浅述香豆素类化合物的抗菌活性
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摘要
香豆素类化合物因其天然资源优势、结构简单、易于合成、活性多样、用途广泛等特点受到研究者的广泛关注。特别是香豆素类化合物具有的优良抗耐药菌活性,再次掀起香豆素抗菌活性的研发热情。基于近年来香豆素类化合物抗菌活性的研究概况,初步总结了香豆素类化合物在医药和农药两方面的抗菌研究进展,并对此类化合物的后续研究和发展趋势进行了简要展望。
Coumarins have attracted much attention due to the natural resource,simple structure,easy synthesis,diverse activities and wide applications. Especially,coumarins have been found to have excellent activity against resistant bacteria,which has aroused researchers' enthusiasm for the development of antibacterial activity of coumarins.Based on the general situation of coumarins' antibacterial activity in recent years,the progress in antibacterial activity of coumarins in medicine and pesticide was summarized,and the follow-up research and development trend of coumarins were prospected.
Coumarins have attracted much attention due to the natural resource,simple structure,easy synthesis,diverse activities and wide applications. Especially,coumarins have been found to have excellent activity against resistant bacteria,which has aroused researchers' enthusiasm for the development of antibacterial activity of coumarins.Based on the general situation of coumarins' antibacterial activity in recent years,the progress in antibacterial activity of coumarins in medicine and pesticide was summarized,and the follow-up research and development trend of coumarins were prospected.
引文
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[12]杨树平,韩立军,潘燕,等.8-(3-或4-氟苯甲酰基)-7-羟基-4-甲基香豆素的合成、晶体结构、抑菌活性、抗氧化活性及其与牛血清白蛋白的相互作用[J].中国科学:化学,2013,43(7):858-868.
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[14]袁明月,刘伟华,张英群,等.微波辐射下N-[4-(香豆素-3-基)噻唑-2-基]芳醛腙类化合物的合成及生物活性研究[J].有机化学,2013,33(5):1 108-1 112.
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[19]HU Y,SHEN Y F,WU X H,et al.Synthesis and biological evaluation of coumarin derivatives containing imidazole skeleton as potential antibacterial agents[J]. Eur. J.Med.Chem.,2018,143:958-969.
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[21]KRALJEVI T G,HAREJ A,SEDIC M,et al.Synthesis,in vitro anticancer and antibacterial activities and in silico studies of new 4-substituted 1,2,3-triazoleecoumarin hybrids[J].Eur.J.Med.Chem.,2016,124:794-808.
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[23]YANG G Y,JIN Q,XU C L,et al.Synthesis,characterization and antifungal activity of coumarin-functionalized chitosan derivatives[J]. Int. J. Biol. Macromol.,2018,(106):179-184.
[24]左经龙,姜桂霞.细菌性病害主要化学防治药剂[J].吉林蔬菜,2016,(3):21-22.
[25]LIU M,LIU Y,HUA X W,et al.Synthesis of osthole derivatives with grignard reagents and their larvicidal activities on mosquitoes[J].Chin.J.Chem.,2015,33(12):1 353-1 358.
[26]章冰川,罗金香,赖婷,等.香豆素类化合物对朱砂叶螨的触杀活性及定量构效关系研究[J].农药学学报,2016,18(1):37-48.
[27]ZHANG R R,LIU J,ZHANG Y,et al.Microwave-assisted synthesis and antifungal activity of novel coumarin derivatives:pyrano[3,2-c]chromene-2,5-diones[J].Eur.J.Med.Chem.,2016,116:76-83.
[28]GUAN A Y,LIU C L,YANG X P,et al.Application of the intermediate derivatization approach in agrochemical discovery[J].Chem.Rev.,2014,114(14):7 079-7 107.
[29]魏艳,邵兴燕,郝双红.7-羟基香豆素硝基衍生物的合成及抑菌活性[J].青岛农业大学学报(自然科学版),2017,34(4):284-287.
[30]王栋,张方贺,孙健,等.8种4-甲基香豆素衍生物的合成及其农药活性[J].中国农学通报,2013,29(15):199-203.
[31]魏艳,于明巧,王栋,等.4-甲基-7-羟基-8-乙酰基香豆素醚化衍生物的合成及其抑菌活性[J].农药,2016,55(11):793-795.
[32]雷震霖,侯文成,骆焱平.7-醚基香豆素衍生物的合成及抑菌活性研究[J].化学试剂,2016,38(2):157-162.
[33]陈美航,张迅,鲁道旺,等.含香豆素的酰胺类衍生物的合成及抑菌活性[J].农药,2016,55(12):884-888.
[34]陈美航,张迅,王晓斌,等.1-芳基-3-(3-(4-氧香豆素基)苯基)硫脲衍生物的合成及抑菌活性[J].应用化学,2017,34(7):774-782.
[35]陈美航,王晓斌,吴文能.新型1-(4-取代苯基)-3-[4-(4-氧香豆素基)苯基]硫脲衍生物的合成及其抑菌活性[J].合成化学,2017,25(3):190-194.
[36]谢颖,雷震霖,骆焱平.6-酯基香豆素衍生物的除草抑菌活性[J].海南大学学报(自然科学版),2014,32(3):233-238.
[37]李标,刘秋霞,周元清,等.二茂铁苯甲酸香豆素类化合物的合成与性质研究[J].有机化学,2017,37(8):2 008-2 014.
[38]覃远根,鲁莲芳,王晓斌,等.含香豆素结构的姜黄素衍生物的合成及生物活性[J].化学研究与应用,2018,30(2):213-218.
[39]WEI J H,SUN Z H. tert-Butyl sulfoxide as a starting point for the synthesis of sulfinyl containing compounds[J].Org.Lett.,2015,17(21):5 396-5 399.
[40]刘明,刘阳,刘艾林,等.含亚磺酸酯或亚磺酰胺基团的香豆素衍生物的合成及生物活性研究[J].有机化学,2016,36(7):1 653-1 661.
[41]KHAN I,IBRAR A,AHMED W,et al.Synthetic approaches,functionalization and therapeutic potential of quinazoline and quinazolinone skeletons:the advances continue[J].Eur.J.Med.Chem.,2015,90:124-169.
[42]冯钰欣,谭官海,周利凯,等.含苯并香豆素的喹唑啉-4-酮衍生物的合成及其抗肿瘤、抗菌活性[J].有机化学,2017,37(2):429-439.
[43]YU X,TENG P,ZHANG Y L,et al. Design,synthesis and antifungal activity evaluation of coumarin-3-carboxamide derivatives[J].Fitoterapia,2018,127:387-395.
[2]AWS M,HAMDY A M,KHADDOUR Z,et al.Synthesis of arylated coumarins by Suzuki-Miyaura cross-coupling reaction and anti-HIV activity[J]. Bioorg. Med. Chem.,2016,24(21):5 115-5 126.
[3]PENG X M,KUMAR K V,DAMU G L V,et al.Coumarin-derived azolyl ethanols:synthesis,antimicrobial evaluation and preliminary action mechanism[J]. Sci. China Chem.,2016,59(7):878-894.
[4]ZHANG M Z,ZHANG R R,WANG J Q,et al.Microwaveassisted synthesis and antifungal activity of novel fused osthole derivatives[J]. Eur. J. Med. Chem.,2016,124:10-16.
[5]DAMU G L V,CUI S F,PENG X M,et al.Synthesis and bioactive evaluation of a novel series of coumarinazoles[J].Bioorg.Med.Chem.Lett.,2014,24(15):3 605-3 608.
[6]PENG X M,DAMU G L V,ZHOU C H.Current developments of coumarin compounds in medicinal chemistry[J].Curr.Pharm.Des.,2013,19(21):3 884-3 930.
[7]DIKPIMAR T,SUZGEC-SELCUK S,CELIK B O,et al.Antimicrobial activity of rhizomes of Ferulago trachycarpa Boiss.and bioguided isolation of active coumarin constituents[J].Ind.Crop.Prod.,2018,123:762-767.
[8]刘建新,连磊凡,张文平.花椒毒酚体外抗菌实验的研究[J].时珍国医国药,2015,26(5):1 087-1 088.
[9]ZUO G Y,WANG C J,HAN J,et al.Synergism of coumarins from the Chinese drug Zanthoxylum nitidum with antibacterial agents against methicillin-resistant Staphylococcus aureus(MRSA)[J]. Phytomedicine,2016,23(14):1 814-1 820.
[10]MADEIRO S A L,BORGES N H P B,SOUTO A L,et al.Modulation of the antibiotic activity against multidrug resistant strains of coumarins isolated from Rutaceae species[J].Microb.Pathog.,2017,104:151-154.
[11]时园,周成合,周向东,等.香豆素苯并三唑的合成、抗微生物活性及其与氯霉素和氟康唑协同作用研究[J].药学学报,2011,46(7):798-810.
[12]杨树平,韩立军,潘燕,等.8-(3-或4-氟苯甲酰基)-7-羟基-4-甲基香豆素的合成、晶体结构、抑菌活性、抗氧化活性及其与牛血清白蛋白的相互作用[J].中国科学:化学,2013,43(7):858-868.
[13]CHHABRIA M T,PATEL S,MODI P,et al.Thiazole:a review on chemistry,synthesis and therapeutic importance of its derivatives[J]. Curr. Top. Med. Chem.,2016,16(26):2 841-2 862.
[14]袁明月,刘伟华,张英群,等.微波辐射下N-[4-(香豆素-3-基)噻唑-2-基]芳醛腙类化合物的合成及生物活性研究[J].有机化学,2013,33(5):1 108-1 112.
[15]何典雄,刘文超,彭知云,等.香豆素噻唑类化合物的合成及其抗菌活性研究[J].化学试剂,2017,39(1):11-14.
[16]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.,2018,1 166:147-154.
[17]PATEL D,KUMARI P,PATEL N B.Synthesis and biological evaluation of coumarin based isoxazoles,pyrimidinthiones and pyrimidin-2-ones[J]. Arab. J. Chem.,2017,10(S2):S3 990-S4 001.
[18]LIU H,REN Z L,WANG W,et al. Novel coumarinpyrazole carboxamide derivatives as potential topoisomeraseⅡinhibitors:design,synthesis and antibacterial activity[J].Eur.J.Med.Chem.,2018,157:81-87.
[19]HU Y,SHEN Y F,WU X H,et al.Synthesis and biological evaluation of coumarin derivatives containing imidazole skeleton as potential antibacterial agents[J]. Eur. J.Med.Chem.,2018,143:958-969.
[20]SHAIKH M H,SUBHEDAR D D,KHAN F A K,et al.1,2,3-Triazole incorporated coumarin derivatives as potential antifungal and antioxidant agents[J].Chin.Chem.Lett.,2016,27(2):295-301.
[21]KRALJEVI T G,HAREJ A,SEDIC M,et al.Synthesis,in vitro anticancer and antibacterial activities and in silico studies of new 4-substituted 1,2,3-triazoleecoumarin hybrids[J].Eur.J.Med.Chem.,2016,124:794-808.
[22]罗礼阳,罗晓星,李明凯.香豆素类化合物的抗菌活性及其作用机制研究进展[J].山东医药,2017,57(28):102-105.
[23]YANG G Y,JIN Q,XU C L,et al.Synthesis,characterization and antifungal activity of coumarin-functionalized chitosan derivatives[J]. Int. J. Biol. Macromol.,2018,(106):179-184.
[24]左经龙,姜桂霞.细菌性病害主要化学防治药剂[J].吉林蔬菜,2016,(3):21-22.
[25]LIU M,LIU Y,HUA X W,et al.Synthesis of osthole derivatives with grignard reagents and their larvicidal activities on mosquitoes[J].Chin.J.Chem.,2015,33(12):1 353-1 358.
[26]章冰川,罗金香,赖婷,等.香豆素类化合物对朱砂叶螨的触杀活性及定量构效关系研究[J].农药学学报,2016,18(1):37-48.
[27]ZHANG R R,LIU J,ZHANG Y,et al.Microwave-assisted synthesis and antifungal activity of novel coumarin derivatives:pyrano[3,2-c]chromene-2,5-diones[J].Eur.J.Med.Chem.,2016,116:76-83.
[28]GUAN A Y,LIU C L,YANG X P,et al.Application of the intermediate derivatization approach in agrochemical discovery[J].Chem.Rev.,2014,114(14):7 079-7 107.
[29]魏艳,邵兴燕,郝双红.7-羟基香豆素硝基衍生物的合成及抑菌活性[J].青岛农业大学学报(自然科学版),2017,34(4):284-287.
[30]王栋,张方贺,孙健,等.8种4-甲基香豆素衍生物的合成及其农药活性[J].中国农学通报,2013,29(15):199-203.
[31]魏艳,于明巧,王栋,等.4-甲基-7-羟基-8-乙酰基香豆素醚化衍生物的合成及其抑菌活性[J].农药,2016,55(11):793-795.
[32]雷震霖,侯文成,骆焱平.7-醚基香豆素衍生物的合成及抑菌活性研究[J].化学试剂,2016,38(2):157-162.
[33]陈美航,张迅,鲁道旺,等.含香豆素的酰胺类衍生物的合成及抑菌活性[J].农药,2016,55(12):884-888.
[34]陈美航,张迅,王晓斌,等.1-芳基-3-(3-(4-氧香豆素基)苯基)硫脲衍生物的合成及抑菌活性[J].应用化学,2017,34(7):774-782.
[35]陈美航,王晓斌,吴文能.新型1-(4-取代苯基)-3-[4-(4-氧香豆素基)苯基]硫脲衍生物的合成及其抑菌活性[J].合成化学,2017,25(3):190-194.
[36]谢颖,雷震霖,骆焱平.6-酯基香豆素衍生物的除草抑菌活性[J].海南大学学报(自然科学版),2014,32(3):233-238.
[37]李标,刘秋霞,周元清,等.二茂铁苯甲酸香豆素类化合物的合成与性质研究[J].有机化学,2017,37(8):2 008-2 014.
[38]覃远根,鲁莲芳,王晓斌,等.含香豆素结构的姜黄素衍生物的合成及生物活性[J].化学研究与应用,2018,30(2):213-218.
[39]WEI J H,SUN Z H. tert-Butyl sulfoxide as a starting point for the synthesis of sulfinyl containing compounds[J].Org.Lett.,2015,17(21):5 396-5 399.
[40]刘明,刘阳,刘艾林,等.含亚磺酸酯或亚磺酰胺基团的香豆素衍生物的合成及生物活性研究[J].有机化学,2016,36(7):1 653-1 661.
[41]KHAN I,IBRAR A,AHMED W,et al.Synthetic approaches,functionalization and therapeutic potential of quinazoline and quinazolinone skeletons:the advances continue[J].Eur.J.Med.Chem.,2015,90:124-169.
[42]冯钰欣,谭官海,周利凯,等.含苯并香豆素的喹唑啉-4-酮衍生物的合成及其抗肿瘤、抗菌活性[J].有机化学,2017,37(2):429-439.
[43]YU X,TENG P,ZHANG Y L,et al. Design,synthesis and antifungal activity evaluation of coumarin-3-carboxamide derivatives[J].Fitoterapia,2018,127:387-395.