2-(hydroxymethyl)-6-phenyl-3(2H)-pyridazinone | 32949-37-4

• 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: 2-(hydroxymethyl)-6-phenyl-3(2H)-pyridazinone
• 英文别名: 2-hydroxymethyl-6-phenyl-2H-pyridazin-3-one；3(2H)-Pyridazinone, 2-(hydroxymethyl)-6-phenyl-；2-(hydroxymethyl)-6-phenylpyridazin-3-one
• CAS: 32949-37-4
• 化学式: C₁₁H₁₀N₂O₂
• 分子量: 202.213
• InChiKey: BVPMMHIYXMVPKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(hydroxymethyl)-6-phenyl-3(2H)-pyridazinone 在 氯化亚砜 、 乙醇 、 sodium 作用下， 以 氯仿 为溶剂， 反应 6.0h， 生成 2-<<(2-amonoethyl)thio>methyl>-6-phenyl-3(2H)-pyridazinone
  参考文献：
  名称：

  Pyridazinones. 3. Synthesis, antisecretory, and antiulcer activities of 2-cyanoguanidine derivatives

  摘要：

  3(2H)-Pyridazinone derivatives having a 2-cyanoguanidine moiety, as well as a sulfur or an oxygen atom in the alkylene side chain, were synthesized and evaluated for gastric antisecretory and antiulcer activities. The key intermediates, free amines having a thioether linkage, were synthesized by the reaction of 2-(omega-chloroalkyl) derivatives with cysteamine, while other intermediates having an ether linkage were synthesized from 2-(omega-chloroalkyl)oxymethyl derivatives. These free amines were converted via the 3-cyano-2-methyl-1-isothiourea derivatives into the desired 2-cyano-3-substituted-1-guanidine derivatives. All compounds synthesized were evaluated for gastric antisecretory activity in the pylorus-ligated rat by the method of Shay, and selected compounds were evaluated in the stress-induced ulcer test in rat. Structure-activity relationships are discussed. The molecular features for the best activities are a phenyl group in the C-6 position of the 3(2H)-pyridazinone ring, a four-atom chain length between the 3(2H)-pyridazinone ring and the 2-cyanoguanidine moiety, and a thioether rather than an ether linkage. Among them, compound 14, 2-[[[2-(2-cyano-3-methyl-1-guanidino)ethyl]thio]methyl]-6-phenyl-3 (2H)-pyridazinone, had the most potent antisecretory and antiulcer activities. These compounds are neither histamine H2 receptor inhibitors nor anticholinergic agents.

  DOI：

  10.1021/jm00362a011
• 作为产物：
  描述：

  聚合甲醛 、 6-苯基-3-哒嗪酮 反应 1.0h， 以88%的产率得到2-(hydroxymethyl)-6-phenyl-3(2H)-pyridazinone
  参考文献：
  名称：

  Pyridazinones. 3. Synthesis, antisecretory, and antiulcer activities of 2-cyanoguanidine derivatives

  摘要：

  3(2H)-Pyridazinone derivatives having a 2-cyanoguanidine moiety, as well as a sulfur or an oxygen atom in the alkylene side chain, were synthesized and evaluated for gastric antisecretory and antiulcer activities. The key intermediates, free amines having a thioether linkage, were synthesized by the reaction of 2-(omega-chloroalkyl) derivatives with cysteamine, while other intermediates having an ether linkage were synthesized from 2-(omega-chloroalkyl)oxymethyl derivatives. These free amines were converted via the 3-cyano-2-methyl-1-isothiourea derivatives into the desired 2-cyano-3-substituted-1-guanidine derivatives. All compounds synthesized were evaluated for gastric antisecretory activity in the pylorus-ligated rat by the method of Shay, and selected compounds were evaluated in the stress-induced ulcer test in rat. Structure-activity relationships are discussed. The molecular features for the best activities are a phenyl group in the C-6 position of the 3(2H)-pyridazinone ring, a four-atom chain length between the 3(2H)-pyridazinone ring and the 2-cyanoguanidine moiety, and a thioether rather than an ether linkage. Among them, compound 14, 2-[[[2-(2-cyano-3-methyl-1-guanidino)ethyl]thio]methyl]-6-phenyl-3 (2H)-pyridazinone, had the most potent antisecretory and antiulcer activities. These compounds are neither histamine H2 receptor inhibitors nor anticholinergic agents.

  DOI：

  10.1021/jm00362a011

文献信息

• Pyridazin (2H)-3-ones, process for their preparation and their use in antihypertensive agents
  申请人：DIAMOND SHAMROCK CORPORATION

  公开号：EP0018063A1

  公开（公告）日：1980-10-29

  Substituted keto-pyridazine compounds of the formula where R, and R7 are substituents selected from atoms and groups as listed in the disclosure and X and Y denote the same or different optional substituents also selected as listed in the disclosure, are new compounds which are useful antihypertensive agents. The methods of preparation and properties of examples of the compounds are given, together with their use as antihypertensive agents.

  式中的取代酮哒嗪化合物 其中 R 和 R7 是选自公开文献中所列原子和基团的取代基，X 和 Y 表示相同或不同的任选取代基，也选自公开文献中所列基团。本文给出了这些化合物的制备方法和性质实例，以及它们作为降压药的用途。
• YAMADA, TOSHIHIRO;SHIMAMURA, HIROSHI;TSUKAMOTO, YOSHITSUGU;YAMAGUCHI, AZU+, J. MED. CHEM., 1983, 26, N 8, 1144-1149
  作者：YAMADA, TOSHIHIRO、SHIMAMURA, HIROSHI、TSUKAMOTO, YOSHITSUGU、YAMAGUCHI, AZU+

  DOI：——

  日期：——
• EP0088128A4
  申请人：——

  公开号：EP0088128A4

  公开（公告）日：1984-04-06
• ANTIINFLAMMATORY AND ANALGETIC 4-PYRIDYLPYRIDAZIN(2H)-3-ONES
  申请人：DIAMOND SHAMROCK CORPORATION

  公开号：EP0088128A1

  公开（公告）日：1983-09-14
• US4238490A
  申请人：——

  公开号：US4238490A

  公开（公告）日：1980-12-09