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 50 条

[1] Synthesis of conformationally constrained lysine analogues
Ganorkar, Rakesh
Natarajan, Amarnath
Mamai, Ahmed
Madalengoitia, Jose S.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (13): : 5004 - 5007
[2] Design and synthesis of conformationally constrained glucagon analogues
Trivedi, D
Lin, Y
Ahn, JM
Siegel, M
Mollova, NN
Schram, KH
Hruby, VJ
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (09) : 1714 - 1722
[3] Synthesis of conformationally constrained analogues of RGD tripeptide
Kumar, Sukeerthi
Wang, Qian
Sasaki, N. Andre
[J]. TETRAHEDRON, 2007, 63 (09) : 2084 - 2092
[4] Asymmetric synthesis of conformationally constrained 4-hydroxyprolines and their applications to the formal synthesis of (+)-epibatidine
Avenoza, A
Cativiela, C
Fernández-Recio, MA
Peregrina, JM
[J]. TETRAHEDRON-ASYMMETRY, 1999, 10 (20) : 3999 - 4007
[5] Design and stereoselective synthesis of conformationally constrained analogues of zimeldine
Cho, WJ
Grunewald, GL
[J]. ARCHIVES OF PHARMACAL RESEARCH, 1996, 19 (02) : 168 - 170
[6] The synthesis of conformationally constrained analogues of the ACE inhibitor Idrapril
Jones, IG
Jones, W
North, M
[J]. TETRAHEDRON, 1999, 55 (01) : 279 - 290
[7] Synthesis and chromatographic resolution of conformationally constrained analogues of homotaurine
Fulco, Maria Carmela
Marinozzi, Maura
Ergun, Burcu Caliskan
Sardella, Roccaldo
Natalini, Benedetto
Pellicciari, Roberto
[J]. TETRAHEDRON, 2009, 65 (42) : 8756 - 8762
[8] Azabicycloalkenes as synthetic intermediates - Synthesis of conformationally constrained glutamate analogues
Maison, Wolfgang
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (14) : 2276 - 2284
[9] Synthesis of (+/-)-epibatidine and its analogues
Bai, DG
Xu, R
Chu, GH
Zhu, XG
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (14): : 4600 - 4606
[10] Synthesis of functionally diverse and conformationally constrained polycyclic analogues of proline and prolinol
Hanessian, S
Papeo, G
Angiolini, M
Fettis, K
Beretta, M
Munro, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (19): : 7204 - 7218

← 1 2 3 4 5 →