(+/-)-(2-furoyl)-cis-octahydroquinoxaline

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (+/-)-(2-furoyl)-cis-octahydroquinoxaline
• 英文别名: 3,4,4a,5,6,7,8,8a-octahydro-2H-quinoxalin-1-yl(furan-2-yl)methanone
• 化学式: C₁₃H₁₈N₂O₂
• 分子量: 234.298
• InChiKey: VLBIPEYDZHRWFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-(2-furoyl)-cis-octahydroquinoxaline 、 (S)-(+)-扁桃酸 以 甲醇 为溶剂， 生成 (+/-)-(2-furoyl)-cis-octahydroquinoxaline (+)-mandelate salt
  参考文献：
  名称：

  USE OF SELECTIVE ANTAGONISTS OF THE ALPHA 1b-ADRENERGIC RECEPTOR FOR IMPROVEMENT OF SEXUAL DYSFUNCTION

  摘要：

  公开号：

  EP1177190B1
• 作为产物：
  描述：

  (+/-)-furan-2-yl(cis-octahydroquinoxalin-1yl)methanone 生成 (+/-)-(2-furoyl)-cis-octahydroquinoxaline
  参考文献：
  名称：

  Synthesis and Biological Profile of the Enantiomers of [4-(4-Amino-6,7-dimethoxyquinazolin-2-yl)-cis-octahydroquinoxalin-1-yl]furan- 2-ylmethanone (Cyclazosin), a Potent Competitive α_1B-Adrenoceptor Antagonist

  摘要：

  The enantiomers of [4-(4-amino-6,7-dimethoxyquinazolin-2-yl)-cis-octahydriquinoxalin-1-yl]furan-2-ylmethanone (cyclazosin, 1) were synthesized from the chiral furan-2-yl(cis-octahydroquinoxalin-1-yl)methanone [(+)-2 and (-)-2], which were obtained by resolution of the racemic amine with (S)-(+)- and (R)-(-)-mandelic acid. The binding profile of the enantiomers of 1 was assessed at alpha(1)-, alpha(2)-, D-2, and 5-HT1A receptors as well as at native alpha(1A)- and alpha(1B)- and cloned alpha(1a)-, alpha(1b)-, and alpha(1d)-adrenoceptor subtypes in comparison with prazosin, spiperone, and AH11110A. (+)-1 displayed a 40-90-fold selectivity for the alpha(1B)(alpha(1b))-adrenoceptor relative to alpha(1A)(alpha(1a)) and old subtypes. A significant enantioselectivity was observed at the alpha(1A)(alpha(1a))-adrenoceptor and particularly at alpha(1d)-adrenoceptors since (-)-1 was 11-14- and 47-fold, respectively, more potent than(+)-1. Furthermore the enantiomer (+)-1 displayed selectivities of 1100-, 19000-, and 12000-fold in binding to alpha(1b)-adrenoceptors relative to alpha(2)-adrenoceptors and 5-HT1A and D-2 receptors. These results indicate that (+)-1, [(+)-cyclazosin] is the most potent and selective ligand for the alpha(1B)-adrenoceptor subtype so far described and may be a valuable tool in the characterization of alpha(1)-adrenoceptor subtypes.

  DOI：

  10.1021/jm960510x

文献信息

• Use of selective antagonists of the alpha1b-adrenergic receptor for improvement of sexual dysfunction
  申请人：Recordati S.A.

  公开号：US20020161009A1

  公开（公告）日：2002-10-31

  Described is the use in the treatment of either male or female sexual dysfunction of selective antagonists of the &agr; 1B -adrenergic receptor and the pharmaceutical compositions containing them as compounds capable of helping the sexual act avoiding at the same time excessive side effects due to acute hypotension.

  本文描述了选择性&agr;1B-肾上腺素受体拮抗剂的使用，以治疗男性或女性性功能障碍，并包含它们的药物组合物作为有助于性行为的化合物，同时避免由于急性低血压而引起的过度副作用。
• US6303606B1
  申请人：——

  公开号：US6303606B1

  公开（公告）日：2001-10-16
• US6355641B1
  申请人：——

  公开号：US6355641B1

  公开（公告）日：2002-03-12
• US6953800B2
  申请人：——

  公开号：US6953800B2

  公开（公告）日：2005-10-11
• [EN] OXAZOLONE DERIVATIVES AND THEIR USE AS ALPHA-1 ADRENORECEPTOR MODULATORS<br/>[FR] DERIVES D'OXAZOLONE ET UTILISATIONS DE CES DERNIERS EN TANT QUE MODULATEURS DU RECEPTEUR ADRENERGIQUE ALPHA-1
  申请人：HOFFMANN LA ROCHE

  公开号：WO2000055143A1

  公开（公告）日：2000-09-21

  Compounds of Formula (I) wherein X is Formula (A), (B) or (C): Z is CH or N; R1 is cycloalkyl, cycloalkenyl, heterocyclic, aryl or heteroaryl; are useful as alpha1- adrenoreceptor modulators, particularly antagonists.