Methyl 5-methoxy-3-nonoxy-1-phenylindole-2-carboxylate | 104961-09-3

• 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: Methyl 5-methoxy-3-nonoxy-1-phenylindole-2-carboxylate
• CAS: 104961-09-3
• 化学式: C₂₆H₃₃NO₄
• 分子量: 423.552
• InChiKey: FULVBYPXUIMKFL-UHFFFAOYSA-N

物化性质

• 沸点：
  509.1±32.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  31
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  49.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl 5-methoxy-3-nonoxy-1-phenylindole-2-carboxylate 在 N,N'-羰基二咪唑 作用下， 反应 18.67h， 生成 5-methoxy-3-(n-nonyloxy)-1-phenyl-N-1H-tetrazol-5-yl-1H-indole-2-carboxamide
  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：

  1-溴壬烷 、 3-hydroxy-5-methoxy-1-phenyl-1H-indole-2-carboxylic acid methyl ester 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 Methyl 5-methoxy-3-nonoxy-1-phenylindole-2-carboxylate
  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

文献信息

• Acidic indole compounds and their use as antiallergy agents
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0186367A2

  公开（公告）日：1986-07-02

  There are disclosed compounds having the following general formula (I): and pharmaceutically acceptable salts thereof, wherein: R' and Q are each, independently, H, an alkyl having from one to twelve carbon atoms, an alkoxy having from one to twelve carbon atoms, mercapto. an alkylthio having from one to four carbon atoms, an alkylsulphinyl having from one to four carbon atoms, an alkylsulphonyl having from one to four carbon atoms, a hydroxy group, a nitro group, an amino group, substituted amino group or a halogen, R' being further chosen from a methylenedioxy radical attached to adjacent carbon atoms of the benzene ring; R2 is H, an alkyl having from one to twelve carbon atoms, a phenyl radical, a substituted phenyl radical or a benzyl radical; R3 is H, an alkyl having from one to twelve carbon atoms, an alkoxy having from one to twelve carbon atoms, mercapto, an alkylthio having from one to four carbon atoms, a phenylthio radical, a substituted phenylthio radical, an alkylsulphinyl having from one to four carbon atoms, a phenylsulphinyl radical, a substituted phenylsulphinyl radical, an alkylsulphonyl hving from one to four carbon atoms, a phenylsolphonyl radical, a substituted phenylsolphonyl radical an amino group, or a substitued amino group; and R4 is Methods of preparing the compounds, compositions comprising the compounds and the pharmaceutical use of the compounds are also disclosed.

  公开了具有以下通式(I)的化合物： 及其药学上可接受的盐类，其中 R'和 Q 各自独立地为 H、1-12 个碳原子的烷基、1-12 个碳原子的烷氧基、1-4 个碳原子的巯基、1-4 个碳原子的烷硫基、1-4 个碳原子的烷基亚磺酰基、1-4 个碳原子的烷基磺酰基、羟基、硝基、氨基、取代氨基或卤素，R'可进一步选自连接到苯环相邻碳原子上的亚甲二氧基； R2 是 H、具有 1 至 12 个碳原子的烷基、苯基、取代苯基或苄基； R3 是 H、具有一至十二个碳原子的烷基、具有一至十二个碳原子的烷氧基、巯基、具有一至四个碳原子的烷硫基、苯硫基、取代的苯硫基、具有一至四个碳原子的烷基亚磺酰基、一个氨基或一个取代氨基；和 R4 是 还公开了制备这些化合物的方法、包含这些化合物的组合物以及这些化合物的药物用途。
• US4675332A
  申请人：——

  公开号：US4675332A

  公开（公告）日：1987-06-23
• Novel indolecarboxamidotetrazoles as potential antiallergy agents
  作者：Paul C. Unangst、David T. Connor、S. Russell Stabler、Robert J. Weikert、Mary E. Carethers、John A. Kennedy、David O. Thueson、James C. Chestnut、Richard L. Adolphson、M. C. Conroy

  DOI：10.1021/jm00126a036

  日期：1989.6

  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.