新型吲哚衍生物及其抗病毒活性研究进展
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摘要
目的综述新型吲哚衍生物及其抗病毒活性的研究进展。方法通过查阅近几年相关文献35篇,对具有抗病毒活性的新型吲哚衍生物进行归纳总结。结果近年来,随着病毒感染性疾病的普遍发生,越来越多的具有抗病毒活性的吲哚衍生物被设计合成;将不同结构的吲哚衍生物分为9大类,并综述其抗病毒活性。结论随着计算机辅助设计等新技术的不断应用,吲哚类衍生物在抗病毒方面的研究取得了惊人的成果,尤其是新型的大环吲哚衍生物的研发具有重要意义和广阔前景。
Objective To review the research progress of new indole derivatives and their antiviral activities.Methods The new indole derivatives with antiviral activity were summarized by referring to 35 relevant literatures in recent years.Results In recent years,with the prevalence of viral infectious diseases,more and more indole derivatives with antiviral activity were designed and synthesized.In this article,indole derivatives with different structures were classified into 9 categories and their antiviral activities were reviewed.Conclusion With the continuous application of new technologies such as computer-aided design,the research of indole derivatives in antiviral field has achieved amazing results,especially the research and development of novel macrocyclic indole derivatives have important significance and broad prospects.
Objective To review the research progress of new indole derivatives and their antiviral activities.Methods The new indole derivatives with antiviral activity were summarized by referring to 35 relevant literatures in recent years.Results In recent years,with the prevalence of viral infectious diseases,more and more indole derivatives with antiviral activity were designed and synthesized.In this article,indole derivatives with different structures were classified into 9 categories and their antiviral activities were reviewed.Conclusion With the continuous application of new technologies such as computer-aided design,the research of indole derivatives in antiviral field has achieved amazing results,especially the research and development of novel macrocyclic indole derivatives have important significance and broad prospects.
引文
[1] ZHANG F,WANG G.A review of non-nucleoside anti-hepatitis B virus agents[J].European Journal of Medicinal Chemistry,2014,75(9):267-281.
[2] VILLALAIN J.Membranotropic effects of arbidol,a broad anti-viral molecule,onphospholipid model membranes[J].Journal of Chemical Physics,2010,114(25):8544-8554.
[3] BRANCATO V,PEDUTOA,WHARTON S,et al.Design of inhibitors of influenza virus membrane fusion:Synthesis,structure-activity relationship and in vitro antiviral activity of a novelindole series[J].Antiviral Research,2013,99(2):125-135.
[4] SCUOTTO M,ABDELNABI R,COLLARILE S,et al.Discovery of novel multi-target indole-based derivatives as potent andselective inhibitors of chikungunya virus replication[J].Bioorganic & Medicinal Chemistry,2016,25(1):327-337.
[5] WILLIAMS T M,CICCARONE T M,MAC S C,et al.5-chloro-3-(phenylsulfonyl)indole-2-carboxamide:a novel,non-nucleosideinhibitor of HIV-1 reverse transcriptase[J].Journal of Medicinal Chemistry,1993,36(9):1291-1294.
[6] REGINA G,COLUCCIA A,BRANCALE A,et al.New nitrogen containing substituents at the indole-2-carboxamide yield high potent and broad spectrum indolylarylsulfone HIV-1 non-nucleoside reverse transcriptase inhibitors[J].Journal of Medicinal Chemistry,2012,55(14):6634-6638.
[7] FAMIGLINI V,REGINA G,COLUCCIA A,et al.Newindolylarylsulfones as highly potent and broad spectrum HIV-1 non-nucleoside reverse transcriptase inhibitors[J].European Journal of Medicinal Chemistry,2014,80:101-111.
[8] ALEXANDRE F R,AMADOR A,BOT S,et al.Synthesis and biological evaluation of aryl-phospho-indole asnovel HIV-1 non-nucleoside reverse transcriptase inhibitors[J].Journal of Medicinal Chemistry,2011,54(1):392-395.
[9] MENG L J,GUO Q L,LIU Y F,et al.Indole alkaloid sulfonic acids from an aqueousextract of Isatis indigotica roots and theirantiviral activity[J].Acta Pharmaceutica Sinica B,2017,7(3):334-341.
[10] ANDREEV I A,MANVAR D,BARRECA M L,et al.Discovery of the 2-phenyl-4,5,6,7-tetrahydro-1H-indole as a novelanti-hepatitis C virus targeting scaffold[J].European Journal of Medicinal Chemistry,2015,96:250-258.
[11] ZHANG M Z,WANG Y,PAUEKSAKON P,et al.Epidermal growth factorreceptor inhibition slows progression of diabetic nephropathy in associationwith a decrease in endoplasmic reticulum stress and an increase in autophagy[J].Diabetes,2014,63(6):2063-2072.
[12] HASSAM M,BASSON A E,LIOTTA D C,et al.Novel cyclopropyl-indole derivatives as HIV non-nucleoside reverse transcriptase inhibitors[J].ACS Medicinal Chemistry Letters,2012,3:470-475.
[13] XUE S T,MA L L,GAO R M,et al.Synthesis and antiviral activity of some novelindole-2-carboxylate derivatives[J].Acta Pharmaceutica Sinica B,2014,4(4):313-321.
[14] PENTA A,CHANDER S,GANGULY S,et al.De novo design and in-silico studies of novel 1-phenyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole -3-carboxylic acid derivatives as HIV-1 reverse transcriptase inhibitors[J].Medicinal Chemistry Research,2014,23:3662-3670.
[15] BAG P,OJHA D,MUKHERJEE H,et al.A dihydropyrido-indole potently inhibits HSV-1 infection by interfering the viral immediate early transcriptional events[J].Antiviral Research,2014,105:126-134.
[16] TICHY M,POHL R,TLOUSTOVA E,et al.Synthesis and biological activity of benzo-fused 7-deazaadenosineanalogues.5- and 6-substituted 4-amino- or 4-alkylpyrimido[4,5-b]indole ribonucleosides[J].Bioorganic & Medicinal Chemistry,2013,21:5362-5372.
[17] TICHY M,POHL R,XU H Y,et al.Synthesis and antiviral activity of 4,6-disubstituted pyrimido[4,5-b]indoleribonucleosides[J].Bioorganic & Medicinal Chemistry,2012,20(20):6123-6133.
[18] FERRO S,GRAZIA S D,LUCA L D,et al.Microwave assisted organic synthesis(MAOS)of small molecules as potential HIV-1 integrase inhibitors[J].Molecules,2011,16(8):6858-6870.
[19] LUCA L D,GRAZIA S D,FERRO S,et al.HIV-1 integrase strand-transfer inhibitors:Design,synthesis and molecularmodeling investigation[J].European Journal of Medicinal Chemistry,2011,46(2):756-764.
[20] ROGOLINO D,CARCELLI M,COMPARI C,et al.Diketoacid chelating ligands asdual inhibitors of HIV-1 integration process[J].European Journal of Medicinal Chemistry,2014,78:425-430.
[21] FERRO S,LUCAL D,SURDO G L,et al.A new potential approach to block HIV-1 replication via proteinprotein interaction and strand-transfer inhibition[J].Bioorganic & Medicinal Chemistry,2014,22(7):2269-2279.
[22] LIU J J,LI W Y,ZHANG L,et al.Recent progress in research on C3 substituted isatin derivatives[J].World Notes on Antibiotics,2013,34(3):116-122.
[23] ZHANG H F,DAI H Q,PAUL J H,et al.Antiviral activity of an isatin derivative via induction of PERK-Nrf2-mediated suppression of cap-independent translation[J].ACS Chemical Biology,2014,9(4):1015-1024.
[24] TONG L,YUW S,COBURN C A,et al.Structure-activity relationships of proline modifications aroundthe tetracyclic-indole class of NS5A inhibitors[J].Bioorganic & Medicinal Chemistry Letters,2016,26(21):5354-5360.
[25] TONG L,YU W S,COBURN C A,et al.Alternative core development around the tetracyclic indole class of HCV NS5A inhibitors[J].Bioorganic & Medicinal Chemistry Letters,2016,26(20):5132-5137.
[26] TONG L,YU W S,CHEN L,et al.Discovery of ruzasvir(MK-8408):apotent,pan-genotype HCV NS5A inhibitor with optimized activity against common resistance associated polymorphisms[J].Journal of Medicinal Chemistry,2017,60(1):290-306.
[27] BALUPURI A,GADHE C G,BALASUBRAMANIAN P K,et al.Insilico study on indole derivatives as anti HIV-1 agents:a combined docking,molecular dynamics and 3D-QSAR study[J].Archives of Pharmacal Research,2014,37(8):1001-1015.
[28] ZHOU G,WU D,HERMEL E,et al.Design,synthesis,andevaluation of indole compounds as novel inhibitors targeting Gp41[J].Bioorganic & Medicinal Chemistry Letters,2010,20(5):1500-1503.
[29] WHITBY L R,BOYLEK E,CAI L,et al.Discovery of HIV fusion inhibitors targeting gp41 using a comprehensive alpha-helix mimeticlibrary[J].Bioorganic & Medicinal Chemistry Letters,2012,22(8):2861-2865.
[30] LEE W G,GALLARDO-MACIAS R,FREY K M,et al.Picomolar inhibitors of HIV reverse transcriptase featuring bicyclic replacement of a cyanovinylphenyl group[J].Journal of the American Chemical Society,2013,135(44):16705-16713.
[31] ISMAIL N S,DINE R S,HATTORI M,et al.Computer baseddesign,synthesis and biological evaluation of novel indole derivatives as HCV NS3-4A serine protease inhibitors[J].Bioorganic & Medicinal Chemistry,2008,16(17):7877-7887.
[32] FLINT O P,NOOR M A,HRUZ P W,et al.The role of protease inhibitors in the pathogenesisof HIV-associated lipodystrophy:cellular mechanisms and clinical implications[J].Toxicologic Pathology,2009,37(1):65-77.
[33] HAN X,OUYANG W,LIU B,et al.Enantioselective inhibition of reverse transcriptase(RT)of HIV-1 by non-racemicindole-based trifluoropropanoates developed by asymmetric catalysis using recyclable organocatalysts[J].Organic & Biomolecular Chemistry,2013,11:8463-8475.
[34] PENG J,LIN T,WANG W,et al.Antiviral alkaloids produced by the mangrove-derived fungus Cladosporium sp.PJX-41[J].Journal of Natural Products,2013,76(6):1133-1140.
[35] CIHAN-USTUNDAG G,GURSOY E,NAESENS L,et al.Synthesis and antiviral properties of novel indole-basedthiosemicarbazides and 4-thiazolidinones[J].Bioorganic & Medicinal Chemistry,2016,24(2):240-246.
[2] VILLALAIN J.Membranotropic effects of arbidol,a broad anti-viral molecule,onphospholipid model membranes[J].Journal of Chemical Physics,2010,114(25):8544-8554.
[3] BRANCATO V,PEDUTOA,WHARTON S,et al.Design of inhibitors of influenza virus membrane fusion:Synthesis,structure-activity relationship and in vitro antiviral activity of a novelindole series[J].Antiviral Research,2013,99(2):125-135.
[4] SCUOTTO M,ABDELNABI R,COLLARILE S,et al.Discovery of novel multi-target indole-based derivatives as potent andselective inhibitors of chikungunya virus replication[J].Bioorganic & Medicinal Chemistry,2016,25(1):327-337.
[5] WILLIAMS T M,CICCARONE T M,MAC S C,et al.5-chloro-3-(phenylsulfonyl)indole-2-carboxamide:a novel,non-nucleosideinhibitor of HIV-1 reverse transcriptase[J].Journal of Medicinal Chemistry,1993,36(9):1291-1294.
[6] REGINA G,COLUCCIA A,BRANCALE A,et al.New nitrogen containing substituents at the indole-2-carboxamide yield high potent and broad spectrum indolylarylsulfone HIV-1 non-nucleoside reverse transcriptase inhibitors[J].Journal of Medicinal Chemistry,2012,55(14):6634-6638.
[7] FAMIGLINI V,REGINA G,COLUCCIA A,et al.Newindolylarylsulfones as highly potent and broad spectrum HIV-1 non-nucleoside reverse transcriptase inhibitors[J].European Journal of Medicinal Chemistry,2014,80:101-111.
[8] ALEXANDRE F R,AMADOR A,BOT S,et al.Synthesis and biological evaluation of aryl-phospho-indole asnovel HIV-1 non-nucleoside reverse transcriptase inhibitors[J].Journal of Medicinal Chemistry,2011,54(1):392-395.
[9] MENG L J,GUO Q L,LIU Y F,et al.Indole alkaloid sulfonic acids from an aqueousextract of Isatis indigotica roots and theirantiviral activity[J].Acta Pharmaceutica Sinica B,2017,7(3):334-341.
[10] ANDREEV I A,MANVAR D,BARRECA M L,et al.Discovery of the 2-phenyl-4,5,6,7-tetrahydro-1H-indole as a novelanti-hepatitis C virus targeting scaffold[J].European Journal of Medicinal Chemistry,2015,96:250-258.
[11] ZHANG M Z,WANG Y,PAUEKSAKON P,et al.Epidermal growth factorreceptor inhibition slows progression of diabetic nephropathy in associationwith a decrease in endoplasmic reticulum stress and an increase in autophagy[J].Diabetes,2014,63(6):2063-2072.
[12] HASSAM M,BASSON A E,LIOTTA D C,et al.Novel cyclopropyl-indole derivatives as HIV non-nucleoside reverse transcriptase inhibitors[J].ACS Medicinal Chemistry Letters,2012,3:470-475.
[13] XUE S T,MA L L,GAO R M,et al.Synthesis and antiviral activity of some novelindole-2-carboxylate derivatives[J].Acta Pharmaceutica Sinica B,2014,4(4):313-321.
[14] PENTA A,CHANDER S,GANGULY S,et al.De novo design and in-silico studies of novel 1-phenyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole -3-carboxylic acid derivatives as HIV-1 reverse transcriptase inhibitors[J].Medicinal Chemistry Research,2014,23:3662-3670.
[15] BAG P,OJHA D,MUKHERJEE H,et al.A dihydropyrido-indole potently inhibits HSV-1 infection by interfering the viral immediate early transcriptional events[J].Antiviral Research,2014,105:126-134.
[16] TICHY M,POHL R,TLOUSTOVA E,et al.Synthesis and biological activity of benzo-fused 7-deazaadenosineanalogues.5- and 6-substituted 4-amino- or 4-alkylpyrimido[4,5-b]indole ribonucleosides[J].Bioorganic & Medicinal Chemistry,2013,21:5362-5372.
[17] TICHY M,POHL R,XU H Y,et al.Synthesis and antiviral activity of 4,6-disubstituted pyrimido[4,5-b]indoleribonucleosides[J].Bioorganic & Medicinal Chemistry,2012,20(20):6123-6133.
[18] FERRO S,GRAZIA S D,LUCA L D,et al.Microwave assisted organic synthesis(MAOS)of small molecules as potential HIV-1 integrase inhibitors[J].Molecules,2011,16(8):6858-6870.
[19] LUCA L D,GRAZIA S D,FERRO S,et al.HIV-1 integrase strand-transfer inhibitors:Design,synthesis and molecularmodeling investigation[J].European Journal of Medicinal Chemistry,2011,46(2):756-764.
[20] ROGOLINO D,CARCELLI M,COMPARI C,et al.Diketoacid chelating ligands asdual inhibitors of HIV-1 integration process[J].European Journal of Medicinal Chemistry,2014,78:425-430.
[21] FERRO S,LUCAL D,SURDO G L,et al.A new potential approach to block HIV-1 replication via proteinprotein interaction and strand-transfer inhibition[J].Bioorganic & Medicinal Chemistry,2014,22(7):2269-2279.
[22] LIU J J,LI W Y,ZHANG L,et al.Recent progress in research on C3 substituted isatin derivatives[J].World Notes on Antibiotics,2013,34(3):116-122.
[23] ZHANG H F,DAI H Q,PAUL J H,et al.Antiviral activity of an isatin derivative via induction of PERK-Nrf2-mediated suppression of cap-independent translation[J].ACS Chemical Biology,2014,9(4):1015-1024.
[24] TONG L,YUW S,COBURN C A,et al.Structure-activity relationships of proline modifications aroundthe tetracyclic-indole class of NS5A inhibitors[J].Bioorganic & Medicinal Chemistry Letters,2016,26(21):5354-5360.
[25] TONG L,YU W S,COBURN C A,et al.Alternative core development around the tetracyclic indole class of HCV NS5A inhibitors[J].Bioorganic & Medicinal Chemistry Letters,2016,26(20):5132-5137.
[26] TONG L,YU W S,CHEN L,et al.Discovery of ruzasvir(MK-8408):apotent,pan-genotype HCV NS5A inhibitor with optimized activity against common resistance associated polymorphisms[J].Journal of Medicinal Chemistry,2017,60(1):290-306.
[27] BALUPURI A,GADHE C G,BALASUBRAMANIAN P K,et al.Insilico study on indole derivatives as anti HIV-1 agents:a combined docking,molecular dynamics and 3D-QSAR study[J].Archives of Pharmacal Research,2014,37(8):1001-1015.
[28] ZHOU G,WU D,HERMEL E,et al.Design,synthesis,andevaluation of indole compounds as novel inhibitors targeting Gp41[J].Bioorganic & Medicinal Chemistry Letters,2010,20(5):1500-1503.
[29] WHITBY L R,BOYLEK E,CAI L,et al.Discovery of HIV fusion inhibitors targeting gp41 using a comprehensive alpha-helix mimeticlibrary[J].Bioorganic & Medicinal Chemistry Letters,2012,22(8):2861-2865.
[30] LEE W G,GALLARDO-MACIAS R,FREY K M,et al.Picomolar inhibitors of HIV reverse transcriptase featuring bicyclic replacement of a cyanovinylphenyl group[J].Journal of the American Chemical Society,2013,135(44):16705-16713.
[31] ISMAIL N S,DINE R S,HATTORI M,et al.Computer baseddesign,synthesis and biological evaluation of novel indole derivatives as HCV NS3-4A serine protease inhibitors[J].Bioorganic & Medicinal Chemistry,2008,16(17):7877-7887.
[32] FLINT O P,NOOR M A,HRUZ P W,et al.The role of protease inhibitors in the pathogenesisof HIV-associated lipodystrophy:cellular mechanisms and clinical implications[J].Toxicologic Pathology,2009,37(1):65-77.
[33] HAN X,OUYANG W,LIU B,et al.Enantioselective inhibition of reverse transcriptase(RT)of HIV-1 by non-racemicindole-based trifluoropropanoates developed by asymmetric catalysis using recyclable organocatalysts[J].Organic & Biomolecular Chemistry,2013,11:8463-8475.
[34] PENG J,LIN T,WANG W,et al.Antiviral alkaloids produced by the mangrove-derived fungus Cladosporium sp.PJX-41[J].Journal of Natural Products,2013,76(6):1133-1140.
[35] CIHAN-USTUNDAG G,GURSOY E,NAESENS L,et al.Synthesis and antiviral properties of novel indole-basedthiosemicarbazides and 4-thiazolidinones[J].Bioorganic & Medicinal Chemistry,2016,24(2):240-246.
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