Synthesis, antibacterial and free radical scavenging activity of some newer N-((10-nitro-1H-indolo [1, 2-c]quinazolin-12-yl)methylene)benzenamines

[1]Al-Hiari YM, Qaisi AM, El-Abadelah MM, Voelter W. Synthesis and antibacterial activity of some substituted 3-(aryl)-and 3-(heteroaryl) indoles. Monatshefte für Chemie/Chemical Monthly. 2006 Feb 1;137(2):243–8.Al-HiariYMQaisiAMEl-AbadelahMMVoelterWSynthesis and antibacterial activity of some substituted 3-(aryl)-and 3-(heteroaryl) indolesMonatshefte für Chemie/Chemical Monthly2006Feb11372243810.1007/s00706-005-0424-6Search in Google Scholar

[2]Andreani A, Burnelli S, Granaiola M et al. Antitumor activity of bis-indole derivatives. J Med Chem. 2008; 51: 4563–4570.AndreaniABurnelliSGranaiolaMAntitumor activity of bis-indole derivativesJ Med Chem2008514563457010.1021/jm800194kSearch in Google Scholar

[3]Bast A, Haenen G, Doelman C. Oxidants and antioxidants: state of the art. Am J Med. 1991; 92 (Suppl. 3C): 2–13.BastAHaenenGDoelmanCOxidants and antioxidants: state of the artAm J Med199192Suppl. 3C21310.1016/0002-9343(91)90278-6Search in Google Scholar

[4]Bhovi MG, Gadaginamath GS. 1, 3-Dipolarcycloaddition reactions: Synthesis and antimicrobial activity of novel 1-triazolylindole and 1-triazolylbenz-[g]indole derivatives. Indian J Chem. 2005; 44B: 1068–1073.BhoviMGGadaginamathGS1, 3-Dipolarcycloaddition reactions: Synthesis and antimicrobial activity of novel 1-triazolylindole and 1-triazolylbenz-[g]indole derivativesIndian J Chem200544B1068107310.1002/chin.200538126Search in Google Scholar

[5]Billimoria AD, Cava MP. Chemistry of Indolo [1, 2-c]quinazoline: An approach to the marine alkaloid Hinckdentine A. J Org Chem. 1994; 59: 6777–6782.BillimoriaADCavaMPChemistry of Indolo [1, 2-c]quinazoline: An approach to the marine alkaloid Hinckdentine AJ Org Chem1994596777678210.1021/jo00101a043Search in Google Scholar

[6]Bulkley GB. Free radicals and other reactive oxygen metabolites: Clinical relevance and the therapeutic efficacy of antioxidant therapy. Surgery. 1993; 113: 479–483.BulkleyGBFree radicals and other reactive oxygen metabolites: Clinical relevance and the therapeutic efficacy of antioxidant therapySurgery1993113479483Search in Google Scholar

[7]Chodvadiya VD, Pambhar KD, Parmar ND, Dhamsaniya AP, Chhatbar PV, Ram HN, Khunt RC, Patel PK. Synthesis and Characterization of N-Methyl Indole Derivatives via Desulfitative Displacement by Various Amines and Its Antimicrobial Activity. World Scientific News. 2019; 120(2):181–91.ChodvadiyaVDPambharKDParmarNDDhamsaniyaAPChhatbarPVRamHNKhuntRCPatelPKSynthesis and Characterization of N-Methyl Indole Derivatives via Desulfitative Displacement by Various Amines and Its Antimicrobial ActivityWorld Scientific News2019120218191Search in Google Scholar

[8]Cihan-Üstündağ G, Naesens L, Şatana D, Erköse-Genç G, Mataracı-Kara E, Çapan G. Design, synthesis, antitubercular and antiviral properties of new spirocyclic indole derivatives. Monatshefte für Chemie-Chemical Monthly. 2019;150(8):1533–44.Cihan-ÜstündağGNaesensLŞatanaDErköse-GençGMataracı-KaraEÇapanGDesign, synthesis, antitubercular and antiviral properties of new spirocyclic indole derivativesMonatshefte für Chemie-Chemical Monthly2019150815334410.1007/s00706-019-02457-9Search in Google Scholar

[9]Cross CE, Vliet A, Neill ACO, Eiserich JP. Reactive oxygen species and the lung. Lancet. 1994; 344: 930–933.CrossCEVlietANeillACOEiserichJPReactive oxygen species and the lungLancet199434493093310.1016/S0140-6736(94)92275-6Search in Google Scholar

[10]Dedon PC, Tannenbaum SR. Reactive nitrogen species in the chemical biology of inflammation. Arch Biochem Biophys. 2004; 423: 12–22.DedonPCTannenbaumSRReactive nitrogen species in the chemical biology of inflammationArch Biochem Biophys2004423122210.1016/j.abb.2003.12.01714989259Search in Google Scholar

[11]Dekker WH, Selling HA, Overeem JC. Structure-activity relationships of some antifungal indoles. J Agric Food Chem. 1975; 23: 785–791.DekkerWHSellingHAOvereemJCStructure-activity relationships of some antifungal indolesJ Agric Food Chem19752378579110.1021/jf60200a0411170225Search in Google Scholar

[12]Demurtas M, Baldisserotto A, Lampronti I, Moi D, Balboni G, Pacifico S, Vertuani S, Manfredini S, Onnis V. Indole derivatives as multifunctional drugs: Synthesis and evaluation of antioxidant, photoprotective and antiproliferative activity of indole hydrazones. Bioorganic chemistry. 2019 Apr 1;85:568–76.DemurtasMBaldisserottoALamprontiIMoiDBalboniGPacificoSVertuaniSManfrediniSOnnisVIndole derivatives as multifunctional drugs: Synthesis and evaluation of antioxidant, photoprotective and antiproliferative activity of indole hydrazonesBioorganic chemistry2019Apr1855687610.1016/j.bioorg.2019.02.00730825715Search in Google Scholar

[13]Donawade DS, Gadaginamath GS. Some electrophilic substitution reactions on 1-substituted-3-acetyl/carbethoxy-5-hydroxy-2-methylindole and antimicrobial activity of these new indole derivatives. Indian J Chem. 2005; 44B: 1679–1685.DonawadeDSGadaginamathGSSome electrophilic substitution reactions on 1-substituted-3-acetyl/carbethoxy-5-hydroxy-2-methylindole and antimicrobial activity of these new indole derivativesIndian J Chem200544B1679168510.1002/chin.200550112Search in Google Scholar

[14]El Sayed MT, Sabry NM, Mahmoud K, Mahrous KF, Ali MM, Mahmoud AE, Voronkov A. Novel Nitro-Heterocycles Sugar and Indoles Candidates as Lead Structures Targeting HepG2 and A549 Cancer Cell Lines. Current Bioactive Compounds. 2018 Dec 1;14(4):434–44.El SayedMTSabryNMMahmoudKMahrousKFAliMMMahmoudAEVoronkovANovel Nitro-Heterocycles Sugar and Indoles Candidates as Lead Structures Targeting HepG2 and A549 Cancer Cell LinesCurrent Bioactive Compounds2018Dec11444344410.2174/1573407213666170621075333Search in Google Scholar

[15]Gadaginamath GS, Kavali RR. Synthesis and antimicrobial activity of novel 4H-pyrano [2, 3-f]-indole derivatives. Indian J Chem. 1999; 38B: 178–182.GadaginamathGSKavaliRRSynthesis and antimicrobial activity of novel 4H-pyrano [2, 3-f]-indole derivativesIndian J Chem199938B178182Search in Google Scholar

[16]Gaikwad R, Bobde Y, Ganesh R, Patel T, Rathore A, Ghosh B, Das K, Gayen S. 2-Phenylindole derivatives as anticancer agents: synthesis and screening against murine melanoma, human lung and breast cancer cell lines. Synthetic Communications. 2019 Jun 17:1–2.GaikwadRBobdeYGaneshRPatelTRathoreAGhoshBDasKGayenS2-Phenylindole derivatives as anticancer agents: synthesis and screening against murine melanoma, human lung and breast cancer cell linesSynthetic Communications2019Jun171210.1080/00397911.2019.1620282Search in Google Scholar

[17]Ghosh AK, Gong G, Grum-Tokars V, Mulhearn DC, Baker SC, Coughlin M, Prabhakar BS, Sleeman K., Johnson ME, Mesecar AD. Design, synthesis and antiviral efficacy of a series of potent chloropyridyl ester-derived SARS-CoV 3CLpro inhibitors. Bioorg Med Chem Lett. 2008; 18: 5684–5688.GhoshAKGongGGrum-TokarsVMulhearnDCBakerSCCoughlinMPrabhakarBSSleemanK.JohnsonMEMesecarADDesign, synthesis and antiviral efficacy of a series of potent chloropyridyl ester-derived SARS-CoV 3CLpro inhibitorsBioorg Med Chem Lett2008185684568810.1016/j.bmcl.2008.08.082274559618796354Search in Google Scholar

[18]Gupta L, Talwar A, Chauhan PMS. Bis and tris indole alkaloids from marine organisms: new leads for drug discovery. Curr Med Chem. 2007; 14: 1789–1803.GuptaLTalwarAChauhanPMSBis and tris indole alkaloids from marine organisms: new leads for drug discoveryCurr Med Chem2007141789180310.2174/9781608054640113060016Search in Google Scholar

[19]Gurkok G, Altanlar N, Suzen S. Investigation of antimicrobial activities of Indole-3-Aldehyde Hydrazide/Hydrazone Derivatives. Chemotherapy. 2009; 55, 15–19.GurkokGAltanlarNSuzenSInvestigation of antimicrobial activities of Indole-3-Aldehyde Hydrazide/Hydrazone DerivativesChemotherapy200955151910.1159/00016699918974644Search in Google Scholar

[20]Halliwell B, Gutteridge M. Free radicals in biology and medicine, third ed. Oxford Science Publications. Oxford University Press. 1998.HalliwellBGutteridgeMFree radicals in biology and medicinethird edOxford Science Publications. Oxford University Press1998Search in Google Scholar

[21]Halliwell B, Hoult JR, Blake DR. Oxidants, inflammation, and anti-inflammatory drugs. FASEB J. 1988; 2: 2867–2873.HalliwellBHoultJRBlakeDROxidants, inflammation, and anti-inflammatory drugsFASEB J198822867287310.1096/fasebj.2.13.28446162844616Search in Google Scholar

[22]Karah N, Gursoy A, Kandemirli F, Shvets N, Kaynak FB, Ozbey S, Kovalishyn V, Dimoglo A. Synthesis and structure-antituberculosis activity relationship of 1H-indole-2,3-dione derivatives. Bioorg Med Chem. 2007; 15: 5888–5891.KarahNGursoyAKandemirliFShvetsNKaynakFBOzbeySKovalishynVDimogloASynthesis and structure-antituberculosis activity relationship of 1H-indole-2,3-dione derivativesBioorg Med Chem2007155888589110.1016/j.bmc.2007.05.06317561405Search in Google Scholar

[23]Kaushik N, Kumar N, Kumar A. Synthesis, antioxidant and antidiabetic activity of 1-[(5-substituted phenyl)-4,5-dihydro-1H-pyrazol-3-yl]-5-phenyl-1H-tetrazole. Indian J Pharm Sci. 2016; 78(3): 352–359.KaushikNKumarNKumarASynthesis, antioxidant and antidiabetic activity of 1-[(5-substituted phenyl)-4,5-dihydro-1H-pyrazol-3-yl]-5-phenyl-1H-tetrazoleIndian J Pharm Sci201678335235910.4172/pharmaceutical-sciences.1000125Search in Google Scholar

[24]Kodisundaram P, Amirthaganesan S, Balasankar T. Antimicrobial evaluation of a set of heterobicyclic methylthiadiazole hydrazones: synthesis, characterization, and SAR studies. Journal of agricultural and food chemistry. 2013 Nov 27;61(49):11952–6KodisundaramPAmirthaganesanSBalasankarTAntimicrobial evaluation of a set of heterobicyclic methylthiadiazole hydrazones: synthesis, characterization, and SAR studiesJournal of agricultural and food chemistry2013Nov27614911952610.1021/jf404537d24251691Search in Google Scholar

[25]Macchia M, Manera C, Nencetti S, Rossello A, Broccali G, Limonta D. Synthesis and antimicrobial activity of benzo[a] dihydrocarbazole and benzotetrahydrocyclohept [1,2b]indole derivatives. Farmaco. 1996; 51: 75–78.MacchiaMManeraCNencettiSRosselloABroccaliGLimontaDSynthesis and antimicrobial activity of benzo[a] dihydrocarbazole and benzotetrahydrocyclohept [1,2b]indole derivativesFarmaco1996517578Search in Google Scholar

[26]Malesani G, Chiarelotto G, Dallacqua F, Vedali D. Antimicrobial properties of some 3-acyl-4,7-disubstituted indoles. Farmaco. 1975; 30: 137–146.MalesaniGChiarelottoGDallacquaFVedaliDAntimicrobial properties of some 3-acyl-4,7-disubstituted indolesFarmaco197530137146Search in Google Scholar

[27]Malviya R, Sharma PK, Dubey SK. Antioxidant potential and emulsifying properties of kheri (Acacia chundra, Mimosaceae) gum polysaccharide. Marm Pharm J. 2017; 21/3: 701–706.MalviyaRSharmaPKDubeySKAntioxidant potential and emulsifying properties of kheri (Acacia chundra, Mimosaceae) gum polysaccharideMarm Pharm J201721370170610.12991/marupj.323594Search in Google Scholar

[28]Mathada BSD, Mathada MBH. Synthesis and antimicrobial activity of some 5-substituted-3-phenyl-Nb-(Substituted-2-oxo-2H-pyrano [2,3-b]quinoline-3-carbonyl)-1H-indole-2-carboxyhydrazide. Chem Pharm Bull. 2009; 57: 557–560.MathadaBSDMathadaMBHSynthesis and antimicrobial activity of some 5-substituted-3-phenyl-Nb-(Substituted-2-oxo-2H-pyrano [2,3-b]quinoline-3-carbonyl)-1H-indole-2-carboxyhydrazideChem Pharm Bull20095755756010.1248/cpb.57.557Search in Google Scholar

[29]McCord JM. Human disease, free radicals, and the oxidant/antioxidant balance, Clin Biochem. 1993; 26: 351–357.McCordJMHuman disease, free radicals, and the oxidant/antioxidant balanceClin Biochem19932635135710.1016/0009-9120(93)90111-ISearch in Google Scholar

[30]Mouithys-Mickalad AML, Zheng SX, Deby-Dupont GP, Deby CM, Lamy MM, Reginster JY, Henrotin YE. Invitro study of the antioxidant properties of nonsteroidal anti-inflammatory drugs by chemiluminescence and electron spin resonance (ESR). Free Radic Res. 2000; 33: 607–621.Mouithys-MickaladAMLZhengSXDeby-DupontGPDebyCMLamyMMReginsterJYHenrotinYEInvitro study of the antioxidant properties of nonsteroidal anti-inflammatory drugs by chemiluminescence and electron spin resonance (ESR)Free Radic Res20003360762110.1080/10715760000301131Search in Google Scholar

[31]Nikolic D, Breemen RB. DNA Oxidation Induced by Cyclooxygenase-2, Chem Res Toxicol. 2001; 14: 351–354.NikolicDBreemenRBDNA Oxidation Induced by Cyclooxygenase-2Chem Res Toxicol20011435135410.1021/tx010004xSearch in Google Scholar

[32]Ningsih IY, Zulaikhah S, Hidayat MA, Kuswandi B. Antioxidant activity of various Kenitu (Chrysophyllum cainito L.) leaves extracts from Jember. Indonesia Agric Sci Procedia. 2016; 9: 378–85.NingsihIYZulaikhahSHidayatMAKuswandiBAntioxidant activity of various Kenitu (Chrysophyllum cainito L.) leaves extracts from JemberIndonesia Agric Sci Procedia201693788510.1016/j.aaspro.2016.02.153Search in Google Scholar

[33]Ran J, Huang N, Xu H, Yang Y, Lv M, Zheng YT. Anti HIV-1 agents 5: Synthesis and anti-HIV-1 activity of some N-arylsulfonyl-3-acetylindoles. Bioorg Med Chem. Lett. 2010; 20: 3534–3536.RanJHuangNXuHYangYLvMZhengYTAnti HIV-1 agents 5: Synthesis and anti-HIV-1 activity of some N-arylsulfonyl-3-acetylindolesBioorg Med Chem. Lett2010203534353610.1016/j.bmcl.2010.04.132Search in Google Scholar

[34]Santrucek M, Krepelka J. Antioxidants from the aspect of their potential use in chemotherapy. Drugs Future. 1988; 37: 121–128.SantrucekMKrepelkaJAntioxidants from the aspect of their potential use in chemotherapyDrugs Future198837121128Search in Google Scholar

[35]Santrucek M, Krepelka J. Of particular interests are the potential protective effects of antioxidants on lipoproteins, since oxidized LDL is thought to be atherogenic, Drugs Future. 1988; 13: 973–996.SantrucekMKrepelkaJOf particular interests are the potential protective effects of antioxidants on lipoproteins, since oxidized LDL is thought to be atherogenicDrugs Future198813973996Search in Google Scholar

[36]Shirinzadeh H, SÜZEN S, Altanlar N, Westwell AD. Antimicrobial Activities of New Indole Derivatives Containing 1, 2, 4-Triazole, 1, 3, 4-Thiadiazole and Carbothioamide. Turkish Journal of Pharmaceutical Sciences. 2018;15(3).ShirinzadehHSÜZENSAltanlarNWestwellADAntimicrobial Activities of New Indole Derivatives Containing 1, 2, 4-Triazole, 1, 3, 4-Thiadiazole and CarbothioamideTurkish Journal of Pharmaceutical Sciences201815310.4274/tjps.55707Search in Google Scholar

[37]Slater MJ, Baxter R, Bonser RW, Cockerill S, Gohil K, Parry N, Robinson E, Randall R, Yeates C, Snowden W, Walters A. Synthesis of N-alkyl substituted indolocarbazoles as potent inhibitors of human cytomegalovirus replication. Bioorg Med Chem Lett. 2001; 11: 1993–95.SlaterMJBaxterRBonserRWCockerillSGohilKParryNRobinsonERandallRYeatesCSnowdenWWaltersASynthesis of N-alkyl substituted indolocarbazoles as potent inhibitors of human cytomegalovirus replicationBioorg Med Chem Lett20011119939510.1016/S0960-894X(01)00352-3Search in Google Scholar

[38]Somei M, Yamada F. Simple indole alkaloids and those with a nonrearranged monoterpenoid unit. Nat Prod Rep. 2003; 20: 216–242.SomeiMYamadaFSimple indole alkaloids and those with a nonrearranged monoterpenoid unitNat Prod Rep20032021624210.1039/b110074m12735698Search in Google Scholar

[39]Sravanthi T, Rani S, Manju S. Synthesis and biological evaluation of 2-(2′/3′/4′/6′-substituted phenyl)-1H-indoles. Int J Pharm Pharmac Sc. 2015; 7(11): 268–73SravanthiTRaniSManjuSSynthesis and biological evaluation of 2-(2′/3′/4′/6′-substituted phenyl)-1H-indolesInt J Pharm Pharmac Sc201571126873Search in Google Scholar

[40]Sreejayan N, Rao MN. Free radical scavenging activity of curcuminoids, Drug Res. 1996; 46: 169–171.SreejayanNRaoMNFree radical scavenging activity of curcuminoidsDrug Res199646169171Search in Google Scholar

[41]Sreenivasulu R, Reddy KT, Sujitha P, Kumar CG, Raju RR. Synthesis, antiproliferative and apoptosis induction potential activities of novel bis (indolyl) hydrazide-hydrazone derivatives. Bioorganic & medicinal chemistry. 2019 Mar 15;27(6):1043–55.SreenivasuluRReddyKTSujithaPKumarCGRajuRRSynthesis, antiproliferative and apoptosis induction potential activities of novel bis (indolyl) hydrazide-hydrazone derivativesBioorganic & medicinal chemistry2019Mar1527610435510.1016/j.bmc.2019.02.00230773423Search in Google Scholar

[42]Tsotinis A, Varvaresou A, Calogeropoulou T, Siatra-Papastaikoudi T, Tiligada A. Synthesis and antimicrobial evaluation of indole containing derivatives of 1,3,4-triazole and their open-chain counterparts. Drug Res. 1997; 47: 307–310.TsotinisAVarvaresouACalogeropoulouTSiatra-PapastaikoudiTTiligadaASynthesis and antimicrobial evaluation of indole containing derivatives of 1,3,4-triazole and their open-chain counterpartsDrug Res199747307310Search in Google Scholar

[43]Turrens JF. Mitochondrial formation of reactive oxygen species. J Physiol. 2003; 552: 335–344.TurrensJFMitochondrial formation of reactive oxygen speciesJ Physiol200355233534410.1113/jphysiol.2003.049478234339614561818Search in Google Scholar

[44]Ugur A, Mercimek B, Ozler MA, Aahin N. Antimicrobial effects of bis (2-imidazolinyl)-5,5V-dioxime and its mono- and tri-nuclear complexes. Transit Met Chem. 2000; 25, 421.UgurAMercimekBOzlerMAAahinNAntimicrobial effects of bis (2-imidazolinyl)-5,5V-dioxime and its mono- and tri-nuclear complexesTransit Met Chem20002542110.1023/A:1007064819271Search in Google Scholar

[45]Vapaatalo H. Free radicals and anti-inflammatory drugs. Med Biol. 1986; 64: 1–7;VapaataloHFree radicals and anti-inflammatory drugsMed Biol19866417Search in Google Scholar

[46]Varvaresou A, Tsantili-Kakoulidou A, Siatra-Papastaikoudi T, Tiligada E. Synthesis and biological evaluation of indole containing derivatives of thiosemicarbazide and their cyclic 1,2,4-triazole and 1,3,4-thiadiazole analogs, Drug Res. 2000; 50: 48–54.VarvaresouATsantili-KakoulidouASiatra-PapastaikoudiTTiligadaESynthesis and biological evaluation of indole containing derivatives of thiosemicarbazide and their cyclic 1,2,4-triazole and 1,3,4-thiadiazole analogsDrug Res200050485410.1055/s-0031-130016310683716Search in Google Scholar

[47]Whitehead CW, Whitesitt AA. Effects of lipophilic substituents on some biological properties of indoles. J Med Chem. 1974; 17: 1298–1304.WhiteheadCWWhitesittAAEffects of lipophilic substituents on some biological properties of indolesJ Med Chem1974171298130410.1021/jm00258a0144214926Search in Google Scholar

[48]Williams JD, Chen JJ, Drach JC, Townsend LB. Synthesis and antiviral activity of 3-formyl- and 3-Cyano-2,5,6-trichloroindole nucleoside derivatives, J Med Chem. 2004; 47: 5766–5772.WilliamsJDChenJJDrachJCTownsendLBSynthesis and antiviral activity of 3-formyl- and 3-Cyano-2,5,6-trichloroindole nucleoside derivativesJ Med Chem2004475766577210.1021/jm040032n15509175Search in Google Scholar

[49]Xu H, Lv M. Developments of indoles as anti-HIV-1 inhibitors. Curr Pharm Des. 2009; 15: 2120–2148.XuHLvMDevelopments of indoles as anti-HIV-1 inhibitorsCurr Pharm Des2009152120214810.2174/13816120978848916819519449Search in Google Scholar