US04353905A1

  公开（公告）日：1982-10-12

  Substituted 4,5-dihydro-6-[4-(1H-imidazol-1-yl)-phenyl]-3(2H)-pyridazinone compounds and 6-[4-(1H-imidazol-1-yl)phenyl]-3(2H)-pyridazinone compounds and pharmaceutically acceptable salts thereof are useful as cardiotonic agents. Said compounds cause a significant increase in myocardial contractility in the anesthetized dog. Said compounds are produced by reacting substituted .gamma.-oxo-benzenebutanoic acids with suitably substituted hydrazines to provide 4,5-dihydro-6-[4-(1H-imidazol-1-yl)phenyl]-3(2H)-pyridazinones which are dehydrogenated to 6-[4-(1H-imidazol-1-yl)phenyl]-3(2H)-pyridazinones. Both the intermediate 4,5-dihydro-6-[4-(1H-imidazol-1-yl)phenyl]-3(2H)-pyridazinones and the 6-[4-(1H-imidazol-1-yl)phenyl]-3(2H)-pyridazinones are useful as cardiotonic agents.

  4,5-二氢-6-[4-(1H-咪唑-1-基)-苯基]-3(2H)-吡啶啉化合物和6-[4-(1H-咪唑-1-基)苯基]-3(2H)-吡啶啉化合物及其药用盐可用作心力衰竭药物。这些化合物可在麻醉狗体内显著增加心肌收缩力。这些化合物是通过将取代的γ-氧代苯丁酸与适当取代的肼反应而制备的，从而得到4,5-二氢-6-[4-(1H-咪唑-1-基)苯基]-3(2H)-吡啶啉，然后将其脱氢为6-[4-(1H-咪唑-1-基)苯基]-3(2H)-吡啶啉。中间体4,5-二氢-6-[4-(1H-咪唑-1-基)苯基]-3(2H)-吡啶啉和6-[4-(1H-咪唑-1-基)苯基]-3(2H)-吡啶啉均可用作心力衰竭药物。
• Synthesis of new 1,2,4-triazolo[4,3-<i>b</i>]pyridazines and related compounds
  作者：Ila Sircar

  DOI：10.1002/jhet.5570220424

  日期：1985.7

  The synthesis of novel 6-[4-(1H-imidazol-1-yl)phenyl]-1,2,4-triazolo[4,3-b]pyridazines 8a-f and related compounds is described. Although the intermediate hydrazine derivatives 7 and 9 possess good positive inotropic activity, the fused bicyclic pyridazines 8a-f are significantly less potent than the 3(2H)-pyridazinone 5. Compounds 8a-f are potent but nonselective inhibitors of cardiac phosphodiesterase

  描述了新型6- [4-（4-（1H-咪唑-1-基）苯基] -1，2，4-三唑并[4，3- b ]哒嗪8a-f和相关化合物的合成。尽管中间体肼衍生物7和9具有良好的正性肌力活性，但是稠合的双环哒嗪8a-f的效力明显低于3（2 H）-哒嗪酮5。化合物8a-f是有效的但非选择性的心脏磷酸二酯酶抑制剂。
• Substituted 4,5-dihydro-6-(substituted)-phenyl-3(2H)-pyridazinones and 6-(substituted)phenyl-3(2H)-pyridazinones
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0075436A1

  公开（公告）日：1983-03-30

  Substituted 4,5-dihydro-6-(substituted)-phenyl-3(2H)-pyridazinone compounds and 6-(substituted)phenyl-3(2H)-pyridazinone compounds and pharmaceutically acceptable salts thereof are useful as cardiotonic and antihypertensive agents. Said compounds cause a significant increase in myocardial contractility in the dog. Said compounds also cause a decrease in blood pressure in the spontaneously hypertensive rat. Said compounds are produced by reacting substituted y-oxobenzene-butanoic acids with suitably substituted hydrazines to provide 4,5-dihydro-6-(substituted)phenyl-3(2H)-pyridazinones which are dehydrogenated to 6-(substituted)phenyl-3(2H)-pyridazinones. Both the 4,5-dihydro-6-(substituted)-phenyl-3(2H)-pyridazinones and the 6-(substituted)-phenyl-3(2H)-pyridazinones are useful as cardiotonic and antihypertensive agents. The compounds have the formula: where represents a double or single bond and A is anyone of five types of heterocyclic ring-containing radicals, and R2, R3 and Y are hydrogen or various substituents.

  取代的 4,5-二氢-6-(取代)苯基-3(2H)-哒嗪酮化合物和 6-(取代)苯基-3(2H)-哒嗪酮化合物及其药学上可接受的盐类可用作强心剂和降压药。 上述化合物可显著增强狗的心肌收缩力。所述化合物还能降低自发性高血压大鼠的血压。所述化合物是通过取代的 y-氧代苯丁酸与适当取代的肼反应生成 4,5-二氢-6-（取代）苯基-3(2H)-哒嗪酮，后者脱氢生成 6-（取代）苯基-3(2H)-哒嗪酮。 4,5-二氢-6-（取代）苯基-3(2H)-哒嗪酮和 6-（取代）苯基-3(2H)-哒嗪酮均可用作强心剂和降压药。这些化合物的化学式如下 其中代表双键或单键，A 是五种含杂环基中的任何一种，R2、R3 和 Y 是氢或各种取代基。
• Substituted 3-mercaptopyridazines, their 3-alkylthio derivatives and processes for their preparation
  申请人：A. Nattermann & Cie. GmbH

  公开号：EP0122419A2

  公开（公告）日：1984-10-24

  The invention relates to new substituted 3-mercaptopyridazines andtheir3-alkylthio derivatives of the formula 1 and processes for their preparation.

  本发明涉及新的取代的 3-巯基哒嗪及其式 1 的 3-烷硫基衍生物，以及它们的制备工艺。 及其制备工艺。