2-Hydroxy-chinolizidin | 54308-62-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹嗪类
• 英文名称: 2-Hydroxy-chinolizidin
• 英文别名: trans-2-Hydroxyquinolizidine；2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-2-ol
• CAS: 54308-62-2
• 化学式: C₉H₁₇NO
• 分子量: 155.24
• InChiKey: AZYHGLMOZYMJGF-UHFFFAOYSA-N

物化性质

• 熔点：
  91-92 °C
• 沸点：
  127-130 °C(Press: 13 Torr)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Hydroxy-chinolizidin 在 lithium aluminium tetrahydride 、 二苯基膦叠氮化物 、 三苯基膦 、 N,N'-羰基二咪唑 、 偶氮二甲酸二乙酯 、 乙硫醇钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Novel quinolizidine salicylamide influenza fusion inhibitors

  摘要：

  A novel series of quinolizidine salicylamides was synthesized as specific inhibitors of the H1 subtype of influenza A viruses. These inhibitors inhibit the pH-induced fusion process, thereby blocking viral entry into host cells. Compound 16 was the most active inhibitor in this series with an EC50 of 0.25 mu g/mL in plaque reduction assay. The synthesis and the SAR of these compounds are discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00361-3

文献信息

• Rhodes; Soine, Journal of the American Pharmaceutical Association (1912), 1956, vol. 45, p. 746,750
  作者：Rhodes、Soine

  DOI：——

  日期：——
• AZABICYCLIC COMPOUNDS AS 5-HT 4? RECEPTOR ANTAGONISTS
  申请人：SMITHKLINE BEECHAM PLC

  公开号：EP0603220A1

  公开（公告）日：1994-06-29
• US5552398A
  申请人：——

  公开号：US5552398A

  公开（公告）日：1996-09-03
• [EN] AZABICYCLIC COMPOUNDS AS 5-HT4 RECEPTOR ANTAGONISTS
  申请人：SMITHKLINE BEECHAM PLC

  公开号：WO1993005040A1

  公开（公告）日：1993-03-18

  (EN) Compounds of formula (I), wherein X is (a), (b), wherein L is N or CRc wherein Rc is hydrogen, alkoxy, halo, alkyl or cyano; Q is NR1, CH2, O or S; Ra is hydrogen, halo, alkyl, amino, nitro or alkoxy; Rb is hydrogen, halo, alkyl or alkoxy; R1 is hydrogen, alkyl, alkenyl, aralkyl, alkanoyl, or alkanoylalkyl; R2 is alkoxy; and R3 is hydrogen, chloro or fluoro; R4 is hydrogen, alkyl, amino optionally substituted by alkyl, halo, hydroxy or alkoxy; R5 is hydrogen, halo, alkyl, alkoxy, nitro, amino or alkylthio; R6 is hydrogen, halo, alkyl, alkoxy or amino; n is 0, 1, 2, 3 or 4; p and m are independently 0, 1 or 2; and Rq is hydrogen or alkyl. The compounds of the present invention are 5-HT4 receptor antagonists and it is thus believed may generally be used in the treatment or prophylaxis of gastrointestinal disorders, cardiovascular disorders and CNS disorders.(FR) Composés de formule (I) où X représente (a), (b), où L représente N ou CRc où Rc représente hydrogène, alcoxy, halo, alkyle ou cyano; Q représente NR1, CH2, O ou S; Ra représente hydrogène, halo, alkyle, amino, nitro ou alcoxy; Rb représente hydrogène, halo, alkyle ou alcoxy; R1 représente hydrogène, alkyle, alcényle, aralkyle, alcanoyle, ou alcanoylalkyle; R2 représente alcoxy; et R3 représente hydrogène, chloro ou fluoro; R4 représente hydrogène, alkyle, amino éventuellement substitué par alkyle, halo, hydroxy ou alcoxy; R5 représente hydrogène, halo, alkyle, alcoxy, nitro, amino ou alkylthio; R6 représente hydrogène, halo, alkyle, alcoxy ou amino; n représente 0, 1, 2, 3 ou 4; p et m sont indifféremment 0, 1 ou 2; et Rq représente hydrogène ou alkyle. Les composés faisant l'objet de la présente invention sont des antagonistes du récepteur 5-HT4 et sont généralement considérés comme utilisables dans le traitement ou la prophylaxie des affections gastro-intestinales et cardio-vasculaires et celles touchant le système nerveux central.
• Novel quinolizidine salicylamide influenza fusion inhibitors
  作者：Kuo-Long Yu、Edward Ruediger、Guangxiang Luo、Christopher Cianci、Stephanie Danetz、Laurence Tiley、Ashok K. Trehan、Ivo Monkovic、Bradley Pearce、Alain Martel、Mark Krystal、Nicholas A. Meanwell

  DOI：10.1016/s0960-894x(99)00361-3

  日期：1999.8

  A novel series of quinolizidine salicylamides was synthesized as specific inhibitors of the H1 subtype of influenza A viruses. These inhibitors inhibit the pH-induced fusion process, thereby blocking viral entry into host cells. Compound 16 was the most active inhibitor in this series with an EC50 of 0.25 mu g/mL in plaque reduction assay. The synthesis and the SAR of these compounds are discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.