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Novel 1,3-oxazine-tetrazole hybrids as mushroom tyrosinase inhibitors and free radical scavengers: Synthesis, kinetic mechanism, and molecular docking studies.
Chem Biol Drug Des. 2019 02; 93(2):123-131.CB

Abstract

A variety of 5-(2H-tetrazol-5-yl)-4-thioxo-2-(substituted phenyl)-4,5-dihydro-1,3-oxazin-6-ones (3a-k) have been synthesized from 1,3-oxazine-5-carbonitriles (2a-k). The protocol represents an efficient, facile, and novel route from easily available precursors to unprecedented structures that share 1,3-oxazine and tetrazole motifs of utmost value. All the synthesized compounds (3a-k) were evaluated for their inhibitory potential against mushroom tyrosinase. Results revealed that all examined 1,3-oxazine-tetrazole hybrids exhibited significant tyrosinase inhibitory activity while compound 3d having 2-bromophenyl moiety was the most potent among the series with IC50 value 0.0371 ± 0.0018 μM as compared to the reference kojic acid (IC50 = 16.832 ± 0.73 μM). Inhibitory kinetics showed that compound 3d behaves as a competitive inhibitor. The molecular docking analysis was performed against target protein to investigate the binding mode. Moreover, compounds 3j and 3k displayed superior DPPH radical scavenging activity than other analogues.

Authors+Show Affiliations

Department of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan.Department of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan.Department of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan.Department of Physiology, University of Sindh, Jamshoro, Pakistan.Department of Biological Sciences, College of Natural Sciences, Kongju National University, Chungnam, Korea.Department of Biological Sciences, College of Natural Sciences, Kongju National University, Chungnam, Korea.Department of Biological Sciences, College of Natural Sciences, Kongju National University, Chungnam, Korea.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

29923689

Citation

Qamar, Rabia, et al. "Novel 1,3-oxazine-tetrazole Hybrids as Mushroom Tyrosinase Inhibitors and Free Radical Scavengers: Synthesis, Kinetic Mechanism, and Molecular Docking Studies." Chemical Biology & Drug Design, vol. 93, no. 2, 2019, pp. 123-131.
Qamar R, Saeed A, Larik FA, et al. Novel 1,3-oxazine-tetrazole hybrids as mushroom tyrosinase inhibitors and free radical scavengers: Synthesis, kinetic mechanism, and molecular docking studies. Chem Biol Drug Des. 2019;93(2):123-131.
Qamar, R., Saeed, A., Larik, F. A., Abbas, Q., Hassan, M., Raza, H., & Seo, S. Y. (2019). Novel 1,3-oxazine-tetrazole hybrids as mushroom tyrosinase inhibitors and free radical scavengers: Synthesis, kinetic mechanism, and molecular docking studies. Chemical Biology & Drug Design, 93(2), 123-131. https://doi.org/10.1111/cbdd.13352
Qamar R, et al. Novel 1,3-oxazine-tetrazole Hybrids as Mushroom Tyrosinase Inhibitors and Free Radical Scavengers: Synthesis, Kinetic Mechanism, and Molecular Docking Studies. Chem Biol Drug Des. 2019;93(2):123-131. PubMed PMID: 29923689.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Novel 1,3-oxazine-tetrazole hybrids as mushroom tyrosinase inhibitors and free radical scavengers: Synthesis, kinetic mechanism, and molecular docking studies. AU - Qamar,Rabia, AU - Saeed,Aamer, AU - Larik,Fayaz Ali, AU - Abbas,Qamar, AU - Hassan,Mubashir, AU - Raza,Hussain, AU - Seo,Sung-Yum, Y1 - 2018/12/03/ PY - 2018/02/02/received PY - 2018/05/17/revised PY - 2018/06/04/accepted PY - 2018/6/21/pubmed PY - 2019/11/15/medline PY - 2018/6/21/entrez KW - 1,3-oxazine-tetrazole hybrids KW - antioxidant activity KW - kinetic studies KW - molecular docking KW - mushroom tyrosinase inhibitors KW - synthesis SP - 123 EP - 131 JF - Chemical biology & drug design JO - Chem Biol Drug Des VL - 93 IS - 2 N2 - A variety of 5-(2H-tetrazol-5-yl)-4-thioxo-2-(substituted phenyl)-4,5-dihydro-1,3-oxazin-6-ones (3a-k) have been synthesized from 1,3-oxazine-5-carbonitriles (2a-k). The protocol represents an efficient, facile, and novel route from easily available precursors to unprecedented structures that share 1,3-oxazine and tetrazole motifs of utmost value. All the synthesized compounds (3a-k) were evaluated for their inhibitory potential against mushroom tyrosinase. Results revealed that all examined 1,3-oxazine-tetrazole hybrids exhibited significant tyrosinase inhibitory activity while compound 3d having 2-bromophenyl moiety was the most potent among the series with IC50 value 0.0371 ± 0.0018 μM as compared to the reference kojic acid (IC50 = 16.832 ± 0.73 μM). Inhibitory kinetics showed that compound 3d behaves as a competitive inhibitor. The molecular docking analysis was performed against target protein to investigate the binding mode. Moreover, compounds 3j and 3k displayed superior DPPH radical scavenging activity than other analogues. SN - 1747-0285 UR - https://www.unboundmedicine.com/medline/citation/29923689/Novel_13_oxazine_tetrazole_hybrids_as_mushroom_tyrosinase_inhibitors_and_free_radical_scavengers:_Synthesis_kinetic_mechanism_and_molecular_docking_studies_ L2 - https://doi.org/10.1111/cbdd.13352 DB - PRIME DP - Unbound Medicine ER -