A brief review of the biological potential of indole derivatives
Tóm tắt
Từ khóa
Tài liệu tham khảo
Lakhdar S, Westermaier M, Terrier F, Goumont R, Boubaker T, Ofial AR, Mayr H (2006) Nucleophilic reactivities of indoles. J Org Chem 71:9088–9095
Sharma V, Pradeep K, Devender P (2010) Biological importance of the indole nucleus in recent years: a comprehensive review. J Heterocycl Chem 47:491–502
Kaushik NK, Kaushik N, Attri P, Kumar N, Kim CH, Verma AK, Choi EH (2013) Biomedical Importance of Indoles. Molecules 18:6620–6662
Xue S, Ma L, Gao R, Lin Y, Linn Z (2014) Synthesis and antiviral activity of some novel indole-2-carboxylate derivatives. Acta Pharmaceutica Sinica B 4(4):313–321
Cihan-Üstündag G, Gürsoy E, Naesens L, Ulusoy-Güzeldemirci N, Çapan G (2016) Synthesis and antiviral properties of novel indole-based thiosemicarbazides and 4-thiazolidinones. Bioorg Med Chem 24:240–246
Sellitto G, Faruolo A, Caprariis PD, Altamura S, Paonessa G, Ciliberto G (2010) Synthesis and anti-hepatitis C virus activity of novel ethyl1H-indole-3-carboxylates in vitro. Bioorg Med Chem 18:6143–6148
Giampieri M, Balbia A, Mazzeia M, Collab PL, Ibba C, Loddo R (2009) Antiviral activity of indole derivatives. Antiviral Res 83:179–185
Tichy M, Pohl R, Xu HY, Chen YL, Yokokawa F, Shi PY, Hocek M (2012) Synthesis and antiviral activity of 4, 6-disubstituted pyrimido[4,5-b]indole ribonucleosides. Bioorgan Med Chem 20:6123–6133
Terzioglu N, Karali N, Gursoy A, Pannecouque C, Leysen P, Paeshuyse J, Neyts J, De Clercq E (2006) Synthesis and primary antiviral activity evaluation of 3-hydrazono-5-nitro-2-indolinone derivatives. Arkivoc 1:109–118
El-Sawy AER, Abo-Salem HM, Zarie ES, Abd-Alla HI, El-Safty MM, Mandour AH (2015) Synthesis and antiviral activity of novel ethyl 2-(3-heterocycle-1H-indol-1-yl) acetate derivatives. Int J Pharm Pharm Sci 7(5):76–83
Abdel-gawad H, Mohamed HA, Dawood KM, Badria FAR (2010) Synthesis and antiviral activity of new indole-based heterocycles. Chem Pharm Bull 58(11):1529–1531
Cihan-Üstündağ G, Naesens L, Şatana D, Erköse-Genç G, Mataracı-Kara E, Çapan G (2019) Design, synthesis, antitubercular and antiviral properties of new spirocyclic indole derivatives. Monatsh Chem 150(8):1533–1544
Ozdemir A, Altıntop MD, Zitouni GT, Çiftçi GA, Ertorun I, Alatas O, Kaplancıklı ZA (2015) Synthesis and evaluation of new indole-based chalcones as potential antiinflammatory agents. Eur J Med Chem 89:304–309
Sarva S, Harinah JS, Sthanikam SP, Ethiraj S, Vaithiyalingam M, Cirandur SR (2016) Synthesis, antibacterial and anti-inflammatory activity of bis(indolyl)methanes. Chinese Chem Lett 27:16–20
Rani P, Srivastava VK, Kumar A (2004) Synthesis and anti-inflammatory activity of heterocyclic indole derivatives. Eur J Med Chem 39:449–452
Pedada SR, Yarla NS, Tambade PJ, Dhananjaya BL, Bishayee A, Arunasree KM, Philip GH, Dharmapuri G, Aliev G, Putta S, Rangaiah G (2016) Synthesis of new secretory phospholipase A2-inhibitory indole containing isoxazole derivatives as anti-inflammatory and anticancer agents. Eur J Med Chem 112:289–297
Misra CS, Honnappa CG, Jitta SR, Gourishetti K, Daram P, Singh MP, Shrungeswara AH, Nayak Y, Unnikrishnan MK (2016) Biological activity of a small molecule indole analog, 1-[(1H-indol-3-yl)methylene]-2-phenylhydrazine (HMPH), in chronic inflammation. Chem Biol Interact 244:71–83
Singh N, Bhati SK, Kumar A (2008) Thiazolyl /oxazolyl formazanyl indoles as potent anti-inflammatory agents. Eur J Med Chem 43:2597–2609
Amin NH, El-Saadi MT, Hefny AA, Abdelazeem AH, Elshemy HA, Abdellatif KR (2018) Anti-inflammatory indomethacin analogs endowed with preferential COX-2 inhibitory activity. Future Med Chem 10(21):2521–2535
Abdellatif KR, Lami PF, Omar HA (2016) 3-Methyl-2-phenyl-1-substituted-indole derivatives as indomethacin analogs: design, synthesis and biological evaluation as potential anti-inflammatory and analgesic agents. J Enzyme Inhib Med Chem 31(2):318–324
Chavan RS, More HN, Bhosale AV (2011) Synthesis, characterization and evaluation of analgesic and anti-inflammatory activities of some novel indoles. Trop J Pharmaceutical Res 10(4):463–473
Prajapati TR, Pandey DP, Gupta V, Joshi B, Dhingra GK (2018) Synthesis and anti-inflammatory activity of some newer potential isoxazoline derivatives of indole. Essence Int J Env Rehab Conserv IX(1):87–93
Mandour A, El-Sawy E, Shaker K, Mustafa M (2010) Synthesis, anti-inflammatory, analgesic and anticonvulsant activities of 1, 8-dihydro-1-ary1-8-alkyl pyrazolo (3, 4-b) indoles. Acta Pharmaceutica 60(1):73–88
Bhat MA, Al-Omar MA, Raish M, Ansari MA, Abuelizz HA, Bakheit AH, Naglah AM (2018) Indole derivatives as cyclooxygenase inhibitors: synthesis, biological evaluation and docking studies. Molecules 23(6):1250
Ugwu DI, Okoro UC, Ukoha PO, Gupta A, Okafor SN (2018) Novel antiinflammatory and analgesic agents: synthesis, molecular docking and invivo studies. J Enzyme Inhib Med Chem 33(1):405–415
Shaker AM, Abdelall EK, Abdellatif KR, Abdel-Rahman HM (2018) Design, synthesis and biological evaluation of 2-(4-(methylsulfonyl) phenyl) indole derivatives with promising COX-2 inhibitory activity. J Appl Pharm Sci 8(11):001–008
Zhuang SH, Lin YC, Chou LC, Hsu MH, Lin HY, Huang CH, Lien JC, Kuo SC, Huang LJ (2013) Synthesis and anticancer activi ty of 2, 4-disubstituted furo[3,2-b]indole derivatives. Eur J Med Chem 66:466–479
Ma J, Bao G, Wang L, Li W, Xu B, Du B, Lv J, Zhai X, Gong P (2015) Design, synthesis, biologicalevaluation and preliminary mechanism study of novel benzothiazole derivatives bearing indole-based moiety as potent antitumor agents. Eur J Med Chem 96:173–186
Gurkan-Alp AS, Mumcuoglu M, Andac CA, Dayanc E, Cetin-Atalay R, Buyukbingol E (2012) Synthesis, anticancer activities and molecular modeling studies of novel indoleretinoid derivatives. Eur J Med Chem 58:346–354
Kumar TOS, Mahadavan KM, Kumara MN (2014) Synthesis and cytotoxic studies of 2, 3-dimethylindoles and tetrahydrocarbazoles. Int J Pharm Pharmaceutical Sci 6(2):2014
Han K, Wang H, Song B, Li Y, Ding WN, Zhao H, Sun H, Teng Y, Yu P (2014) Design, synthesis and biological activity evaluation of novel anticancer agent 5-(2-carboxyethenyl)indole derivatives. J Chem Pharm Res. 6(9):376–380
Akkoc MK, Y¨Uksel MY, Durmaz I, Atalay RC (2012) Design, synthesis, and biological evaluation of indole-based 1, 4-disubstituted piperazines as cytotoxic agents. Turk J Chem 36:515–525
Kumar D, Kumar NM, Chang KH, Gupta R, Shah K (2011) Synthesis and in-vitro anticancer activity of 3, 5-bis (indolyl)-1, 2, 4-thiadiazoles. Bioorg Med Chem Lett 21:5897–5900
Choppara P, Prasad YV, Rao CV, Krishna KH, Trimoorthulu G, Rao GUM, Rao JV, Bethu MS, Murthy YLN (2015) Design, synthesis of novel N- prenylated indole-3-carbazones and evaluation of invitro cytotoxicity and 5-LOX inhibition activities. Arab J Chem xxx:xxx
Kaur H, Singh J, Narasimhan B (2019) Indole hybridized diazenyl derivatives: synthesis, antimicrobial activity, cytotoxicity evaluation and docking studies. BMC Chem 13(1):65
Yousif MN, Hussein HA, Yousif NM, El-Manawaty MA, El-Sayed WA (2019) Synthesis and anticancer activity of novel 2-phenylindole linked imidazolothiazole, thiazolo-s-triazine and imidazolyl-sugar systems. J Appl Pharm Sci 9(01):006–014
Kasralikar HM, Jadhavar SC, Bhusare SR (2015) Synthesis and molecular docking studies of oxochromenyl xanthenone and indolyl xanthenone derivatives as anti-HIV-1 RT inhibitors. Bioorg Med Chem Lett 25:3882–3886
Ran JQ, Huang N, Xu H, Yang LM, Lv M, Zheng YT (2010) Anti HIV-1 agents 5: Synthesis and anti-HIV-1 activity of some N-arylsulfonyl-3-acetylindoles invitro. Bioorg Med Chem Lett 20:3534–3536
Selvam P, Chandramohan M, Clercq ED, Witvrouw M, Pannecouque C (2001) Synthesis and anti-HIV activity of 4-[(1, 2-dihydro-2-oxo-3H-indol-3-ylidene) amino]-N (4, 6-dimethyl-2-pyrimidinyl)-benzene sulfonamide and its derivatives. Eur J Pharm Sci 14:313–316
Che Z, Tian Y, Liu S, Hu M, Chen G (2018) Discovery of N-arylsulfonyl-3-acylindole benzoyl hydrazone derivatives as anti-HIV-1 agents. Brazilian J Pharmaceutical Sci 54(3)e17044:1-7
Ashok P, Lu CL, Chander S, Zheng YT, Murugesan S (2015) Design, synthesis, and biological evaluation of 1-(thiophen-2-yl)-9H-pyrido [3, 4-b] indole derivatives as anti-HIV-1 agents. Chem Biol Drug Des 85(6):722–728
Han X, Wu H, Wang W, Dong C, Tien P, Wu S, Zhou HB (2014) Synthesis and SARs of indole-based α-amino acids as potent HIV-1 non-nucleoside reverse transcriptase inhibitors. Org Biomol Chem 12(41):8308–8317
Sanna G, Madeddu S, Giliberti G, Piras S, Struga M, Wrzosek M, Kubiak-Tomaszewska G, Koziol AE, Savchenko O, Lis T, Stefanska J (2018) Synthesis and biological evaluation of novel indole-derived thioureas. Molecules 23(10):2554
Ragno R, Coluccia A, La Regina G, De Martino G, Piscitelli F, Lavecchia A, Novellino E, Bergamini A, Ciaprini C, Sinistro A, Maga G (2006) Design, molecular modeling, synthesis, and anti-HIV-1 activity of new indolyl aryl sulfones. Novel derivatives of the indole-2-carboxamide. J Med Chem 49(11):3172–3184
Chai H, Zhao Y, Zhao C, Gong P (2006) Synthesis and invitro anti-hepatitis B virus activities of some ethyl 6-bromo-5-hydroxy-1H-indole-3-carboxylates. Bioorgan Med Chem 14:911–917
Zhao C, Zhao Y, ChaiH GP (2006) Synthesis and in vitro anti-hepatitis B virus activities of some ethyl 5-hydroxy-1H-indole-3-carboxylates. Bioorgan Med Chem 14:2552–2558
Jiang T, Kuhen KL, Wolff K, Yin H, Bieza K, Caldwell J, Bursulaya B, Tuntland T, Zhang K, Karanewsky D, He Y (2006) Design, synthesis, and biological evaluations of novel oxindoles as HIV-1 non-nucleoside reverse transcriptase inhibitors. Part 2. Bioorg Med Chem Lett 16:2109–2112
Zhao Z, Wolkenberg SE, Lu M, Munshi V, Moyer G, Feng M, Carella AV, Ecto LT LT, Gabryelski LJ, Ming-Tain Lai MT, Prasad SG, Yan Y, McGaughey GB, Miller MD, Lindsley CW, Hartman GD, Vacca JP, Williams TM (2008) Novel indole-3-sulfonamides as potent HIV non-nucleoside reverse transcriptase inhibitors (NNRTIs). Bioorg Med Chem Lett 18:554–559
Chiummiento L, Funicello M, Lupattelli P, Tramutola F, Campaner P (2009) New indolic non-peptidic HIV protease inhibitors from (S)-glycidol: synthesis and preliminary biological activity. Tetrahedron 65:5984–5989
Ferro S, Luca LD, Barreca ML, Grazia SD, Christ F, Zeger Debyser Z, Chimirri A (2010) New chloro, fluorobenzylindole derivatives as integrase strand-transfer inhibitors (INSTIs) and their mode of action. Bioorgan Med Chem 18:5510–5518
Silveira CC, Mendes SR, Soares JR, Victoria FN, Martinez DM, Savegnago L (2013) Synthesis and antioxidant activity of new C-3 sulfenyl indoles. Tetrahedron Lett 54:4926–4929
Gurer-Orhan H, Karaaslan C, Ozcan S, Firuzi O, Tavakkoli M, Saso L, Suzen S (2016) Novel indole-based melatonin analogues: Evaluation of antioxidant activity and protective effect against amyloid b-induced damage. Bioorg Med Chem 24:1658–1664
Biradar JS, Sasidhar BS, Parveen R (2010) Synthesis, antioxidant and DNA cleavage activities of novel indole derivatives. Eur J Med Chem 45:4074–4078
Estevao MS, Carvalho LC, Ribeiro D, Couto D, Freitas M, Gomes A, Ferreira LM, Fernandes B, Marques MMB (2010) Antioxidant activity of unexplored indole derivatives: Synthesis and screening. Eur J Med Chem 45:4869–4878
Bakherad Z, Safavi M, Fassihi A, Sadeghi-Aliabadi H, Bakherad M, Rastegar H, Mahdavi M (2019) Anti-cancer, anti-oxidant and molecular docking studies of thiosemicarbazone indole-based derivatives. Res Chemical Intermediate 45(5):2827–2854
Suzen S, Tekiner-Gulbas B, Shirinzadeh H, Uslu D, Gurer-Orhan H, Gumustas M, Ozkan SA (2013) Antioxidant activity of indole-based melatonin analogues in erythrocytes and their voltammetric characterization. J Enzyme Inhib Med Chem 28(6):1143–1155
Yılmaz AD, Coban T, Suzen S (2012) Synthesis and antioxidant activity evaluations of melatonin-based analogue indole-hydrazide/hydrazone derivatives. J Enzyme Inhib Med Chem 27(3):428–436
Ummadi N, Gundala S, Venkatapuram P, Adivireddy P (2017) Synthesis and antioxidant activity of a new class of pyrazolyl indoles, thiazolyl pyrazolyl indoles. Med Chem Res 26(7):1574–1584
Ates-Alagoz Z, Coban T, Buyukbingol E (2006) Synthesis and antioxidant activity of new tetrahydro-naphthalene-indole derivatives as retinoid and melatonin analogs. Arch Pharm 339(4):193–200
Dixit A, Pathak D, Sharma GK (2020) Synthesis, antibacterial and free radical scavenging activity of some newer N-((10-nitro-1H-indolo [1, 2-c] quinazolin-12-yl) methylene) benzenamines. Eur Pharmaceutical J 1 (ahead-of-print)
Xu H, Fan LL (2011) Antifungal agents. Part 4: Synthesis and antifungal activities of novel indole[1,2-c]-1,2,4-benzotriazine derivatives against phytopathogenic fungi invitro. Eur J Med Chem 46:364–369
Shi Z, Zhao Z, Huang M, Fu X (2015) Ultrasound-assisted, one-pot, three-component synthesis and antibacterial activities of novel indole derivatives containing 1,3,4-oxadiazole and 1,2,4-triazole moieties. C R Chimie 18:1320–1327
Tiwari RK, Singh D, Singh J, Yadav V, Pathak AK, Dabur R, Chhillar AK, Singh R, Sharma GL, Chandra R, Verma AK (2006) Synthesis and antibacterial activity of substituted1, 2, 3, 4-tetrahydropyrazino [1, 2-a] indoles. Bioorg Med Chem Lett 16:413–416
Hong W, Li J, Chang Z, Tan X, Yang H, Ouyang Y, Yang Y, Kaur S, Paterson IC, Ngeow YF, Wang H (2017) Synthesis and biological evaluation of indole core-based derivatives with potent antibacterial activity against resistant bacterial pathogens. J Antibiotics 70:832–844
Ozturk A, Abdullah M (2006) Toxicological effect of indole and its azo dye derivatives on some microorganisms under aerobic conditions. Sci Total Environ 358:137–142
Scribner A, Moore JA III, Ouvry G, Fisher M, Wyvratt M, Leavitt P, Liberator P, Gurnett A, Brown C, Mathew J, Thompson D, Schmatz D, Biftu T (2009) Synthesis and biological activity of anticoccidial agents: 2,3-diarylindoles. Bioorg Med Chem Lett 19:1517–1521
Singh P, Verma P, Yadav B, Komath SS (2011) Synthesis and evaluation of indole-based new scaffolds for antimicrobial activities and Identification of promising candidates. Bioorg Med Chem Lett 21:3367–3372
Desai NC, Somani H, Trivedi A, Bhatt K, Nawale L, Khedkar VM, Jha PC, Sarkar D (2016) Synthesis, biological evaluation and molecular docking study of some novel indole and pyridine based 1, 3, 4-oxadiazole derivatives as potential antitubercular agents. Bioorg Med Chem Lett 26:1776–1783
Guo S, Tipparaju SK, Pegan SD, Wanc B, Moa S, Orjala J, Mesecar AD AD, Franzblau SG, Kozikowski AP (2009) Natural product leads for drug discovery: Isolation, synthesis and biological evaluation of 6-cyano-5-methoxyindolo[2,3-a]carbazole based ligands as antibacterial agents. Bioorgan Med Chem 17:7126–7130
Velezheva V, Brennan P, Ivanov P, Kornienko A, Lyubimov S, Kazarian K, Nikonenko B, Majorov K, Apt A (2016) Synthesis and antituberculosis activity of indole–pyridine derived hydrazides, hydrazide–hydrazones, and thiosemicarbazones. Bioorg Med Chem Lett 26(3):978–985
Walmik P, Saundane AR (2014) Synthesis of novel indolyl-azetidinone and thiazolidinone derivatives as a potent antioxidant, antimicrobial and antitubercular agents. Der Pharma Chemica 6(4):70–79
Rathod AS, Godipurge SS, Biradar JS (2017) Synthesis of indole, coumarinyl and pyridinyl derivatives of isoniazid as potent antitubercular and antimicrobial agents and their molecular docking studies. Int J Pharm Pharm Sci 9:233–240
Kondreddi RR, Jiricek J, Rao SP, Lakshminarayana SB, Camacho LR, Rao R, Herve M, Bifani P, Ma NL, Kuhen K, Goh A, Chatterjee AK, Dick T, Diagana TT, Manjunatha UN, Smith PW (2013) Design, synthesis, and biological evaluation of indole-2-carboxamides: a promising class of antituberculosis agents. J Med Chem 56(21):8849–8859
Ramesh D, Joji A, Vijayakumar BG, Sethumadhavan A, Mani M, Kannan T (2020) Indole chalcones: Design, synthesis, invitro and insilico evaluation against Mycobacterium tuberculosis. Eur J Med Chem 198:112358. https://doi.org/10.1016/j.ejmech.2020.112358
Naidu KM, Srinivasarao S, Agnieszka N, Ewa AK, Kumar MMK, Sekhar KVGC (2016) Seeking potent anti-tubercular agents: Design, synthesis, anti-tubercular activity and docking study of various ((triazoles/indole)-piperazin-1-yl/1, 4-diazepan-1-yl) benzo [d] isoxazole derivatives. Bioorg Med Chem Lett 26(9):2245–2250
Bingul M, Ercan S, Boga M (2020) The design of novel 4, 6-dimethoxyindole based hydrazide-hydrazones: Molecular modeling, synthesis and anticholinesterase activity. J Mol Struct 1213:128202
Prochnow T, Maroneze A, Back DF, Jardim NS, Nogueira CW, Zeni G (2018) Synthesis and anticholinesterase activity of 2-substituted-N-alkynylindoles. Org Biomol Chem 16(42):7926–7934
Mohammadi-Farani A, Ahmadi A, Nadri H, Aliabadi A (2013) Synthesis, docking and acetylcholinesterase inhibitory assessment of 2-(2-(4-Benzylpiperazin-1-yl) ethyl) isoindoline-1, 3-dione derivatives with potential anti-Alzheimer effects. DARU J Pharma Sci 21(1):47
Bingül M (2019) Synthesis and characterisation of novel 4, 6-dimethoxyindole-7-and-2-thiosemicarbazone derivatives: Biological evaluation as antioxidant and anticholinesterase candidates. J Chem Res 43(9-10):399–406
Ismail MM, Kamel MM, Mohamed LW, Faggal SI (2012) Synthesis of new indole derivatives structurally related to donepezil and their biological evaluation as acetylcholinesterase inhibitors. Molecules 17(5):4811–4823
Aliabadi A, Foroumadi A, Mohammadi-Farani A, Mahvar MG (2013) Synthesis and evaluation of anti-acetylcholinesterase activity of 2-(2-(4-(2-Oxo-2-phenylethyl) piperazin-1-yl) ethyl) isoindoline-1, 3-dione derivatives with potential anti-Alzheimer effects. Iran J Basic Medl sci 16(10):1049
Denya I, Malan SF, Enogieru AB, Omoruyi SI, Ekpo OE, Kapp E, Zindo FT, Joubert J (2018) Design, synthesis and evaluation of indole derivatives as multifunctional agents against Alzheimer's disease. Med Chem Comm 9(2):357–370
Vasconcelos SN, Meissner KA, Ferraz WR, Trossini GH, Wrenger C, Stefani HA (2019) Indole-3-glyoxyl tyrosine: synthesis and antimalarial activity against Plasmodium falciparum. Future Med Chem 11(6):525–538
Luthra T, Nayak AK, Bose S, Chakrabarti S, Gupta A, Sen S (2019) Indole based antimalarial compounds targeting the melatonin pathway: their design, synthesis and biological evaluation. Eur J Med Chem 168:11–27
Schuck DC, Jordão AK, Nakabashi M, Cunha AC, Ferreira VF, Garcia CR (2014) Synthetic indole and melatonin derivatives exhibit antimalarial activity on the cell cycle of the human malaria parasite Plasmodium falciparum. Eur J Med Chem 78:375–382