(E)-3-(2-nitrovinyl)-1H-indole-5-carbonitrile | 1452838-22-0

• 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: (E)-3-(2-nitrovinyl)-1H-indole-5-carbonitrile
• 英文别名: 5-Cyano-3-(2-nitrovinyl)indole；3-[(E)-2-nitroethenyl]-1H-indole-5-carbonitrile
• CAS: 1452838-22-0
• 化学式: C₁₁H₇N₃O₂
• 分子量: 213.195
• InChiKey: CQDDYYRKWJNSCZ-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  85.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-(2-nitrovinyl)-1H-indole-5-carbonitrile 在 盐酸 、 sodium tetrahydroborate 、 锌 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 3-(2-aminoethyl)-1H-indole-5-carbonitrile
  参考文献：
  名称：

  Gold and BINOL-Phosphoric Acid Catalyzed Enantioselective Hydroamination/N-Sulfonyliminium Cyclization Cascade

  摘要：

  A highly enantioselective hydroamination/N-sulfonyliminium cyclization cascade is reported using a combination of gold(I) and chiral phosphoric acid catalysts. An initial 5-exo-dig hydroamination and a subsequent phosphoric acid catalyzed cyclization process provide access to complex sulfonamide scaffolds in excellent yield and high enantiocontrol. The method can be extended to lactam derivatives, with excellent yields and enantiomeric excesses of up to 93% ee.

  DOI：

  10.1021/ol401784h
• 作为产物：
  描述：

  5-氰基吲哚 在 ammonium acetate 、 三氯氧磷 作用下， 反应 1.08h， 生成 (E)-3-(2-nitrovinyl)-1H-indole-5-carbonitrile
  参考文献：
  名称：

  Gold and BINOL-Phosphoric Acid Catalyzed Enantioselective Hydroamination/N-Sulfonyliminium Cyclization Cascade

  摘要：

  A highly enantioselective hydroamination/N-sulfonyliminium cyclization cascade is reported using a combination of gold(I) and chiral phosphoric acid catalysts. An initial 5-exo-dig hydroamination and a subsequent phosphoric acid catalyzed cyclization process provide access to complex sulfonamide scaffolds in excellent yield and high enantiocontrol. The method can be extended to lactam derivatives, with excellent yields and enantiomeric excesses of up to 93% ee.

  DOI：

  10.1021/ol401784h

文献信息

• [EN] SEPIAPTERIN REDUCTASE INHIBITORS FOR THE TREATMENT OF PAIN<br/>[FR] INHIBITEURS DE SÉPIAPTÉRINE RÉDUCTASE POUR LE TRAITEMENT DE LA DOULEUR
  申请人：HERCULES TECHNOLOGY MAN CO V INC

  公开号：WO2011047156A1

  公开（公告）日：2011-04-21

  Disclosed herein are small molecule heterocyclic inhibitors of sepiapterin reductase (SPR), and prodrugs and pharmaceutically acceptable salts thereof. The Also featured are pharmaceutical compositions of the compounds and uses of these compounds for the treatment or prevention of pain (e.g., inflammatory pain, nociceptive pain, functional pain, and neuropathic pain).

  本文介绍的是对丝氨酸脱氢酶（SPR）的小分子杂环抑制剂，以及它们的前药和药用盐。还包括这些化合物的药物组合物以及这些化合物用于治疗或预防疼痛（如炎症性疼痛、伤害性疼痛、功能性疼痛和神经病理性疼痛）的用途。
• N-(2-arylethyl) benzylamines as antagonists of the 5-ht6 receptor
  申请人：Chen Zhaogen

  公开号：US20060009511A9

  公开（公告）日：2006-01-12

  The present invention provides compounds of formula (I), which are antagonists of the 5-HT 6 receptor.

  本发明提供了式(I)的化合物，它们是5-HT6受体的拮抗剂。
• N-(2-ARYLETHYL)BENZYLAMINES AS ANTAGONISTS OF THE 5-HT6 RECEPTOR
  申请人：Chen Zhaogen

  公开号：US20070099909A1

  公开（公告）日：2007-05-03

  The present invention provides compounds of formula (I), which are antagonists of the 5-HT 6 receptor.

  本发明提供了公式（I）的化合物，它们是5-HT6受体的拮抗剂。
• N-(2-ARYLETHYL) BENZYLAMINES AS ANTAGONISTS OF THE 5-HT6 RECEPTOR
  申请人：ELI LILLY AND COMPANY

  公开号：EP1859798B1

  公开（公告）日：2015-12-30
• SEPIAPTERIN REDUCTASE INHIBITORS FOR THE TREATMENT OF PAIN
  申请人：Children's Medical Center Corporation

  公开号：US20160031812A1

  公开（公告）日：2016-02-04

  Disclosed herein are small molecule heterocyclic inhibitors of sepiapterin reductase (SPR), and prodrugs and pharmaceutically acceptable salts thereof. The Also featured are pharmaceutical compositions of the compounds and uses of these compounds for the treatment or prevention of pain (e.g., inflammatory pain, nociceptive pain, functional pain, and neuropathic pain).