151
Views
5
CrossRef citations to date
0
Altmetric
Research Article

Design, Synthesis and Antiproliferative Activity of Novel Heterocycles from 6-Iodo-2-phenyl-4H-benzo[d][1,3]thiazine-4-thione

ORCID Icon, & ORCID Icon
Pages 251-263 | Received 05 May 2020, Accepted 27 Oct 2020, Published online: 26 Nov 2020

References

  • Gao C, Ye TH, Wang NY, et al. Synthesis and structure–activity relationships evaluation of benzothiazinone derivatives as potential anti-tubercular agents. Bioorg Med Chem Lett. 2013;23:4919–4922.
  • Majewski MW, Tiwaria R, Miller PA, et al. Design, syntheses, and anti-tuberculosis activities of conjugates of piperazino-1,3-benzothiazin-4-ones (pBTZs) with 2,7dimethylimidazo[1,2-a]pyridine-3-carboxylic acids and 7phenylacetyl cephalosporins. Bioorg Med Chem Lett. 2016 Apr 15;26(8):2068–2071.
  • Peng CT, Gao C, Wang NY, et al. Synthesis and antitubercular evaluation of 4-carbonyl piperazine substituted 1,3-benzothiazin-4-one derivatives. Bioorg Med Chem Lett. 2015 Apr 1;25(7):1373–1376.
  • He D, Wang M, Zhao S, et al. Pharmaceutical prospects of naturally occurring quinazolinone and its derivatives. Fitoterapia. 2017;119:136–149.
  • Patel MB, Kumar SP, Valand NN, et al. Synthesis and biological evaluation of cationic fullerene quinazolinone conjugates and their binding mode with modeled Mycobacterium tuberculosis hypoxanthine-guanine phosphoribosyltransferase enzyme. J Mol Model. 2013;19(8):3201–3217.
  • Kubo K, Shimizu T, Ohyama S, et al. Novel potent orally active selective VEGFR-2 tyrosine kinase inhibitors: synthesis, structure-activity relationships, and antitumor activities of N-phenyl-N'-{4-(4-quinolyloxy)phenyl}ureas. J Med Chem. 2005;48(5):1359–1366.
  • El-Hashash MAM, Salem MS, Al-Mabrook SAM. Synthesis and anticancer activity of novel quinazolinone and benzamide derivatives. Res Chem Intermed. 2018;44(4):2545–2559. DOI:10.1007/s11164-017-3245-4
  • Marzouk MI, Shaker SA, Farghaly T A, et al. Synthesis of some novel quinazolinone derivatives with anticipated biological activity. J Heterocyclic Chem. 2017;54:3331–3341.
  • Radwan TM, El-Hashash MA, Wasfy AAF, et al. Synthesis and characteristics of metastable 2-benzyl-4H-3,1-benzoxazin-4-one as anticancer agent and its Comparison with other heterocyclic compounds. Chemistry Select. 2019;4:14056–14062.
  • Song F, Ren B, Yu K, et al. Quinazolin-4-one coupled with pyrrolidin-2-iminium alkaloids from marine-derived fungus Penicillium aurantiogriseum. Mar Drugs. 2012;10(6):1297–1306.
  • Khodarahmi G, Jafari E, Hakimelahi G, et al. Synthesis of some new quinazolinone derivatives and evaluation of their antimicrobial activities. Iran J Pharm Res. 2012;11(3):789–797.
  • Patil A, Barge M, Rashinkar G, et al. Aqueous hydrotrope: an efficient and reusable medium for a green one-pot, diversity-oriented synthesis of quinazolinone derivatives. Mol Divers. 2015;19(3):435–445.
  • El-Hashash MA, El-Naggar AM, El-Bordany EA, et al. 6-Iodo-2-isopropyl-4H-3,1-benzoxazin-4-one as building block in heterocyclic synthesis. Synth Commun. 2016;46(24):2009–2021.
  • Kubicová L, Ustr M, Kráľová K, et al. Synthesis and biological evaluation of quinazoline-4-thiones. Molecules. 2003;8:756–769.
  • El-Feky SA, Thabet HK, Ubeid MT. Synthesis, molecular modeling and anti-inflammatory screening of novel fluorinated quinoline incorporated benzimidazole derivatives using the Pfitzinger reaction. J Fluorine Chem. 2014;161:87–94.
  • Andrzejewskaa M, Yepez-Mulia L, Tapia A, et al. Synthesis, and antiprotozoal and antibacterial activities of S-substituted 4,6-dibromo- and 4,6-dichloro-2-mercaptobenzimidazoles. Eur J Pharm Sci. 2004;21:323–329.
  • Camacho J, Barazarte A, Gamboa N, et al. Synthesis and biological evaluation of benzimidazole-5-carbohydrazide derivatives as antimalarial, cytotoxic and antitubercular agents. Bioorg Med Chem. 2011;19:2023–2029.
  • Gong Y, Karakaya SS, Guo X, et al. Benzimidazole-based compounds kill Mycobacterium tuberculosis. Eur J Med Chem. 2014;75:336–353.
  • Abonia R, Cortes E, Insuasty B, et al. Synthesis of novel 1,2,5-trisubstituted benzimidazoles as potential antitumor agents. Eur J Med Chem. 2011;46:4062–4070.
  • Fonseca T, Gigante B, Marques MM, et al. Synthesis and antiviral evaluation of benzimidazoles, quinoxalines and indoles from dehydroabietic acid. Bioorg Med Chem. 2004;12:103–112.
  • Kaur N, Kaur A, Bansal Y, et al. Design, synthesis, and evaluation of 5-sulfamoyl benzimidazole derivatives as novel angiotensin II receptor antagonists. Bioorg Med Chem. 2008;16:10210–10215.
  • Falco JL, Pique M, Gonzalez M, et al. Synthesis, pharmacology and molecular modeling of N-substituted 2-phenyl-indoles and benzimidazoles as potent GABAA agonists. Eur J Med Chem. 2006;41:985–990.
  • Futatsugi K, Mascitti V, Guimarães CR, et al. From partial to full agonism: Identification of a novel 2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole as a full agonist of the human GPR119 receptor. Bioorg Med Chem Lett. 2013;23:194–197.
  • Jia H, Bai F, Liu N, et al. Design, synthesis and evaluation of pyrazole derivatives as non-nucleoside hepatitis B virus inhibitors. Eur J Med Chem. 2016;123:202–210.
  • Liu GN, Luo RH, ZhouY ZXJ, et al. Synthesis and anti-HIV-1 activity evaluation for novel 3a,6a-dihydro-1H-pyrrolo[3,4-c]pyrazole-4,6-dione derivatives. Molecules. 2016;21:1198–1209.
  • Hassan GS, Abou-Seri SM, Kamel G, et al. Celecoxib analogs bearing benzofuran moiety as cyclooxygenase-2 inhibitors: design, synthesis and evaluation as potential anti-inflammatory agents. Eur J Med Chem. 2014;76:482–493.
  • Karrouchi K, Chemlal L, Doudach L, et al. Synthesis, anti-inflammatory and antioxidant activities of some new pyrazole derivatives. J Pharm Res. 2014;8:1171–1177.
  • Madkour HMF, El-Hashash MAM, Salem MS, et al. Synthesis, antileishmanial and cytotoxicity activities of fused and nonfused tetrahydroquinoline derivatives. Res Chem Intermed. 2018;44:3349–3364.
  • Radwan TM, El-Hashash MAM, Wasfy AAF, et al. Antitumor, cytotoxic, and antioxidant evaluation of six heterocyclic compounds containing different heterocycle moieties. J Heterocyclic Chem. 2020;57(3):1111–1122.
  • Madkour HMF, El-Hashash MAM, Salem MS, et al. Design, synthesis, and in vitro antileishmanial and antitumor activities of new tetrahydroquinolines. J Heterocyclic Chem. 2018;55:391–401.
  • Khlosy TA, Salem MS, Ali AT, et al. Synthesis and cytotoxic activity against human tumor cells of heterocyclic systems derived from 2-thioxo-1,2-dihydro-4H-3,1-benzothazin-4-one. J Heterocyclic Chem. 2020;57:60–68.
  • Salem MS, El-Helw E AE, Derbala HAY. Development of promising chromones-pyrazoles based anticancer agents. Russ J Bioorg Chem. 2020;46(1):77–84.
  • Salem MS, Hussein RA, El-Sayed WM. Substitution at phenyl rings of chalcone and schiff base moieties accounts for their antiproliferative activity. Anticancer Agents Med Chem. 2019;19(5):620–626.
  • El-Helw EAE, Derbala HAY, El-Shahawi MM, et al. Synthesis and In Vitro antitumor activity of novel chromenones bearing benzothiazole moiety. Russ J Bioorg Chem. 2019;45(1):42–53.
  • El-Hashash MA, Assy MG, Aly A, et al. Behavior of 6-Iodobenzoxazinone towards some nitrogen nucleophiles and evaluation of 4(3H) – quinazolinones derivatives as potential antimicrobial agents. Nat Sci. 2016;14(5):76–84.
  • Mohamed AMM, Ismail MF, Madkour HMF, et al. Straightforward synthesis of 2-chloro-N-(5-(cyanomethyl)-1,3,4-thiadiazol-2-yl)benzamide as a precursor for synthesis of novel heterocyclic compounds with insecticidal activity. Synth Commun. 2020. DOI:10.1080/00397911.2020.1802652.
  • Salem MS, Al-Mabrook SAM, El-Hashash MAM. Synthesis and antiproliferative evaluation of some novel quinazolin-4(3H)-one derivatives, J Heterocyclic Chem. 2020. in press.
  • Ozturk T, Ertas E, Mert O. A berzellus reagent; P4S10 in organic syntheses. Chem Rev. 2010;110:3419–3478.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.