phenyl N-[6-(pyrazin-2-ylmethoxy)pyridin-3-yl]carbamate | 216019-43-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: phenyl N-[6-(pyrazin-2-ylmethoxy)pyridin-3-yl]carbamate
• CAS: 216019-43-1
• 化学式: C₁₇H₁₄N₄O₃
• 分子量: 322.323
• InChiKey: HTUVYEIEVMSZHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  86.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-甲基-6-三氟甲基吲哚啉 、 phenyl N-[6-(pyrazin-2-ylmethoxy)pyridin-3-yl]carbamate 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 N-[6-(2-Pyrazinylmethoxy)-3-pyridinyl]-5-methyl-6-(trifluoromethyl)indoline-1-carboxamide
  参考文献：
  名称：

  1-[2-[(Heteroarylmethoxy)aryl]carbamoyl]indolines are selective and orally active 5-HT2C receptor inverse agonists

  摘要：

  Bisarylmethoxyethers have been identified with nanomolar 5-HT2C affinity and selectivity over both 5-HT2A and 5-HT2B receptors. Compounds such as 1, 2, 8, 12, 14 and 18 have potent oral activity in a centrally mediated pharmacodynamic model of 5-HT2C function and their therapeutic potential is currently under further investigation. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00365-6
• 作为产物：
  描述：

  2-羟甲基吡嗪 在 盐酸 、 sodium hydride 、 三乙胺 、 tin(ll) chloride 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 phenyl N-[6-(pyrazin-2-ylmethoxy)pyridin-3-yl]carbamate
  参考文献：
  名称：

  1-[2-[(Heteroarylmethoxy)aryl]carbamoyl]indolines are selective and orally active 5-HT2C receptor inverse agonists

  摘要：

  Bisarylmethoxyethers have been identified with nanomolar 5-HT2C affinity and selectivity over both 5-HT2A and 5-HT2B receptors. Compounds such as 1, 2, 8, 12, 14 and 18 have potent oral activity in a centrally mediated pharmacodynamic model of 5-HT2C function and their therapeutic potential is currently under further investigation. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00365-6

文献信息

• INDOLINE DERIVATIVES AS 5HT2C RECEPTOR ANTAGONISTS
  申请人：SMITHKLINE BEECHAM PLC

  公开号：EP0984956A1

  公开（公告）日：2000-03-15
• [EN] INDOLINE DERIVATIVES AS 5HT2C RECEPTOR ANTAGONISTS<br/>[FR] DERIVES D'INDOLINE COMME ANTAGONISTES DU RECEPTEUR 5HT2C
  申请人：SMITHKLINE BEECHAM PLC

  公开号：WO1998052943A1

  公开（公告）日：1998-11-26

  (EN) A compound of formula (I) or a salt thereof, wherein: R1 is hydrogen or C1-6alkyl; R2, R3 and R4 groups are independently hydrogen, halogen or C1-6alkyl optionally substituted by one or more fluorine atoms. R5 and R6 groups are independently hydrogen or C1-6alkyl; X and Y are independently CH or nitrogen, provided that X is nitrogen when Y is nitrogen and both R5 and R6 are hydrogen. The compounds exhibit enhanced 5HT2C receptor antagonist activity profile. 5HT2C receptor antagonists are believed to be of potential use in the treatment of CNS disorders such as anxiety, depression, epilepsy, obsessive compulsive disorders, migraine, Alzheimer's disease, sleep disorders, feeding disorders such as anorexia and bulimia, panic attacks, withdrawal from drug abuse such as cocaine, ethanol, nicotine and benzodiazepines, schizophrenia, and also disorders associated with spinal trauma and/or head injury such as hydrocephalus. Compounds of the invention are also expected to be of use in the treatment of glaucoma, certain GI (gastrointestinal) disorders such as IBS (Irritable Bowel Syndrome) as well as microvascular diseases such as macular oedema and retinopathy.(FR) L'invention concerne un composé présentant la formule (I) ou un sel de ce dernier. Dans la formule, R1 est de l'hydrogène ou alkyle C1-6; les groupes R2, R3 et R4 sont indépendamment de l'hydrogène, halogène, ou alkyle C1-6 éventuellement substitué par un ou plusieurs atomes de fluor.Les groupes R5 et R6 sont indépendamment de l'hydrogène ou alkyle C1-6. X et Y sont indépendamment CH ou azote, à condition que X représente de l'azote lorsque Y est de l'azote et R5 et R6 sont tous deux de l'hydrogène. Les composés présentent un effet antagoniste du récepteur 5HT2C amélioré. Ces antagonistes du récepteur 5HT2C présentent une utilité potentielle pour traiter les troubles du SNC tels que l'anxiété, la dépression, l'épilepsie, les troubles obssessivo-compulsifs, la migraine, la maladie d'Alzheimer, les troubles du sommeil, les troubles de l'alimentation tels que l'anorexie et la boulimie, les attaques de panique, le sevrage lors de l'abus de drogues telles que la cocaïne, l'éthanol, la nicotine et les benzodiazépines, la schizophrénie, et également des troubles associés à un trauma de la colonne vertébrale et/ou une blessure de la tête comme l'hydrocéphalie. Les composés selon l'invention peuvent permettre également de traiter le glaucome, certains troubles gastro-intestinaux comme le syndrome du côlon irritable ainsi que les maladies microvasculaires comme l'oedème maculaire et la rétinopathie.
• 1-[2-[(Heteroarylmethoxy)aryl]carbamoyl]indolines are selective and orally active 5-HT2C receptor inverse agonists
  作者：Steven M. Bromidge、Susannah Davies、D.Malcolm Duckworth、Ian T. Forbes、Graham E. Jones、Jerome Jones、Frank D. King、Thomas P. Blackburn、Vicky Holland、Guy A. Kennett、Sean Lightowler、Derek N. Middlemiss、Graham J. Riley、Brenda Trail、Martyn D. Wood

  DOI：10.1016/s0960-894x(00)00365-6

  日期：2000.8

  Bisarylmethoxyethers have been identified with nanomolar 5-HT2C affinity and selectivity over both 5-HT2A and 5-HT2B receptors. Compounds such as 1, 2, 8, 12, 14 and 18 have potent oral activity in a centrally mediated pharmacodynamic model of 5-HT2C function and their therapeutic potential is currently under further investigation. (C) 2000 Elsevier Science Ltd. All rights reserved.