Structure-Activity Relationships of Synthetic Coumarins As HIV-1 Inhibitors

Overview

Journal Bioinorg Chem Appl

Publisher Wiley

Date 2007 May 15

PMID 17497014

Citations 36

Authors

I Kostova

S Raleva

P Genova

R Argirova

Affiliations

Soon will be listed here.

Abstract

HIV/AIDS pandemics is a serious threat to health and development of mankind, and searching for effective anti-HIV agents remains actual. Considerable progress has been made in recent years in the field of drug development against HIV. A lot of structurally different coumarins were found to display potent anti-HIV activity. The current review demonstrates the variety of synthetic coumarins having unique mechanism of action referring to the different stages of HIV replication. Recent studies based on the account of various synthetic coumarins seem to indicate that some of them serve as potent non-nucleoside RT-inhibitors, another as inhibitors of HIV-integrase or HIV-protease. The merits of selecting potential anti-HIV agents to be used in rational combination drugs design and structure-activity relationships are discussed.The scientific community is looking actively for new drugs and combinations for treatment of HIV infection effective for first-line treatment, as well as against resistant mutants. The investigation on chemical anti-HIV agents gives hope and optimism about it. This review article describes recent progress in the discovery, structure modification, and structure-activity relationship studies of potent anti-HIV coumarin derivatives.

Citing Articles

Novel Fluorescent Benzothiazolyl-Coumarin Hybrids as Anti-SARS-COVID-2 Agents Supported by Molecular Docking Studies: Design, Synthesis, X-ray Crystal Structures, DFT, and TD-DFT/PCM Calculations.

Abdallah A, Abdel-Latif S, Elgemeie G ACS Omega. 2023; 8(22):19587-19602.

PMID: 37284548 PMC: 10237303. DOI: 10.1021/acsomega.3c01085.

Plant Coumarins with Anti-HIV Activity: Isolation and Mechanisms of Action.

Sharapov A, Fatykhov R, Khalymbadzha I, Zyryanov G, Chupakhin O, Tsurkan M Int J Mol Sci. 2023; 24(3).

PMID: 36769163 PMC: 9917851. DOI: 10.3390/ijms24032839.

Corrosion mitigation for steel in acid environment using novel -phenylenediamine and benzidine coumarin derivatives: synthesis, electrochemical, computational and SRB biological resistivity.

Elaryian H, Bedair M, Bedair A, Aboushahba R, Fouda A RSC Adv. 2022; 12(45):29350-29374.

PMID: 36320746 PMC: 9558558. DOI: 10.1039/d2ra05803k.

An Update on Synthesis of Coumarin Sulfonamides as Enzyme Inhibitors and Anticancer Agents.

Rubab L, Afroz S, Ahmad S, Hussain S, Nawaz I, Irfan A Molecules. 2022; 27(5).

PMID: 35268704 PMC: 8911621. DOI: 10.3390/molecules27051604.

Immunostimulants for shrimp aquaculture: paving pathway towards shrimp sustainability.

Kumar S, Verma A, Singh S, Awasthi A Environ Sci Pollut Res Int. 2022; 30(10):25325-25343.

PMID: 35025041 PMC: 8755978. DOI: 10.1007/s11356-021-18433-y.

References

Bourinbaiar A, Tan X, Nagorny R . Inhibitory effect of coumarins on HIV-1 replication and cell-mediated or cell-free viral transmission. Acta Virol. 1993; 37(4):241-50. View

Yu D, Suzuki M, Xie L, Morris-Natschke S, Lee K . Recent progress in the development of coumarin derivatives as potent anti-HIV agents. Med Res Rev. 2003; 23(3):322-45. DOI: 10.1002/med.10034. View

Mao P, Mouscadet J, Leh H, Auclair C, Hsu L . Chemical modification of coumarin dimer and HIV-1 integrase inhibitory activity. Chem Pharm Bull (Tokyo). 2002; 50(12):1634-7. DOI: 10.1248/cpb.50.1634. View

Ishikawa T, Kotake K, Ishii H . Synthesis of toddacoumaquinone, a coumarin-naphthoquinone dimer, and its antiviral activities. Chem Pharm Bull (Tokyo). 1995; 43(6):1039-41. DOI: 10.1248/cpb.43.1039. View

Boggetto N, Doucet C, de Rosny E, Vergely I, Thierry N, Amour A . [Synthetic inhibitors targeting serine and aspartic acid proteases]. J Pharm Belg. 1996; 51(3):161-4. View

Wang H, Ng T . Examination of lectins, polysaccharopeptide, polysaccharide, alkaloid, coumarin and trypsin inhibitors for inhibitory activity against human immunodeficiency virus reverse transcriptase and glycohydrolases. Planta Med. 2001; 67(7):669-72. DOI: 10.1055/s-2001-17359. View

Zhao H, Neamati N, Hong H, Mazumder A, Wang S, Sunder S . Coumarin-based inhibitors of HIV integrase. J Med Chem. 1997; 40(2):242-9. DOI: 10.1021/jm960450v. View

Xu Z, Flavin M, Jenta T . Calanolides, the naturally occurring anti-HIV agents. Curr Opin Drug Discov Devel. 2009; 3(2):155-66. View

Flavin M, Rizzo J, Khilevich A, Kucherenko A, SHEINKMAN A, Vilaychack V . Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (+/-)-calanolide A and its enantiomers. J Med Chem. 1996; 39(6):1303-13. DOI: 10.1021/jm950797i. View

10.

Martyanov I, Zakharova O, Sottofattori E, Maksakova G, Pyshnyi D, Mazzei M . HIV-1 reverse transcriptase is capable of elongating derivatives of sequence specific noncomplementary oligodeoxynucleotides. Biochem Mol Biol Int. 1998; 45(5):857-64. DOI: 10.1002/iub.7510450502. View

11.

Kirkiacharian S, Thuy D, Sicsic S, Bakhchinian R, Kurkjian R, Tonnaire T . Structure-activity relationships of some 3-substituted-4-hydroxycoumarins as HIV-1 protease inhibitors. Farmaco. 2002; 57(9):703-8. DOI: 10.1016/s0014-827x(02)01264-8. View

12.

Xie L, Yu D, Wild C, Allaway G, Turpin J, Smith P . Anti-AIDS agents. 52. Synthesis and anti-HIV activity of hydroxymethyl (3'R,4'R)-3',4'-di-O-(S)-camphanoyl-(+)-cis-khellactone derivatives. J Med Chem. 2004; 47(3):756-60. DOI: 10.1021/jm030416y. View

13.

Xu Z, Kern E, Westbrook L, Allen L, Buckheit Jr R, Tseng C . Plant-derived and semi-synthetic calanolide compounds with in vitro activity against both human immunodeficiency virus type 1 and human cytomegalovirus. Antivir Chem Chemother. 2000; 11(1):23-9. DOI: 10.1177/095632020001100102. View

14.

Xie L, Takeuchi Y, Cosentino L, Lee K . Anti-AIDS agents. 37. Synthesis and structure-activity relationships of (3'R,4'R)-(+)-cis-khellactone derivatives as novel potent anti-HIV agents. J Med Chem. 1999; 42(14):2662-72. DOI: 10.1021/jm9900624. View

15.

Kashman Y, Gustafson K, Fuller R, Cardellina 2nd J, McMahon J, Currens M . The calanolides, a novel HIV-inhibitory class of coumarin derivatives from the tropical rainforest tree, Calophyllum lanigerum. J Med Chem. 1992; 35(15):2735-43. DOI: 10.1021/jm00093a004. View

16.

Xie L, Takeuchi Y, Cosentino L, McPhail A, Lee K . Anti-AIDS agents. 42. Synthesis and anti-HIV activity of disubstituted (3'R,4'R)-3',4'-di-O-(S)-camphanoyl-(+)-cis-khellactone analogues. J Med Chem. 2001; 44(5):664-71. DOI: 10.1021/jm000070g. View

17.

Galinis D, Fuller R, McKee T, Cardellina 2nd J, Gulakowski R, McMahon J . Structure-activity modifications of the HIV-1 inhibitors (+)-calanolide A and (-)-calanolide B. J Med Chem. 1996; 39(22):4507-10. DOI: 10.1021/jm9602827. View

18.

Martyanov I, Zakharova O, Sottofattori E, Pyshnyi D, Yurchenko E, Babbi P . Interaction of oligonucleotides conjugated to substituted chromones and coumarins with HIV-1 reverse transcriptase. Antisense Nucleic Acid Drug Dev. 1999; 9(5):473-80. DOI: 10.1089/oli.1.1999.9.473. View

19.

Lunney E, Hagen S, Domagala J, Humblet C, Kosinski J, Tait B . A novel nonpeptide HIV-1 protease inhibitor: elucidation of the binding mode and its application in the design of related analogs. J Med Chem. 1994; 37(17):2664-77. DOI: 10.1021/jm00043a006. View

20.

El-Subbagh H, Mahran M, Badria F, Al-Obaid A . Synthesis and biological evaluation of certain alpha,beta-unsaturated ketones and their corresponding fused pyridines as antiviral and cytotoxic agents. J Med Chem. 2000; 43(15):2915-21. DOI: 10.1021/jm000038m. View