A review on pharmacological properties of coumarins

Mini-Reviews in Medicinal Chemistry

Volumn 16, Issue , 2016, Pages

  Srikrishna, Devulapally ^a   Godugu, Chandraiah ^b   Kumar Dubey, Pramod ^a,b  

^a JNTUH COLLEGE OF ENGINEERING   (India)

^b NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

Author keywords

Anti inflammatory; Anticancer; Anticonvulsant; Antimicrobial; Antioxidant; Coumarin; MAO inhibitory; Pharmacological properties

Indexed keywords

2 IMINO N PHENYL 2H CHROMENE 3 CARBOXAMIDE; 2 OXO N PHENYL 2H CHROMENE 3 CARBOXAMIDE; 3 (1H BENZO[D] IMIDAZOL 2 YL) 2H CHROMEN 2 ONE; 3 ARYL COUMARIN DERIVATIVE; 3 ARYL FURO[3,2 C]COUMARIN DERIVATIVE; 3 ARYLCOUMARIN DERIVATIVE; 3 CYANOCOUMARIN DERIVATIVE; 3 ETHOXYCARBONYL 4 HYDROXYCOUMARIN; 3 HETEROARYL AZO 4 HYDROXYCOUMARIN DERIVATIVE; 3 HETERYL 4 HYDROXYCOUMARIN DERIVATIVE; 3,4 SUBSTITUTED COUMARIN DERIVATIVE; 4 (3 COUMARINYL) 3 BENZYL 4 THIAZOLIN 2 ONEBENZYLIDENEHYDRAZONE DERIVATIVE; 4 HETEROARYLAMINOCOUMARIN DERIVATIVE; 4 HYDROXY 3 (2 PHENYL 2,3 DIHYDRO 1H BENZO[B][1,4]DIAZEPIN 4 YL) 2H CHROMEN 2 ONE; 4 HYDROXY 3 (2 PHENYL 2,3 DIHYDROBENZO[B][1,4]THIAZEPIN 4 YL) 2H CHROMEN 2 ONE; 4 METHYLCOUMARIN DERIVATIVE; 4 PHENYLHYDROXYCOUMARIN DERIVATIVE; 6 (DIETHYLAMINO) 2 OXO 4 PHENYL 2H CHROMENE 3 CARBONITRILE DERIVATIVE; 6 ACYL 4 ALKYL 5,7 DIHYDROXYCOUMARIN; 6 ACYL 4 ARYL 5,7 DIHYDROXYCOUMARIN; 7 (2 OXOALKOXY)COUMARIN DERIVATIVE; COUMARIN 3 CARBOXAMIDE; COUMARIN 4 ACETIC ACID BENZYLIDENE HYDRAZIDE DERIVATIVE; COUMARIN DERIVATIVE; COUMARINYLTHIAZOLE DERIVATIVE; HETEROAROYL 2H CHROMENE 2 THIONE DERIVATIVE; N (1H BENZO[D] IMIDAZOL 2 YL) 2 OXO 2H CHROMENE 3 CARBOXAMIDE; STREPTOMYCIN; THIADIAZINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; ANTICONVULSIVE AGENT; ANTIINFECTIVE AGENT; ANTINEOPLASTIC AGENT; MONOAMINE OXIDASE INHIBITOR; NONSTEROID ANTIINFLAMMATORY AGENT; TUBERCULOSTATIC AGENT;

ANTICOAGULATION; ANTICONVULSANT ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; CARRAGEENAN-INDUCED PAW EDEMA; CHEMICAL MODIFICATION; CYTOTOXICITY; DOSE RESPONSE; DPPH RADICAL SCAVENGING ASSAY; DRUG EFFICACY; DRUG POTENCY; DRUG SYNTHESIS; ELECTRON TRANSPORT; GROWTH INHIBITION; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; IC50; NONHUMAN; OXIDATIVE STRESS; REVIEW; TUBERCULOSIS; ANIMAL; CHEMISTRY; HUMAN; SYNTHESIS;

ANIMALS; ANTI-HIV AGENTS; ANTI-INFECTIVE AGENTS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; ANTICONVULSANTS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; ANTITUBERCULAR AGENTS; COUMARINS; HUMANS; MONOAMINE OXIDASE INHIBITORS;

EID: 84989154985     PISSN: 13895575     EISSN: 18755607     Source Type: Journal    
DOI: 10.2174/1389557516666160801094919     Document Type: Review

References (66)

1. Vogel, A. On the existence of benzoic acid in the tonka bean and in the flowers of melilot. Journal de Pharmacie., 1820, 6, 305-309.
2. Guibourt, N.J.B.G. Histoire abrégée des droques simples (Abridged history of simple drugs). 1st ed.; Volume 2.; L. Colas: Paris, 1820. pp. 160-161.
3. Perkin, W.H. On the artificial production of coumarin and formation of its homologues. J. Chem. Soc., 1868, 21, 53-63.
4. Takeda, S.; Aburada, M. The choleretic mechanism of coumarin compounds and phenolic compounds. J. Pharmacobiodyn. 1981, 4, 724-734.
5. Deana, A.A.; Stokker, G.E.; Schultz, E.M.; Smith, R.L.; Cragoe, E.J.; Russo, H.F.; Watson, L.S. 2-(Aminomethyl)phenols, a new class of saluretic agents. 5. Fused-ring analogs J. Med. Chem. 1983, 26, 580-585.
6. Lake, B.G. Coumarin metabolism, toxicity and carcinogenicity: relevance for human risk assessment. Food Chem. Toxicol. 1999, 37, 423-453.
7. Vilar, S.; Quezada, E.; Santana, L.; Uriarte, E.; Yanez, M.; Fraiz, N.; Alcaide, C.; Cano, E.; Orallo, F. Design, synthesis, and vasorelaxant and platelet antiaggregatory activities of coumarinresveratrol hybrids. Bioorg. Med. Chem. Lett. 2006, 16, 257-261.
8. Song, H.Y.; Ngai, M.H.; Song, Z.Y.; MacAry, P.A.; Hobley, J.; Lear, M.J. Practical synthesis of maleimides and coumarin-linked probes for protein and antibody labelling via reduction of native disulfides. Org. Biomol. Chem. 2009, 7, 3400-3406.
9. Finn, G.; Kenealy, E.; Creaven, B.; Egan, D. In vitro cytotoxic potential and mechanism of action of selected coumarins, using human renal cell lines. Cancer Lett., 2002, 183, 61-68.
10. Egan, D.; Kennedy, R.; Moran, E.; Cox, D.; Prosser, E.; Thornes, R.D. The Pharmacology, metabolism, analysis and applications of coumarin and coumarin-related compounds. Drug Metab. Rev., 1990, 22, 503-529.
11. Hisalkar, P.J.; Patne, A.B.; Fawade, M.M.; Karnik, A.C. Evaluation of plasma superoxide dismutase and glutathione peroxidase in type 2 diabetic patients. Biology and Medicine, 2012, 4 65-72.
12. Khalid, M. Studies on free radicals, antioxidants, and co-factors. Clin. Interv. Aging. 2007, 2, 219-236.
13. Tomas, F.; Michal, R.; Katerina, M.; Eva, A.; Jana, K.; Mladenka, P. Antioxidant effects of coumarins include direct radical scavenging, metal chelation and inhibition of ROS-producing enzymes. Curr. Top. Med. Chem. 2015, 15, 415-431.
14. Roussaki, M.; Christos, A.; Kontogiorgis, H.L.D.; Hamilakis, S.; Detsi, A. A novel synthesis of 3-aryl coumarins and evaluation of their antioxidant and lipoxygenase inhibitory activity. Bio-org. Med. Chem. Lett., 2010, 20, 3889-3892.
15. Sreekanth, T.; Kavitha, N.; Anusha, S.; Rajeshwar, Y. Design, synthesis, characterization, antioxidant and in vitro cytotoxic activities of novel coumarin thiazole derivatives. Med. Chem. Res., 2015, 24, 1162-1169.
16. Milan, C.; Valentina, P.; Maja, M.; Bojan, S.; Elizabeta, H.S. Design and synthesis of some new 1,3,4-thiadiazines with coumarin moieties and their antioxidative and antifungal activity. Molecules, 2014, 19, 1163-1177.
17. Veselinovic, J.B.; Veselinovic, A.M.; Vitnik, Z.J.; Vitnik, V.D.; Nikolic, G.M. Antioxidant properties of selected 4-phenylhydroxycoumarins: Integrated in vitro and computational studies. Chem. Biol. Interact., 2014, 214, 49-56.
18. Gouda, M.A. Synthesis and antioxidant activity of a novel series of pyrazolotriazine, coumarin, oxoazinone, and pyrazinopyrimidine derivatives. Arch. Pharm. Chem. Life Sci., 2013, 346, 626-634.
19. Singh, O.M.; Devi, N.S.; Singh, D.T.; Sharma, G.J. Novel 3-alkanoyl/aroyl/heteroaroyl-2H-chromene-2-thiones: Synthesis and evaluation of their antioxidant activities. Eur. J. Med. Chem., 2010, 45, 2250-2257.
20. Georgia, M.; Antreas, A.; Olga, I.M.; Anastasia, D.; Maria, K.; Christos, K.; Dimitra, J.H.L. Synthesis and evaluation of the antioxidant and anti-inflammatory activity of novel coumarin-3-aminoamides and their alpha-lipoic acid adducts. Eur. J. Med. Chem., 2009, 44, 3020-3026.
21. Pedersen, J.Z.; Oliveira, C.; Incerpi, S.; Kumar, V.; Fiore, A.M.; Vito, P.D.; Prasad, A.K.; Malhotra, S.V.; Parmar, V.S.; Saso, L. Antioxidant activity of 4-methylcoumarins. J. pharm. pharmcol., 2007, 59, 1721-1728.
22. Lin, C.M.; Huang, S.T.; Lee, F.W.; Kuoa, H.S.; Lin, M.H. 6-Acyl-4-aryl/alkyl-5,7-dihydroxycoumarins as anti-inflammatory agents. Bio-org. Med.Chem., 2006, 14, 4402-4409.
23. Pu, W.; Lin, Y.; Zhang, J.; Wang, F.; Wang, C.; Zhang, G. 3-Arylcoumarins: Synthesis and potent anti-inflammatory activity. Bio-org. Med. Chem. Lett., 2014, 24, 5432-5434.
24. Bylov, I.E.; Vasylyev, M.V.; Bilokin, Y.V. Synthesis and antiinflammatory activity of N-substituted 2-oxo-2H-1-benzopyran-3-carboxamides and their 2-iminoanalogues. Eur. J. Med. Chem., 1999, 34, 997−1001.
25. Arora, R.K.; Kaur, N.; Bansal, Y.; Bansal, G. Novel coumarinbenzimidazole derivatives as antioxidants and safer antiinflammatory agents. Acta. Pharm. Sinica B., 2014, 4(5), 368-375.
26. Timonen, J.; Vuolteenaho, K.; Leppanen, T.; Nieminen, R.; Eeva, M.; Paula, A.; Janne, J. 7-(2-Oxoalkoxy)coumarins: Synthesis and anti-inflammatory activity of a series of substituted coumarins. J. Het. Chem., In press, (2014). DOI: 10.1002/jhet.2173.
27. Ankit, R.K.; Rakesh, R.G.; Varun, G.B., Hemali, J.P.; Dinkar, I.B.; Microwave assisted synthesis and biological activity of 3-arylfuro [ 3,2-c]coumarins. Arab. J. Chem., (2013) In press. DOI:10.1016/j.arabjc.2013.01.017.
28. Sahoo, J.; Suman, K.M.; Paidesetty, S.K. Synthesis, spectral characterization of some new 3-heteroaryl azo 4-hydroxy coumarin derivatives and their antimicrobial evaluation. J. Taibah Univ. Sci., 2015, 9, 187-195.
29. Mulwad, V.V.; Rupesh, B.P. Synthesis of some antibacterial compounds from 4-hydroxycoumarin. Indian J. Chem., 2003, 42B, 2091-2096.
30. Biljana, R.D.; Niko, S.R.; Vidoslav, S.D.; Rastko, D.V.; Radosav, M.P. Synthesis and antimicrobial activity of new 4-heteroarylaminocoumarin derivatives containing nitrogen and sulfur as heteroatoms. Molecules, 2010, 15, 2246-2256.
31. Nermien, M.S.; Hany, M.M.; Essam, S.; Khattab, A.E.H.; Shymaa, S.M.; Ahmed, M.E. Synthesis of 4H-chromene, coumarin, 12Hchromeno[ 2,3-d]pyrimidine derivatives and some of their antimicrobial and cytotoxicity activities. Eur. J.Med. Chem., 2011, 46, 765-772.
32. Atul, M.; Malde, A.; Verma, J.; Virsodia, V.; Mishra, A.; Kuldip, U.; Hrishikesh, A.; Evans, C.; Shah, A.; Synthesis, anti-tubercular activity and 3D-QSAR study of coumarin-4-acetic acid benzylidene hydrazides. Eur. J. Med. Chem., 2008, 43, 2395-2403.
33. Gursoy, A.; Karali, N. Synthesis, characterization and primary antituberculosis activity evaluation of 4-(3-coumarinyl)-3-benzyl-4-thiazolin-2-onebenzylidenehydrazones. Turk. J. Chem., 2003, 27, 545-551.
34. Kuldip, U.; Atul, M.; Kena, R.; Sudhir, J.; Jalpa, T.; Ravi, C.; Shah, A. Evaluation of structurally diverse benzoazepines clubbed with coumarins as mycobacterium tuberculosis agents. Chem. Biol. Drug. Des., 2012, 80, 1003-1008.
35. Angelova, V.T.; Valcheva, V.; Stavrakov, G. Antimycobacterial activity of 4-and 3,4-substituted coumarins. Pharmacia, 2014, 61, 3-6.
36. Patel, K.S.; Patel, J.C.; Hitesh, R.D.; Vishal, K.P.; Kanuprasad, D.P.; Synthesis of Cu(II), Ni(II), Co(II), and Mn(II) complexes with ciprofloxacin and their evaluation of antimicrobial, antioxidant and anti-tubercular activity. Open J. Metal., 2012, 2, 49-59.
37. Kostova, I. Coumarins as inhibitors of HIV reverse transcriptase. Curr. HIV Res. 2006, 4, 347-363.
38. Kostova, I.; Raleva, S.; Genova, P.; Argirova, R. Structure-Activity relationships of synthetic coumarins as HIV-1 inhibitors, Bioinorg. Chem. Appl. 2006, 68274, 1-9.
39. Mao, P.C.M.; Mouscadet, J.F.; Herve, L.; Christian, A.; Ling-Yih, H. Chemical modification of coumarin dimer and HIV-1 integrase inhibitory activity. Chem. Pharm. Bull., 2002, 50(12), 1634-1637.
40. Mahajan, D.H.; Christophe, P.; Erik, D.C.; Kishor, H.C. Synthesis and studies of new 2-(coumarin-4-yloxy)-4,6-(substituted)-striazine derivatives as potential anti-HIV agents. Arch. Pharm. Chem. Life Sci., 2009, 342, 281-290.
41. Temitope, O.O.; Salerwe, M.; Rosalyn, K.; Telisha, T.J.; Judy, C.; Raymond, H.; Perry, T.K.; Novel furocoumarins as potential HIV-1 integrase inhibitors. Bio-org. Chem., 2014, 57, 1-4.
42. Chiang, C.C.; Mouscadet, J.F.; Tsai, H.J.; Liu, C.T.; Hsu, L.Y.; Synthesis and HIV-1 integrase inhibition of novel bis-or tetracoumarin analogues. Chem. Pharm. Bull., 2007, 55(12), 1740-1743.
43. Yaseen, A.A.S.; Haitham, H.A.S.; Houssain, A.S.A.; Kifah, S.M.S.; Mohammad, S. M.; Najim, A.A.M.; Ihsan, H.J. Synthesis, characterization and anti-HIV and antitumor activities of new coumarin derivatives. Z. Naturforsch., 2008, 63b, 83-89.
44. Emami, S.; Dadashpour, S. Current developments of coumar in based anti-cancer agents in medicinal chemistry. Eur. J. Med. Chem. 2015,102, 611-630.
45. Musa, M.A.; Cooperwood, J.S.; Omar, M.F.K. A review of coumarin derivatives in pharmacotherapy of breast cancer, Curr. Med. Chem. 2008, 15, 2664-2679
46. Nasr, T.; Bondock, S.; Mahmoud, Y. Anticancer activity of new coumarins substituted hydrazide-hydrazone derivatives. Eur. J. Med. Chem., 2014, 76, 539-548.
47. Amin, K.M.; Amal A.M. Eissa, Sahar M. Abou-Seri, Fadi M. Awadallah, Ghaneya S. Hassan, Synthesis and biological evaluation of novel coumarin-pyrazoline hybrids endowed with phenylsulfonyl moiety as antitumor agents. Eur. J. Med. Chem., 2013, 60, 187-198.
48. Pingaew, R.; Amporn, S.; Prasit, M.; Chanin, N.; Supaluk, P.; Somsak, R.; Virapong, P. Synthesis, biological evaluation and molecular docking of novel chalcone-coumarin hybrids as anticancer and antimalarial agents. Eur. J. Med. Chem., 2014, 85, 65-76.
49. Musiliyu, A.M.; Veera, B.; Lekan, M.L.; John, C.; Andre, S.; Ahkinyala, A. Cytotoxic activity of new acetoxycoumarin derivatives in cancer cell lines. Anticancer Res., 2011, 31, 2017-2022.
50. Songsiang, U.; Tula, T.; Pornsilp, Z.; Veerapol, K.; Chantana, B.; Jinda, W.; Chavi, Y.; Antioxidant activity and cytotoxicity against cholangiocarcinoma of carbazoles and coumarins from Clausena harmandiana. Science Asia, 2012, 38, 75-81.
51. Kostova, I.; Manolov, I.; Nicolova, I.; Konstantinov, S.; Karaivanova, M. New lanthanide complexes of 4-methyl-7-hydroxycoumarin and their pharmacological activity. Eur. J. Med. Chem. 2001, 36, 339-347.
52. Manolov, I.; Kostova, I.; Netzeva, T.; Konstantinov, S.; Karaivanova, M. Cytotoxic activity of cerium complexes with coumarin derivatives. Molecular modeling of the ligands. Arch. Pharm. Pharm. Med. Chem. 2000, 333, 93-98.
53. Saso, L.; Miri, R.; Nejati, M.; Khakdan, F.; Parshad, B.; Mathur, D.; Parmar, V.S.; Bracke, M.E.; Prasad, A.K.; Sharma, S.K.; Firuzi, O. Structure-activity relationship studies of 4-methylcoumarin derivatives as anticancer agents. Pharm. Biol. 2016, 54, 105-110.
54. Loring, D.W.; Cognitive side effects of antiepileptic drugs in children. Psychiatric Times, 2005, 22(10).
55. Siddiqui, N.; Arshad, M.F.; Suroor, A.K. Synthesis of some new coumarin incorporated thiazolyl semicarbazones as anticonvulsants. Acta Poloniae Pharmaceutica-Drug Res., 2009, 66, 161-167.
56. Bhat, M.A.; Mohammed, A.A.O.; Coumarin incorporated triazoles: a new class of anticonvulsants. Acta Poloniae Pharmaceutica-Drug Res., 2011, 68, 889-895.
57. Amin, K.M.; Doaa, E.A.R.; Yasmin, A.A.E. Synthesis and preliminary evaluation of some substituted coumarins as anticonvulsant agents. Bioorg. Med. Chem., 2008, 16, 5377-5388.
58. Bhat, M.A.; Nadeem, S.; Suroor, A.K. Synthesis of novel 3-(4-acetyl-5H/methyl-5-substitutedphenyl-4,5-dihydro-1,3,4-oxadiazol-2-yl)-2h-chromen-2-ones as potential anticonvulsant agents. Acta Poloniae Pharmaceutica-Drug Res., 2008, 65, 235-239.
59. Delogu, G.L.; Silvia, S.; Elias, Q.; Eugenio, U.; Santiago, V.; Nicholas, P.T. Dolores, V. Monoamine oxidase (MAO) inhibitory activity: 3-phenylcoumarins versus 4-hydroxy-3-phenylcoumarins. Chem. Med. Chem., 2014, 9, 1-5.
60. Ferino, G.; Enzo, C.; Maria, J.M.; Elias, Q.; Eugenio, U.; Lourdes, S.; Santiago, V.; Nicholas, P.T.; Matilde, Y.C.; Dolores, V.; Carmen, P.; Silvia, S.; Giovanna, D. MAO inhibitory activity of 2-arylbenzofurans versus 3-arylcoumarins: synthesis, in vitro study and docking calculations. Chem. Med. Chem., 2013, 8(6), 956-966.
61. Jeong, S.H.; Xiang, H.H.; Seong, S.H.; Ji, S.H.; Ji, H.H.; Dongho, L.; Myung, K.L.; Jai, S.R.; Bang, Y.H. Monoamine oxidase inhibitory coumarins from the aerial parts of dictamnus albus. Arch. Pharm. Res., 2006, 29, 1119-1124.
62. He, X.; Yan-Yan, C.; Jing-Bo, S.; Wen-Jiang, T.; Zhi-Xiang, P.; Zhi-Qiang, D.; Bao-An, S.; Li, J.; Xin-Hua, L. New coumarin derivatives: Design, synthesis and use as inhibitors of hMAO. Bioorg. Med. Chem., 2014, 22, 3732-3738.
63. Varala, V.N.R.; Kotra, V.; Zubaidha, P.K. Synthesis and anticoagulant activity of C3-and O-alkylated 4-hydroxycoumarin derivatives. Research and Reviews: Journal of Chemistry, 2013, 2(1), 1-6.
64. Manolova, I.; Danchevb, N.D. Synthesis and pharmacological investigations of some 4-hydroxycoumarin derivatives. Arch. Pharm. Pharm. Med. Chem. 2003, 2, 83-94.
65. Abdelhafez, O.M.; Amin, K.M.; Batran, R.Z.; Maher, T.J.; Nada, S.A.; Sethumadhavan, S. Synthesis, anticoagulant and PIVKA-II induced by new 4-hydroxycoumarin derivatives. Bioorg. Med. Chem. 2010, 18, 3371-3378.
66. Manolov, I.; Caecilia M.; Danchev, N. Synthesis, structure, toxicological and pharmacological investigations of 4-hydroxycoumarin derivatives. Eur. J. Med. Chem. 2006, 41, 882-890.