2,2-dimethyl-5-hydroxy-7-pentyl-2,3-dihydro-4H-1-benzothiopyran-4-one | 88880-07-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫铬烷
• 英文名称: 2,2-dimethyl-5-hydroxy-7-pentyl-2,3-dihydro-4H-1-benzothiopyran-4-one
• 英文别名: 2,2-dimethyl-5-hydroxy-7-pentyl-4H-2,3-dihydrobenzothiopyran-4-one；5-hydroxy-2,2-dimethyl-7-pentyl-3H-thiochromen-4-one
• CAS: 88880-07-3
• 化学式: C₁₆H₂₂O₂S
• 分子量: 278.415
• InChiKey: MVSUEHRYKXAWGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-5-hydroxy-7-pentyl-2,3-dihydro-4H-1-benzothiopyran-4-one 、 异丙醇胺 以 乙醇 为溶剂， 以83%的产率得到2,2-dimethyl-5-hydroxy-7-pentyl-4-(2'-hydroxypropylimino)-4H-2,3-dihydrobenzothiopyran
  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 在 四氢吡咯 、 aluminum tri-bromide 作用下， 以 甲苯 、 苯 为溶剂， 反应 2.0h， 生成 2,2-dimethyl-5-hydroxy-7-pentyl-2,3-dihydro-4H-1-benzothiopyran-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

• Substituted iminoderivatives of dihydrobenzopyran and
  申请人：Farmitalia Carlo Erba S.p.A.

  公开号：US04497820A1

  公开（公告）日：1985-02-05

  Substituted imino derivatives of 4 H-2, 3-dihydrobenzopyran and 4 H-2, 3-dihydrobenzothiopyran, and pharmaceutical compositions containing them. The compounds are active on the central nervous system, in particular as central nervous system depressants, i.e., sedatives, anticonvulsive agents, tranquilizers and sleep-inducing agents.

  4 H-2,3-二氢苯并吡喃和4 H-2,3-二氢苯并硫吡喃的取代亚胺衍生物，以及含有它们的药物组合物。这些化合物对中枢神经系统具有活性，特别是作为中枢神经系统抑制剂，即镇静剂、抗惊厥药、镇定剂和催眠药。
• Arnoldi; Merlini; Quadri, Il Farmaco, 1991, vol. 46, # 5, p. 629 - 638
  作者：Arnoldi、Merlini、Quadri、Bonsignori、Melloni、Varasi

  DOI：——

  日期：——
• 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：——
• US4497820A
  申请人：——

  公开号：US4497820A

  公开（公告）日：1985-02-05
• Synthesis and anticonvulsant and sedative-hypnotic activity of 4-(alkylimino)-2,3-dihydro-4H-1-benzopyrans and benzothiopyrans
  作者：Anna Arnoldi、Alberto Bonsignori、Piero Melloni、Lucio Merlini、Maria Luisa Quadri、Alessandro C. Rossi、Mariella Valsecchi

  DOI：10.1021/jm00172a030

  日期：1990.10

  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).