Quinazoline pharmacophore in therapeutic medicine

Authors

  • Olayinka Oyewale Ajani Department of Chemistry, Covenant University, CST, Canaanland, Km 10 Idiroko Road, P.M.B. 1023, Ota, Ogun State http://orcid.org/0000-0002-3422-3478
  • Damilola Victoria Aderohunmu Department of Chemistry, Covenant University, CST, Canaanland, Km 10 Idiroko Road, P.M.B. 1023, Ota, Ogun State http://orcid.org/0000-0002-3563-2919
  • Ejike Nzube Umeokoro Department of Chemistry, Covenant University, CST, Canaanland, Km 10 Idiroko Road, P.M.B. 1023, Ota, Ogun State
  • Ayodele Ojo Olomieja Department of Chemistry, Ogun State Institute of Technology, Igbesa, Ogun State http://orcid.org/0000-0002-5281-8141

DOI:

https://doi.org/10.3329/bjp.v11i3.25731

Keywords:

Antidiabetic, Antimicrobial, Heterocyclic compound, Kinase inhibitor, Quinazoline scaffold

Abstract

This present study comprehensively expatiates the functionalized utilization of quinazoline scaffolds in drug development and furnishes latest updates in pharmacological appositeness of its derivatives in order to reveal novel pathways for therapeutic targets. It traverses numerous biological potentials of quinazoline in the contemporary time to allow researchers unhindered access to the beneficial role of quinazoline in fighting infectious diseases for future drug discovery. This work provides broad overview of medicinal survey of quinazoline chemistry valuable in the discovery of more efficient clinical trials and to summarize the most promising molecular targets for drug design.  

Downloads

Download data is not yet available.
Abstract
7673
Download
3231

Author Biography

Olayinka Oyewale Ajani, Department of Chemistry, Covenant University, CST, Canaanland, Km 10 Idiroko Road, P.M.B. 1023, Ota, Ogun State

Senior Lecturer

References

Ahmed OM, Hussein AM, Ahmed RR. Antidiabetic and anti-oxidant effects of newly synthesized pyrimido[1,6-a]pyrimidine derivatives in neonatal streptozotocin-induced diabetic Rats. Med Chem. 2012; 2: 20-28.

Ajani OO. Present status of quinoxaline motifs: Excellent pathfinders in therapeutic medicine. Eur J Med Chem. 2014; 85: 688-715.

Ajani OO, Nwinyi OC. Synthesis and evaluation of antimicrobial activity of phenyl and furan-2-yl[1,2,4]triazolo[4,3-a]quinoxalin-4(5H)-one and their hydrazone precursors. Canadian J Pure Appl Sci. 2009; 3: 983-92.

Alafeefy AM, Ceruso M, Al-Tamimi AMS, Prete SD, Capasso C, Supuran, CT. Quinazolinesulfonamides with potent inhibitory activity against the ?-carbonic anhydrase from Vibrio cholera. Bioorg Med Chem. 2014; 22: 5133-40.

Al-Azawi K. Synthesis, characterization and anti-oxidant studies of quinazolin derivatives. Orient J Chem. 2016; 32: 585-90.

Ali MA, Shaharyar M, De Clercq E. Synthesis of 5-(4-hydroxy-3-methylphenyl)-5-(substitutedphenyl)-4, 5-dihydro-1H-1-pyrazolyl-4-pyridylmethanone derivatives with antiviral activity. J Enzym Inhib Med Chem. 2007; 22: 702-08.

Al-Omary FA, Hassan GS, El-Messery SM, El-Subbagh HI. Substituted thiazoles V. synthesis and antitumor activity of novel thiazolo[2,3-b]quinazoline and pyrido[4,3-d]thiazolo[3,2-a]pyrimidine analogues. Eur J Med Chem. 2012; 47: 65-72.

Al-Salahi R, Abuelizz HA, Ghabbour HA, El-Dib R, Marzouk M. Molecular docking study and antiviral evaluation of 2-thioxo-benzo[g]quinazolin-4(3H)-one derivatives. Chem Cent J. 2016; 10: 21.

Aly MM, Mohamed YA, El-Bayouki KM, Basyouni WM, Abbas S.Y. Synthesis of some new 4(3H)-quinazolinone-2-carboxaldehyde thiosemicarbazones and their metal complexes and a study on their anticonvulsant, analgesic, cytotoxic and antimicrobial activities. Eur J Med Chem. 2010; 45: 3365-73.

Anand T, Sivaraman G, Chellappa D. Quinazoline copper(II) ensemble as turn-on fluorescence sensor for cysteine and chemodosimeter for NO. J Photochem Photobiol A: Chem. 2014; 281: 47-52.

Ankita W, Pranay W, Nishi G, Rai AK, Srivastav RS. Novel class of semi synthetic natural products derived from lupeol as antitubercular agents. Stand Res J Pharm Pharmacol. 2014; 2: 40-45.

Antonello A, Tarozzi A, Morroni F, Cavalli A, Rosini M, Hrelia P, Bolognesi ML, Melchiorre C. Multitarget-directed drug design strategy: A novel molecule designed to block epidermal growth factor receptor (EGFR) and to exert proapoptotic effects. J Med Chem. 2006; 49: 6642-45.

Antypenko LM, Kovalenko SI, Antypenko OM, Katsev AM, Achkasova AM. Design and evaluation of novel antimicrobial and anti-cancer agents among tetrazolo[1,5-c]quinazo line-5-thiones derivatives. Sci Pharm. 2013; 81: 15-52.

Armarego WLF. The chemistry of heterocyclic compounds: Fused pyrimidines, Part 1, quinazolines. New Jersey, John Wiley and Sons Inc., 1967, 24, p 11, 12, 270, 391.

Arya K, Tomar R, Rawat DS. Greener synthesis and photo-anti-proliferative activity of novel fluorinated benzothiazolo[2,3-b]quinazoline. Med Chem Res. 2014; 23: 896-904.

Asif M. Chemical characteristics, synthetic methods, and biological potential of quinazoline and quinazolinone derivatives. Int J Med Chem. 2014; 2014: p 27.

Barbosa MLC, Lima LM, Tesch R, SantAnna CMR, Totzke F, Kubbutat MHG, Schächtele C, Laufer SA, Barreiro EJ. Novel 2-chloro-4-anilino-quinazoline derivatives as EGFR and VEGFR-2 dual inhibitors. Eur J Med Chem. 2014; 71: 1-14.

Bartha E, Solti I, Kereskai L, Lantos J, Plozer, E, Magyar K, Szabados E, Kalai T, Hideg K, Halmosi R, Sumegi B, Kalman T. PARP inhibition delays transition of hypertensive cardiopathy to heart failure in spontaneously hypertensive rats. Cardiovasc Res. 2009; 83: 501-10.

Birhan YS, Bekhit AA, Hymete A. In vivo antimalarial evaluation of some 2,3-disubstituted-4(3H)-quinazolinone derivatives. BMC Res Notes 2015; 8: 589-94.

Bolden JE, Peart MJ, Johnstone RW. Anti-cancer activities of histone deacetylase inhibitors. Nat Rev Drug Discovery. 2006; 5: 769-84.

Bukowska A, Zacharias I, Weinert S, Skopp K, Hartmann C, Huth C, Goette A. Coagulation factor Xa induces an inflammatory signaling by activation of protease-activated receptors in human atrial tissue. Eur J Pharmacol. 2013; 718: 114-23.

Bursavich MG, Dastrup D, Shenderovich M, Yager KM, Cimbora DM, Williams B., Kumar DV. Novel Mps1 kinase inhibitors: From purine to pyrrolopyrimidine and quinazoline leads. Bioorg Med Chem Lett. 2013; 23: 6829-33.

Cai J, Sun M, Wu X, Chen J, Wang P, Zong X, Ji M. Design and synthesis of novel 4-benzothiazole amino quinazolines dasatinib derivatives as potential antitumor agents. Eur J Med Chem. 2013; 63: 702-12.

Chandrika PM, Yakaiah T, Narsaiah B, Sridhar V, Venugopal G, Rao JV, Kumar KP, Murthy USN, Rao ARR. Synthesis leading to novel 2,4,6-trisubstituted quinazoline derivatives, their antibacterial and cytotoxic activity against THP-1, HL-60 and A375 cell lines. Indian J Chem. 2009; 48B: 840-47.

Chandrika PM, Yakaiah T, Rao ARR, Narsaiah B, Reddy NC, Sridhar V, Rao JV. Synthesis of novel 4,6-disubstituted quinazoline derivatives, their anti-inflammatory and anti-cancer activity (cytotoxic) against U937 leukemia cell lines. Eur J Med Chem. 2008; 43: 846-52.

Chang FR, Lee YH, Yang YL, Hsieh PW, Khalil AT, Chen CY, Wu YC. Secoiridoid glycoside and alkaloid constituents of hydrangea chinensis. J Nat Prod. 2003; 66: 1245-48.

Chen L, Sun YX, Chai YK, Lee JS, Song MS, Quan ZS. Synthesis and anticonvulsant evaluation of 4-(4-alkoxylphenyl)-3-ethyl-4H-1,2,4-triazoles as open-chain analogues of 7-alkoxyl-4,5-dihydro-1,2,4-triazolo[4,3-a]quinolines. Bioorg Med Chem. 2007; 15: 6775-81.

Cheng D. Prevalence, predisposition and prevention of type II diabetes. Nutr Metab. 2005; 2: 29-39.

Connolly DJ, Cusack D, Sullivan TPO, Guiry PJ. Synthesis of quinazolinones and quinazolines. Tetrahedron. 2005; 61: 10153-202.

Corbett EL, Watt CJ, Walker N, Maher D, Williams BG, Raviglione MC, Dye C. The growing burden of tuberculosis: Global trends and interactions with the HIV epidemic. Arch Intern Med. 2003; 163: 1009-21.

Deepakumari HN, Jayanna BK, Prashanth MK, Revanasiddappa HD, Veeresh B. Synthesis and anticonvulsant activity of N-(substituted)-1-methyl-2,4-dioxo-1,2-dihydro-quinazoline -3(4H)-carboxamides. Arch Pharm. 2016.

Deedwania PC, Blood pressure control in diabetes mellitus: Is lower always better, and how low should it go? Circulation 2011; 123: 2776-78.

Ding MW, Yang SJ, Chen YF. Synthesis and fungicidal activities of 2-alkoxy-3H-quinazolin-4-ones. Chinese J Org Chem. 2004; 24: 923-1026.

Dongamanti A, Gadiparthi R, Redamala R, Anireddy J, Burri N, Vantikommu J. Synthesis, antibacterial, anti-asthmatic and anti-diabetic activities of novel 3-substituted quinazolin-4-ones using 1-butyl-3-methyl-imidazoliumtetrafluoro borate [BMIM+][BF4-] as a green, efficient and reusable catalyst under solvent free conditions. J Chem Pharm Res. 2012; 4: 3991-4000.

Du J, Kang Y, Zhao Y, Zheng W, Zhang Y, Lin Y, Wang Z, Wang Y, Luo Q, Wu K, Wang F. Synthesis, characterization, and in vitro antitumor activity of ruthenium(ii) polypyridyl complexes tethering EGFR-inhibiting 4-anilinoquinazolines. Inorg Chem. 2016; 55: 4595-605.

Eicher T, Hauptmann S. The chemistry of heterocycles: Structure, reactions, syntheses, and applications. 2nd edn. 2003.

El-Azab AS, Abdel-Hamide SG, Sayed-Ahmed MM, Hassan GS, El-Hadiyah TM, Al-Shabanah OA, Al-Deeb OA, El-Subbagh HI Novel 4(3H)-quinazolinone analogs: Synthesis and anticonvulsant activity. Med Chem Res. 2013; 22: 2815-27.

El-Azab AS, ElTahir KEH. Design, synthesis and anticonvulsant evaluation of novel 8-substituted-4(3H)-quinazolines. Med Chem Res. 2012; 21: 3785-96.

Elkamhawy A, Lee J, Park BG, Park I, Pae AN, Roh EJ. Novel quinazoline-urea analogues as modulators for A?-induced mitochondrial dysfunction: Design, synthesis, and molecular docking study. Eur J Med Chem. 2014; 84: 466-75.

Famiglini V, Silvestri R. Focus on chirality of HIV-1 non-nucleoside reverse transcriptase inhibitors. Molecules 2016; 21: 221-39.

Farag AA, Khalifa EM, Sadik NA, Abbas SY, Al-Sehemi AG, Ammar YA. Synthesis, characterization, and evaluation of some novel 4(3H)-quinazolinone derivatives as anti-inflammatory and analgesic agents. Med Chem Res. 2013; 22: 440-52.

Fares M, Eldehna WM, Abou-Seri SM, Abdel-Aziz HA, Aly MH, Tolba MF. Design, synthesis and in vitro anti-proliferative activity of novel isatin-quinazoline hybrids. Arch Pharm (Weinheim). 2015; 348: 144-54.

Franklin BS, Ishizaka ST, Lamphier M, Gusovsky F, Hansen H, Rose J, Zheng W, Ataíde MA, de Oliveira RB, Golenbock DT, Gazzinelli RT. Therapeutical targeting of nucleic acid-sensing Toll-like receptors prevents experimental cerebral malaria. Proc Natl Acad Sci USA. 2011; 108: 3689-94.

Fung C, Grandis JR. Emerging drugs to treat squamous cell carcinomas of the head and neck. Expert Opin Emerg Drugs. 2010; 15: 355-73.

Gali R, Banothu J, Porika M, Velpula R, Hnamte S, Bavantula R, Abbagani S, Busi S. Indolyl methylenebenzo[h]thiazolo[2,3-b]quinazolinones: Synthesis, characterization and evaluation of anti-cancer and antimicrobial activities. Bioorg Med Chem Lett. 2014; 24: 4239-42.

Garofalo A, Goossens L, Lemoine A, Ravez S, Six P, Howsam, M, Farce A, Depreux P. [4-(6,7-Disubstituted quinazolin-4-ylamino)phenyl] carbamic acid esters: A novel series of dual EGFR/VEGFR-2 tyrosine kinase inhibitors. Med Chem Commun. 2011; 2: 65-72.

Ghorab MM, Alsaid MS, Al-Dosari MS, El-Gazzar MG, Parvez MK. Design, synthesis and anti-cancer evaluation of novel quinazoline-sulfonamide hybrids. Molecules 2016; 21: 189-200.

Guan J, Zhang Q, ONeil M, Obaldia III N, Ager A, Gerena L, Lin AJ. Antimalarial activities of new pyrrolo[3,2-f]quinazoline-1,3-diamine derivatives. Antimicrob Agent Chemother. 2005; 49: 4928-33.

Hassan GS, Georgey HH, Ibrahim NA, Zaki SS. Synthesis of novel substituted quinazoline and quinazolin-4(3H)-one derivatives of expected antitumor activity. Der Pharm Chem. 2015; 7: 106-19.

Högberg T, Frimurer TM, Sasmal PK. Melanin-concentrating hormone receptor 1 (MCHR1) antagonists Still a viable approach for obesity treatment. Bioorg Med Chem Lett. 2012; 22: 6039-47

Humphrey JM, Yang E, am Ende CW, Arnold EP, Head JL, Jenkinson S, Lebel LA, Liras S, Pandit J, Samas B, Vajdos F, Simons SP, Evdokimov A, Mansour M, Menniti FS. Small-molecule phosphodiesterase probes: Discovery of potent and selective CNS-penetrable quinazoline inhibitors of PDE1. Med Chem Commun. 2014; 5: 1290-96.

Hurt RT, Kulisek C, Buchanan LA, McClave SA. the obesity epidemic: Challenges, health initiatives, and implications for gastroenterologists. Gastroenterol Hepatol (N Y). 2010; 6: 780-92.

Hynes NE, Lane HA. ERBB receptors and cancer: The complexity of targeted inhibitors. Nat Rev Cancer. 2005; 5: 341-54.

Islam MS, Loots DT. Experimental rodent models of type 2 diabetes: A review. Methods Find Exp Pharmacol. 2009; 31: 249-61.

Jabir NR, Tabrez S, Ashraf GMd, Shakil S, Damanhouri GA, Kamal MA. Nanotechnology-based approaches in anti-cancer research. Int J Nanomed. 2012; 7: 4391-408.

Jafari E, Khajouei MR, Hassanzadeh F, Hakimelahi GH, Khodarahmi GA. Quinazolinone and quinazoline derivatives: Recent structures with potent antimicrobial and cytotoxic activities. Res Pharm Sci. 2016; 11: 1-14.

Jaime MFV, Redko F, Muschietti LV, Campos RH, Martino VS, Cavallaro LV. In vitro antiviral activity of plant extracts from Asteraceae medicinal plants. Virol J. 2013; 10: 245.

Jantova S, Ovadekova R, Letasiova S, Spirkova K, Stankovsky S. Antimicrobial activity of some substituted triazoloquinazolines. Folia Microbiol. 2005; 50: 90-94.

Jäntschi L, Bolboac? S. Molecular descriptors family on structure activity relationships 5. Antimalarial activity of 2,4-diamino-6-quinazoline sulfonamide derivates. Leonardo J Sci. 2006; 8: 77-88.

Jeon MK, Cheon HG. Promising strategies for obesity pharmacotherapy: Melanocortin-4 (MC-4)receptor agonists and melanin concentrating hormone (MCH) receptor-1 antagonists. Curr Top Med Chem. 2009; 9: 504-38.

Jindal DP, Bhatti RS, Ahlawat S, Gupta R. Synthesis and bronchodilatory activity of some nitrogen bridgehead compounds. Eur J Med Chem. 2002; 37: 419-25.

Joule JA, Mills K. Heterocyclic chemistry. 4th edn. Oxford, Wiley-Blackwell Publishers, 2000, pp 12-18.

Kanuma K, Omodera K, Nishiguchi M, Funakoshi T, Chaki S, Semple G, Tran TA, Kramer B, Hsu D, Casper M, Thomsen B, Sekiguchi Y. Lead optimization of 4-(dimethyl amino) quinazolines, potent and selective antagonists for the melanin-concentrating hormone receptor 1. Bioorg Med Chem Lett. 2005; 15: 3853-56.

Kashaw SK, Kashaw V, Mishra P, Jain NK, Stables JP. Synthesis, anticonvulsant and CNS depressant activity of some new bioactive 1-(4-substituted-phenyl)-3-(4-oxo-2-phenyl /ethyl -4H-quinazolin-3-yl)-urea. Eur J Med Chem. 2009; 44: 4335-43.

Khan I, Ibrar A, Abbas N, Saeed A. Recent advances in the structural library of functionalized quinazoline and quinazolinone scaffolds: Synthetic approaches and multifarious applications. Eur J Med Chem. 2014; 76: 193-244.

Khan I, Ibrar A, Ahmed W, Saeed A. Synthetic approaches, functionalization and therapeutic potential of quinazolineand quinazolinone skeletons: Advance continue. Eur J Med Chem. 2015; 90: 124-69.

King AM, Marc DR, Rafal K, Anne V, James PS, Harold K. Defining the structural parameters that confer anticonvulsant activity by the site-by-site modification of (R)-N-benzyl 2-amino-3-methylbutanamide. J Med Chem. 2011; 54: 6432-42.

Kolavenko SI, Nosulenko IS, Voskoboynik AY, Berest GG, Antypenko LN. Antypenko AN, Katsev AM. Novel N-aryl(alkaryl)-2-[(3-R-2-oxo-2H-[1,2,4]triazino[2,3-c]quinazoline-6-yl)thio]acetamides: Synthesis, cytotoxicity, anticancer activity, compare analysis and docking. Med Chem Res. 2013; 22: 2610-32.

Kramer OH. HDAC2: A critical factor in health and disease. Trends Pharmacol Sci. 2009; 30: 647-55.

Kumar A, Ito A, Hirohama M, Yoshida M, Zhang KYJ. Identification of quinazolinyloxy biarylurea as a new class of SUMO activating enzyme 1 inhibitors. Bioorg Med Chem Lett. 2013; 23: 5145-49.

Kumar A, Sharma S, Bajaj AK, Sharma S, Panwar H, Singh T, Srivastava VK. Some new 2, 3, 6-trisubstituted quinazolinones as potent anti-inflammatory, analgesic and COX-II inhibitors. Bioorg Med Chem. 2003; 11: 5293-99.

Kumar KS, Ganguly S, Veerasamy R, De Clercq E. Synthesis, antiviral activity and cytotoxicity evaluation of Schiff bases of some 2-phenyl quinazoline-4(3H)-ones. Eur J Med Chem. 2010; 45: 5474-79.

Lim CJ, Oh KS, Ha JD, Lee JH, Seo HW, Chae CH, Kim DG, Lee MJ, Lee BH. 4-Substituted quinazoline derivatives as novel EphA2 receptor tyrosine kinase inhibitors. Bioorg Med Chem Lett. 2014; 24: 4080-83.

Lin Z, Bishop KS, Sunderland H, Marlow G, Murray P, Dennya WA, Ferguson LR. Aquinazoline-based HDAC inhibitor affects gene expression pathways involved in cholesterol biosynthesis and mevalonate in prostate cancer cells. Mol BioSyst. 2016; 12: 839-49.

Lin Z, Murray PM, Ding Y, Denny WA, Ferguson LR. Quinazolines as novel anti-inflammatory histone deacetylase inhibitors. Mutation Res. 2010; 690: 81-88.

Liu J, Xie YQ, Lin Q, Shi BB, Zhang P, Zhang YM, Wei TB. Dipodal fluorescent chemosensor for Fe3+ and resultant complex as a chemosensor for fluoride. Sensor Actuator B Chem. 2013; 186: 657-65.

Liu Y, Li XM, Meng LH, Wang BG. N-Formyllapatin A, a new N-formylspiro quinazoline derivative from the marine-derived fungus Penicillium adametzioides AS-53. Phytochem Lett. 2014; 10: 145-48.

Luo H, Yang S, Cai Y, Peng Z, Liu T. Synthesis and biological evaluation of novel 6-chloro-quinazoline derivatives as potential antitumor agents. Eur J Med Chem. 2014; 84: 746-52.

Magyar K, Deres L, Eros K, Bruszt K, Seress L, Hamar J, Hideg K, Balogh A, Gallyas Jr, F, Sumegi B, Toth K, Halmosi R. A quinazoline-derivative compound with PARP inhibitory effect suppresses hypertension-induced vascular alterations in spontaneously hypertensive rats. Biochim Biophys Acta Mol Basis Dis. 2014; 1842: 935-44.

Mahato AK, Srivastava B, Nithya S. Chemistry, structure activity relationship and biological activity of quinazoline-4(3H)-one derivatives. Inventi Rapid Med Chem. 2011; 2.

Maheswari CU, Kumar GS, Venkateshwar M, Kumar RA, Kantam ML, Reddy KR. Highly efficient one?pot synthesis of 2?substituted quinazolines and 4H?benzo[d][1,3]oxazines via cross dehydrogenative coupling using sodium hypochlorite. Adv Syn Catal. 2010; 352: 341-46

Manasa K, Sidhaye RV, Radhika G, Nalini CN. Synthesis, anti-oxidant and anti-cancer activity of quinazoline derivatives. Curr Pharma Res. 2011; 1: 101-05.

Maskey RP, Shaaban M, Grün-Wollny I, Laatsch H. Quinazolin-4-one derivatives from Streptomyces isolates. J Nat Prod. 2004; 67: 1131-34.

Mathew B, Ross L, Reynolds RC. A novel quinoline derivative that inhibits mycobacterial FtsZ. Tuberculosis 2013; 93: 398-400.

Maurya HK, Verma R, Alam S, Pandey S, Pathak V, Sharma S, Srivastava KK, Negi AS, Gupta A. Studies on substituted benzo[h]quinazolines, benzo[g]indazoles, pyrazoles, 2,6-diaryl pyridines as anti-tubercular agents. Bioorg Med Chem Lett. 2013; 23: 5844-49.

McLaughlin NP, Evans P, Pines M. The chemistry and biology of febrifugine and halofuginone. Bioorg Med Chem. 2014; 2: 1993-2004.

Mendoza-Martínez C, Galindo-Sevilla N, Correa-Basurto J, Ugalde-Saldivar VM, Rodríguez-Delgado RG, Hernández-Pineda J, Padierna-Mota C, Flores-Alamo M, Hernández-Luis F. Antileishmanial activity of quinazoline derivatives: Synthesis, docking screens, molecular dynamic simulations and electrochemical studies. Eur J Med Chem. 2015; 92: 314-31.

Mhaske SB, Argade NP. The chemistry of recently isolated naturally occurring quinazolinone alkaloids. Tetrahedron 2006; 62: 9787-826.

Minkovsky N, Berezov A. BIBW-2992, a dual receptor tyrosine kinase inhibitor for the treatment of solid tumors. Curr Opin Invest Drug. 2008; 9: 1336-46.

Miolo G, Salvador A, Mazzoli A, Spalletti A, Marzaro G, Chilin A. Photochemical and photobiological studies on furoquinazolines as new psoralen analogs. J Photochem Photobiol B Biol. 2014; 138: 43-54.

Modh RP, De Clercq E, Pannecouque C, Chikhalia KH Design, synthesis, antimicrobial activity and anti-HIV activity evaluation of novel hybrid quinazoline-triazine derivatives. J Enzyme Inhib Med Chem. 2014; 29: 100-08.

Mohamed HA, Lake BR, Laing T, Phillips RM, Willans CE. Synthesis and anti-cancer activity of silver(I)-N-heterocyclic carbene complexes derived from the natural xanthine products caffeine, theophylline and theobromine. Dalton Trans. 2015; 44: 7563-69.

Mohamed MA, Ghanem HM, Abd El-Ghaffar NF, Mohamed SS. Biological evaluation and molecular docking of substituted quinazolinones as antimicrobial agents. Aust J Basic Appl Sci. 2013; 7: 263-74.

Mohamed YA, Amr AEE, Mohamed SF, Abdalla MM, Al-Omar MA, Shfik SH. Cytotoxicity and anti-HIV evaluations of some new synthesized quinazoline and thioxopyrimidine derivatives using 4-(thiophen-2-yl)-3,4,5,6-tetrahydrobenzo[h]quinazoline-2(1H)-thione as synthon. J Chem Sci. 2012; 124: 693-702.

Murgan V, Thomas CC, Rama B, Sarma GVS, Kumar EP. Synthesis of 2-substituted quinazolin-4(3H)-ones as a new class of anti-cancer agents. Indian J Pharm Sci. 2003; 65: 386-89.

Nayyar AP, Arpanarana M. An updated review: Newer quinazoline derivatives under clinical trial. Int J Pharm Biol Arch. 2011; 2: 1651-57.

Olliaro P, Wells TN. The global portfolio of new antimalarial medicines under development. Clin Pharmacol Ther. 2009; 85: 584-95.

Omori K, Kotera J. Overview of PDEs and their regulation. Circ Res. 2007; 100: 309-27.

Ouahrouch A, Taourirte M, Engels JW, Benjelloun S, Lazre HB. Synthesis of new 1,2,3-triazol-4-yl-quinazoline nucleoside and acyclonucleoside analogues. Molecules 2014; 19: 3638-53.

Palop JA, Plano D, Moreno E, Sanmartín C. Novel quinazoline and pyrido[2,3-d]pyrimidine derivatives and their hydroselenite salts as antitumoral agents. Arkivoc 2013; ii: 187-206.

Patel NB, Patel JC. Synthesis and antimicrobial activity of Schiff bases and 2-azetidinones derived from quinazolin-4(3H)-one. Arabian J Chem. 2011; 4: 403-11.

Pathak SR, Malhotra V, Nath R, Shanker K. Synthesis and antihypertensive activity of novel quinazolin-4(3H)-one derivatives. Cent Nerv Syst Agents Med Chem. 2014; 14: 34-38.

Pathania D, Sechi M, Palomba M, Sanna V, Berrettini F, Sias A, Taheri L, Neamati N. Design and discovery of novel quinazolinedione-based redox modulators as therapies for pancreatic cancer. Biochim Biophys Acta. 2014; 1840: 332-43.

Pickup M, Novitskiy S, Moses HL. The role of TGF? in the tumour microenvironment. Nat Rev Cancer. 2013; 13: 788-99.

Popkin, BM, Adair LS, Ng SW. Global nutrition transition and the pandemic of obesity in developing countries. Nutr Rev. 2012; 70: 3-21.

Portela-Cubillo F, Scott JS, Walton JC. Microwave-promoted syntheses of quinazolines and dihydroquinazolines from 2-aminoarylalkanone o-phenyl oxime. J Org Chem. 2009; 74: 4934-42.

Radnai B, Antus C, Racz B, Engelmann P, Priber JK, et al., Protective effect of the poly (ADP-ribose) polymerase inhibitor PJ34 on mitochondrial depolarization-mediated cell death in hepatocellular carcinoma cells involves attenuation of c-Jun N-terminal kinase-2 and protein kinase B/Akt activation. Mol Cancer. 2012; 11: 34-45.

Raghav N, Singh M. Design, synthesis and docking studies of bischalcones based quinazoline-2(1H)-ones and quinazoline-2(1H)-thiones derivatives as novel inhibitors of cathepsin B and cathepsin H. Eur J Pharm Sci. 2014; 54: 28-39.

Rajput R, Mishra AP. A review on biological activity of quinazolinones. Int J Pharm Pharm Sci. 2012; 4: 66-70.

Redondo M, Zarruk JG, Ceballos P, Pérez DI, Pérez C, Perez-Castillo A, Moro MA, Brea J, Val C, Cadavid MI, Loza MI, Campillo NE, Martínez A, Gil C. Neuroprotective efficacy of quinazoline type phosphodiesterase 7 inhibitors in cellular cultures and experimental stroke model. Eur J Med Chem. 2012; 47: 175-85.

Rojas-Aguirre Y, Hernández-Luis F, Mendoza-Martínez C, Sotomayor CP, Aguilar LF, Villena, F, Castillo I, Hernández DJ, Suwalsky M. Effects of an antimalarial quinazoline derivative on human erythrocytes and on cell membrane molecular models. Biochim Biophys Acta. 2012; 1818: 738-46.

Ryu CK, Kim YH, Im HA, Kim JY, Yoon JH, Kim A. Synthesis and antifungal activity of 6,7-bis(arylthio)-quinazoline-5,8-diones and furo[2,3-f]quinazolin-5-ols. Bioorg Med Chem Lett. 2012; 22: 500-03.

Sasmal S, Balaji G, Kanna RHR, Balasubrahmanyam D, Srinivas G, Kyasa S, Sasmal PK, Khanna I, Talwar R, Suresh J, Jadhav VP, Muzeeb S, Shashikumar D, Harinder RK, Sebastian VJ, Frimurer TM, Rist Ø, Elster L, Högberg T. Design and optimization of quinazoline derivatives as melanin concentrating hormone receptor 1 (MCHR1) antagonists. Bioorg Med Chem Lett. 2012; 22: 3157-62.

Sánchez AI, Martínez-Barrasa V, Burgos C, Vaquero JJ, Alvarez-Builla J, Terricabras E, Segarra V. Synthesis and evaluation of quinazoline derivatives as phosphodiesterase 7 inhibitors. Bioorg Med Chem. 2013; 21: 2370-78.

Sangshetti JN, Khan FAK, Kulkarni AA, Aroteb R, Patil RH. Antileishmanial drug discovery: Comprehensive review of the last 10 years. RSC Adv. 2015; 5: 32376-415.

Selvam P, Sridharan D, Murugesh N, Chandramohan M, Witurouw M. Synthesis and anti-HIV activity of some novel 2,3-disubstituted quinazolin-4(3H)-ones. Int J Chem Sci. 2008; 6: 1196-201.

Selvam TP, Kumar PV. Quinazoline marketed drugs: A review. Res Pharm. 2011; 1: 1-21.

Sergey I, Igor F, Vadim V, Oksana V. Synthesis of 2-(3,4-dihydro-3-oxo-2H-[1,2,4]triazino[4,3-c]quinazolin-4-yl)acetic acid derivatives as potential anti-oxidants in nitrosative stress model. Farmacia 2010; 58: 145-57.

Serya RAT, Abbas AH, Ismail NSM, Esmat A, El Ella DAA. Design, synthesis and biological evaluation of novel quinazoline-based anti-inflammatory agents acting as PDE4B inhibitors. Chem Pharm Bull. 2015; 63: 102-16.

Sharma A, Luxami V, Paul K. Synthesis, single crystal and antitumor activities of benzimidazolequinazoline hybrids. Bioorg Med Chem Lett. 2013a; 23: 3288-94.

Sharma A, Luxami V, Saxena S, Paul K. Benzimidazole-based quinazolines: In vitro evaluation, quantitative structure-activity relationship, and molecular modeling as aurora kinase inhibitors. Arch Pharm. 2016; 349: 193-201.

pulák M, Pourová J, Voprálová M, Mikuek J, Kune J, Vacek J, Ghavre M, Gathergood N, Pour M. Novel bronchodilatory quinazolines and quinoxalines: Synthesis and biological evaluation. Eur J Med Chem. 2014; 74: 65-72.

Srivastav MK, Shantakumar SM. Design and synthesis of novel 2-trichloromethyl-4-substituted quinazoline derivatives as anti-tubercular agents. Chem Sci Trans. 2013; 2: 1056-62.

Susín C, Morales-Garcia JA, Aguilar-Morante D, Palomo V, Sanz-Sancristobal M, Alonso-Gil S, Gil C, Santos A, Martinez A, Perez-Castillo A. The new iminothiadiazole derivative VP1.14 ameliorates hippocampal damage after an excitotoxic injury. J Neurochem. 2012; 122: 1193-202.

Takase Y, Saeki T, Watanabe N, Saito I. Cyclic GMP phosphodiesterase inhibitors. 2. Requirement of 6-substitution of quinazoline derivatives for potent and selective inhibitory activity. J Med Chem. 1994; 37: 2106-11.

Tan F, Shen X, Wang D, Xie G, Zhang X, Ding L, Hu Y, He W, Wang Y, Wang Y. Icotinib (BPI-2009H), a novel EGFR tyro-sine kinase inhibitor, displays potent efficacy in preclinical studies. Lung Cancer. 2012; 76: 177-82.

Tang L, Zhou P, Zhong K, Hou S. Fluorescence relay enhancement sequential recognition of Cu2+ and CN? by a new quinazoline derivative. Sensor Actuator. B. 2013; 182: 439-45.

Tinker AC, Beaton HG, Smith NB, Cook TR, Cooper SL, Rae LF, Hallam K, Hamley P, McInally T, Nicholls DJ, Pimm AD, Wallace AV. 1,2-dihydro-4-quinazolinamines: Potent, highly selective inhibitors of inducible nitric oxide synthase which show anti-inflammatory activity in vivo. J Med Chem. 2003; 46: 913-16.

Tiumana TS, Santos AO, Ueda-Nakamuraa T, Dias Filhoa BP, Nakamuraa CV. Recent advances in leishmaniasis treatment. Int J Infect Dis. 2011; 15: e525-32.

Vagdevi HM, Lokesh MR, Gowdarshivannanavar BC. Synthesis and anti-oxidant activity of 3-substituted schiff bases of quinazoline-2,4-diones. Int J Chem Tech Res. 2012; 4: 1527-33.

Vijayakumar K, Ahamed AJ, Thiruneelakandan G. Synthesis, antimicrobial, and anti-HIV1 activity of quinazoline-4(3H)-one derivatives. J Appl Chem. 2013: 5.

Wan Z, Hu D, Li P, Xie D, Gan X. Synthesis, antiviral bioactivity of novel 4-thioquinazoline derivatives containing chalcone moiety. Molecules 2015; 20: 11861-74.

Wang C, Sun Y, Zhu X, Wu B, Wang Q, Zhen Y, Shu X, Liu K, Zhou Y, Ma X. Novel quinazoline bearing various 4-aniline moieties as potent EGFR inhibitors with enhanced activity against NSCLC cell line. Cell Biol Drug Des. 2016; 87: 635-43.

Wang D, Gao F. Quinazoline derivatives: Synthesis and bioactivities. Chem Central J. 2013; 7: 95-115.

Wang X, Li ZN, Yin J, He M, Xue W, Chen ZW, Song BA. Synthesis and bioactivity evaluation of novel arylimines containing 3-aminoethyl-2-[(p-trifluoromethoxy)anilino]-4(3H)-quinazolinone moiety. J Agric Food Chem. 2013; 61: 9575-958.

Wang X, Yin J, Shi L, Zhang G, Song B. Design, synthesis, and antibacterial activity of novel Schiff base derivatives of quinazolin-4(3H)-one. Eur J Med Chem. 2014; 77: 65-74.

Werbel LM, Degnan MJ. Synthesis and antimalarial and antitumor effects of 2-amino-4-(hydrazino and hydroxyamino)-6-[(aryl)thio]quinazolines. J Med Chem. 1987; 30: 2151-54.

WHO, World Health Organization. Control of the Leishmaniases. WHO Technical Report Series. Retrieved online on February 7, 2016 at http://www.who.int/leishmaniasis/resources/en.

WHO, World Health Organization. HIV/AIDS, Fact Sheet n. 360, Updated Nov. 2015. Retrieved online on Dec. 7, 2015 at http://www.who.int/mediacentre/factsheets/fs360/en/

Williams CH, Hong CC. Making models work: Library annotation through phenoclustering. Drug Discov Today Dis Model. 2013; 10: e5e9.

Yassen ASA, Elshihawy HEAEA, Said MMA, Abouzid KAM. Molecular modelling and synthesis of quinazoline-based compounds as potential anti-proliferative agents. Chem Pharm Bull. 2014; 62: 454-66.

Yu H, Li Y, Ge Y, Song Z, Wang C., Huang S, Jin Y, Han X, Zhen Y, Liu K, Zhou Y, Ma X. Novel 4-anilinoquinazoline derivatives featuring an 1-adamantyl moiety as potent EGFR inhibitors with enhanced activity against NSCLC cell lines. Eur J Med Chem. 2016; 110: 195-203.

Yves LJ. Antituberculosis drugs: Ten years of research. Bioorg Med Chem. 2007; 15: 2479-513.

Zayed MF. New fluorinated quinazolinone derivatives as anticonvulsant agents. J Taibah Univ Med Sci. 2014; 9: 104-09.

Zhang J, Liu J, Ma Y, Ren D, Cheng P, Zhao J, Zhang F, Yao Y. One-pot synthesis and antifungal activity against plant pathogens of quinazolinone derivatives containing an amide moiety. Bioorg Med Chem Lett. 2016; 26: 2273-77.

Zhang X, Peng T, Ji X, Li J, Tong L, Li Z, Yang W, Xu Y, Li M, Ding J, Jiang H, Xie H, Liu H. Design, synthesis and biological evaluation of novel 4-anilinoquinazolines with C-6 urea-linked side chains as inhibitors of the epidermal growth factor receptor. Bioorg Med Chem. 2013a; 21: 7988-98.

Zhang X, Su S, Chen Y, Li J, Lu W. The design and synthesis of a new class of RTK/ HDAC dual-targeted inhibitors. Molecules 2013b; 18: 6491-503.

Downloads

Published

2016-08-14

How to Cite

Ajani, O. O., D. V. Aderohunmu, E. N. Umeokoro, and A. O. Olomieja. “Quinazoline Pharmacophore in Therapeutic Medicine”. Bangladesh Journal of Pharmacology, vol. 11, no. 3, Aug. 2016, pp. 716-33, doi:10.3329/bjp.v11i3.25731.

Issue

Vol. 11 No. 3 (2016)

Section

Mini Review

License

Authors who publish with this journal agree to the following terms:

  1. Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.
  2. Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal.
  3. Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (See The Effect of Open Access).