2-(2-chloroethyl)-6-phenyl-3(2H)-pyridazinone | 74316-74-8

• 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-(2-chloroethyl)-6-phenyl-3(2H)-pyridazinone
• 英文别名: 2-(2-chloroethyl)-6-phenylpyridazin-3-one
• CAS: 74316-74-8
• 化学式: C₁₂H₁₁ClN₂O
• 分子量: 234.685
• InChiKey: ZODAHQVRSITQTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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-(2-chloroethyl)-6-phenyl-3(2H)-pyridazinone 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以85%的产率得到2-Vinyl-6-phenyl-3-pyridazone
  参考文献：
  名称：

  Vinylation of 3-pyridazones

  摘要：

  DOI：

  10.1007/bf02401732
• 作为产物：
  描述：

  2-(2-羟基乙基)-6-苯基-3(2H)-吡嗪酮 在 氯化亚砜 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以89%的产率得到2-(2-chloroethyl)-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

• Arylpiperazinylalkyl-3(2-H)-pyridazinones
  申请人：FAES, Fabrica Espanola de Productos Quimicos y Farmaceuticos, S.A.

  公开号：US06413966B1

  公开（公告）日：2002-07-02

  A description is given of new arylpiperazinylalkyl-3(2H)-pyridazinones of general formula (I) and their preparation and their addition salts with pharmaceutically acceptable acids, in which R1 is a methyl or phenyl radical, R2 is a hydrogen atom or a methyl radical, n takes values between 2 and 4, and R3 is a naphthyl radical or a phenyl radical, which are substituted by a radical such as methoxyl, trifluoromethyl and chlorine. The compounds have affinity for serotonin 5HT1A and 5HT2 receptors and for dopamine D2 receptors, and can be useful as antipsychotics.

  提供了新的芳基哌嗪基烷基-3（2H）-吡啶嗪酮（通式（I））及其制备和与药学上可接受的酸形成的加合物的描述，其中R1是甲基或苯基基团，R2是氢原子或甲基基团，n取2至4之间的值，而R3是萘基或苯基基团，这些基团被甲氧基、三氟甲基和氯等基团取代。这些化合物具有亲和力，可以用作抗精神病药物，可以与血清素5HT1A和5HT2受体以及多巴胺D2受体结合。
• Arylpiperazinylalkyl-3(2H)-pyridazinones as serotonin 5HT and dopamine D2 receptor agonists
  申请人：FAES, Fabrica Espanola de Productos Quimicos y Farmaceuticos, S.A.

  公开号：EP1057820A1

  公开（公告）日：2000-12-06

  A description is given of new arylpiperazinylalkyl-3(2H)-pyridazinones of general formula (I) and their preparation and their addition salts with pharmaceutically acceptable acids, in which R1 is a methyl or phenyl radical, R2 is a hydrogen atom or a methyl radical, n takes values between 2 and 4, and R3 is a naphthyl radical or a phenyl radical, which are substituted by a radical such as methoxyl, trifluoromethyl and chlorine. The compounds present affinity for serotonin 5HT1A and 5HT2 receptors and for dopamine D2 receptors, and can be useful as antipsychotics.

  本文介绍了通式(I)的新芳基哌嗪基烷基-3(2H)-哒嗪酮及其制备方法，以及它们与药学上可接受的酸的加成盐、 其中 R1 是甲基或苯基，R2 是氢原子或甲基，n 取值在 2 和 4 之间，R3 是萘基或苯基，它们被甲氧基、三氟甲基和氯等基团取代。 这些化合物对血清素 5HT1A 和 5HT2 受体以及多巴胺 D2 受体具有亲和力，可用作抗精神病药物。
• Synthesis of some new 2,6-disubstituted-3(2H)-pyridazinone derivatives and investigation of their analgesic, anti-inflammatory and antimicrobial activities
  作者：Didem Tiryaki、Murat Sukuroglu、Deniz S. Dogruer、Esra Akkol、Selda Ozgen、M. Fethi Sahin

  DOI：10.1007/s00044-012-0253-1

  日期：2013.6

  In this study, 12 new 3(2H)-pyridazinone derivatives carrying 4-substituted phenylpiperazinylethyl moiety on lactam nitrogen were synthesized and their chemical structures were confirmed by H-1-NMR, mass, and elemental analysis. Analgesic and anti-inflammatory activities of the synthesized compounds were evaluated in mice. Among the synthesized compounds, compound 9c showed the best analgesic and anti-inflammatory activities without causing any gastric effect in stomachs of tested animals. In addition, the synthesized compounds were screened for their antibacterial and antifungal activities against some pathogenic strains.
• SHATALOV G. V.; GRIDCHIN S. A.; MIXANTEV B. I., XIMIYA GETEROTSIKL. SOEDIN., 1980, HO 3, 394-397
  作者：SHATALOV G. V.、 GRIDCHIN S. A.、 MIXANTEV B. I.

  DOI：——

  日期：——
• MATYUS, PETER;MAKK, NANDOR;KASZTREINER, ENDRE;JERKOVICH, GYULE, HETEROCYCLES, 29,(1989) N, C. 67-77
  作者：MATYUS, PETER、MAKK, NANDOR、KASZTREINER, ENDRE、JERKOVICH, GYULE

  DOI：——

  日期：——