Ethyl 6-bromopyrazine-2-carboxylate | 1258268-99-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: Ethyl 6-bromopyrazine-2-carboxylate
• CAS: 1258268-99-3
• 化学式: C₇H₇BrN₂O₂
• 分子量: 231.049
• InChiKey: KNUHCBGLQPLEGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  52.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethyl 6-bromopyrazine-2-carboxylate 、 4-三氟甲氧基苯硼酸 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium carbonate 作用下， 以 异丙醇 为溶剂， 生成
  参考文献：
  名称：

  Subtype-selective Nav1.8 sodium channel blockers: Identification of potent, orally active nicotinamide derivatives

  摘要：

  A series of aryl-substituted nicotinamide derivatives with selective inhibitory activity against the Na(v)1.8 sodium channel is reported. Replacement of the furan nucleus and homologation of the anilide linker in subtype-selective blocker A-803467 (1) provided potent, selective derivatives with improved aqueous solubility and oral bioavailability. Representative compounds from this series displayed efficacy in rat models of inflammatory and neuropathic pain. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.121

文献信息

• [4-(1,2-EPOXYCYCLOHEXANYL) BUT-3-EN-1-YNYL] AROMATIC AND HETEROAROMATIC ACIDS AND DERIVATIVES HAVING RETINOID-LIKE BIOLOGICAL ACTIVITY
  申请人：Allergan

  公开号：EP0737190A1

  公开（公告）日：1996-10-16
• US5426118A
  申请人：——

  公开号：US5426118A

  公开（公告）日：1995-06-20
• US5618836A
  申请人：——

  公开号：US5618836A

  公开（公告）日：1997-04-08
• [EN] [4-(1,2-EPOXYCYCLOHEXANYL) BUT-3-EN-1-YNYL] AROMATIC AND HETEROAROMATIC ACIDS AND DERIVATIVES HAVING RETINOID-LIKE BIOLOGICAL ACTIVITY<br/>[FR] ACIDES [4-(1,2-EPOXYCYCLOHEXANYLE) BUT-3-EN-1-YNYLE] AROMATIQUES ET HETEROAROMATIQUES ET DERIVES DESDITS ACIDES AYANT UNE ACTIVITE BIOLOGIQUE DE TYPE RETINOIDE.
  申请人：ALLERGAN

  公开号：WO1995018120A1

  公开（公告）日：1995-07-06

  (EN) Compounds of Formula (1) where R1-R7 are hydrogen, lower alkyl of 1-6 carbons, or halogen; Y is phenyl, pyridyl, furyl, thienyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl ou oxazolyl; A is (CH2)n, where n is 0-5, lower branched chain alkyl having 3-6 carbons, cycloalkyl having 3-6 carbons, alkenyl having 2-6 carbons and 1 or 2 double bonds, alkynyl having 2-6 carbons and 1 or 2 triple bonds; B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR8, CONR9R10, -CH2OH, CH2OR11, CH2OCOR11, CHO, CH(OR12)2, CHOR13O, -COR14, CR14(OR12)2, or CR14OR13O, where R8 is an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5-10 carbons, or R8 is phenyl or lower alkylphenyl, R9 and R10 independently are hydrogen, an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5-10 carbons, or phenyl or lower alkylphenyl, R11 is lower alkyl, phenyl or lower alkylphenyl, R12 is lower alkyl, R13 is divalent alkyl radical of 2-5 carbons and R14 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons, have retinoid-like biological activity.(FR) Composés de formule (1) dans laquelle R1 - R7 sont hydrogène, alkyle inférieur ayant de 1 à 6 atomes de carbone, ou halogène; Y est phényle, pyridyle, furyle, thiényle, pyridazinyle, pyrimidinyle, pyrazinyle, thiazolyle ou oxazolyle; A est (CH2)n, n valant de 0 à 5, alkyle inférieur à chaîne ramifiée ayant 3 à 6 atomes de carbone, cycloalkyle ayant 3 à 6 atomes de carbone, alcényle ayant 2 à 6 atomes de carbone et 1 ou 2 liaisons doubles, alcynyle ayant 2 à 6 atomes de carbone et 1 ou 2 liaisons triples; B est hydrogène, COOH ou un sel pharmaceutiquement acceptable de ladite substance, COOR8, CONR9R10, -CH2OH, CH2OR11, CH2OCOR11, CHO, CH(OR12)2, CHOR13O, -COR14, CR14(OR12)2, ou CR14OR13O, R8 étant un groupe alkyle ayant 1 à 10 atomes de carbone, ou un groupe cycloalkyle ayant 5 à 10 atomes de carbone, ou un groupe cycloalkyle ayant 5 à 10 atomes de carbon, ou bien R8 étant phényle ou alkylphényle inférieur, R9 et R10 étant indépendamment hydrogène, un groupe alkyle de 1 à 10 atomes de carbone, ou un groupe cycloalkyle ayant 5 à 10 atomes de carbone, ou phényle ou alkylphényle inférieur, R11 étant alkyle inférieur, phényle ou alkylphényle inférieur, R12 étant alkyle inférieur, R13 étant un radical alkyle divalent ayant 2 à 5 atomes de carbone et R14 étant un groupe alkyle, cycloalkyle ou alcényle contenant 1 à 5 atomes de carbone. Ces composés présentent une activité biologique de type rétinoïde.
• Subtype-selective Nav1.8 sodium channel blockers: Identification of potent, orally active nicotinamide derivatives
  作者：Michael E. Kort、Robert N. Atkinson、James B. Thomas、Irene Drizin、Matthew S. Johnson、Matthew A. Secrest、Robert J. Gregg、Marc J.C. Scanio、Lei Shi、Ahmed H. Hakeem、Mark A. Matulenko、Mark L. Chapman、Michael J. Krambis、Dong Liu、Char-Chang Shieh、XuFeng Zhang、Gricelda Simler、Joseph P. Mikusa、Chengmin Zhong、Shailen Joshi、Prisca Honore、Rosemarie Roeloffs、Stephen Werness、Brett Antonio、Kennan C. Marsh、Connie R. Faltynek、Douglas S. Krafte、Michael F. Jarvis、Brian E. Marron

  DOI：10.1016/j.bmcl.2010.08.121

  日期：2010.11

  A series of aryl-substituted nicotinamide derivatives with selective inhibitory activity against the Na(v)1.8 sodium channel is reported. Replacement of the furan nucleus and homologation of the anilide linker in subtype-selective blocker A-803467 (1) provided potent, selective derivatives with improved aqueous solubility and oral bioavailability. Representative compounds from this series displayed efficacy in rat models of inflammatory and neuropathic pain. (C) 2010 Elsevier Ltd. All rights reserved.