1-(1,2-Dihydroxyethyl)-phenoxathiin-10,10-dioxide | 135865-60-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: 1-(1,2-Dihydroxyethyl)-phenoxathiin-10,10-dioxide
• 英文别名: 1-(10,10-dioxophenoxathiin-1-yl)ethane-1,2-diol
• CAS: 135865-60-0；143285-19-2；207451-34-1
• 化学式: C₁₄H₁₂O₅S
• 分子量: 292.312
• InChiKey: PKTQHXZCHYIMFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  92.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  吩恶噻 10,10-二氧化物 在 正丁基锂 、 甲酸 、 氯化亚砜 、 双氧水 作用下， 以 二氯甲烷 为溶剂， 反应 21.25h， 生成 1-(1,2-Dihydroxyethyl)-phenoxathiin-10,10-dioxide
  参考文献：
  名称：

  Selective Inhibitors of Monoamine Oxidase (MAO). 5. 1-Substituted Phenoxathiin Inhibitors Containing No Nitrogen That Inhibit MAO A by Binding It to a Hydrophobic Site

  摘要：

  It is believed that a monoamine oxidase (MAO) inhibitor specific for MAO A, which is reversibly bound to this enzyme and displaceable:by tyramine, will be an antidepressant which will not cause a rise in blood pressure when tyramine-containing foods are ingested. Some linear tricyclic compounds with a larger and a smaller group forming the central ring and with a lipophilic group ortho to the larger group (here mostly the SO2 function of phenoxathiin 10, -10-dioxide) are reported to have the sought properties. Potency appears to require short length and relatively small cross section for the substituent. The 1-ethyl (13), 1-vinyl (22), 1-trifluoromethyl (27), and 1-iodo (76) phenoxathiin dioxides had the best profiles. Structure-activity relationships, syntheses, and a possible rationale for the selectivity of these compounds and related tricyclics are given. Compound 13 was selected for further development. A summary of pharmacological data for 13 is given.

  DOI：

  10.1021/jm970862j

文献信息

• 1-SUBSTITUTED PHENOXATHIIN DERIVATIVES AS ANTIDEPRESSANTS
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0550518A1

  公开（公告）日：1993-07-14
• [EN] 1-SUBSTITUTED PHENOXATHIIN DERIVATIVES AS ANTIDEPRESSANTS
  申请人：——

  公开号：WO1992004897A1

  公开（公告）日：1992-04-02

  [EN] Compounds of formula (I), wherein R<4> is hydrogen and either R<5> is hydrogen and R<6> is hydroxyl or R<5>, R<6> and the carbon to which they are attached together form a carbonyl group; or R<6> is hydrogen and R<4> and R<5> together form a bond; or R<4> is hydroxyl, R<5> is hydrogen and R<6> is hydrogen or hydroxyl inhibit monoamine oxidase-A and are useful in the treatment of disorders such as depression.
  [FR] Composés de la formule (I), où R4 représente hydrogène et, soit R5 représente hydrogène et R6 représente hydroxyle, soit R5, R6 et le carbone auquel ils sont combinés forment ensemble un groupe carbonyle; ou bien R6 représente hydrogène et R4 et R5 forment ensemble une liaison; ou R4 représente hydroxyle, R5 représente hydrogène et R6 représente hydrogène ou hydroxyle. Ces composés inhibent la monoamine-oxydase-A et sont utiles dans le traitement d'affections telles que la dépression.
• Selective Inhibitors of Monoamine Oxidase (MAO). 5. 1-Substituted Phenoxathiin Inhibitors Containing No Nitrogen That Inhibit MAO A by Binding It to a Hydrophobic Site
  作者：Morton Harfenist、Daniel P. C. McGee、Mark D. Reeves、Helen L. White

  DOI：10.1021/jm970862j

  日期：1998.6.1

  It is believed that a monoamine oxidase (MAO) inhibitor specific for MAO A, which is reversibly bound to this enzyme and displaceable:by tyramine, will be an antidepressant which will not cause a rise in blood pressure when tyramine-containing foods are ingested. Some linear tricyclic compounds with a larger and a smaller group forming the central ring and with a lipophilic group ortho to the larger group (here mostly the SO2 function of phenoxathiin 10, -10-dioxide) are reported to have the sought properties. Potency appears to require short length and relatively small cross section for the substituent. The 1-ethyl (13), 1-vinyl (22), 1-trifluoromethyl (27), and 1-iodo (76) phenoxathiin dioxides had the best profiles. Structure-activity relationships, syntheses, and a possible rationale for the selectivity of these compounds and related tricyclics are given. Compound 13 was selected for further development. A summary of pharmacological data for 13 is given.