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Novel 4(3H)Quinazolinones Based Azo Dyes: Synthesis, Investigations, Solvatochromic UV–Vis Absorption, Antioxidant and Biological Assessments

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Abstract

This study focused on efficiently, synthesizing novel derivatives of azo-4-(3H) quinazolinone and azo diamides. Azo diamides derivatives were synthesized by rapidly opening the ring of azo benzoxazine-4-one in the presence of primary aromatic amines, attempts to dehydrate diamides into azo quinazolinones were failed, while azo quinazolinones were synthesized from azo-benzo[d][1,3]oxazin-4-one by using freshly fused sodium acetate in acetic acid The structures of the newly synthesized compounds were characterized using FT-IR, UV–visible, 1H-NMR, and13C-NMR. A solvatochromic UV–Vis absorption study was conducted on the newly synthesized azo quinazolinones using various solvents. The optical band gap of these compounds was subsequently determined. The compounds were then subjected to in vitro anti-microbial screening, measuring their inhibition zones against bacteria (S. aureus, E. coli) and fungus (C. albicans) using well diffusion assays. The newly synthesized azo quinazolinones were also evaluated for their anti-cancer activity against MCF-7 cell lines, revealing moderate to excellent anti-proliferative activity. Additionally, anti-oxidant activity was assessed using the DPPH method and the results revealed that the compounds showed good anti-oxidant properties.

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References

  1. Gupta V, Singh J, Kinger M, Arora AK, Jaswal VS (2015) Synthesis and antiviral activities of some 2, 3-di-substituted quinazoline derivatives. Synthesis 1:2

    Google Scholar 

  2. Mahajan PG, Dige NC, Vanjare BD, Raza H, Hassan M, Seo S-Y, Kim C-H, Lee KH (2019) Facile synthesis of new quinazolinone benzamides as potent tyrosinase inhibitors: Comparative spectroscopic and molecular docking studies. J Mol Struct 1198:126915

    Article  Google Scholar 

  3. Ansari S, Mohammadi-Khanaposhtani M, Asgari MS, Esfahani EN, Biglar M, Larijani B, Rastegar H, Hamedifar H, Mahdavi M, Tas R (2021) Design, synthesis, in vitro and in silico biological assays of new quinazolinone-2-thio-metronidazole derivatives. J Mol Struct 1244:130889

    Article  CAS  Google Scholar 

  4. Gatadi S, Pulivendala G, Gour J, Malasala S, Bujji S, Parupalli R, Shaikh M, Godugu C, Nanduri S (2020) Synthesis and evaluation of new 4 (3H)-quinazolinone derivatives as potential anticancer agents. J Mol Struct 1200:127097

    Article  Google Scholar 

  5. Abd El-Dayem NS, Mostafa MA, Hassan SY, Yacout GA, El Sadek MM (2020) Synthesis: antioxidant and antiproliferative activities of novel quinazolinone derivatives. J Appl Chem 13:49–64

    Google Scholar 

  6. Kakoulidou C, Gritzapis PS, Hatzidimitriou AG, Fylaktakidou KC, Psomas G (2020) Zn(II) complexes of (E)-4-(2-(pyridin-2-ylmethylene) hydrazinyl) quinazoline in combination with non-steroidal anti-inflammatory drug sodium diclofenac: structure, DNA binding and photo-cleavage studies, antioxidant activity and interaction with albumin. J Inorg Biochem 211:111194

    Article  CAS  PubMed  Google Scholar 

  7. Xu Z, Zhang Y, Fu H, Zhong H, Hong K, Zhu W (2011) Antifungal quinazolinones from marine-derived Bacillus cereus and their preparation. Bio Med Chem Lett 21(13):4005–4007

    Article  CAS  Google Scholar 

  8. Zhang J, Liu J, Ma Y, Ren D, Cheng P, Zhao J, Zhang F, Yao Y (2016) One-pot synthesis and antifungal activity against plant pathogens of quinazolinone derivatives containing an amide moiety. Bio Med Chem Lett 26(9):2273–2277

    Article  CAS  Google Scholar 

  9. Ran L, Yang H, Luo L, Huang M, Hu D (2020) Discovery of potent and novel quinazolinone sulfide inhibitors with anti-ToCV activity. J Agric Food Chem 68(19):5302–5308

    Article  CAS  PubMed  Google Scholar 

  10. Saul S, Pu S-Y, Zuercher WJ, Einav S, Asquith CR (2020) Potent antiviral activity of novel multi-substituted 4-anilinoquin (az) olines. Bio Med Chem Lett 30(16):127284

    Article  CAS  Google Scholar 

  11. Wang M, Zhang G, Wang Y, Wang J, Zhu M, Cen S, Wang Y (2020) Design, synthesis and anti-influenza A virus activity of novel 2, 4-disubstituted quinazoline derivatives. Bio Med Chem Lett 30(11):127143

    Article  CAS  Google Scholar 

  12. Zhang G, Wang M, Zhao J, Wang Y, Zhu M, Wang J, Cen S, Wang Y (2020) Design, synthesis and in vitro anti-influenza A virus evaluation of novel quinazoline derivatives containing S-acetamide and NH-acetamide moieties at C-4. Eur J Med Chem 206:112706

    Article  CAS  PubMed  Google Scholar 

  13. Zu G, Gan X, Xie D, Yang H, Zhang A, Li S, Hu D, Song B (2020) Design, synthesis, and anti-ToCV activity of novel 4 (3 H)-quinazolinone derivatives bearing dithioacetal moiety. J Agric Food Chem 68(20):5539–5544

    Article  CAS  PubMed  Google Scholar 

  14. El-Shafey HW, Gomaa RM, El-Messery SM, Goda FE (2020) Quinazoline based HSP90 inhibitors: synthesis, modeling study and ADME calculations towards breast cancer targeting. Bio Med Chem Lett 30(15):127281

    Article  CAS  Google Scholar 

  15. Hoan DQ, Hoa LT, Huan TT, Dinh NH (2020) Synthesis and transformation of 4-(1-chloro-1-nitroethyl)-6, 7-dimethoxy-2-methylquinazoline: spectral characterization and anti-cancer properties of some novel quinazoline derivatives. J Het Chem 57(4):1720–1728

    Article  CAS  Google Scholar 

  16. Le Y, Gan Y, Fu Y, Liu J, Li W, Zou X, Zhou Z, Wang Z, Ouyang G, Yan L (2020) Design, synthesis and in vitro biological evaluation of quinazolinone derivatives as EGFR inhibitors for antitumor treatment. J Enzyme Inhib Med Chem 35(1):555–564

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  17. Ramadan SK, Elrazaz EZ, Abouzid KA, El-Naggar AM (2020) Design, synthesis and in silico studies of new quinazolinone derivatives as antitumor PARP-1 inhibitors. RSC Adv 10(49):29475–29492

    Article  CAS  PubMed  PubMed Central  ADS  Google Scholar 

  18. Yang L, Liu S, Chu J, Miao S, Wang K, Zhang Q, Wang Y, Xiao Y, Wu L, Liu Y (2021) Novel anilino quinazoline-based EGFR tyrosine kinase inhibitors for treatment of non-small cell lung cancer. Biomater Sci 9(2):443–455

    Article  CAS  PubMed  Google Scholar 

  19. Noser AA, El-Naggar M, Donia T, Abdelmonsef AH (2020) Synthesis, in silico and in vitro assessment of new quinazolinones as anticancer agents via potential AKT inhibition. Mol 25(20):4780

    Article  CAS  Google Scholar 

  20. Du H, Ding M, Luo N, Shi J, Huang J, Bao X (2021) Design, synthesis, crystal structure and in vitro antimicrobial activity of novel 1, 2, 4-triazolo [1, 5-a] pyrimidine-containing quinazolinone derivatives. Mol Div 25:711–722

    Article  CAS  Google Scholar 

  21. Norouzbahari M, Salarinejad S, Güran M, Şanlıtürk G, Emamgholipour Z, Bijanzadeh HR, Toolabi M, Foroumadi A (2020) Design, synthesis, molecular docking study, and antibacterial evaluation of some new fluoroquinolone analogues bearing a quinazolinone moiety. DARU J Pharm Sci 28:661–672

    Article  Google Scholar 

  22. Xu Z (2020) 1,2,3-triazole-containing hybrids with potential antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA). Eur J Med Chem 206:112686

    Article  CAS  PubMed  Google Scholar 

  23. Le-Nhat-Thuy G, Thi NN, Pham-The H, Thi TAD, Thi HN, Thi THN, Hoang SN, Van Nguyen T (2020) Synthesis and biological evaluation of novel quinazoline-triazole hybrid compounds with potential use in Alzheimer’s disease. Bio Med Chem Lett 30(18):127404

    Article  CAS  Google Scholar 

  24. Prinsloo IF, Zuma NH, Aucamp J, N’Da DD (2021) Synthesis and in vitro antileishmanial efficacy of novel quinazolinone derivatives. Chem Biol Drug Des 97(2):383–398

    Article  CAS  PubMed  Google Scholar 

  25. Sharma M, Chauhan K, Shivahare R, Vishwakarma P, Suthar MK, Sharma A, Gupta S, Saxena JK, Lal J, Chandra P (2013) Discovery of a new class of natural product-inspired quinazolinone hybrid as potent antileishmanial agents. J Med Chem 56(11):4374–4392

    Article  CAS  PubMed  Google Scholar 

  26. Eskikanbur S, Sayin K, Kose M, Zengin H, McKee V, Kurtoglu M (2015) Synthesis of two new azo-azomethines; spectral characterization, crystal structures, computational and fluorescence studies. J Mol Struct 1094:183–194

    Article  CAS  ADS  Google Scholar 

  27. Herbst W, Hunger K (2006) Industrial organic pigments: production, properties, applications. Wiley, New York

    Google Scholar 

  28. Kirk RE, Othmer DF, Grayson M, Eckroth D (1985) Kirk-Othmer concise encyclopedia of chemical technology. (No Title)

  29. Lazar T (2005) Industrial dyes—chemistry, properties, applications. Wiley Online Library, New York

    Book  Google Scholar 

  30. Zollinger H (2003) Color chemistry: syntheses, properties, and applications of organic dyes and pigments. Wiley, New York

    Google Scholar 

  31. Benkhaya S, M'rabet S, El Harfi A (2020) Classifications, properties, recent synthesis and applications of azo dyes. Heliyon 6(1)

  32. Favre-Besse F-C, Poirel O, Bersot T, Kim-Grellier E, Daumas S, El Mestikawy S, Acher FC, Pietrancosta N (2014) Design, synthesis and biological evaluation of small-azo-dyes as potent vesicular glutamate transporters inhibitors. Eur J Med Chem 78:236–247

    Article  CAS  PubMed  Google Scholar 

  33. Mi Y, Zhang J, Han X, Tan W, Miao Q, Cui J, Li Q, Guo Z (2021) Modification of carboxymethyl inulin with heterocyclic compounds: synthesis, characterization, antioxidant and antifungal activities. Int J Biol Macromol 181:572–581

    Article  CAS  PubMed  Google Scholar 

  34. Singh K, Pal R, Khan SA, Kumar B, Akhtar MJ (2021) Insights into the structure activity relationship of nitrogen-containing heterocyclics for the development of antidepressant compounds: an updated review. J Mol Struct 1237:130369

    Article  CAS  Google Scholar 

  35. Patel DR, Patel KC (2010) Synthesis, characterization and application of quinazolinone based reactive dyes for various fibers. Fiband Pol 11:537–544

    Article  CAS  Google Scholar 

  36. Levy PR, Stephen H (1956) Syntheses in the quinazolone series. Part I. Synthesis of 2: 3-diaryl-4-quinazolones. J Chem Soc 205:985–988

    Article  Google Scholar 

  37. Patel DR, Patel KC (2011) Synthesis and characterization of reactive dyes based on 2-phenyl-3-[4′-(4″-aminophenylsulphonamido)] phenyl-4 (3H)-quinazolinone-6-sulphonic acid. Arab J Chem 4(3):279–285

    Article  CAS  Google Scholar 

  38. Patel M, Patel V (1987) Azo dyes with 4-quinazolinone ring for dyeing nylon, wool, cotton and viscose rayon fibres. Ind J Tex Res 12:3–16

    Google Scholar 

  39. Fried B, Sherma J (1982) Thin-layer chromatography: techniques and applications

  40. Kareem Samad M (2017) Synthesis, characterization and dying performance studies of some azo dyes derived from m-phenylenediamine. Zanco J Pure Appl Sci 28(6):148–157

    ADS  Google Scholar 

  41. Ayoob MM, Hawaiz FE (2022) Design, synthesis, molecular docking ADMET and anti-bacterial activities of some new benzamides and their corresponding quinazolinone derivatives. Egypt J Chem 65(132):1517–1530

    Google Scholar 

  42. El-Sawy AA, Mohamed SK, Eissa AE-MM, Tantawy AH, Issac YA (2012) Synthesis, reactions and biological evaluation of pentadecanyl benzoxazinone and pentadecanyl quinazolinone derivatives. J Chem Pharm Res 4(5):2755–2762

    CAS  Google Scholar 

  43. Ayoob M, Hawaiz F, Dege N, Kansız S (2023) Structural investigation and hirshfeld surface analysis of N-(3-chloro-4-methylphenyl)-2-(3-nitrobenzamido) benzamide. J Str Chem 64(6):1049–1058

    Article  CAS  Google Scholar 

  44. Al-Majidi SM, Al-tamimy HM (2017) Synthesis, identification and surface active properties of some nonionic surfactants containing quinazolinone ring. J Appl Chem 10(5):37–46

    CAS  Google Scholar 

  45. Banerjee M, Behera CC, Pradhan GC, Azam MA, Sahu SK (2009) Synthesis and biological evaluation of some anthranilic acid and 2-phenylquinazoline-4 (3H)-one analogues. S Af J Chem 62:134–142

    CAS  Google Scholar 

  46. Madkour H (2004) Reactivity of 4H-3, 1-benzoxazin-4-ones towards nitrogen and carbon nucleophilic reagents: applications to the synthesis of new heterocycles. Ark 1:36–54

    Google Scholar 

  47. Mohammed SJ, Salih AK, Rashid MAM, Omer KM, Abdalkarim KA (2020) Synthesis, spectroscopic studies and keto-enol tautomerism of novel 1,3,4-thiadiazole derivative containing 3-mercaptobutan-2-one and quinazolin-4-one moieties. Mol 25(22):5441

    Article  CAS  Google Scholar 

  48. Sumathy A, Palanisamy S (2017) Synthesis of some novel quinazoline derivatives having anti-cancer activity. Int J Pharm Pharm Sci 3(2):48–52

    Google Scholar 

  49. Rajput CS, Singhal S (2013) Synthesis, characterization, and anti inflamatory activity of newer quinazolinone analogs. J Pharm 2013:907525

    Google Scholar 

  50. Ayoob MM, Hussein AJ, Samad MK, Dege N, Hawaiz FE, Mohamed SK, Hussain FH (2021) Synthesis, anti-bacterial and anti-oxidant activity of azo-oxazolone and their ring opening azo-benzamide derivatives. Curr Org Synth 18(5):493–505

    Article  CAS  PubMed  Google Scholar 

  51. Ayoob MM, Hawaiz FE, Hussein A, Samad MK, Hussain F, Mohamed SK (2020) Synthesis, spectroscopic investigation, anti-bacterial and antioxidant activites of some new azo-benzofuran derivatives. Egypt J Chem 63(7):2617–2629

    Google Scholar 

  52. Jiménez-Estrada M, Velázquez-Contreras C, Garibay-Escobar A, Sierras-Canchola D, Lapizco-Vázquez R, Ortiz-Sandoval C, Burgos-Hernández A, Robles-Zepeda RE (2013) In vitro antioxidant and antiproliferative activities of plants of the ethnopharmacopeia from northwest of Mexico. BMC Complement Altern Med 13:1–8

    Article  Google Scholar 

  53. López-Romero JC, Torres-Moreno H, Rodríguez-Martínez KL, Ramírez-Audelo V, Vidal-Gutiérrez M, Hernández J, Robles-Zepeda RE, Ayala-Zavala JF, González-Ríos H, Valenzuela-Melendres M (2022) Fouquieria splendens: a source of phenolic compounds with antioxidant and antiproliferative potential. Eur J Integr Med 49:102084

    Article  Google Scholar 

  54. Charitos G, Trafalis DT, Dalezis P, Potamitis C, Sarli V, Zoumpoulakis P, Camoutsis C (2019) Synthesis and anticancer activity of novel 3,6-disubstituted 1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazole derivatives. Arab J Chem 12(8):4784–4794

    Article  CAS  Google Scholar 

  55. El-Hashash MAE-AM, Salem MS, Al-Mabrook SAM (2018) Synthesis and anticancer activity of novel quinazolinone and benzamide derivatives. Res Chem Intermed 44:2545–2559

    Article  CAS  Google Scholar 

  56. Desai N, Dodiya AM (2014) Synthesis, characterization and antimicrobial screening of quinoline based quinazolinone-4-thiazolidinone heterocycles. Arab J Chem 7(6):906–913

    Article  CAS  Google Scholar 

  57. Rakesh K, Kumara H, Ullas B, Shivakumara J, Gowda DC (2019) Amino acids conjugated quinazolinone-Schiff’s bases as potential antimicrobial agents: synthesis, SAR and molecular docking studies. Bio Chem 90:103093

    Article  CAS  Google Scholar 

  58. Ramilo-Gomes F, Addis Y, Tekamo I, Cavaco I, Campos DL, Pavan FR, Gomes CS, Brito V, Santos AO, Domingues F (2021) Antimicrobial and antitumor activity of S-methyl dithiocarbazate Schiff base zinc(II) complexes. J Inorg Biochem 216:111331

    Article  CAS  PubMed  Google Scholar 

  59. Al-Obaid A, Abdel-Hamide S, El-Kashef H, Abdel-Aziz A, El-Azab A, Al-Khamees H, El-Subbagh H (2009) Synthesis, in vitro antitumor activity and molecular modelling study of certain 2-thieno-4(3H)-quinazolinone analogs. Eur J Med Chem 44:2379–2391

    Article  CAS  PubMed  Google Scholar 

  60. Al-Omary FA, Abou-Zeid LA, Nagi MN, Habib E-SE, Alaa A-M, El-Azab AS, Abdel-Hamide SG, Al-Omar MA, Al-Obaid AM, El-Subbagh HI (2010) Non-classical antifolates. Part 2: synthesis, biological evaluation, and molecular modeling study of some new 2, 6-substituted-quinazolin-4-ones. Bioorg Med Chem 18(8):2849–2863

    Article  CAS  PubMed  Google Scholar 

  61. Al-Rashood ST, Aboldahab IA, Nagi MN, Abouzeid LA, Abdel-Aziz AA, Abdel-Hamide SG, Youssef KM, Al-Obaid AM, El-Subbagh HI (2006) Synthesis, dihydrofolate reductase inhibition, antitumor testing, and molecular modeling study of some new 4 (3H)-quinazolinone analogs. Bioorg Med Chem 14(24):8608–8621

    Article  CAS  PubMed  Google Scholar 

  62. Airinei A, Homocianu M, Dorohoi DO (2010) Changes induced by solvent polarity in electronic absorption spectra of some azo disperse dyes. J Mol Liq 157(1):13–17

    Article  CAS  Google Scholar 

  63. Zakerhamidi M, Ahmadi-Kandjani S, Moghadam M, Ortyl E, Kucharski S (2011) Substituent and solvent effects on the dipole moments and photophysical properties of two azo sulfonamide dyes. J Mol Struct 996(1–3):95–100

    Article  CAS  ADS  Google Scholar 

  64. Kakanejadifard A, Azarbani F, Zabardasti A, Kakanejadifard S, Ghasemian M, Esna-ashari F, Omidi S, Shirali S, Rafieefar M (2013) The synthesis, structural characterization and antibacterial properties of some 2-((4-amino-1, 2, 5-oxadiazol-3-ylimino) methyl)-4-(phenyldiazenyl) phenol. Dyes Pigm 97(1):215–221

    Article  CAS  Google Scholar 

  65. Ghasemian M, Kakanejadifard A, Azarbani F, Zabardasti A, Kakanejadifard S (2014) Spectroscopy and solvatochromism studies along with antioxidant and antibacterial activities investigation of azo–azomethine compounds 2-(2-hydroxyphenylimino) methyl)-4-phenyldiazenyl) phenol. Spectrochim Acta A Mol Biomol 124:153–158

    Article  CAS  Google Scholar 

  66. Kakanejadifard A, Azarbani F, Zabardasti A, Rezayat A, Ghasemian M, Kakanejadifard S (2013) Spectroscopic and solvatochromism studies along with antioxidant and antibacterial activities investigation of 2-((2-mercaptophenylimino) methyl)-4-(phenyldiazenyl) phenol. Spectrochim Acta A Mol Biomol 114:404–409

    Article  CAS  ADS  Google Scholar 

  67. Khanmohammadi H, Abdollahi A (2012) New diaminomaleonitrile-based azo-azomethine dyes; synthesis, characterization and spectral properties. Dyes Pigm 94(1):163–168

    Article  CAS  Google Scholar 

  68. Kumar N, Mahadevan K, Nagaraju G (2020) Development and detection of level II and III features of latent fingerprints using highly sensitive AIE based coumarin fluorescent derivative. J Sci Adv Mater Devi 5(4):520–526

    CAS  Google Scholar 

  69. Manjunatha B, Bodke YD (2021) Novel isoxazolone based azo dyes: synthesis, characterization, computational, solvatochromic UV–Vis absorption and biological studies. J Mol Struct 1244:130933

    Article  Google Scholar 

  70. Nagaraju G, Shubha J, Manjunath K, Dupont J (2018) Ionothermal synthesis of TiO2 nanoparticles for enhanced photocatalytic H2 generation. Int J Hydrog 43(8):4028–4035

    Article  CAS  Google Scholar 

  71. Samad MK, Hawaiz FE (2019) Synthesis, characterization, antioxidant power and acute toxicity of some new azo-benzamide and azo-imidazolone derivatives with in vivo and in vitro antimicrobial evaluation. Bio Chem 85:431–444

    Article  CAS  Google Scholar 

  72. Ahmed D, Khan MM, Saeed R (2015) Comparative analysis of phenolics, flavonoids, and antioxidant and antibacterial potential of methanolic, hexanic and aqueous extracts from Adiantum caudatum leaves. Antiox 4(2):394–409

    Article  CAS  Google Scholar 

  73. Idhayadhulla A, Xia L, Lee YR, Kim SH, Wee Y-J, Lee C-S (2014) Synthesis of novel and diverse mollugin analogues and their antibacterial and antioxidant activities. Bio Chem 52:77–82

    Article  CAS  Google Scholar 

  74. Allam HA, Aly EE, Farouk AK, El Kerdawy AM, Rashwan E, Abbass SE (2020) Design and synthesis of some new 2,4,6-trisubstituted quinazoline EGFR inhibitors as targeted anticancer agents. Bio Chem 98:103726

    Article  CAS  Google Scholar 

  75. Haredi Abdelmonsef A, Eldeeb Mohamed M, El-Naggar M, Temairk H, Mohamed Mosallam A (2020) Novel quinazolin-2,4-dione hybrid molecules as possible inhibitors against malaria: synthesis and in silico molecular docking studies. Fron Mol Biosci 7:105

    Article  Google Scholar 

  76. Metwally NH, Abdelrazek FM, Eldaly SM (2018) Synthesis, molecular docking, and biological evaluation of some novel bis-heterocyclic compounds based N,N′-([1,1′-biphenyl]-4,4′-diyl)bis(2-cyanoacetamide) as potential anticancer agents. J Heterocycl Chem 55(12):2668–2682

    Article  CAS  Google Scholar 

  77. Plaeyao K, Kampangta R, Korkokklang Y, Talodthaisong C, Saenchoopa A, Thammawithan S, Latpala K, Patramanon R, Kayunkid N, Kulchat S (2023) Gingerol extract-stabilized silver nanoparticles and their applications: colorimetric and machine learning-based sensing of Hg(II) and antibacterial properties. RSC Adv 13(29):19789–19802

    Article  CAS  PubMed  PubMed Central  ADS  Google Scholar 

  78. Hemalatha K, Madhumitha G, Ravi L, Khanna VG, Al-Dhabi NA, Arasu MV (2016) Binding mode of dihydroquinazolinones with lysozyme and its antifungal activity against Aspergillus species. J Photochem Photobiol B Biol 161:71–79

    Article  CAS  Google Scholar 

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Acknowledgements

This work was supported by Salahaddin University-Erbil, Erbil, Kurdistan-Iraq as the PhD program (No. 3/1/5/1520 at 6/10/2020). The authors would like to thank Dr. Mohammed K. Samad, Dr. Aveen F. Jalal and Dr. Rebwar Muhammad Hamasalih for the excellent technical assistance performed in vitro biochemical assays.

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  1. Department of Chemistry, College of Education, Salahaddin University-Erbil, Kirkuk Road, Erbil, KRG, Iraq

    Mzgin Mohammed Ayoob & Farouq Emam Hawaiz

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Ayoob, M.M., Hawaiz, F.E. Novel 4(3H)Quinazolinones Based Azo Dyes: Synthesis, Investigations, Solvatochromic UV–Vis Absorption, Antioxidant and Biological Assessments. Chemistry Africa 7, 623–642 (2024). https://doi.org/10.1007/s42250-023-00803-3

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