5-Methyl-thiopyrano<3,2-b>indol-4(5H)-on | 61164-54-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-Methyl-thiopyrano<3,2-b>indol-4(5H)-on
• 英文别名: 5-methyl-5H-thiopyrano[3,2-b]indol-4-one；5-methylthiopyrano[3,2-b]indol-4(5H)-one；5-methylthiopyrano[3,2-b]indol-4-one
• CAS: 61164-54-3
• 化学式: C₁₂H₉NOS
• 分子量: 215.276
• InChiKey: UOIDSPQWWZJAPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  47.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-Methyl-thiopyrano<3,2-b>indol-4(5H)-on-2-carbonsaeuremethylester 在 sodium hydroxide 作用下， 反应 12.0h， 生成 5-Methyl-thiopyrano<3,2-b>indol-4(5H)-on
  参考文献：
  名称：

  Anellierte Thiopyrone，2. 手套。Thiopyrano[3,2-b]indol-4(5H)-on- 和 Thiopyrano[2,3-b]indol-4(9H)-on-2-carbonsäuren

  摘要：

  Die (3-Indoyl-thio)-fumarsäuren 2 cyclisieren mit Polyphosphorsäure (PPA) zu den isomeren Titelverbindungen 6 和 8。

  DOI：

  10.1002/ardp.19863190408

文献信息

• Anellierte Thiopyrone, 1. Mitt. Thiopyrano[3,2-b]indol-4(5H)-one, Thiopyrano[2,3-b]indol-4(9H)-one als Nebenprodukte
  作者：Klaus Görlitzer、Detlef Hölscher

  DOI：10.1002/ardp.19863190206

  日期：——

  Die 3‐(3‐Indolyl‐thio)‐acrylsäuren 3 cyclisieren mit Polyphosphorsäure (PPA) zu den isomeren Titelverbindungen 4 und 5, die als Sulfone, Thione und Oxonole charakterisiert werden.

  3-(3-吲哚基-硫代)-丙烯酸 3 与多磷酸 (PPA) 环化，得到异构的标题化合物 4 和 5，其特征为砜、硫酮和氧代醇。
• Indolothiopyrones
  申请人：Warner-Lambert Company

  公开号：US03971806A1

  公开（公告）日：1976-07-27

  This invention relates to novel indolothiopyrones having the formula: ##SPC1## Wherein R.sub.1 is hydrogen, lower alkyl or aryl; R.sub.2 is hydrogen or halogen; and R.sub.7 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, nitro-substituted-aryl, or .omega.-substituted lower alkyl wherein the substituent is: ##EQU1## --COOH, or ##EQU2## wherein R.sub.4 and R.sub.5 each represent hydrogen, lower alkyl, or together with the nitrogen atom, form a heterocyclic ring; and R.sub.6 is lower alkoxy or amino, and novel intermediates used in their preparation. The indolothiopyrones are prepared by reacting a 3-mercaptoindole with sodium propiolate or a substituted sodium propiolate followed by acidification to obtain an intermediate acid; the intermediate acid cyclizes in the presence of an acid catalyst to obtain the indolothiopyrone structure which may be additionally subjected to halogenation, alkylation or hydrolysis to obtain derivatives having the various substituent groups disclosed. The compounds of this invention are useful in the treatment of angina pectoris and conditions benefiting from the depression of the central nervous system.

  本发明涉及具有以下式子的新型吲哚硫吡喃：##SPC1## 其中R.sub.1是氢、低烷基或芳基；R.sub.2是氢或卤素；R.sub.7是氢、低烷基、低烯基、低炔基、硝基取代的芳基或ω-取代的低烷基，其中取代基是：##EQU1## --COOH，或##EQU2## 其中R.sub.4和R.sub.5分别表示氢、低烷基或与氮原子一起形成杂环环；R.sub.6是低烷氧基或氨基，并且本发明中使用的新型中间体用于它们的制备。通过将3-硫代吲哚与丙炔酸钠或取代的丙炔酸钠反应，然后酸化以获得中间酸；在酸催化剂存在下，中间酸环化以获得吲哚硫吡喃结构，该结构可以进一步经过卤化、烷基化或水解以获得具有所述各种取代基的衍生物。本发明中的化合物在治疗心绞痛和需要抑制中枢神经系统的情况下有用。
• Morpholino containing indolothiopyrones
  申请人：Warner-Lambert Company

  公开号：US04064123A1

  公开（公告）日：1977-12-20

  This invention relates to novel indolothiopyrones having the formula: ##STR1## wherein R.sub.1 is hydrogen, lower alkyl or aryl; R.sub.2 is hydrogen or halogen; and R.sub.7 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, nitro-substituted-aryl, or .omega.-substituted lower alkyl wherein the substituent is: ##STR2## wherein R.sub.4 and R.sub.5 each represent hydrogen, lower alkyl, or together with the nitrogen atom, form a heterocyclic ring; and R.sub.6 is lower alkoxy or amino, and novel intermediates used in their preparation. The indolothiopyrones are prepared by reacting a 3-mercaptoindole with sodium propiolate or a substituted sodium propiolate followed by acidification to obtain an intermediate acid; the intermediate acid cyclizes in the presence of an acid catalyst to obtain the indolothiopyrone structure which may be additionally subjected to halogenation, alkylation or hydrolysis to obtain derivatives having the various substituent groups disclosed. The compounds of this invention are useful in the treatment of angina pectoris and conditions benefiting from the depression of the central nervous system.

  本发明涉及一种新型的吲哚硫吡酮，其化学式为：##STR1## 其中R.sub.1为氢，低烷基或芳基；R.sub.2为氢或卤素；R.sub.7为氢、低烷基、低烯基、低炔基、硝基取代的芳基或ω-取代的低烷基，其中取代基为：##STR2## 其中R.sub.4和R.sub.5分别表示氢、低烷基或与氮原子一起形成杂环环；R.sub.6为低烷氧基或氨基，以及用于它们制备的新型中间体。这些吲哚硫吡酮是通过将3-巯基吲哚与丙炔酸钠或取代的丙炔酸钠反应，然后酸化以得到中间酸；在酸催化剂存在下，中间酸环化以得到吲哚硫吡酮结构，该结构可以进一步接受卤素化、烷基化或水解以获得具有所披露的各种取代基的衍生物。本发明的化合物在治疗心绞痛和受益于中枢神经系统抑制的情况下有用。
• Process for the preparation of indolothiopyrones and indolylthio acid
  申请人：Warner-Lambert Company

  公开号：US04092328A1

  公开（公告）日：1978-05-30

  This invention relates to novel indolothiopyrones having the formula: ##STR1## wherein R.sub.1 is hydrogen, lower alkyl or aryl; R.sub.2 is hydrogen or halogen; and R.sub.7 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, nitro-substituted-aryl, or .omega.-substituted lower alkyl wherein the substituent is: ##STR2## wherein R.sub.4 and R.sub.5 each represent hydrogen, lower alkyl, or together with the nitrogen atom, form a heterocyclic ring; and R.sub.6 is lower alkoxy or amino, and novel intermediates used in their preparation. The indolothiopyrones are prepared by reacting a 3-mercaptoindole with sodium propiolate or a substituted sodium propiolate followed by acidification to obtain an intermediate acid; the intermediate acid cyclizes in the presence of an acid catalyst to obtain the indolothiopyrone structure which may be additionally subjected to halogenation, alkylation or hydrolysis to obtain derivatives having the various substituent groups disclosed. The compounds of this invention are useful in the treatment of angina pectoris and conditions benefiting from the depression of the central nervous system.

  本发明涉及新颖的吲哚硫吡酮，其化学式为： ##STR1## 其中R.sub.1为氢、较低的烷基或芳基；R.sub.2为氢或卤素；R.sub.7为氢、较低的烷基、较低的烯基、较低的炔基、硝基取代的芳基或ω-取代的较低烷基，其中取代基为： ##STR2## 其中R.sub.4和R.sub.5分别表示氢、较低的烷基或与氮原子一起形成杂环环；R.sub.6为较低的烷氧基或氨基，以及用于它们的制备的新型中间体。通过将3-巯基吲哚与丙炔酸钠或取代的丙炔酸钠反应，然后酸化以获得中间酸；在酸催化剂的存在下，中间酸环化以获得吲哚硫吡酮结构，该结构可进一步经过卤代、烷基化或水解以获得具有所述各种取代基的衍生物。本发明的化合物在治疗心绞痛和需要抑制中枢神经系统的情况下有用。
• US3971806A
  申请人：——

  公开号：US3971806A

  公开（公告）日：1976-07-27