[3-(1,3-Benzodioxol-5-yl)-1-(hydroxymethyl)-4-(4-methylsulfonylphenyl)cyclopent-3-en-1-yl]methanol | 1027322-10-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: [3-(1,3-Benzodioxol-5-yl)-1-(hydroxymethyl)-4-(4-methylsulfonylphenyl)cyclopent-3-en-1-yl]methanol
• CAS: 1027322-10-6
• 化学式: C₂₁H₂₂O₆S
• 分子量: 402.468
• InChiKey: JHINKPYUSLNTIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [3-(1,3-Benzodioxol-5-yl)-1-(hydroxymethyl)-4-(4-methylsulfonylphenyl)cyclopent-3-en-1-yl]methanol 在 吡啶 、 sodium iodide 、 锌 作用下， 以 乙二醇二甲醚 为溶剂， 反应 3.0h， 生成 5-[6-(4-Methanesulfonyl-phenyl)-spiro[2.4]hept-5-en-5-yl]-benzo[1,3]dioxole
  参考文献：
  名称：

  Diarylspiro[2.4]heptenes as Orally Active, Highly Selective Cyclooxygenase-2 Inhibitors:  Synthesis and Structure−Activity Relationships

  摘要：

  A novel series of 5,6-diarylspiro[2.4]hept-5-enes was shown to provide highly potent and selective cyclooxygenase-2 (COX-2) inhibitors. A study of structure-activity relationships in this series suggests that 3,4-disubstituted phenyl analogs are generally more selective than 4-substituted phenyl analogs and that replacement of the methyl sulfone group on the B-phenyl ring with a sulfonamide moiety results in compounds with superior in vivo pharmacological properties, although with lower COX-2 selectivity, Several compounds have been shown to possess promising pharmacological properties in adjuvant-induced arthritis and edema analgesia models. The absence of gastrointestinal (GI) toxicity at 200 mpk of several selected compounds in rats and mice corresponds well with the weak potency for inhibition of COX-1 observed in the enzyme assay. Methyl sulfone 55 and sulfonamide 24 were shown to have superior in vivo pharmacological profiles, low GI toxicity, and good oral bioavailability and duration of action.

  DOI：

  10.1021/jm950664x
• 作为产物：
  描述：

  4-甲硫基苯乙酮 在 盐酸 、 titanium(III) chloride 、 溴 、 二异丁基氢化铝 、 potassium carbonate 、 间氯过氧苯甲酸 、 potassium iodide 、 锌 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 7.25h， 生成 [3-(1,3-Benzodioxol-5-yl)-1-(hydroxymethyl)-4-(4-methylsulfonylphenyl)cyclopent-3-en-1-yl]methanol
  参考文献：
  名称：

  Diarylspiro[2.4]heptenes as Orally Active, Highly Selective Cyclooxygenase-2 Inhibitors:  Synthesis and Structure−Activity Relationships

  摘要：

  A novel series of 5,6-diarylspiro[2.4]hept-5-enes was shown to provide highly potent and selective cyclooxygenase-2 (COX-2) inhibitors. A study of structure-activity relationships in this series suggests that 3,4-disubstituted phenyl analogs are generally more selective than 4-substituted phenyl analogs and that replacement of the methyl sulfone group on the B-phenyl ring with a sulfonamide moiety results in compounds with superior in vivo pharmacological properties, although with lower COX-2 selectivity, Several compounds have been shown to possess promising pharmacological properties in adjuvant-induced arthritis and edema analgesia models. The absence of gastrointestinal (GI) toxicity at 200 mpk of several selected compounds in rats and mice corresponds well with the weak potency for inhibition of COX-1 observed in the enzyme assay. Methyl sulfone 55 and sulfonamide 24 were shown to have superior in vivo pharmacological profiles, low GI toxicity, and good oral bioavailability and duration of action.

  DOI：

  10.1021/jm950664x