2,2-dimethyl-5-(benzylthio)-7-pentyl-2,3-dihydro-4H-1-benzopyran-4-one | 129679-06-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2,2-dimethyl-5-(benzylthio)-7-pentyl-2,3-dihydro-4H-1-benzopyran-4-one
• 英文别名: 5-benzylsulfanyl-2,2-dimethyl-7-pentyl-3H-chromen-4-one
• CAS: 129679-06-7
• 化学式: C₂₃H₂₈O₂S
• 分子量: 368.54
• InChiKey: ZHVGDNQTBJETTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.46
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-5-(benzylthio)-7-pentyl-2,3-dihydro-4H-1-benzopyran-4-one 在 aluminum tri-bromide 作用下， 以 苯 为溶剂， 反应 1.0h， 以15 mg的产率得到2,2-dimethyl-5-mercapto-7-pentyl-2,3-dihydro-4H-1-benzopyran-4-one
  参考文献：
  名称：

  Synthesis and anticonvulsant and sedative-hypnotic activity of 4-(alkylimino)-2,3-dihydro-4H-1-benzopyrans and benzothiopyrans

  摘要：

  A series of 4-(alkylimino)-5-hydroxy-7-alkyl-2,3-dihydro-4H-1-benzopyrans and -thiopyrans were synthesized and evaluated for anticonvulsant activity. Preliminary screening of these compounds revealed that 2,2-dimethyl-4-[(2-hydroxyalkyl)imino]-5-hydroxy-7-pentyl-2,3- dihydro-4H-1-benzopyrans 19 and 29, the 7-butyl analogue 34, and the corresponding 7-pentyl-4H-1-benzothiopyrans 38 and 39 had the most promising anticonvulsant activity. Synthesis of both enantiomers of 29 and 39 indicated that the R isomers 30 and 40 were the most active and showed very good protection against MES, pentylenetetrazole, and mercaptopropionic acid induced seizures after oral administration in mice. In the Irwin test these compounds showed a generalized depressant activity but at dosages higher than those showing anticonvulsant activity, whereas acute toxicity after oral administration was low (LD50 higher than 400 mg/kg).

  DOI：

  10.1021/jm00172a030
• 作为产物：
  描述：

  2-(benzylthio)-6-hydroxy-4-pentylacetophenone 、 丙酮 在 四氢吡咯 作用下， 以 甲苯 为溶剂， 反应 1.5h， 以150 mg的产率得到2,2-dimethyl-5-(benzylthio)-7-pentyl-2,3-dihydro-4H-1-benzopyran-4-one
  参考文献：
  名称：

  Synthesis and anticonvulsant and sedative-hypnotic activity of 4-(alkylimino)-2,3-dihydro-4H-1-benzopyrans and benzothiopyrans

  摘要：

  A series of 4-(alkylimino)-5-hydroxy-7-alkyl-2,3-dihydro-4H-1-benzopyrans and -thiopyrans were synthesized and evaluated for anticonvulsant activity. Preliminary screening of these compounds revealed that 2,2-dimethyl-4-[(2-hydroxyalkyl)imino]-5-hydroxy-7-pentyl-2,3- dihydro-4H-1-benzopyrans 19 and 29, the 7-butyl analogue 34, and the corresponding 7-pentyl-4H-1-benzothiopyrans 38 and 39 had the most promising anticonvulsant activity. Synthesis of both enantiomers of 29 and 39 indicated that the R isomers 30 and 40 were the most active and showed very good protection against MES, pentylenetetrazole, and mercaptopropionic acid induced seizures after oral administration in mice. In the Irwin test these compounds showed a generalized depressant activity but at dosages higher than those showing anticonvulsant activity, whereas acute toxicity after oral administration was low (LD50 higher than 400 mg/kg).

  DOI：

  10.1021/jm00172a030

文献信息

• ARNOLDI, ANNA;BONSIGNORI, ALBERTO;MELLONI, PIERO;MERLINI, LUCIO;QUADRI, M+, J. MED. CHEM., 33,(1990) N0, C. 2865-2869
  作者：ARNOLDI, ANNA、BONSIGNORI, ALBERTO、MELLONI, PIERO、MERLINI, LUCIO、QUADRI, M+

  DOI：——

  日期：——