Quantitative Structure-Activity Relationship and Density Functional Theory Studies on Some Derivatives of 3′-Azido-3′-Deoxythymidine

被引：3

作者：

Al-Masoudi, Najim A. ^{[2
]}

Essa, Ali H. ^{[1
]}

机构：

[1] Univ Basrah, Dept Chem, Coll Sci, Basrah 42010, Iraq

[2] Univ Konstanz, Fachbereich Chem, D-78457 Constance, Germany

来源：

JOURNAL OF COMPUTATIONAL AND THEORETICAL NANOSCIENCE | 2008年 / 5卷 / 11期

关键词：

3'-Azido-3'-Deoxythymidine (AZT); Density Functional Theory (DFT); QSAR; Semi-Empirical AM1 Method;

D O I：

10.1166/jctn.2008.1122

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The QSAR and DFT properties of eleven derivatives of azidothymidine (AZT) substituted by thio and methyl groups at C-5' as well as AZT itself have been investigated theoretically by applying semiempirical molecular orbital theory and density functional theory (B3LYP/6-31G**). The substituents are: OH, H, SH, SCl, SF3, SCN, SOMe, SO2Me, SMe, SSMe, SCOMe, SEt, and SO2Et. The result indicates that the selected analogues possess the same electronic properties, and some show higher activity than AZT.

引用

页码：2216 / 2220

页数：5

共 50 条

[21] INFLUENCE OF TEMPLATE PRIMARY STRUCTURE ON 3'-AZIDO-3'-DEOXYTHYMIDINE TRIPHOSPHATE INCORPORATION INTO DNA
BRIDGES, EG
LEBOEUF, RB
WEIDNER, DA
SOMMADOSSI, JP
ANTIVIRAL RESEARCH, 1993, 21 (02) : 93 - 102
[22] Synthesis and antiretroviral evaluation of new alkoxy and aryloxy phosphate derivatives of 3'-azido-3'-deoxythymidine
Tsotinis, A
Calogeropoulou, T
Koufaki, M
Souli, C
Balzarini, J
DeClercq, E
Makriyannis, A
JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (17) : 3418 - 3422
[23] SYNTHETIC AND ANTIVIRAL STUDIES OF CERTAIN ACYCLIC 3'-AZIDO-3'-DEOXYTHYMIDINE (AZT) ANALOGS
LEE, KH
CHEN, YL
HUANG, BR
TZENG, CC
ZHU, QY
CHOU, TC
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 1991, 10 (06): : 1407 - 1416
[24] Quantitative Structure-activity Relationship Studies and Nonlinear Optical Properties of 2-Phenylbenzofuran Derivatives: A Density Functional Theory Study
Benhalima, N.
Touhami, M.
Khelfaoui, F.
Cherif, F. Yahia
Chouaih, A. K.
PHYSICAL CHEMISTRY RESEARCH, 2022, 10 (01): : 105 - 125
[25] STRUCTURE AND CONFORMATION OF 3'-AZIDO-3'-DEOXYTHYMIDINE (AZT), AN INHIBITOR OF THE HIV (AIDS) VIRUS
BIRNBAUM, GI
GIZIEWICZ, J
GABE, EJ
LIN, TS
PRUSOFF, WH
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1987, 65 (09): : 2135 - 2139
[26] Density Functional Theory Based Quantitative Structure-Activity Relationship Study of Cycloguanil Derivatives Acting as Plasmodium falciparum
Hmamouchi, Rachid
Larif, Majdouline
Chtita, Samir
Bouachrine, Mohammed
Lakhlifi, Tahar
MOROCCAN JOURNAL OF CHEMISTRY, 2016, 4 (04): : 1061 - 1075
[27] SYNTHESIS AND ANTI-HIV ACTIVITY OF STEROIDAL PRODRUGS OF 3'-AZIDO-3'-DEOXYTHYMIDINE (AZT)
BALAGOPALA, MI
OLLAPALLY, AP
LEE, HJ
CELLULAR AND MOLECULAR BIOLOGY, 1995, 41 : S1 - S7
[28] ANTIBACTERIAL ACTIVITY AND MECHANISM OF ACTION OF 3'-AZIDO-3'-DEOXYTHYMIDINE (BW-A509U)
ELWELL, LP
FERONE, R
FREEMAN, GA
FYFE, JA
HILL, JA
RAY, PH
RICHARDS, CA
SINGER, SC
KNICK, VB
RIDEOUT, JL
ZIMMERMAN, TP
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1987, 31 (02) : 274 - 280
[29] Phosphoramidate conjugates of 3′-azido-3′-deoxythymidine glycerolipid derivatives and amino acid esters: synthesis and anti-HIV activity
Elizaveta S. Darnotuk
Andrei E. Siniavin
Nikolay V. Shulga
Eduard V. Karamov
Natal’ya S. Shastina
Medicinal Chemistry Research, 2021, 30 : 664 - 671
[30] Synthesis and anti-HIV activities of bis-(cycloSaligenyl) pronucleotides derivatives of 3′-fluoro-3′-deoxythymidine and 3′-azido-3′-deoxythymidine
Ahmadibeni, Yousef
Tiwari, Rakesh
Swepson, Chelsie
Pandhare, Jui
Dash, Chandravanu
Doncel, Gustavo F.
Parang, Keykavous
TETRAHEDRON LETTERS, 2011, 52 (07) : 802 - 805

← 1 2 3 4 5 →