3-Hydroxy-5-methoxy-1-methyl-1H-indole-2-carboxylic acid methyl ester | 104961-15-1

• 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: 3-Hydroxy-5-methoxy-1-methyl-1H-indole-2-carboxylic acid methyl ester
• 英文别名: methyl 3-hydroxy-5-methoxy-1-methyl-1H-indole-2-carboxylate；methyl 3-hydroxy-5-methoxy-1-methylindole-2-carboxylate
• CAS: 104961-15-1
• 化学式: C₁₂H₁₃NO₄
• 分子量: 235.24
• InChiKey: AJTYWTHOBKYBKZ-UHFFFAOYSA-N

物化性质

• 沸点：
  384.7±37.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  60.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-Hydroxy-5-methoxy-1-methyl-1H-indole-2-carboxylic acid methyl ester 在 氢氧化钾 、 potassium tert-butylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 5-methoxy-1-methyl-3-(1-methylethoxy)-1H-indole-2-carboxylic acid
  参考文献：
  名称：

  Novel indolecarboxamidotetrazoles as potential antiallergy agents

  摘要：

  The synthesis and antiallergic potential of a series of novel indolecarboxamidotetrazoles are described. A number of compounds inhibit the release of histamine from anti-IgE-stimulated basophilic leukocytes obtained from allergic donors. Optimal inhibition is exhibited by compounds with 3-alkoxy, 5-methoxy, and 1-phenyl substituents on the indole core structure. Compound 8d (5-methoxy-3-(1-methylethoxy)-1-phenyl-N-1H-tetrazol-5-yl-1H -indole-2-carboxamide; designated CI-949) is a potent inhibitor of histamine release from human basophils and from guinea pig and human chopped lung.

  DOI：

  10.1021/jm00126a036
• 作为产物：
  描述：

  2-[羧甲基(甲基)氨基]-5-甲氧基苯甲酸 在 sodium hydroxide 、 sodium methylate 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 3-Hydroxy-5-methoxy-1-methyl-1H-indole-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Unangst, Paul C.; Connor, David T.; Stabler, S. Russell, Journal of Heterocyclic Chemistry, 1987, vol. 24, p. 811 - 815

  摘要：

  DOI：

文献信息

• [EN] USE OF THIAZEPINE, OXAZEPINE AND DIAZEPINE COUMPOUNDS FOR INHIBITING HIV, HERPESVIRUS AND SUPPRESSING THE IMMUNE SYSTEM<br/>[FR] EMPLOI DE COMPOSES DE THIAZEPINE, OXAZEPINE ET DIAZEPINE POUR INHIBER LE VIH, L'HERPESVIRUS ET DEPRIMER LE SYSTEME IMMUNITAIRE
  申请人：WARNER-LAMBERT COMPANY

  公开号：WO1996029077A1

  公开（公告）日：1996-09-26

  (EN) Benzothiophene, benzofuran and indole-thiazepinones, oxazepinones, and diazepinones are effective therapeutic agents for treating viral diseases, including those caused by herpesvirus and HIV.(FR) Le benzothiophène, le benzofurane et les indolethiazepinones, les oxazépinones et les diazépinones sont des agents thérapeutiques efficaces pour le traitement des maladies virales, y compris celles causées par les virus du herpèsvirus et le VIH.

  (中) 苯并噻吩、苯并呋喃和吲哚噻吩酮、噁唑酮和二氮杂环酮是有效的治疗剂，可用于治疗病毒性疾病，包括由疱疹病毒和HIV引起的疾病。
• [EN] BENZOTHIOPHENE, BENZOFURAN AND INDOLETHIAZEPINONES, OXAZEPINONES AND DIAZEPINONES AS INHIBITORS OF CELL ADHESION AND AS INHIBITORS OF HIV<br/>[FR] THIAZEPINONES DE BENZOTHIOPHENE, DE BENZOFURANE ET D'INDOLE, OXAZEPINONES ET DIAZEPINONES UTILISEES COMME INHIBITEURS D'ADHERENCE CELLULAIRE ET DU VIH
  申请人：WARNER-LAMBERT COMPANY

  公开号：WO1995024408A1

  公开（公告）日：1995-09-14

  (EN) Benzothiophene, benzofuran and indolethiazepinones, oxazepinones and diazepinones of formula (I) as well as methods of preparation thereof are described as agents which inhibit leukocyte adherence to vascular endothelium and, as such, are effective therapeutic agents for treating inflammatory diseases; these compounds also inhibit the activation of human immunodeficiency virus (HIV).(FR) L'invention concerne des thiazépinones de benzothiophène, de benzofurane et d'indole, des oxazépinones et des diazépinones de la formule (I) ainsi que leurs procédés de production. Ces composés sont utilisés comme inhibiteurs d'adhérence des leucocytes à l'endothélium vasculaire et, constituent, en tant que tels, des principes thérapeutiques efficaces pour traiter les maladies inflammatoires. Ces composés inhibent également l'activation du virus de l'immunodéficience humaine (VIH).

  描述了式(I)的苯并噻吩、苯并呋喃和吲哚噻吩酮、噁唑酮和二氮杂环酮，以及其制备方法，作为抑制白细胞黏附于血管内皮的药物，并且作为治疗炎症性疾病的有效治疗剂；这些化合物还抑制人类免疫缺陷病毒（HIV）的激活。
• Methods for inhibiting and controlling viral growth
  申请人：Warner-Lambert Company

  公开号：US05612330A1

  公开（公告）日：1997-03-18

  Benzothiophene, benzofuran and indolethiazepinones, oxazepinones, and diazepinones are effective therapeutic agents for treating viral diseases, including those caused by herpesvirus and HIV.

  苯并噻吩，苯并呋喃和吲哚噻唑酮，噁唑酮和二氮杂噻唑酮是治疗病毒性疾病的有效药物，包括由疱疹病毒和HIV引起的疾病。
• Method for inhibiting and controlling viral growth
  申请人：Warner-Lambert Company

  公开号：US05703069A1

  公开（公告）日：1997-12-30

  Benzothiophene, benzofuran and indole-thiazepinones, oxazepinones, and diazepinones are effective therapeutic agents for treating viral diseases, including those caused by herpesvirus and HIV.

  苯并噻吩、苯并呋喃和吲哚-噻唑烷酮、噁唑烷酮和二氮杂噻唑烷酮是治疗病毒性疾病的有效药物，包括由疱疹病毒和HIV引起的疾病。
• Benzothiophene, benzofuran and indole-thiazepinones, oxazepinones and
  申请人：Warner-Lambert Company

  公开号：US05565446A1

  公开（公告）日：1996-10-15

  Benzothiophene, benzofuran and indolethiazepinones, oxazepinones and diazepinones as well as methods of preparation thereof are described as agents which inhibit leukocyte adherence to vascular endothelium and, as such, are effective therapeutic agents for treating inflammatory diseases; these compounds also inhibit the activation of human immunodeficiency virus (HIV).

  本文描述了苯并噻吩、苯并呋喃和吲哚噻唑烷酮、噁唑烷酮和二氮杂噻唑烷酮等代理，它们可以抑制白细胞附着于血管内皮，因此是治疗炎症性疾病的有效治疗药物；这些化合物也可以抑制人类免疫缺陷病毒（HIV）的激活。