2-(chloromethyl)-6-methyl-3(2H)-pyridazinone | 34477-79-7

• 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-(chloromethyl)-6-methyl-3(2H)-pyridazinone
• 英文别名: 1-Chlormethyl-6-methyl-3(2H)-pyridazinon；2-chloromethyl-6-methyl-2H-pyridazin-3-one；2-(Chloromethyl)-6-methylpyridazin-3-one
• CAS: 34477-79-7
• 化学式: C₆H₇ClN₂O
• mdl: MFCD19232566
• 分子量: 158.587
• InChiKey: MUUCTJGIIHBMOH-UHFFFAOYSA-N

物化性质

• 熔点：
  96-97 °C
• 沸点：
  236.6±42.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(chloromethyl)-6-methyl-3(2H)-pyridazinone 在 乙醇 、 sodium 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 methyl N-cyano-N'-[2-[(3-methyl-6-oxopyridazin-1-yl)methylsulfanyl]ethyl]carbamimidothioate
  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：

  2-hydroxymethyl-6-methyl-2H-pyridazin-3-one 在 氯化亚砜 作用下， 以 氯仿 为溶剂， 反应 1.0h， 生成 2-(chloromethyl)-6-methyl-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

• 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：——
• TSUCHIYA T.; ARAI H.; HASEBE M.; IGETA H., CHEM. AND PHARM. BULL. <CPBT-AL>, 1974, 22, NO 10, 2301-2305
  作者：TSUCHIYA T.、 ARAI H.、 HASEBE M.、 IGETA H.

  DOI：——

  日期：——
• N-iso-Propyl-S-(1,6-dihydro-6-(thi)oxo-pyridazin(1)-yl-methyl)-thiolphosphorsäure-esteramide, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel
  申请人：BAYER AG

  公开号：EP0010612B1

  公开（公告）日：1981-09-16
• US4010157A
  申请人：——

  公开号：US4010157A

  公开（公告）日：1977-03-01
• Pyridazinones. 3. Synthesis, antisecretory, and antiulcer activities of 2-cyanoguanidine derivatives
  作者：Toshihiro Yamada、Hiroshi Shimamura、Yoshitsugu Tsukamoto、Azuma Yamaguchi、Masahiko Ohki

  DOI：10.1021/jm00362a011

  日期：1983.8

  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.