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Synthesis, biological evaluation and docking studies of some novel isatin-3-hydrazonothiazolines

机译：一些新型Isatin-3-肼噻唑啉的合成，生物学评估和对接研究

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A new series of thirty nine 5-trifluoromethoxy/fluoro/chloro-isatin 3-hydrazonothiazolines 5a-n, 6a-o and 7a-j were synthesized by cyclization of the corresponding intermediate N-4-aryl-substituted isatin-3-thiosemicarbazones 3 (prepared by condensation of appropriate isatin 1 with appropriate N-4-aryl-substituted 3-thiosemicarbazides 2) with 4-chlorophenacyl bromide 4 in absolute ethanol or ethanolbenzene mixture and screened for their cytotoxicity, phytotoxicity, antifungal and urease inhibitory potential. All the synthesized compounds were found to be almost inactive in a brine shrimp (Artemia salina) bioassay, demonstrating IC50 values > 1.62 x 10(-4) to 2.17 x 10(-4) M. In a phytotoxicity assay, out of thirty-nine compounds tested, six i.e. 5i, 6h, 6i, 6k, 7c and 7h proved to be active, showing weak or non-significant (5-30%) activity at the highest tested concentration (500 mu g mL(-1)). Similarly, in antifungal assay, twenty-six compounds i.e. 5a, 5b, 5d-f, 5h-j, 5m, 6a, 6b, 6d, 6j, 6l-o, 7a, 7b and 7d-j were found to be active against one, two, or three selected fungal strains, exhibiting weak or non-significant inhibition (10-30%). Of these, 6d and 6o displayed a relatively better activity profile in terms of the number of organisms inhibited. On the other hand, in a urease inhibition bioassay, all the synthesized hydrazonothiazolines proved to be potent enzyme inhibitors, demonstrating inhibitory activity with IC50 values ranging from 3.70 +/- 0.62 to 849 +/- 2.26 mu M. Compounds 5c, 5g-i, 5k, 5n, 6b, 6c, 6i, 6k, 6l, 6n, 6o, 7a, 7e, 7i and 7j were, however, found to be relatively very potent, displaying outstanding enzymatic activity (IC50 = 3.70 +/- 0.62 to 20.9 +/- 0.57 mu M), even better than the reference inhibitor thiourea (IC50 = 22.3 +/- 1.12 mu M), and may thus act as valid leads for further studies. Molecular docking studies of the synthesized isatin-thiazolines 5a-n, 6a-o and 7a-j were also carried out to elucidate their relationship with the binding pockets of the enzyme. This study offers the first example of exhibition of urease inhibitory potential by isatin-thiazolines and as such provides a solid basis for further research on these compounds to develop more potent antiurease compounds of medicinal/agricultural interest.
机译：通过相应中间体N-4-芳基取代的Isatin-3-Thiosimerbazones 3，通过环化合成了新的三十九个5-三氟甲氧基/氟/氯含量5a-ind10氢噻唑啉5a-n，6a-o和7a-j （通过用适当的N-4-芳基取代的3-硫代吡啶脱硫4）用绝对乙醇或乙醇苯并混合物用4-氯苯基溴4-硫化物缩合，并筛选它们的细胞毒性，植物毒性，抗真菌和释放释放尿素抑制潜力。发现所有合成的化合物在盐水虾（Artemia Salina）生物测定中几乎无活性，将IC50值> 1.62×10（-4）〜2.17×10（-4）米。在植物毒性测定中，从三十 - 经过九个化合物，六即5i，6h，6i，6k，7c和7h被证明是活性的，在最高测试浓度（500μmgml（-1））下显示弱或非显着（5-30％）活性。同样地，在抗真菌测定中，发现二十六种化合物，即5A，5B，5D-F，5H-J，5M，6A，6B，6D，6J，6L-O，7A，7B和7D-J是活性的一种，两种或三种选定的真菌菌株，表现出弱或不显着的抑制（10-30％）。其中，6D和6o在抑制的生物体的数量方面显示了相对更好的活动概况。另一方面，在脲酶抑制生物测定中，所有合成的肼噻唑嗪被证明是有效的酶抑制剂，证明IC50值的抑制活性范围为3.70 +/- 0.62至849 +/- 2.26 mu M.化合物5c，5g-1然而，5K，5N，6B，6C，6I，6K，6L，6N，60，7A，7E，7I和7J发现是相对非常有效的，显示出优异的酶活性（IC50 = 3.70 +/- 0.62 20.9 +/- 0.57 mu m），甚至比参考抑制剂硫脲（IC50 = 22.3 +/- 1.12 mu m）更好，因此可以作为进一步研究的有效铅。还进行了合成的Isatin-噻唑啉5A-N，6A-O和7A-J的分子对接研究，以阐明它们与酶的结合口袋的关系。本研究提供了由Isatin-噻唑啉的释放释放潜力展览的第一个例子，并为进一步研究这些化合物提供了坚实的基础，以产生更多有效的药/农业利益化合物。

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  • 来源
    《RSC Advances》 |2016年第65期|共19页
  • 作者

    Ahmad Maqbool; Pervez Humayun; Zaib Sumera; Yaqub Muhammad; Naseer Muhammad Moazzam; Khan Shafi Ullah; Iqbal Jamshed;

  • 作者单位

    Bahauddin Zakariya Univ Div Organ Chem Inst Chem Sci Multan 60800 Pakistan;

    Bahauddin Zakariya Univ Div Organ Chem Inst Chem Sci Multan 60800 Pakistan;

    COMSATS Inst Informat Technol Ctr Adv Drug Res Abbottabad 22060 Pakistan;

    Bahauddin Zakariya Univ Div Organ Chem Inst Chem Sci Multan 60800 Pakistan;

    Quaid I Azam Univ Dept Chem Islamabad 45320 Pakistan;

    COMSATS Inst Informat Technol Ctr Adv Drug Res Abbottabad 22060 Pakistan;

    COMSATS Inst Informat Technol Ctr Adv Drug Res Abbottabad 22060 Pakistan;

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  • 正文语种 eng
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