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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
Chemical Biology & Drug Design ( IF 3.2 ) Pub Date : 2018-12-03 , DOI: 10.1111/cbdd.13352 Rabia Qamar 1 , Aamer Saeed 1 , Fayaz Ali Larik 1 , Qamar Abbas 2 , Mubashir Hassan 3 , Hussain Raza 3 , Sung-Yum Seo 3
Chemical Biology & Drug Design ( IF 3.2 ) Pub Date : 2018-12-03 , DOI: 10.1111/cbdd.13352 Rabia Qamar 1 , Aamer Saeed 1 , Fayaz Ali Larik 1 , Qamar Abbas 2 , Mubashir Hassan 3 , Hussain Raza 3 , Sung-Yum Seo 3
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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.
中文翻译：
新型1,3-恶嗪-四唑杂化物作为蘑菇酪氨酸酶抑制剂和自由基清除剂：合成，动力学机理和分子对接研究
已合成了多种5-（2 H-四唑-5-基）-4-硫代氧-2-（取代的苯基）-4,5-二氢-1,3-恶嗪-6-6（3a-k）由1,3-恶嗪-5-腈（2a–k）该协议代表了一种有效，便捷，新颖的途径，从易于获得的前体到前所未有的结构，这些结构共享具有最大价值的1,3-恶嗪和四唑基序。评价所有合成的化合物（3a–k）对蘑菇酪氨酸酶的抑制潜力。结果表明，所有检测的1,3-恶嗪-四唑杂种均表现出显着的酪氨酸酶抑制活性，而具有2-溴苯基部分的化合物3d在具有IC 50的系列中最有效与参比曲酸（IC 50 = 16.832±0.73μM）相比，其值为0.0371± 0.0018μM。抑制动力学表明，化合物3d表现为竞争性抑制剂。针对靶蛋白进行了分子对接分析以研究结合模式。此外，化合物3j和3k显示出比其他类似物优异的DPPH自由基清除活性。
更新日期：2018-12-03
中文翻译：
新型1,3-恶嗪-四唑杂化物作为蘑菇酪氨酸酶抑制剂和自由基清除剂：合成，动力学机理和分子对接研究
已合成了多种5-（2 H-四唑-5-基）-4-硫代氧-2-（取代的苯基）-4,5-二氢-1,3-恶嗪-6-6（3a-k）由1,3-恶嗪-5-腈（2a–k）该协议代表了一种有效，便捷，新颖的途径，从易于获得的前体到前所未有的结构，这些结构共享具有最大价值的1,3-恶嗪和四唑基序。评价所有合成的化合物（3a–k）对蘑菇酪氨酸酶的抑制潜力。结果表明，所有检测的1,3-恶嗪-四唑杂种均表现出显着的酪氨酸酶抑制活性，而具有2-溴苯基部分的化合物3d在具有IC 50的系列中最有效与参比曲酸（IC 50 = 16.832±0.73μM）相比，其值为0.0371± 0.0018μM。抑制动力学表明，化合物3d表现为竞争性抑制剂。针对靶蛋白进行了分子对接分析以研究结合模式。此外，化合物3j和3k显示出比其他类似物优异的DPPH自由基清除活性。
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