Design and Synthesis of Bicyclo[4.3.0]nonene Nucleoside Analogues

被引：0

作者：

Scheeff, Stephan ^{[1
]}

Wang, Yan ^{[2
,5
]}

Lyu, Mao-Yun ^{[1
]}

Ahmadabadi, Behzad Nasiri ^{[2
,5
]}

Hau, Sam Chun Kit ^{[3
]}

Hui, Tony K. C. ^{[4
]}

Zhang, Yufeng ^{[1
]}

Zuo, Zhong ^{[1
]}

Chan, Renee Wan Yi ^{[2
,5
,6
,7
]}

Ng, Billy Wai-Lung ^{[1
,6
]}

机构：

[1] Chinese Univ Hong Kong, Fac Med, Sch Pharm, Shatin, Hong Kong, Peoples R China

[2] Chinese Univ Hong Kong, Fac Med, Dept Paediat, Shatin, Hong Kong, Peoples R China

[3] Chinese Univ Hong Kong, Dept Chem, Shatin, Hong Kong, Peoples R China

[4] Primemax Biotech Ltd, Shatin, Hong Kong, Peoples R China

[5] Chinese Univ Hong Kong, Hong Kong Hub Paediat Excellence, Kowloon Bay, Hong Kong, Peoples R China

[6] Chinese Univ Hong Kong, Li Ka Shing Inst Hlth Sci, Fac Med, Shatin, Hong Kong, Peoples R China

[7] Chinese Univ Hong Kong, Fac Med, SH Ho Res Ctr Infect Dis, Shatin, Hong Kong, Peoples R China

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 50期

关键词：

DIELS-ALDER REACTIONS; CARBOCYCLIC NUCLEOSIDES; SUGAR RING; POTENT; DISCOVERY; CRYSTAL; FORMS;

D O I：

10.1021/acs.orglett.3c03590

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nucleoside analogues are effective antiviral agents, and the continuous emergence of pathogenic viruses demands the development of novel and structurally diverse analogues. Here, we present the design and synthesis of novel nucleoside analogues with a carbobicyclic core, which mimics the conformation of natural ribonucleosides. Employing a divergent synthetic route featuring an intermolecular Diels-Alder reaction, we successfully synthesized carbobicyclic nucleoside analogues with high antiviral efficacy against respiratory syncytial virus.

引用

页码：9002 / 9007

页数：6

共 50 条

[1] Synthesis of complex carbobicyclic compounds from sugar allyltins: functionalization of the allylic position in bicyclo[4.3.0]nonene derivatives
Jarosz, S
Boryczko, B
Cmoch, P
Gomez, AM
Lopez, C
TETRAHEDRON-ASYMMETRY, 2005, 16 (02) : 513 - 518
[2] SYNTHESIS OF 1-BICYCLO[3.2.2]NONENE AND 1(7)-BICYCLO[3.2.2]NONENE BY INTRAMOLECULAR WITTIG REACTION
BECKER, KB
CHAPPUIS, JL
HELVETICA CHIMICA ACTA, 1980, 63 (07) : 1812 - 1822
[3] Synthesis of Complex Bicyclo[4.3.0]nonene Derivatives from Sugar Allyltins; Sugar Mimetics Derived from D-Glucose
Jarosz, S.
Jedra, S.
POLISH JOURNAL OF CHEMISTRY, 2009, 83 (10) : 1757 - 1764
[4] Synthesis of Novel Nucleoside Analogues Built on a Bicyclo[4.1.0]heptane Scaffold
Dominguez-Perez, Beatriz
Ferrer, Eric
Figueredo, Marta
Marechal, Jean-Didier
Balzarini, Jan
Alibes, Ramon
Busque, Felix
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (19): : 9495 - 9505
[5] Chemoenzymatic synthesis of carbocyclic nucleoside analogues with bicyclo[3.1.0]hexyl residues
Theil, F
Ballschuh, S
vonJantaLipinski, M
Johnson, RA
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (03): : 255 - 258
[6] Chemoenzymatic synthesis of carbocyclic nucleoside analogues with bicyclo[3.1.0]hexyl residues
Theil, F.
Ballschuh, S.
Von Janta-Lipinski, M.
Johnson, R. A.
Jornal of the Chemical Society. Perkin Transactions 1, (03):
[7] EFFECTS OF ANNULATION ON THE MASS-SPECTRAL BEHAVIOR OF BICYCLO[4.3.0]-3-NONENE DERIVATIVES - ALDEHYDES
TURECEK, F
HANUS, V
ORGANIC MASS SPECTROMETRY, 1979, 14 (11): : 618 - 623
[8] Synthesis and structure of a bicyclo[2.4.0]-2-nonene
Mague, JT
Ensley, HE
Chen, GQ
JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, 2001, 31 (7-8) : 363 - 367
[9] THE SYNTHESIS OF 2 BICYCLO[4.3.0]NONANE DERIVATIVES
BIRD, CW
COOPER, R
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1993, 25 (02) : 237 - 240
[10] Synthesis and structure of a bicyclo[2.4.0]-2-nonene
Joel T. Mague
Harry E. Ensley
Guoqing Chen
Journal of Chemical Crystallography, 2001, 31 : 363 - 367

← 1 2 3 4 5 →