Synthesis of conformationally constrained spirodihydrofuropyridine analogues of epibatidine

被引：14

作者：

Abe, H ^{[1
]}

Arai, Y ^{[1
]}

Aoyagi, S ^{[1
]}

Kibayashi, C ^{[1
]}

机构：

[1] Tokyo Univ Pharm & Life Sci, Sch Pharm, Tokyo 1920392, Japan

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 14期

关键词：

D O I：

10.1016/S0040-4039(03)00395-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Conformationally constrained spirofuropyridine analogues of epibatidine, syn-2 and anti-2, in which the 7-azabicyclo[2.2.1]heptane system and the 2-chloropyridine ring are held rigidly with the shorter and longer N-N distances, respectively, were synthesized from N-Boc-7-azabicyclo[2.2.1]heptan-2-one. The preliminary binding studies suggested that syn-2 has stronger binding affinity for nAChRs than anti-2. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：2971 / 2973

页数：3

共 33 条

[1] Enantioselective approach to 7-azabicyclo[2.2.1]heptane ring systems using D-(-)-quinic acid as the chiral educt: Application to the formal synthesis of (+)-epibatidine
Albertini, E
Barco, A
Benetti, S
DeRisi, C
Pollini, GP
Zanirato, V
[J]. TETRAHEDRON LETTERS, 1997, 38 (04) : 681 - 684
[2] Synthesis of enantiopure analogues of 3-hydroxyproline and derivatives
Avenoza, A
Barriobero, JI
Busto, JH
Cativiela, C
Peregrina, JM
[J]. TETRAHEDRON-ASYMMETRY, 2002, 13 (06) : 625 - 632
[3] Synthesis, activity and theoretical study of ABT-418 analogues
Avenoza, A
Busto, JH
Cativiela, C
Dordal, A
Frigola, J
Peregrina, JM
[J]. TETRAHEDRON, 2002, 58 (22) : 4505 - 4511
[4] BADIO B, 1994, MOL PHARMACOL, V45, P563
[5] Mono- and disubstituted-3,8-diazabicyclo[3.2.1]octane derivatives as analgesics structurally related to epibatidine: Synthesis, activity, and modeling
Barlocco, D
Cignarella, G
Tondi, D
Vianello, P
Villa, S
Bartolini, A
Ghelardini, C
Galeotti, N
Anderson, DJ
Kuntzweiler, TA
Colombo, D
Toma, L
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (05) : 674 - 681
[6] Approaches to the synthesis of (+)- and (-)-epibatidine
Barros, MT
Maycock, CD
Ventura, MR
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (02): : 166 - 173
[7] Neuronal nAChR stereoselectivity to non-natural epibatidine derivatives
Bertrand, S
Patt, JT
Spang, JE
Westera, G
Schubiger, PA
Bertrand, D
[J]. FEBS LETTERS, 1999, 450 (03): : 273 - 279
[8] Synthesis of bridged analogs of epibatidine. 3-chloro-5,7,8,9,9a,10-hexahydro-7,10-methanopyrrolo[1,2-b]-2,6-naphthyridine and 2-chloro-5,5a,6,7,8,10-hexahydro-5,8-methanopyrrolo[2,1-b]-1,7-naphthyridine
Brieaddy, LE
Mascarella, SW
Navarro, HA
Atkinson, RN
Damaj, MI
Martin, BR
Carroll, FI
[J]. TETRAHEDRON LETTERS, 2001, 42 (23) : 3795 - 3797
[9] An expeditious formal synthesis of(-)-epibalidine
Cabanal-Duvillard, I
Berrien, JF
Royer, J
[J]. TETRAHEDRON-ASYMMETRY, 2000, 11 (12) : 2525 - 2529
[10] A formal asymmetric synthesis of (-)-epibatidine using a highly diastereoselective hetero Diels-Alder reaction
Cabanal-Duvillard, I
Berrien, JF
Ghosez, L
Husson, HP
Royer, J
[J]. TETRAHEDRON, 2000, 56 (23) : 3763 - 3769

← 1 2 3 4 →