BIOMAT Database Logo BIOMAT Database Logo

Synthesis and evaluation of coumarin derivatives as potential dual-action HIV-1 protease and reverse transcriptase inhibitors. 2013

Temitope O Olomola, and Rosalyn Klein, and Nicodemus Mautsa, and Yasien Sayed, and Perry T Kaye
Department of Chemistry and Centre for Chemico- and Biomedicinal Research, Rhodes University, Grahamstown 6140, South Africa.

Baylis-Hillman-derived 3-(benzylaminomethyl)coumarins have been treated, sequentially, with chloroacetyl chloride and propargylamine to afford alkynylated coumarins as substrates for Click Chemistry reactions with azidothymidine (AZT) in the presence of a Cu(I) catalyst. The dual-action HIV-1 protease (PR) and reverse transcriptase (RT) inhibition potential of the resulting N-benzylated cycloaddition products, and a series of non-benzylated analogues, has been explored using saturation transfer difference (STD) NMR, computer modelling and enzyme inhibition techniques.

UI MeSH Term Description Entries
D008958 Models, Molecular Models used experimentally or theoretically to study molecular shape, electronic properties, or interactions; includes analogous molecules, computer-generated graphics, and mechanical structures. Molecular Models,Model, Molecular,Molecular Model
D003374 Coumarins Synthetic or naturally occurring substances related to coumarin, the delta-lactone of coumarinic acid. 1,2-Benzopyrone Derivatives,1,2-Benzopyrones,Coumarin Derivative,Coumarine,1,2-Benzo-Pyrones,Benzopyran-2-ones,Coumarin Derivatives,Coumarines,1,2 Benzo Pyrones,1,2 Benzopyrone Derivatives,1,2 Benzopyrones,Benzopyran 2 ones,Derivative, Coumarin,Derivatives, 1,2-Benzopyrone,Derivatives, Coumarin
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D015215 Zidovudine A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia. AZT (Antiviral),Azidothymidine,3'-Azido-2',3'-Dideoxythymidine,3'-Azido-3'-deoxythymidine,AZT Antiviral,AZT, Antiviral,BW A509U,BWA-509U,Retrovir,3' Azido 2',3' Dideoxythymidine,3' Azido 3' deoxythymidine,Antiviral AZT,BWA 509U,BWA509U
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
D015658 HIV Infections Includes the spectrum of human immunodeficiency virus infections that range from asymptomatic seropositivity, thru AIDS-related complex (ARC), to acquired immunodeficiency syndrome (AIDS). HTLV-III Infections,HTLV-III-LAV Infections,T-Lymphotropic Virus Type III Infections, Human,HIV Coinfection,Coinfection, HIV,Coinfections, HIV,HIV Coinfections,HIV Infection,HTLV III Infections,HTLV III LAV Infections,HTLV-III Infection,HTLV-III-LAV Infection,Infection, HIV,Infection, HTLV-III,Infection, HTLV-III-LAV,Infections, HIV,Infections, HTLV-III,Infections, HTLV-III-LAV,T Lymphotropic Virus Type III Infections, Human
D016333 HIV Protease Enzyme of the human immunodeficiency virus that is required for post-translational cleavage of gag and gag-pol precursor polyproteins into functional products needed for viral assembly. HIV protease is an aspartic protease encoded by the amino terminus of the pol gene. HIV Proteinase,HTLV-III Protease,p16 pol gene product, HIV,p16 protease, HIV,HIV p16 protease,HTLV III Protease,Protease, HIV,Protease, HTLV-III
D017320 HIV Protease Inhibitors Inhibitors of HIV PROTEASE, an enzyme required for production of proteins needed for viral assembly. HIV Protease Inhibitor,Inhibitor, HIV Protease,Inhibitors, HIV Protease,Protease Inhibitor, HIV,Protease Inhibitors, HIV
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

Temitope O Olomola, and Rosalyn Klein, and Nicodemus Mautsa, and Yasien Sayed, and Perry T Kaye
Fullerene derivatives as dual inhibitors of HIV-1 reverse transcriptase and protease.
January 2021, Bioorganic & medicinal chemistry letters,
Temitope O Olomola, and Rosalyn Klein, and Nicodemus Mautsa, and Yasien Sayed, and Perry T Kaye
Structure based design and evaluation of benzoheterocycle derivatives as potential dual HIV-1 protease and reverse transcriptase inhibitors.
January 2023, European journal of medicinal chemistry,
Temitope O Olomola, and Rosalyn Klein, and Nicodemus Mautsa, and Yasien Sayed, and Perry T Kaye
Synthesis and evaluation of oligo-1,3-thiazolecarboxamide derivatives as HIV-1 reverse transcriptase inhibitors.
May 2000, Bioorganic & medicinal chemistry,
Temitope O Olomola, and Rosalyn Klein, and Nicodemus Mautsa, and Yasien Sayed, and Perry T Kaye
Design and biological evaluation of cinnamic and phenylpropionic amide derivatives as novel dual inhibitors of HIV-1 protease and reverse transcriptase.
August 2021, European journal of medicinal chemistry,
Temitope O Olomola, and Rosalyn Klein, and Nicodemus Mautsa, and Yasien Sayed, and Perry T Kaye
Synthesis and evaluation of quinoxalinones as HIV-1 reverse transcriptase inhibitors.
August 2000, Bioorganic & medicinal chemistry letters,
Temitope O Olomola, and Rosalyn Klein, and Nicodemus Mautsa, and Yasien Sayed, and Perry T Kaye
Synthesis of novel uracil non-nucleoside derivatives as potential reverse transcriptase inhibitors of HIV-1.
November 2009, Archiv der Pharmazie,
Temitope O Olomola, and Rosalyn Klein, and Nicodemus Mautsa, and Yasien Sayed, and Perry T Kaye
Design, synthesis, and biological evaluation of novel 2H-pyran-2-one derivatives as potential HIV-1 reverse transcriptase inhibitors.
January 2015, Archiv der Pharmazie,
Temitope O Olomola, and Rosalyn Klein, and Nicodemus Mautsa, and Yasien Sayed, and Perry T Kaye
Design and synthesis of tetrahydrophthalimide derivatives as inhibitors of HIV-1 reverse transcriptase.
August 2013, Organic and medicinal chemistry letters,
Temitope O Olomola, and Rosalyn Klein, and Nicodemus Mautsa, and Yasien Sayed, and Perry T Kaye
Design, synthesis, and biological evaluation of 1,3-diarylpropenones as dual inhibitors of HIV-1 reverse transcriptase.
August 2014, ChemMedChem,
Temitope O Olomola, and Rosalyn Klein, and Nicodemus Mautsa, and Yasien Sayed, and Perry T Kaye
Synthesis and biological evaluation of (±)-benzhydrol derivatives as potent non-nucleoside HIV-1 reverse transcriptase inhibitors.
August 2011, Bioorganic & medicinal chemistry,
Copied contents to your clipboard!