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

[41] Electronic Structure of the Azide Group in 3′-Azido-3′-deoxythymidine (AZT) Compared to Small Azide Compounds
Chen, Fang-Fang
Wang, Feng
MOLECULES, 2009, 14 (07): : 2656 - 2668
[42] Inhibition of cell growth and telomerase activity of breast cancer cells in vitro by 3′-azido-3′-deoxythymidine
Melana, SM
Holland, JF
Pogo, BGT
CLINICAL CANCER RESEARCH, 1998, 4 (03) : 693 - 696
[43] 3'-Azido-3'-deoxythymidine (AZT) induces apoptosis and alters metabolic enzyme activity in human placenta
Collier, AC
Helliwell, RJA
Keelan, JA
Paxton, JW
Mitchell, MD
Tingle, MD
TOXICOLOGY AND APPLIED PHARMACOLOGY, 2003, 192 (02) : 164 - 173
[44] SYNTHESIS, IN-VITRO BIOLOGICAL STABILITY, AND ANTI-HIV ACTIVITY OF 6-HALO-6-ALKOXY(OR AZIDO)-5,6-DIHYDRO-3'-AZIDO-3'-DEOXYTHYMIDINE DIASTEREOMERS AS POTENTIAL PRODRUGS TO 3'-AZIDO-3'-DEOXYTHYMIDINE (AZT)
KUMAR, R
WANG, LL
WIEBE, LI
KNAUS, EE
JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (25) : 4297 - 4306
[45] REDUCTION OF 3'-AZIDO-3'-DEOXYTHYMIDINE TO 3'-AMINO-3'-DEOXYTHYMIDINE IN HUMAN LIVER-MICROSOMES AND ITS RELATIONSHIP TO CYTOCHROME-P450
PLACIDI, L
CRETTON, EM
PLACIDI, M
SOMMADOSSI, JP
CLINICAL PHARMACOLOGY & THERAPEUTICS, 1993, 54 (02) : 168 - 176
[46] Amino acid phosphoramidate monoesters of 3′-azido-3′-deoxythymidine:: Relationship between antiviral potency and intracellular metabolism
Chang, SL
Griesgraber, W
Southern, PJ
Wagner, CR
JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (02) : 223 - 231
[47] Synthesis, properties, and Anti-HIV activity of new lipophilic 3′-azido-3′-deoxythymidine conjugates containing functional phosphoric linkages
N. S. Shastina
T. Yu. Maltseva
L. N. D’yakova
O. A. Lobach
M. S. Chataeva
D. N. Nosik
V. I. Shvetz
Russian Journal of Bioorganic Chemistry, 2013, 39 : 161 - 169
[48] Synthesis, properties, and Anti-HIV activity of new lipophilic 3'-azido-3'-deoxythymidine conjugates containing functional phosphoric linkages
Shastina, N. S.
Maltseva, T. Yu
D'yakova, L. N.
Lobach, O. A.
Chataeva, M. S.
Nosik, D. N.
Shvetz, V. I.
RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY, 2013, 39 (02) : 161 - 169
[49] Synthesis, structure-activity relationship studies using density functional theory and in silico molecular docking on substituted benzohydrazide derivatives
Gurubasavaraj, Prabhuodeyara M.
Sajjan, Vinodkumar P.
Munoz-Flores, Blanca M.
Perez, Victor M. Jimenez
Patil, Dhanashree
Patil, Parutagouda Shankaragouda
Gummagol, Neelamma B.
JOURNAL OF MOLECULAR STRUCTURE, 2024, 1299
[50] SOME NOVEL NUCLEOSIDE REARRANGEMENTS EFFECTED BY (DIETHYLAMINO)SULPHUR TRIFLUORIDE - SYNTHESIS AND ANTIVIRAL PROPERTIES OF SOME FLUORINE-CONTAINING 3'-AZIDO-3'-DEOXYTHYMIDINE DERIVATIVES
LLOYD, AE
COE, PL
WALKER, RT
HOWARTH, OW
JOURNAL OF FLUORINE CHEMISTRY, 1993, 62 (2-3) : 145 - 160

← 1 2 3 4 5 →