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Design,Synthesis, and Molecular Docking Study of Some New Tris-Hetero Cyclic Compounds( Pyridyl, 1, 3, 4-Oxadiazole, and 1,3- Oxazepine ) as Possible Antimicrobial Agent | ||
| Journal of University of Anbar for Pure Science | ||
| Volume 18, Issue 1, June 2024, Pages 165-179 PDF (904.1 K) | ||
| Document Type: Research Paper | ||
| DOI: 10.37652/juaps.2023.143811.1146 | ||
| Authors | ||
| Vian Jawhar Faris* 1; Ayad Saad Hameed2; Fadhil Dawood Khalid2 | ||
| 1Food Technology, College of Agricultural Engineering Sciences, Salahaddin University , Erbil, Iraq | ||
| 2Department of Chemistry, College of Science, University of Tikrit , Tikrit , Iraq | ||
| Abstract | ||
| The study describes synthesis of compounds with a tris heterocyclic rings of (Pyridyl, 1, 3, 4-Oxadiazole, and 1,3- Oxazepine) derived from isoniazid (INH) (V2-V23). The structures of synthesized compounds were characterized using several spectroscopic approaches, including IR, 1H-NMR, and 13C-NMR, and the results are consistent with the assigned structures. Compounds (V1-V23) were examined for antibacterial activity in vitro, and the findings showed that some compounds are more active than conventional medicines. Molecular docking was used to investigate the inhibitory impact of synthesized compounds (V18-V23) (structure - reactivity relationship) on the activity of the E-Coli biotin carboxylase (PDB: ID:3jzf) and some compounds (V1-V17) on the activity of S-aureus biotin protein ligase (PDB: ID:4dqz). The tested and molecular docking results indicated that the introducing 1,3,4-oxadiazol, hydrazine group, and 1,3- Oxazepine in the structure of parent bioactive drug compound (Isoniazid) enhancing the antimicrobial activity. Finally, in vitro, antioxidant of the synthesized compounds (V1, V5, V7, V9, V13, V14, and V16-V23) were evaluated, and molecular docking of compounds (V18-V23) with human heme oxygenase-1 (PDB code: 3CZY) were studied and compared with standard natural antioxidant [ascorbic acid and 1(adamantan1yl)2(1Himidazol1yl)ethanone (Std)] respectively and the results indicated that these compounds exhibit excellent to moderate activity. | ||
| Keywords | ||
| 3- Oxazepine,,; ,،Molecular Docking,,; ,،and biological activity | ||
| References | ||
|
[1] T. Aboul-Fadl, F. A. H. Mohammed, and E. A. S. Hassan, “Synthesis, antitubercular activity and pharmacokinetic studies of some Schiff bases derived from 1- alkylisatin and isonicotinic acid hydrazide (INH),” Arch. Pharm. Res., vol. 26, no. 10, pp. 778–784, 2003, doi: 10.1007/BF02980020.
[2] B. K. Kaymakçioǧlu and S. Rollas, “Synthesis, characterization and evaluation of antituberculosis activity of some hydrazones,” Farmaco, vol. 57, no. 7, pp. 595–599, 2002, doi: 10.1016/S0014-827X(02)01255-7.
[3] F. Martins et al., “Design, synthesis and biological evaluation of novel isoniazid derivatives with potent antitubercular activity,” Eur. J. Med. Chem., vol. 81, pp. 119–138, 2014, doi: 10.1016/j.ejmech.2014.04.077.
[4] L. Xia et al., “Benzaldehyde Schiff bases regulation to the metabolism, hemolysis, and virulence genes expression in vitro and their structure-microbicidal activity relationship,” Eur. J. Med. Chem., vol. 97, pp. 83–93, 2015, doi: 10.1016/j.ejmech.2015.04.042.
[5] R. Ci, K. Zhang, A. Zhu, and W. Zang, “Dendrobine attenuates isoniazid- and rifampicin-induced liver injury by inhibiting miR-295-5p,” Hum. Exp. Toxicol., vol. 39, no. 12, pp. 1671–1680, 2020, doi: 10.1177/0960327120937047.
[6] M. Malhotra, S. Sharma, and A. Deep, “Synthesis, characterization and antimicrobial evaluation of novel derivatives of isoniazid,” Med. Chem. Res., vol. 21, no. 7, pp. 1237–1244, 2012, doi: 10.1007/s00044-011-9634-0.
[7] A. J. Crowle and M. H. May, “Inhibition of tubercle bacilli in cultured human macrophages by chloroquine used alone and in combination with streptomycin, isoniazid, pyrazinamide, and two metabolites of vitamin D3,” Antimicrob. Agents Chemother., vol. 34, no. 11, pp. 2217–2222, 1990, doi: 10.1128/AAC.34.11.2217.
[8] R. de Aguiar Cordeiro et al., “Synthesis and in vitro antifungal activity of isoniazid-derived hydrazones against Coccidioides posadasii,” Microb. Pathog., vol. 98, pp. 1–5, 2016, doi: 10.1016/j.micpath.2016.06.022.
[9] M. X. Wei, L. Feng, X. Q. Li, X. Z. Zhou, and Z. H. Shao, “Synthesis of new chiral 2,5-disubstituted 1,3,4-thiadiazoles possessing γ-butenolide moiety and preliminary evaluation of in vitro anticancer activity,” Eur. J. Med. Chem., vol. 44, no. 8, pp. 3340–3344, 2009, doi: 10.1016/j.ejmech.2009.03.023.
[10] G. Nigade, P. Chavan, and M. Deodhar, “Synthesis and analgesic activity of new pyridine-based heterocyclic derivatives,” Med. Chem. Res., vol. 21, no. 1, pp. 27–37, 2012, doi: 10.1007/s00044-010-9489-9.
[11] В. П. Андрианов, Н. Г. Веселов, and И. И. Мирзоева, “No TitleОрганизация ортопедической и травматологической помощи детям,” vol. 48, p. 240, 1988.
[12] Y. Zhang et al., “Isoniazid promotes the anti-inflammatory response in zebrafish associated with regulation of the PPARγ/NF-κB/AP-1 pathway,” Chem. Biol. Interact., vol. 316, p. 108928, 2020, doi: 10.1016/j.cbi.2019.108928.
[13] S. D. Satyanarayanajois and R. A. Hill, “Medicinal chemistry for 2020,” Future Med. Chem., vol. 3, no. 14, pp. 1765–1786, 2011, doi: 10.4155/fmc.11.135.
[14] G. Verma, A. Marella, M. Shaquiquzzaman, M. Akhtar, M. R. Ali, and M. M. Alam, “A review exploring biological activities of hydrazones,” J. Pharm. Bioallied Sci., vol. 6, no. 2, pp. 69–80, 2014, doi: 10.4103/0975-7406.129170.
[15] W. Neamah and N. Mezaal, “Synthesis and characterization of new derivatives using Schiff ’ s bases for alcoholic extract of ( Cordia myxa ) medical plant,” no. June, pp. 1054–1061, 2022.
[16] H. G. Aslan, S. Özcan, and N. Karacan, “The antibacterial activity of some sulfonamides and sulfonyl hydrazones, and 2D-QSAR study of a series of sulfonyl hydrazones,” Spectrochim. Acta - Part A Mol. Biomol. Spectrosc., vol. 98, pp. 329–336, 2012, doi: 10.1016/j.saa.2012.08.043.
[17] W. H. Majeed, S. R. Baqer, and S. A. Alsahib, “Synthesis and Biological Study of Some Transition Metal Ions Complexes of Schiff-Mannich Base Derived from 2-Amino-5-Mercpto-1,3,4 Thiadiazole,” J. Med. Chem. Sci., vol. 6, no. 4, pp. 789–802, 2023, doi: 10.26655/JMCHEMSCI.2023.4.10.
[18] S. Shaabani, A. Shaabani, M. Kucerakova, and M. Dusek, “A One-Pot Synthesis of Oxazepine-Quinazolinone bis-Heterocyclic Scaffolds via Isocyanide-Based Three-Component Reactions,” Front. Chem., vol. 7, no. September, 2019, doi: 10.3389/fchem.2019.00623.
[19] A. W. Naser, A. J. Al-musawi, A. A. Fadhil, and N. N. Al-shawi, “SYNTHESIS , CHARACTERIZATION AND ANTI-INFLAMMATORY EVALUATION OF SOME NEW 2- ( 3-FLUOROBIPHENYL-4-YL ) PROPANOIC ACID DERIVATIVES SYNTHESIS , CHARACTERIZATION AND ANTI-INFLAMMATORY EVALUATION OF SOME NEW 2- ( 3-FLUOROBIPHENYL-4-YL ) PROPANOIC ACID DERIVAT,” no. January, 2017, doi: 10.13040/IJPSR.0975-8232.8(4).1000-08.
[20] M. H. Serrano-Wu et al., “Sordarin oxazepine derivatives as potent antifungal agents,” Bioorganic Med. Chem. Lett., vol. 12, no. 19, pp. 2757–2760, 2002, doi: 10.1016/S0960-894X(02)00529-2.
[21] J. K. Mishra, K. Samanta, M. Jain, M. Dikshit, and G. Panda, “Amino acid based enantiomerically pure 3-substituted benzofused heterocycles: A new class of antithrombotic agents,” Bioorganic Med. Chem. Lett., vol. 20, no. 1, pp. 244–247, 2010, doi: 10.1016/j.bmcl.2009.10.126.
[22] T. E. Salt, I. F. Tulloch, and D. S. Walter, “Anti-epileptic properties of sodium valproate in rat amygdaloid kindling,” Br. J. Pharmacol., vol. 68, no. 1, 1980.
[23] G. Sharma, J. Y. Park, and M. S. Park, “Synthesis and anticonvulsant evaluation of 6-amino-1,4-oxazepane-3,5-dione derivatives,” Arch. Pharm. Res., vol. 31, no. 7, pp. 838–842, 2008, doi: 10.1007/s12272-001-1235-0.
[24] E. A. Hallinan, A. Stapelfeld, and M. A. Savage, “SC-51322 : A potent PGE2 Antagonist and analgesic,” Bioorg. Med. Chem. Lett., vol. 4, no. 93, pp. 509–514, 1994.
[25] “Synthesis , Biological Activity , Antioxidant Activity , and Molecular Docking Study of Some New and 1 , 3-Oxazepine ) Ring System Which Derived from Bioactive Drug Isoniazid ( INH ),” 2008.
[26] M. M. Heravi, V. Zadsirjan, and B. Farajpour, “Applications of oxazolidinones as chiral auxiliaries in the asymmetric alkylation reaction applied to total synthesis,” RSC Adv., vol. 6, no. 36, pp. 30498–30551, 2016, doi: 10.1039/C6RA00653A.
[27] A. Çetin and E. Çalişkan, “The Synthesis of Acid Derived Compounds Bearing 1,3,4-oxadiazole-2-thion Ring as Potential Antimicrobial Agents,” pp. 1–7, [Online]. Available: http://www.bingol.edu.tr/documents/oemt-1.pdf
[28] F. Zhang et al., “Synthesis, molecular modeling and biological evaluation of N-benzylidene-2-((5-(pyridin-4-yl)-1,3,4-oxadiazol-2-yl)thio)acetohydrazide derivatives as potential anticancer agents,” Bioorganic Med. Chem., vol. 22, no. 1, pp. 468–477, 2014, doi: 10.1016/j.bmc.2013.11.004.
[29] R. M. Kaddoura, “Wu : U,” pp. 1–121, 2020.
[30] I. K. Naeem and E. H. Zimam, “ISSN 0975-413X CODEN (USA): PCHHAX Synthesis, Characterization and Study Antibacterial Activity of some New 1,3- oxazepine and 1,3-diazepine Derivatives,” Pharma Chem., vol. 9, no. 921, pp. 86–93, 2017, [Online]. Available: http://www.derpharmachemica.com/archive.html
[31] A. H. Dalaf, F. H. Jumaa, and I. A. Yass, “Synthesis, Characterization, Biological Evaluation, Molecular Docking, Assess Laser Efficacy, Thermal Performance and Optical Stability Study for New Derivatives of Bis-1, 3-Oxazepene and 1, 3-Diazepine,” AIP Conf. Proc., vol. 2394, 2022, doi: 10.1063/5.0121213.
[32] I. Q. Abd, H. I. Ibrahim, H. M. Jirjes, and A. H. Dalaf, “Synthesis and identification of new compounds have antioxidant activity beta-carotene, from natural auxin phenyl acetic acid,” Res. J. Pharm. Technol., vol. 13, no. 1, pp. 40–46, 2020, doi: 10.5958/0974-360X.2020.00007.4.
[33] K. Abou-Melha, “Synthesis, molecular docking and modeling of new acenaphthenequinones clubbed of anticancer,” J. Mol. Struct., vol. 1224, p. 129215, 2021, doi: 10.1016/j.molstruc.2020.129215.
[34] Dawood ZA, Khalid FD, Hameed AS. Synthesis,
radical scavenging activity, antibacterial activity
and molecular docking of a new thiazolidine-4-
one and 1,3,4oxadiazole derivatives of
tolfenamic acid. Teikyo Med J. 2022;45(2):5017–
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