SYNTHESIS AND ANTI-HIV ACTIVITY OF NOVEL 2′-Deoxy-2′-β-Fluoro-THREOSYL NUCLEOSIDE PHOSPHONIC ACID ANALOGUES

被引：4

作者：

Kim, Seyeon ^{[1
]}

Hong, Joon Hee ^{[1
]}

机构：

[1] Chosun Univ, Coll Pharm, Project Team BK 21, Kwangju 501759, South Korea

来源：

NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS | 2015年 / 34卷 / 12期

关键词：

Anti-HIV agents; 2-deoxy-2-fluoro-threose-phosphonic acid analogue; Vorbruggen reaction; VIRUS; GS-9148; DNA;

D O I：

10.1080/15257770.2015.1076840

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Novel 2-deoxy-2--fluoro-threose purine phosphonic acid analogues were designed and racemically synthesized from 2-propanone-1,3-diacetate. Condensation successfully proceeded from a glycosyl donor 9 under Vorbruggen conditions. Cross-metathesis of vinyl analogues 13 and 23 with diethyl vinylphosphonate yielded the desired nucleoside phosphonate analogues 14 and 24, respectively. Ammonolysis and hydrolysis of phosphonates yielded the nucleoside phosphonic acid analogues 16, 19, 26, and 29. The synthesized nucleoside analogues were subjected to antiviral screening against human immunodeficiency virus (HIV)-1. Adenine analogue 18 exhibited weak in vitro activities against human immunodeficiency virus (HIV)-1.

引用

页码：815 / 833

页数：19

共 50 条

[41] In vitro and in vivo antitumor activity of a novel nucleoside, 4'-thio-2'-deoxy-2'-methylidenecytidine
Miura, S
Tanaka, M
Yoshimura, Y
Satoh, H
Sakata, S
Machida, H
Matsuda, A
Sasaki, T
BIOLOGICAL & PHARMACEUTICAL BULLETIN, 1996, 19 (10) : 1311 - 1315
[42] SYNTHESIS　OF　DI－（2＇－DEOXY－2＇－FLUORO）PYRIMIDINENUCLEOSIDE　PHOSPHATES　AND　PHOSPHOROTIOATES
Zheng Fu WANG
Yi Bing ZHANG
Yao Quan CHEN (Laboratory of Bio-organic and Natural Products Chemistry Shanghai Institute of Organic Chemistry
Chinese Chemical Letters, 1994, (11) : 917 - 920
[43] Synthesis and antiviral activity of L-2′-deoxy-2′-up-fluoro-4′-thionucleosides
Jeong, LS
Moon, HR
Yoo, SJ
Lee, SN
Kim, HD
Chun, MW
NUCLEOSIDES & NUCLEOTIDES, 1999, 18 (4-5): : 571 - 572
[44] SYNTHESIS AND ANTIPROLIFERATIVE AND ANTIVIRAL ACTIVITY OF 2'-DEOXY-2'-FLUOROARABINOFURANOSYL ANALOGS OF THE NUCLEOSIDE ANTIBIOTICS TOYOCAMYCIN AND SANGIVAMYCIN
KRAWCZYK, SH
NASSIRI, MR
KUCERA, LS
KERN, ER
PTAK, RG
WOTRING, LL
DRACH, JC
TOWNSEND, LB
JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (20) : 4106 - 4114
[45] An efficient and scalable synthesis of arabinosylguanine and 2'-deoxy-2'-fluoro-guanosine
Ross, BS
Springer, RH
Sprankle, KG
Vasquez, G
NUCLEOSIDES & NUCLEOTIDES, 1997, 16 (7-9): : 1645 - 1647
[46] NOVEL MECHANISM OF ACTION OF NUCLEOSIDE ANALOGS WITH ANTI-HIV ACTIVITY
BUCKHEIT, RW
GERMANY, JM
SHANNON, W
JOURNAL OF ACQUIRED IMMUNE DEFICIENCY SYNDROMES, 1991, 4 (03) : 351 - 351
[47] Synthesis and anti-HIV activity of L-2′-fluoro-2′,3′-unsaturated purine nucleosides
Choi, YS
Lee, KO
Hong, JH
Schinazi, RF
Chu, CK
TETRAHEDRON LETTERS, 1998, 39 (25) : 4437 - 4440
[48] Synthesis and anti-HIV activity of glutamate-nucleoside conjugates
Agarwal, Hitesh Kumar
Doncel, Gustavo F.
Parang, Keykavous
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238
[49] Novel β-L-1,3-thiazolidine pyrimidine nucleoside analogues: Design, synthesis, molecular docking, and anti-HIV activity
Sriharsha, Shimoga Nagaraj
Jainab, N. . Habeela
Biradar, Mahalakshmi Suresha
Thapa, Shankar
Venkatesh, E. S.
Bidye, Durgesh Paresh
Pujar, Gurubasavaraj
Dixit, Sheshagiri
JOURNAL OF MOLECULAR STRUCTURE, 2023, 1294
[50] CHEMISTRY AND ANTI-HIV ACTIVITY OF 2'-BETA-FLUORO-2',3'-DIDEOXYGUANOSINE
FORD, H
DRISCOLL, JS
SIDDIQUI, M
KELLEY, JA
MITSUYA, H
SHIRASAKA, T
JOHNS, DG
MARQUEZ, VE
NUCLEOSIDES & NUCLEOTIDES, 1994, 13 (1-3): : 213 - 234

← 1 2 3 4 5 →