8-aminobicyclo[3.2.1]octanes: synthesis and anti-viral activity

被引：8
|
作者：
Miller, JA [1 ]
Ullah, GM [1 ]
Welsh, GM [1 ]
Hall, AC [1 ]
机构：
[1] Wellcome Res Labs, Dept Med Chem, Beckenham BR3 3BS, Kent, England
来源：
TETRAHEDRON LETTERS | 2001年 / 42卷 / 42期
关键词：
allyl cation; 3+2] cycloaddition; 8-aminobicyclo[3.2.1]octanes and 6-enes; anti-viral activity versus influenza-A and -B; respiratory syncytial virus;
D O I：
10.1016/S0040-4039(01)01593-3
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of 8-chlorobicyclo[3,2,1]oct-6-enes has been prepared from cyclohexenyl chlorides and simple alkynes via a one-step [3+2] cycloaddition methodology. and then converted into the corresponding bicyclic amines. Against influenza-A virus a number of these showed in vitro activity. and amine (2) was comparable to amantadine in vivo. Good activity against influenza-B virus was less common, and none of the amines showed high potency against both viruses. Amines (20) and (23) showed significant activity versus respiratory syncytial virus. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：7503 / 7507
页数：5
相关论文
共 50 条
  • [1] Synthesis of a novel series of tetracyclic opioid antagonists incorporating an 8-aminobicyclo[3.2.1]oct-6-ene sub-unit
    Miller, JA
    Pope, SA
    Riddall, DR
    Ullah, GM
    Welsh, GM
    TETRAHEDRON LETTERS, 2003, 44 (46) : 8411 - 8415
  • [2] SYNTHESIS AND ANTI-VIRAL ACTIVITY OF HALOGENATED ADAMANTYLPHENOLS
    SHVEDOV, VI
    SAFONOVA, OA
    KORSAKOVA, IY
    BOGDANOVA, NS
    NIKOLAEVA, IS
    PETERS, VV
    PERSHIN, GN
    KHIMIKO-FARMATSEVTICHESKII ZHURNAL, 1980, 14 (02): : 54 - 57
  • [3] SYNTHESIS AND ANTI-VIRAL ACTIVITY OF REMANTADIN DERIVATIVES
    GRAVA, IY
    POLIS, YY
    LIDAK, MY
    INDULEN, MK
    ZAMYATINA, NA
    KHIMIKO-FARMATSEVTICHESKII ZHURNAL, 1980, 14 (10): : 42 - 45
  • [4] Synthesis and biological activity of 2-carbomethoxy-3-catechol-8-azabicyclo[3.2.1]octanes
    Meltzer, PC
    McPhee, M
    Madras, BK
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (22) : 4133 - 4137
  • [5] SYNTHESIS OF HBB ANALOGS WITH POTENTIAL ANTI-VIRAL ACTIVITY
    SAWLEWICZ, J
    SACZEWSKI, F
    ACTA POLONIAE PHARMACEUTICA, 1978, 35 (04): : 507 - 507
  • [6] ANTI-VIRAL ACTIVITY OF INTERFERONS
    FRIEDMAN, RM
    BACTERIOLOGICAL REVIEWS, 1977, 41 (03) : 543 - 567
  • [7] SYNTHESIS OF SOME 8-THIA-3-AZABICYCLO[3.2.1]OCTANES
    BALIAH, V
    CHANDRASEKHARAN, J
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1977, 15 (04): : 379 - 379
  • [8] SYNTHESIS OF SUBSTITUTED 6-AZA-8-OXABICYCLO[3.2.1]-OCTANES
    SINGH, SM
    SINGH, S
    RAO, RB
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1980, 19 (04): : 310 - 312
  • [9] SYNTHESIS AND ANTI-VIRAL ACTIVITY OF S-ALKYNYLDERIVATIVES OF MERCAPTOPURINES
    RATSINO, EV
    RADCHENKO, SI
    SHTILBANS, EB
    RACHKOVSKAYA, LA
    SOKOLOV, LB
    ALEXEEVA, GE
    SHNEIDER, MA
    KHIMIKO-FARMATSEVTICHESKII ZHURNAL, 1981, 15 (08): : 65 - 67
  • [10] Anti-Viral Activity of Indian Plants
    Dhawan, B. N.
    PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES INDIA SECTION B-BIOLOGICAL SCIENCES, 2012, 82 (01) : 209 - 224
12345