SYNTHESIS AND ANTI-HIV ACTIVITY OF 4′-MODIFIED CYCLOPENTENYL PYRIMIDINE C-NUCLEOSIDES

被引：5

作者：

Liu, Lian Jin ^{[1
]}

Hong, Joon Hee ^{[1
]}

机构：

[1] Chosun Univ, Coll Pharm, Project Team BK21, Kwangju 501759, South Korea

来源：

NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS | 2009年 / 28卷 / 04期

关键词：

Cyclopentenyl C-nucleoside; antiviral agents; S(N)2 alkylation; ANTIVIRAL ACTIVITY; ENANTIOSELECTIVE SYNTHESIS; CARBOCYCLIC ANALOGS; 9-DEAZAADENOSINE; ANTITUMOR; CYTIDINE;

D O I：

10.1080/15257770902946058

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 syntheses of 4-modified cyclopentenyl pyrimidine C-nucleosides were performed via C-C bond formation using S(N)2 alkylation via the key intermediate mesylates 6 and 16, which were prepared,from acyclic ketone derivatives. When antiviral evaluation of synthesized, compound was performed against various viruses such as HIV-1, HSV-1 and HSV-2, isocytidine analogue 20 showed, moderate anti-HIV activity in CEM cell line (EC50 = 13.1 mu mol).

引用

页码：303 / 314

页数：12

共 50 条

[1] Enantioselective synthesis and antiviral activity of purine and pyrimidine cyclopentenyl C-nucleosides
Rao, Jagadeeshwar R.
Schinazi, Raymond F.
Chu, Chung K.
BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (02) : 839 - 846
[2] Simple synthesis and anti-HIV activity of novel 3'-vinyl branched apiosyl pyrimidine nucleosides
Oh, Chang Hyun
Kim, Jin Woo
Hong, Joon Hee
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2006, 25 (08) : 871 - 878
[3] New acyclic quinoxaline nucleosides. Synthesis and anti-HIV activity
Ali, Ibrahim A. I.
Al-Masoudi, Iman A.
Aziz, Nazik M.
Al-Masoudi, Najim A.
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2008, 27 (02) : 146 - 156
[4] Synthesis, Anti-HIV Activity Studies, and in silico Rationalization of Cyclobutane-Fused Nucleosides
Figueras, Antoni
Miralles-Lluma, Rosa
Flores, Ramon
Rustullet, Albert
Busque, Felix
Figueredo, Marta
Font, Josep
Alibes, Ramon
Marechal, Jean-Didier
CHEMMEDCHEM, 2012, 7 (06) : 1044 - 1056
[5] Synthesis and Anti-HIV Evaluation of 3'-Triazolo Nucleosides
Roy, Vincent
Obikhod, Aleksandr
Zhang, Hong-Wang
Coats, Steven J.
Herman, Brian D.
Sluis-Cremer, Nicolas
Agrofoglio, Luigi A.
Schinazi, Raymond F.
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2011, 30 (04) : 264 - 270
[6] Synthesis and Antiviral Activity of Novel Thieno[2,3-d]pyrimidine Hydrazones and Their C-Nucleosides
R. R. Khattab
A. A. Hassan
O. M. Kutkat
K. M. Abuzeid
N. A. Hassan
Russian Journal of General Chemistry, 2019, 89 : 1707 - 1717
[7] Synthesis and Antiviral Activity of Novel Thieno[2,3-d]pyrimidine Hydrazones and Their C-Nucleosides
Khattab, R. R.
Hassan, A. A.
Kutkat, O. M.
Abuzeid, K. M.
Hassan, N. A.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2019, 89 (08) : 1707 - 1717
[8] Synthesis of Modified C-Nucleosides of Therapeutic Significant: A Succinct Account
Hudait, Nandagopal
Sakander, Norein
Kundu, Sanchari
Rasool, Bisma
Sengupta, Jhimli
Mukherjee, Debaraj
SYNLETT, 2024, 35 (06) : 635 - 648
[9] Synthesis and In-vitro Activity of 4′-Modified Analogues of ddA as Potent Anti-HIV Agents
Hong, Joon Hee
Oh, Chang Hyun
ARCHIV DER PHARMAZIE, 2009, 342 (10) : 600 - 604
[10] Approaches to the synthesis of heterocyclic C-nucleosides
Mukhin, E. M.
Savateev, K. V.
Rusinov, V. L.
RUSSIAN CHEMICAL BULLETIN, 2023, 72 (02) : 425 - 481

← 1 2 3 4 5 →