4-(2-chlorophenyl)-2-[2-(4-n-butylphenyl)ethyl]-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine | 117279-67-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻烯杂卓类
• 英文名称: 4-(2-chlorophenyl)-2-[2-(4-n-butylphenyl)ethyl]-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine
• 英文别名: 2-[2-(4-butylphenyl)ethyl]-4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine；4-[2-(4-Butylphenyl)ethyl]-7-(2-chlorophenyl)-13-methyl-3-thia-1,8,11,12-tetrazatricyclo[8.3.0.02,6]trideca-2(6),4,7,10,12-pentaene
• CAS: 117279-67-1
• 化学式: C₂₇H₂₇ClN₄S
• 分子量: 475.057
• InChiKey: KYAWBGDNKNBOJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  71.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2-chlorophenyl)-2-[2-(4-n-butylphenyl)ethyl]-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine 生成 [5-[2-(4-butylphenyl)ethyl]-2-[3-[(dimethylamino)methyl]-5-methyl-1,2,4-triazol-4-yl]thiophen-3-yl]-(2-chlorophenyl)methanone
  参考文献：
  名称：

  MORIVAKI, MINORU;NAKADZIMA, TORU;TEHRASAVA, MITIO;TAXARA, TEHTSUXARU

  摘要：

  DOI：
• 作为产物：
  描述：

  丁苯 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 氢氧化钾 、 sodium hypochlorite 、 sodium tetrahydroborate 、 三氯化铝 、 tetraphosphorus decasulfide 、 三氟化硼乙醚 、 氨 、 碳酸氢钠 、 sulfur 、 一水合肼 、 溶剂黄146 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 乙二醇 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 异丙醇 、 甲苯 为溶剂， 反应 43.5h， 生成 4-(2-chlorophenyl)-2-[2-(4-n-butylphenyl)ethyl]-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine
  参考文献：
  名称：

  Structural optimization of 4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f]-[1,2,4]triazolo[4,3-a][1,4]diazepines as antagonists for platelet activating factor: pharmacological contribution of substituents at the 2- and 6-positions of a condensed ring system

  摘要：

  A series of 4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine derivatives bearing substituents at the 2- and 6-positions were synthesized, and evaluated in vitro for their inhibitory activity on rabbit platelet aggregation induced by platelet activating factor (PAF) and in vivo for their preventing effect on PAF-induced mortality in mice. The length of alkyl or arylalkyl side chain at the 2-position was responsible for enhancing the affinity for the PAF receptor. The simultaneous substitution at both the 2- and 6-positions resulted in a successful separation of the affinity for the PAF receptor from that for the benzodiazepine (BZ) receptor. Thus, (+/-)-4-(2-chlorophenyl)-2-[2-(4-isobutylphenyl)ethyl]-6,9-dimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine (Y-24180) was confirmed to be a specific antagonist for the PAF receptor and is currently under clinical trials.

  DOI：

  10.1016/0223-5234(96)85877-6

文献信息

• Thienotriazolodiazepines as platelet-activating factor antagonists. Steric limitations for the substituent in position 2
  作者：Armin Walser、Thomas Flynn、Carl Mason、Herman Crowley、Catherine Maresca、Margaret O'Donnell

  DOI：10.1021/jm00108a031

  日期：1991.4

  substituted ethynyl group at the 2-position, and the corresponding cis-olefins and fully saturated analogues are described. The compounds were evaluated as potential antagonists of platelet-activating factor (PAF) in in vitro and in vitro test models. The new thienotriazolodiazepines are compared with known related compounds such as WEB 2086 (compound 6) and the phenylethyl derivatives 27 and 28.

  描述了在2-位带有取代的乙炔基的噻吩并氮杂二氮杂卓的制剂，以及相应的顺式烯烃和完全饱和的类似物。在体外和体外测试模型中，将这些化合物评估为血小板活化因子（PAF）的潜在拮抗剂。将新的噻吩并氮杂二氮杂卓与已知的相关化合物如WEB 2086（化合物6）和苯乙基衍生物27和28进行了比较。
• MORIVAKI, MINORU;NAKADZIMA, TORU;TEHRASAVA, MITIO;TAXARA, TEHTSUXARU
  作者：MORIVAKI, MINORU、NAKADZIMA, TORU、TEHRASAVA, MITIO、TAXARA, TEHTSUXARU

  DOI：——

  日期：——
• EP0268242B1
  申请人：——

  公开号：EP0268242B1

  公开（公告）日：1992-03-18
• US4820703A
  申请人：——

  公开号：US4820703A

  公开（公告）日：1989-04-11
• Structural optimization of 4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f]-[1,2,4]triazolo[4,3-a][1,4]diazepines as antagonists for platelet activating factor: pharmacological contribution of substituents at the 2- and 6-positions of a condensed ring system
  作者：Y Kawakami、H Kitani、S Yuasa、M Abe、M Moriwaki、M Kagoshima、M Terasawa、T Tahara

  DOI：10.1016/0223-5234(96)85877-6

  日期：1996.1

  A series of 4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine derivatives bearing substituents at the 2- and 6-positions were synthesized, and evaluated in vitro for their inhibitory activity on rabbit platelet aggregation induced by platelet activating factor (PAF) and in vivo for their preventing effect on PAF-induced mortality in mice. The length of alkyl or arylalkyl side chain at the 2-position was responsible for enhancing the affinity for the PAF receptor. The simultaneous substitution at both the 2- and 6-positions resulted in a successful separation of the affinity for the PAF receptor from that for the benzodiazepine (BZ) receptor. Thus, (+/-)-4-(2-chlorophenyl)-2-[2-(4-isobutylphenyl)ethyl]-6,9-dimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine (Y-24180) was confirmed to be a specific antagonist for the PAF receptor and is currently under clinical trials.