Nanocatalyzed Synthetic Approach for the Quinazolinone and Quinazoline Derivatives: A Review (2015 – Present)
Abstract
Due to their diverse chemical reactivities and essential range of biological action, quinazolines and their derivatives rank among the most significant heterocyclic compounds. Quinazoline and quinazolinone scaffolds pharmacological properties have sparked medicinal chemists' interest in creating original medications or drug candidates. The growth of quinazoline hybrid lead compounds and the related heterocycles is summarised in the current review of medicinal chemistry. Additionally, by shedding light on the potential significance of these hybridised pharmacophoric characteristics in the demonstrating a range of pharmacological activities, the review contributes to the acceleration of the drug development process.
Keywords: Fused Heterocycles, Quinazolinone and Quinazoline Derivatives, Drug Development
Keywords:
Fused Heterocycles, Quinazolinone and Quinazoline Derivatives, Drug Development
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References
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30) Bansal R, Design and Synthesis of Some Quinazoline Derivatives as Anti-Inflammatory Agents, Int J Engg Tech Sci Res, 2017; 4:61-62
31) El-Gazzar YI, Georgey HH, El-Messery SM, Ewida HA, Hassan GS, Raafat MM, Synthesis, biological evaluation and molecular modeling study of new (1,2,4-triazole or 1,3,4-thiadiazole)-methylthioderivatives of quinazolin-4(3H)-one as DHFR inhibitors, Bioorganic Chemistry, 2017; 72:282-292. https://doi.org/10.1016/j.bioorg.2017.04.019
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40) Venkatesh R, Ramaiah MJ, Gaikwad HK, Janardhan S, Bantu R, Nagarapu L, Luotonin-a based quinazolinones cause apoptosis and senescence via HDAC inhibition and activation of tumor suppressor proteins in HeLa cells, European Journal of Medicinal Chemistry, 2015; 94:87-101. https://doi.org/10.1016/j.ejmech.2015.02.057
41) Malinowski Z, Fornal E, Nowak M, Kontek R, Gajek G, Borek B, Synthesis and biological evaluation of some amino- and sulfanyl-3H-quinazolin-4- one derivatives as potential anticancer agents, Monatshefte fuer Chemie, 2015; 146:1723-1731. https://doi.org/10.1007/s00706-015-1508-6
42) Hemalath K, Madhumith G, Vasavi CS, Munusami PJ, 2, 3-Dihydroquinazolin-4 (1H)-ones, Visible light mediated synthesis, solvatochromism, biological activity, Journal of Photochemistry and Photobiology B, Biology, 2015; 143:139-147. https://doi.org/10.1016/j.jphotobiol.2014.12.028
43) Al-Salem HS, Hegazy GH, El-Taher KF, El-Messery SM, Al-Obaid AM, El-Subbagh HI, Synthesis anticonvulsant activity, molecular modeling study of some new hydrazinecarbothioamide, benzenesulfonohydrazide, phenacylacetohydrazide analogues of 4(3H)-quinazolinone, Bioorganic & Medicinal Chemistry Letters, 2015; 25:1490-1499. https://doi.org/10.1016/j.bmcl.2015.02.025
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45) Javaid K, Saad SM, Rasheed S, Moin ST, Syed N, Fatima I, 2-Arylquinazolin-4(3H)-ones, A new class of α-glucosidase inhibitors, Bioorganic & Medicinal Chemistry, 2015; 23:7417-7421. https://doi.org/10.1016/j.bmc.2015.10.038
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2) Kaur P, Kaur A, Kaur R, Kaur K, Quinazolinone peptides are the new approach as potent Medicinal agents, J Global Pharm Technol, 2010; 2:35-39
3) Wang D, Gao F, Quinazoline derivatives Synthesis and bioactivities, Chem Cent J, 2013; 7: 1-15 https://doi.org/10.1186/1752-153X-7-95
4) Connolly DJ, Cusack D, Sullivan TPO, Guiry PJ, Synthesis of quinazolinones and quinazolines, Tetrahedron, 2005; 61(43):10153-10202 https://doi.org/10.1016/j.tet.2005.07.010
5) Raziyeh Bakhshali-Dehkordi, Mohammad Ali Ghasemzadeh, javad safaei-ghomi, Multicomponent Preparation of Quinazolinone Derivatives, 2022; 42(3): 960-972 https://doi.org/10.1080/10406638.2020.1759661
6) Jiangnan Yang, Zongboxie, Liang jin, Xuehua Chen, Zhanggao Le, Synthesis of quinazoline by decarboxylation of 2-aminobenzylamine and α-keto acid under visible light catalysis, Jou of organic & biomolecular chemistry, 2022; 20:3558-3563 https://doi.org/10.1039/D2OB00219A
7) Wali HA, Anwar, Synthesis in vitro and in silico studies of newly functionalized quinazolinone analogs for the identification of potent αglucosidase inhibitors, Journal of the Iranian Chemical Societ, 2021; 3(2):1-18 https://doi.org/10.1007/s13738-021-02159-2
8) Ansari SM, Mohammadi-Khanaposhtani, Design synthesis in vitro and in silico biological assays of the new quinazolinone-2-thio-metronidazole derivatives, Journal of Molecular Structure, 2021; 3(2):130889 https://doi.org/10.1016/j.molstruc.2021.130889
9) Mahesh S, Narasaiah BP, Rostamnia S, Padhy H, Vijay V, Balaji GL, Sunflower Assisted Bio-Derived ZnO-NPs as an Efficient Nanocatalyst for Synthesis of Novel Quinazolines with Highly Antioxidant Activities, 2021; 2(3):234-245
10) Rao TN, Krishnarao N, Ahmed F, Alomar SY, Albalawi F, Mani P, Aljaafari A, Parvatamma B, Arshi N, Kumar S, One-pot Synthesis of 7,7-Dimethyl-4-Phenyl-2 Thioxo-2,3,4,6,7,8-Hexahydro-1H-Quinazoline-5-Ones, Using Zinc Ferrite Nanocatalyst and its Bio Evaluation Catalysts, 2021; 11:431 https://doi.org/10.3390/catal11040431
11) Tokalı FS, Taslimi P, Design, synthesis, molecular docking, and several metabolic enzyme inhibition properties of the novel quinazolinone and its derivatives, Archiv der Pharmazie, 2021; 354(5): 2000455. https://doi.org/10.1002/ardp.202000455
12) Emami L, Faghih Z, Design, synthesis, molecular simulation, biological activities of the novel quinazolinone-pyrimidine hybrid derivatives as dipeptidyl peptidase-4 inhibitors and anti-cancer agents, New Journal of Chemistry, 2020; 44(45):19515-19531. https://doi.org/10.1039/D0NJ03774E
13) Azizi S, Soleymani J, Hasanzadeh M, KCC1, Pr-SO3H, An capable Heterogeneous Catalyst for Green and One-Pot Synthesis of the 2,3-Dihydroquinazolin-4(1H)-One Nanocomposites, 2020; 6:31-40. https://doi.org/10.1080/20550324.2019.1708634
14) Bisht, AS, Negi, JS, Sharma, DK, Chemistry and activity of the quinazoline moiety, A systematic review study, Int J Pharm Chem Anal, 2020; 7:61-65. https://doi.org/10.18231/j.ijpca.2020.009
15) Sharif M, Quinazolin-4(3H)-ones, A tangible synthesis procedure via an oxidative olefin bond cleavage using the metal-catalyst free conditions, Appl Sci, 2020; 10:2815. https://doi.org/10.3390/app10082815
16) Saeedi M, Mohammadi-Khanaposhtani M, Pourrabia P, Razzaghi N, Ghadimi R, Imanparast S, Design and synthesis of novel quinazolinone-1,2,3-triazole hybrids as new anti-diabetic agents, In vitro is α-glucosidase inhibition, kinetic, and docking study, Bioorganic Chemistry, 2019; 83:161-169. https://doi.org/10.1016/j.bioorg.2018.10.023
17) Sunil Kumar A, Kudva J, Lahtinen M, Peuronen A, Sadashiva R, Naral D, Synthesis, characterization, crystal structures and biological screening of the 4-amino quinazoline sulfonamide derivatives, J Mol Struct, 2019; 1190: 29- 36. https://doi.org/10.1016/j.molstruc.2019.04.050
18) Allam HA, Aly EE, Farouk AKBAW, El-Kerdawy AM, Rashwan E, Abbass SES, Design and Synthesis of some new 2,4,6-trisubstituted quinazoline and EGFR inhibitors as targeted anticancer agents, Bioorg Chem, 2020; 98:103726. https://doi.org/10.1016/j.bioorg.2020.103726
19) Patel TS, Vanparia SF, Patel UH, Dixit RB, Chudasama CJ, Patel BD, Dixit BC, Eur J Med Chem, 2020; 129:251-265. https://doi.org/10.1016/j.ejmech.2017.02.012
20) Misra A, Dwivedi J, Shukla S, Kishore D, Sharma S, Bacterial cell outflow to potential of newly synthesized quinazoline derivatives of 1,5-benzodiazepines analogue, J Heterocycl Chem, 2020; 57:1545-1558. https://doi.org/10.1002/jhet.3879
21) Espinosa Valdes MP, Borbolla Alvarez S, Delgado-Espinosa A E, Sanchez-Tejeda JF, Ceron Nava A, Quintana Romero OJ, Ariza Castolo A, Garcia Del Rio DF, Loza Mejia MA, Synthesis, in silico, and in vitro evaluation of long chain alkyl amides from 2-Amino-4-quinolone derivatives as biofilm inhibitors, Molecules 2019; 24(2):0340-390. https://doi.org/10.3390/molecules24020327
22) Leven M, Held J, Duffy S, Alves Avelar LA, Meister S, Delves M, Plouffe D, Kuna K, Tschan S, Avery VM, Winzeler EA, Mordmuller B, Kurz T, 8-aminoquinolines with an aminoxyalkyl side chain exert in vitro dual-stage antiplasmodial activity, Chem Med Chem, 2019; 14(4):501-511. https://doi.org/10.1002/cmdc.201800691
23) Saeedi M, Mohammadi Khanaposhtani M, Pourrabia P, Razzaghi N, Ghadimi R, Imanparast S, Design and synthesis of novel quinazolinone-1,2,3-triazole hybrids as new anti-diabetic agents, In vitro α-glucosidase inhibition, kinetic, and docking study, Bioorganic Chemistry, 2019; 83:161-169. https://doi.org/10.1016/j.bioorg.2018.10.023
24) Xie D, Shi J, Zhang A, Lei Z, Zu G, Fu Y, Gan X, Yin L, Song B, Hu D, Syntheses, antiviral activities and induced resistance mechanisms of novel quinazoline derivatives containing a dithioacetal moiety, Bioorg Chem, 2018; 80:433-443. https://doi.org/10.1016/j.bioorg.2018.06.026
25) Fan Z, Shi J, Bao X, Synthesis and antimicrobial evaluation of novel 1,2,4-triazole thioether derivatives bearing a quinazoline moiety, Mol Divers, 2018; 22:657-667. https://doi.org/10.1007/s11030-018-9821-8
26) El-Shehry MF, Ghorab MM, Abbas SY, Fayed EA, Shedid SA, Ammar YA Quinoline derivatives bearing pyrazole moiety:synthesis and biological evaluation as possible antibacterial andantifungal agents, Eur J Med Chem, 2018; 143:1463-1473. https://doi.org/10.1016/j.ejmech.2017.10.046
27) Qhobosheane MA, Petzer A, Petzer JP, Legoabe LJ, Synthesis and evaluation of 2-substituted 4(3H)-quinazolinone thioether derivatives as monoamine oxidase inhibitors, Bioorganic & Medicinal Chemistry, 2018; 26:5531-5537. https://doi.org/10.1016/j.bmc.2018.09.032
28) Abuelizz HA, Marzouk M, Ghabbour H, Al-Salahi R, Synthesis and anticancer activity of new quinazoline derivatives, Saudi Pharm J, 2017; 25:1047-1054. https://doi.org/10.1016/j.jsps.2017.04.022
29) Zhang GP, Pan JK, Zhang J, Wu ZX, Liu DY, Zhao L, Design, Synthesis, Antiviral Activities of Novel Phosphonate Derivatives Containing Quinazoline Based on Chalone Motif, J Heterocycl Chem, 2017; 54:2548-2555. https://doi.org/10.1002/jhet.2849
30) Bansal R, Design and Synthesis of Some Quinazoline Derivatives as Anti-Inflammatory Agents, Int J Engg Tech Sci Res, 2017; 4:61-62
31) El-Gazzar YI, Georgey HH, El-Messery SM, Ewida HA, Hassan GS, Raafat MM, Synthesis, biological evaluation and molecular modeling study of new (1,2,4-triazole or 1,3,4-thiadiazole)-methylthioderivatives of quinazolin-4(3H)-one as DHFR inhibitors, Bioorganic Chemistry, 2017; 72:282-292. https://doi.org/10.1016/j.bioorg.2017.04.019
32) Zhang J, Liu J, Ma Y, Ren D, Cheng P, Zhao J, One-pot synthesis and antifungal activityagainst plant pathogens of quinazolinone derivatives containing an amide moiety,Bioorganic, Medicinal Chemistry Letters, 2016; 6(9):2273-2277. https://doi.org/10.1016/j.bmcl.2016.03.052
33) Sugden R, Kelly R, Davies S, Combating antimicrobial resistance globally, Nature Microbiology, 2016; 1:16187-16187. https://doi.org/10.1038/nmicrobiol.2016.187
34) Gokhale N, Panathur N, Dalimba U, Nayak PG, Pai KSR, J Heterocycl Chem, 2016; 53:513-524. https://doi.org/10.1002/jhet.2403
35) Popova E, Kostov M, Kupenova P, Effects of dopamine D1 receptor blockade on the ERG b, d waves during blockade of ionotropic GABA receptors, Eye and Vision, London, 2016; 3:32. https://doi.org/10.1186/s40662-016-0064-4
36) El-Gazzar YI, Georgey HH, El-Messery SM, Ewida HA, Hassan GS, Raafat MM, Synthesis, biological evaluation, molecular modeling study of new (1,2,4-triazole or 1,3,4-thiadiazole)-methylthioderivatives of quinazolin-4(3H)-one as DHFR inhibitors, Bioorganic Chemistry, 2017; 72:282-292. https://doi.org/10.1016/j.bioorg.2017.04.019
37) Birhan YS, Bekhit AA, Hymete A, In vivo antimalarial evaluation of some 2,3-disubstituted-4(3H)-quinazolinone derivatives, BMC Research Notes, 2015; 8:589. https://doi.org/10.1186/s13104-015-1578-x
38) Liu S, Wang W, Jiang L, Wan S, Zhang L, Yu R, 2-Pyridinyl-4(3H)- quinazolinone, A scaffold for antiinfluenza a virus compounds, Chemical Biology & Drug Design, 2015; 86:1221-1225. https://doi.org/10.1111/cbdd.12589
39) Singh M, Raghav N, 2,3-Dihydroquinazolin-4(1H)-one derivatives as potential non-peptidyl inhibitors of cathepsins B and H, Bioorganic Chemistry, 2015; 59:12-22. https://doi.org/10.1016/j.bioorg.2015.01.005
40) Venkatesh R, Ramaiah MJ, Gaikwad HK, Janardhan S, Bantu R, Nagarapu L, Luotonin-a based quinazolinones cause apoptosis and senescence via HDAC inhibition and activation of tumor suppressor proteins in HeLa cells, European Journal of Medicinal Chemistry, 2015; 94:87-101. https://doi.org/10.1016/j.ejmech.2015.02.057
41) Malinowski Z, Fornal E, Nowak M, Kontek R, Gajek G, Borek B, Synthesis and biological evaluation of some amino- and sulfanyl-3H-quinazolin-4- one derivatives as potential anticancer agents, Monatshefte fuer Chemie, 2015; 146:1723-1731. https://doi.org/10.1007/s00706-015-1508-6
42) Hemalath K, Madhumith G, Vasavi CS, Munusami PJ, 2, 3-Dihydroquinazolin-4 (1H)-ones, Visible light mediated synthesis, solvatochromism, biological activity, Journal of Photochemistry and Photobiology B, Biology, 2015; 143:139-147. https://doi.org/10.1016/j.jphotobiol.2014.12.028
43) Al-Salem HS, Hegazy GH, El-Taher KF, El-Messery SM, Al-Obaid AM, El-Subbagh HI, Synthesis anticonvulsant activity, molecular modeling study of some new hydrazinecarbothioamide, benzenesulfonohydrazide, phenacylacetohydrazide analogues of 4(3H)-quinazolinone, Bioorganic & Medicinal Chemistry Letters, 2015; 25:1490-1499. https://doi.org/10.1016/j.bmcl.2015.02.025
44) Khadka DB, Tran GH, Shin S, Nguyen HTM, Cao HT, Zhao C, Substituted 2-arylquinazolinones, Design, synthesis, and evaluation of cytotoxicity and inhibition of topoisomerases, European Journal of Medicinal Chemistry, 2015;103:69-79. https://doi.org/10.1016/j.ejmech.2015.08.040
45) Javaid K, Saad SM, Rasheed S, Moin ST, Syed N, Fatima I, 2-Arylquinazolin-4(3H)-ones, A new class of α-glucosidase inhibitors, Bioorganic & Medicinal Chemistry, 2015; 23:7417-7421. https://doi.org/10.1016/j.bmc.2015.10.038
46) Javaid S, Saad SM, Perveen S, Khan KM, Choudhary MI, 2-Arylquinazolin-4(3H)-ones, A novel class of thymidine phosphorylase inhibitors, Bioorganic Chemistry, 2015; 63:142-151. https://doi.org/10.1016/j.bioorg.2015.10.006
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Vishwakarma LKK, Kashaw V. Nanocatalyzed Synthetic Approach for the Quinazolinone and Quinazoline Derivatives: A Review (2015 – Present). JDDT [Internet]. 15Mar.2023 [cited 22Mar.2023];13(3):171-83. Available from: https://jddtonline.info/index.php/jddt/article/view/5765
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