香豆素类化合物生物活性研究进展
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摘要
香豆素是一类重要杂环化合物,具多种生物活性,在医药、食品等领域有重要用途。本文综述了近年来香豆素生物活性研究进展,并简单介绍了含有苯并吡喃酮化合物的合成方法,为香豆素类化合物生物活性的深入研究提供依据。
Coumarin is a kind of important heterocyclic compound with broad biologi-cal activity.Coumarin compounds have important application in medicine and food fields.In this paper,coumarin biological activities are reviewed.The synthesis methods are also summarized.In order to provide basis for further research on coumarin biological activities.
Coumarin is a kind of important heterocyclic compound with broad biologi-cal activity.Coumarin compounds have important application in medicine and food fields.In this paper,coumarin biological activities are reviewed.The synthesis methods are also summarized.In order to provide basis for further research on coumarin biological activities.
引文
[1]姚新生,吴立君.天然药物化学[M].4版.北京:人民卫生出版社,2004.
[2]Albratty M,El-Sharkawy K A,Alam S.Synthesis and antitumor activity of some novel thiophene,pyrimidine,coumarin,pyrazole and pyridine derivatives[J].Acta Pharm,2017,67(1):15-33.
[3]Jovana B,Jelena S,Aleksandar M.et al.Coumarin structure as a lead scaffold for antibacterial agents molecular docking study[J].Biologica Nyssana,2016,7(2):167-170.
[4]Kamauchi H,Noji M,Kinoshita K,et al.Coumarins with an unprecedented tetracyclic skeleton and coumarin dimers from chemically engineered extracts of a marine-derived fungus[J].Tetrahedron,2018,74(23):2846-2856.
[5]Elizabeth G J,Anita R,Stephen B,et al.Development of an in silico model of DPPH and free radical scavenging capacity:prediction of antioxidant activity of coumarin type compounds[J].Int J Mol Sci,2016,17(6):1073-1080.
[6]Kurapati K,Atluri V S,Thangavel S,et al.Natural products as anti-HIV agents and role in HIV-associated neurocognitive disorders (HAND):A brief overview[J].Front Microbiol,2015,6(212):1-14.
[7]Wang Y,Liu H,Lu P,et al.Design,synthesis,and in vitro evaluation of novel 3,7-disubstituted coumarin derivatives as potent anticancer agents.[J].Chem Biol Drug Des,2015,6:1444-1497.
[8]Holiyachi M,Shastri S L,Chougala B M,et al.Design,synthesis and structure-activity relationship study of coumarin benzimidazole hybrid as potent antibacterial and anticancer agents[J].Chemistry Select,2016,1(15):4638-4644.
[9]Gabr M T,Elgohary N S,Elbendary E R.et al.Microwave-assisted synthesis and antitumor evaluation of a new series of thiazolylcoumarin derivatives[J].Excli J,2017,16:1114-1131.
[10]Luo G,Muyaba M,Lyu W,et al.Design,synthesis and biological evaluation of novel 3-substituted 4-anilino-coumarin derivatives as antitumor agents[J].Bioorg Med Chem Lett,2017,27(4):867-874.
[11]Lingaraju G S,Balaji K S,Jayarama K,et al.Synthesis of new coumarin tethered isoxazolines as potential anticancer agents[J].Bioorg Med Chem Lett,2018,28(23):3606-3612.
[12]Manojkumar P,Ravi T,Subbuchettiar G.Synthesis of coumarin heterocyclic derivatives with antioxidant activity and in vitro cytotoxic activity against tumour cells[J].Acta Pharm,2009,59(2):159-170.
[13]Wang S F,Yin Y,Qiao F,et al.Synthesis,molecular docking and biological evaluation of metronidazole derivatives containing piperazine skeleton as potential antibacterial agents[J].Bioorg Med Chem,2014,22(8):2409-2415.
[14]Sined M S,Anis R,Mejda D R,et al.Synthesis and antimicrobial activity of novel coumarin derivatives from 4-methylumbelliferone[J].Med Chem Res,2015,24(8):3247-3257.
[15]Rodanant P,Khetkam P,Suksamrarn A,et al.Coumarins and flavonoid from Murraya paniculata (L.) Jack:Antibacterial and anti-inflammation activity[J].Pak J Pharm Sci,2015,28(6):1947-1951.
[16]Ji Q,Ge Z,Ge Z,et al.Synthesis and biological evaluation of novel phosphoramidate derivatives of coumarin as chitin synthase inhibitors and antifungal agents[J].Eur J Med Chem,2016,108:166-176.
[17]Desai N C,Satodiya H M,Rajpara K M,et al.A microwave-assisted facile synthesis of novel coumarin derivatives containing cyanopyridine and furan as antimicrobial agents[J].J Saudi Chem Soc,2017,21:S153-S156.
[18]Chavan R R,Hosamani K M.Microwave-assisted synthesis,computational studies and antibacterial/ anti-inflammatory activities of compounds based on coumarin-pyrazole hybrid[J].Roy Soc Open Sci,2018,5(5):1-16.
[19]Kassim N K,Rahmani M,Ismail A,et al.Antioxidant activity-guided separation of coumarins and lignan from Melicope glabra (Rutaceae)[J].Food Chem,2013,139(4):87-92.
[20]Roussaki M,Zelianaios K,Kavetsou E,et al.Structural modifications of coumarin derivatives:Determination of antioxidant and lipoxygenase (LOX) inhibitory activity[J].Bioorg Med Chem,2014,22(23):6586-6594.
[21]Niu H,Wang W,Li J,et al.A novel structural class of coumarin-chalcone fibrates as PPARα/γ agonists with potent antioxidant activities:Design,synthesis,biological evaluation and molecular docking studies[J].Eur J Med Chem,2017,138:212-220.
[22]Osman H,Yusufzai S K,Khan M S,et al.New thiazolyl-coumarin hybrids:Design,synthesis,characterization,X-ray crystal structure,antibacterial and antiviral evaluation[J].J Mol Struct,2018,1166:147-154.
[23]Hamdy A M,Hamdy A M,Khaddour Z,et al.Synthesis of arylated coumarins by Suzuki-Miyaura cross-coupling.Reactions and anti-HIV activity[J].Bioorg Med Chem,2016,24(21):5115-5126.
[24]Chao W,Hao Z,Fengrong X,et al.Substituted 3-Benzylcoumarins as Allosteric MEK1 Inhibitors:Design,Synthesis and Biological Evaluation as Antiviral Agents[J].Molecules,2013,18(5):6057-6091.
[25]王洁.抗HIV香豆素类化合物的结构改造及生物活性研究[D].上海:复旦大学药学院药物化学,2010:1-70.
[26]权彦,李小蓉,刘靖丽.4-羟基香豆素衍生物的微波合成、表征及抗凝血研究[J].中国新药杂志,2018(8):921-926.
[27]Pintus F,Matos M J,Vilar S,et al.New insights into highly potent tyrosinase inhibitors based on 3-heteroarylcoumarins:Anti-melanogenesis and antioxidant activities,and computational molecular modeling studies[J].Bioorg Med Chem,2017,25(5):1687-1695.
[2]Albratty M,El-Sharkawy K A,Alam S.Synthesis and antitumor activity of some novel thiophene,pyrimidine,coumarin,pyrazole and pyridine derivatives[J].Acta Pharm,2017,67(1):15-33.
[3]Jovana B,Jelena S,Aleksandar M.et al.Coumarin structure as a lead scaffold for antibacterial agents molecular docking study[J].Biologica Nyssana,2016,7(2):167-170.
[4]Kamauchi H,Noji M,Kinoshita K,et al.Coumarins with an unprecedented tetracyclic skeleton and coumarin dimers from chemically engineered extracts of a marine-derived fungus[J].Tetrahedron,2018,74(23):2846-2856.
[5]Elizabeth G J,Anita R,Stephen B,et al.Development of an in silico model of DPPH and free radical scavenging capacity:prediction of antioxidant activity of coumarin type compounds[J].Int J Mol Sci,2016,17(6):1073-1080.
[6]Kurapati K,Atluri V S,Thangavel S,et al.Natural products as anti-HIV agents and role in HIV-associated neurocognitive disorders (HAND):A brief overview[J].Front Microbiol,2015,6(212):1-14.
[7]Wang Y,Liu H,Lu P,et al.Design,synthesis,and in vitro evaluation of novel 3,7-disubstituted coumarin derivatives as potent anticancer agents.[J].Chem Biol Drug Des,2015,6:1444-1497.
[8]Holiyachi M,Shastri S L,Chougala B M,et al.Design,synthesis and structure-activity relationship study of coumarin benzimidazole hybrid as potent antibacterial and anticancer agents[J].Chemistry Select,2016,1(15):4638-4644.
[9]Gabr M T,Elgohary N S,Elbendary E R.et al.Microwave-assisted synthesis and antitumor evaluation of a new series of thiazolylcoumarin derivatives[J].Excli J,2017,16:1114-1131.
[10]Luo G,Muyaba M,Lyu W,et al.Design,synthesis and biological evaluation of novel 3-substituted 4-anilino-coumarin derivatives as antitumor agents[J].Bioorg Med Chem Lett,2017,27(4):867-874.
[11]Lingaraju G S,Balaji K S,Jayarama K,et al.Synthesis of new coumarin tethered isoxazolines as potential anticancer agents[J].Bioorg Med Chem Lett,2018,28(23):3606-3612.
[12]Manojkumar P,Ravi T,Subbuchettiar G.Synthesis of coumarin heterocyclic derivatives with antioxidant activity and in vitro cytotoxic activity against tumour cells[J].Acta Pharm,2009,59(2):159-170.
[13]Wang S F,Yin Y,Qiao F,et al.Synthesis,molecular docking and biological evaluation of metronidazole derivatives containing piperazine skeleton as potential antibacterial agents[J].Bioorg Med Chem,2014,22(8):2409-2415.
[14]Sined M S,Anis R,Mejda D R,et al.Synthesis and antimicrobial activity of novel coumarin derivatives from 4-methylumbelliferone[J].Med Chem Res,2015,24(8):3247-3257.
[15]Rodanant P,Khetkam P,Suksamrarn A,et al.Coumarins and flavonoid from Murraya paniculata (L.) Jack:Antibacterial and anti-inflammation activity[J].Pak J Pharm Sci,2015,28(6):1947-1951.
[16]Ji Q,Ge Z,Ge Z,et al.Synthesis and biological evaluation of novel phosphoramidate derivatives of coumarin as chitin synthase inhibitors and antifungal agents[J].Eur J Med Chem,2016,108:166-176.
[17]Desai N C,Satodiya H M,Rajpara K M,et al.A microwave-assisted facile synthesis of novel coumarin derivatives containing cyanopyridine and furan as antimicrobial agents[J].J Saudi Chem Soc,2017,21:S153-S156.
[18]Chavan R R,Hosamani K M.Microwave-assisted synthesis,computational studies and antibacterial/ anti-inflammatory activities of compounds based on coumarin-pyrazole hybrid[J].Roy Soc Open Sci,2018,5(5):1-16.
[19]Kassim N K,Rahmani M,Ismail A,et al.Antioxidant activity-guided separation of coumarins and lignan from Melicope glabra (Rutaceae)[J].Food Chem,2013,139(4):87-92.
[20]Roussaki M,Zelianaios K,Kavetsou E,et al.Structural modifications of coumarin derivatives:Determination of antioxidant and lipoxygenase (LOX) inhibitory activity[J].Bioorg Med Chem,2014,22(23):6586-6594.
[21]Niu H,Wang W,Li J,et al.A novel structural class of coumarin-chalcone fibrates as PPARα/γ agonists with potent antioxidant activities:Design,synthesis,biological evaluation and molecular docking studies[J].Eur J Med Chem,2017,138:212-220.
[22]Osman H,Yusufzai S K,Khan M S,et al.New thiazolyl-coumarin hybrids:Design,synthesis,characterization,X-ray crystal structure,antibacterial and antiviral evaluation[J].J Mol Struct,2018,1166:147-154.
[23]Hamdy A M,Hamdy A M,Khaddour Z,et al.Synthesis of arylated coumarins by Suzuki-Miyaura cross-coupling.Reactions and anti-HIV activity[J].Bioorg Med Chem,2016,24(21):5115-5126.
[24]Chao W,Hao Z,Fengrong X,et al.Substituted 3-Benzylcoumarins as Allosteric MEK1 Inhibitors:Design,Synthesis and Biological Evaluation as Antiviral Agents[J].Molecules,2013,18(5):6057-6091.
[25]王洁.抗HIV香豆素类化合物的结构改造及生物活性研究[D].上海:复旦大学药学院药物化学,2010:1-70.
[26]权彦,李小蓉,刘靖丽.4-羟基香豆素衍生物的微波合成、表征及抗凝血研究[J].中国新药杂志,2018(8):921-926.
[27]Pintus F,Matos M J,Vilar S,et al.New insights into highly potent tyrosinase inhibitors based on 3-heteroarylcoumarins:Anti-melanogenesis and antioxidant activities,and computational molecular modeling studies[J].Bioorg Med Chem,2017,25(5):1687-1695.