BIOMAT Database Logo BIOMAT Database Logo

Synthesis and biological evaluation of novel C5 halogen-functionalized S-DABO as potent HIV-1 non-nucleoside reverse transcriptase inhibitors. 2010

Hua Qin, and Chang Liu, and Ying Guo, and Ruiping Wang, and Jianfang Zhang, and Liying Ma, and Zhili Zhang, and Xiaowei Wang, and Yuxin Cui, and Junyi Liu
State key Laboratory of National and Biomimetic Drug, Peking University, Beijing 100191, PR China.

A series of novel S-DABO analogues (4a1-5a12) have been synthesized by an efficient method and evaluated as inhibitors of human immunodeficiency virus type-1 (HIV-1). The biological testing results clearly indicated that the substitution of halogen at the C5 position of pyrimidine ring could increase the anti-HIV-1 RT activity. The most active compounds showed activity in the low micromole range with IC(50) values (IC(50) 0.18-3.03 microM) comparable to nevirapine (IC(50) 4.12 microM). The docking showed that a new halogen bond was formed between halogen and carbonyl of TYR188 in the HIV-I RT.

UI MeSH Term Description Entries
D009682 Magnetic Resonance Spectroscopy Spectroscopic method of measuring the magnetic moment of elementary particles such as atomic nuclei, protons or electrons. It is employed in clinical applications such as NMR Tomography (MAGNETIC RESONANCE IMAGING). In Vivo NMR Spectroscopy,MR Spectroscopy,Magnetic Resonance,NMR Spectroscopy,NMR Spectroscopy, In Vivo,Nuclear Magnetic Resonance,Spectroscopy, Magnetic Resonance,Spectroscopy, NMR,Spectroscopy, Nuclear Magnetic Resonance,Magnetic Resonance Spectroscopies,Magnetic Resonance, Nuclear,NMR Spectroscopies,Resonance Spectroscopy, Magnetic,Resonance, Magnetic,Resonance, Nuclear Magnetic,Spectroscopies, NMR,Spectroscopy, MR
D011744 Pyrimidinones Heterocyclic compounds known as 2-pyrimidones (or 2-hydroxypyrimidines) and 4-pyrimidones (or 4-hydroxypyrimidines) with the general formula C4H4N2O. Pyrimidinone,Pyrimidone,Pyrimidones
D006219 Halogens A family of nonmetallic, generally electronegative, elements that form group 17 (formerly group VIIa) of the periodic table. Halogen,Group 17 Elements,Elements, Group 17
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D013455 Sulfur An element that is a member of the chalcogen family. It has an atomic symbol S, atomic number 16, and atomic weight [32.059; 32.076]. It is found in the amino acids cysteine and methionine. Sulfur-16,Sulfur 16
D015195 Drug Design The molecular designing of drugs for specific purposes (such as DNA-binding, enzyme inhibition, anti-cancer efficacy, etc.) based on knowledge of molecular properties such as activity of functional groups, molecular geometry, and electronic structure, and also on information cataloged on analogous molecules. Drug design is generally computer-assisted molecular modeling and does not include PHARMACOKINETICS, dosage analysis, or drug administration analysis. Computer-Aided Drug Design,Computerized Drug Design,Drug Modeling,Pharmaceutical Design,Computer Aided Drug Design,Computer-Aided Drug Designs,Computerized Drug Designs,Design, Pharmaceutical,Drug Design, Computer-Aided,Drug Design, Computerized,Drug Designs,Drug Modelings,Pharmaceutical Designs
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D015497 HIV-1 The type species of LENTIVIRUS and the etiologic agent of AIDS. It is characterized by its cytopathic effect and affinity for the T4-lymphocyte. Human immunodeficiency virus 1,HIV-I,Human Immunodeficiency Virus Type 1,Immunodeficiency Virus Type 1, Human
D054303 HIV Reverse Transcriptase A reverse transcriptase encoded by the POL GENE of HIV. It is a heterodimer of 66 kDa and 51 kDa subunits that are derived from a common precursor protein. The heterodimer also includes an RNAse H activity (RIBONUCLEASE H, HUMAN IMMUNODEFICIENCY VIRUS) that plays an essential role the viral replication process. Reverse Transcriptase, HIV,Reverse Transcriptase, Human Immunodeficiency Virus,Transcriptase, HIV Reverse
D018894 Reverse Transcriptase Inhibitors Inhibitors of reverse transcriptase (RNA-DIRECTED DNA POLYMERASE), an enzyme that synthesizes DNA on an RNA template. Reverse Transcriptase Inhibitor,Inhibitors, Reverse Transcriptase,Inhibitor, Reverse Transcriptase,Transcriptase Inhibitor, Reverse

Related Publications

Hua Qin, and Chang Liu, and Ying Guo, and Ruiping Wang, and Jianfang Zhang, and Liying Ma, and Zhili Zhang, and Xiaowei Wang, and Yuxin Cui, and Junyi Liu
Non-nucleoside HIV-1 reverse transcriptase inhibitors: synthesis and biological evaluation of novel quinoxalinylethylpyridylthioureas as potent antiviral agents.
March 2000, Antiviral chemistry & chemotherapy,
Hua Qin, and Chang Liu, and Ying Guo, and Ruiping Wang, and Jianfang Zhang, and Liying Ma, and Zhili Zhang, and Xiaowei Wang, and Yuxin Cui, and Junyi Liu
Synthesis and biological evaluation of (±)-benzhydrol derivatives as potent non-nucleoside HIV-1 reverse transcriptase inhibitors.
August 2011, Bioorganic & medicinal chemistry,
Hua Qin, and Chang Liu, and Ying Guo, and Ruiping Wang, and Jianfang Zhang, and Liying Ma, and Zhili Zhang, and Xiaowei Wang, and Yuxin Cui, and Junyi Liu
Synthesis and biological evaluation of imidazole thioacetanilides as novel non-nucleoside HIV-1 reverse transcriptase inhibitors.
August 2009, Bioorganic & medicinal chemistry,
Hua Qin, and Chang Liu, and Ying Guo, and Ruiping Wang, and Jianfang Zhang, and Liying Ma, and Zhili Zhang, and Xiaowei Wang, and Yuxin Cui, and Junyi Liu
Synthesis and biological evaluation of aryl-phospho-indole as novel HIV-1 non-nucleoside reverse transcriptase inhibitors.
January 2011, Journal of medicinal chemistry,
Hua Qin, and Chang Liu, and Ying Guo, and Ruiping Wang, and Jianfang Zhang, and Liying Ma, and Zhili Zhang, and Xiaowei Wang, and Yuxin Cui, and Junyi Liu
Development of novel S-N3-DABO derivatives as potent non-nucleoside reverse transcriptase inhibitors with improved potency and selectivity.
February 2023, European journal of medicinal chemistry,
Hua Qin, and Chang Liu, and Ying Guo, and Ruiping Wang, and Jianfang Zhang, and Liying Ma, and Zhili Zhang, and Xiaowei Wang, and Yuxin Cui, and Junyi Liu
Synthesis and biological evaluations of sulfanyltriazoles as novel HIV-1 non-nucleoside reverse transcriptase inhibitors.
August 2006, Bioorganic & medicinal chemistry letters,
Hua Qin, and Chang Liu, and Ying Guo, and Ruiping Wang, and Jianfang Zhang, and Liying Ma, and Zhili Zhang, and Xiaowei Wang, and Yuxin Cui, and Junyi Liu
Synthesis and biological evaluation of CHX-DAPYs as HIV-1 non-nucleoside reverse transcriptase inhibitors.
June 2014, Bioorganic & medicinal chemistry,
Hua Qin, and Chang Liu, and Ying Guo, and Ruiping Wang, and Jianfang Zhang, and Liying Ma, and Zhili Zhang, and Xiaowei Wang, and Yuxin Cui, and Junyi Liu
Novel tight binding PETT, HEPT and DABO-based non-nucleoside inhibitors of HIV-1 reverse transcriptase.
August 2006, Journal of enzyme inhibition and medicinal chemistry,
Hua Qin, and Chang Liu, and Ying Guo, and Ruiping Wang, and Jianfang Zhang, and Liying Ma, and Zhili Zhang, and Xiaowei Wang, and Yuxin Cui, and Junyi Liu
Design, synthesis, and biological evaluations of novel quinolones as HIV-1 non-nucleoside reverse transcriptase inhibitors.
August 2006, Bioorganic & medicinal chemistry letters,
Hua Qin, and Chang Liu, and Ying Guo, and Ruiping Wang, and Jianfang Zhang, and Liying Ma, and Zhili Zhang, and Xiaowei Wang, and Yuxin Cui, and Junyi Liu
Design, synthesis, and evaluation of diarylpyridines and diarylanilines as potent non-nucleoside HIV-1 reverse transcriptase inhibitors.
December 2010, Journal of medicinal chemistry,
Copied contents to your clipboard!