Aims:: Synthesis of novel 4-bromobenzoic acid-based hydrazone-Schiff base derivatives and to screen them for their α-amylase inhibitory activity. Objective:: The biological activities of hydrazone-Schiff base compounds encouraged us to evaluate the synthesized derivatives (4-32) for in-vitro inhibition activity against the α-amylase enzyme. Methods:: In current research work twenty-nine Schiff base derivatives (4-32) of 4-bromobenzoic acid were synthesized in worthy yields by treating various replaced aldehydes with 4- bromobenzohydrazide using methanol solvent in catalytic quantity of acetic acid. The products were structurally described through the support of several spectroscopic methods (EI-MS and 1HNMR) and finally evaluated against α-amylase enzyme. Results:: All the made derivatives exhibited worthy inhibition potential from IC50 = 0.21 ± 0.01 to 5.50 ± 0.01 μM when equated to the usual acarbose drug having IC50 = 1.34 ± 0.01 μM. Compound 21 (IC50 = 0.21 ± 0.01 μM) was established as the most active inhibitor among the series better than standard. The structure-activity relationship study showed that the alteration in the activity of the produced products might be due to the attached position and nature of the substituents. Furthermore, in-silico study supported the effects of groups attached on the binding interaction with α-amylase enzyme. Conclusion:: A series of substituted hydrazone Schiff bases based on 4-bromobenzoic acid were produced, confirmed the structures by EI-MS and 1H-NMR spectroscopic methods and lastly tested for their in-vitro α-amylase inhibitory potential. Among the series, twenty-four products indicated brilliant inhibition potential having IC50 values from 0.21 ± 0.01 to 1.30 ± 0.01 μM. The structure-activity relationship study showed that the alteration in the activity of the synthesized products might be due to the attached position and nature of the substituents. On the other hand, in silico studies advocated that the synthesized Schiff base derivatives have prevalent interactions of binding within the active site of the α-amylase enzyme, and because of their various attached substituent, their conformation is altered in the active site of the enzyme. The current study recognized a number of lead candidates derived from 4-bromobenzoic acid. Additional investigation of the synthesized derivatives for coming research to get novel α-amylase inhibitors.

中文翻译：

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一些新型 4-溴苯甲酸棒状腙席夫碱衍生物作为有效 α-淀粉酶抑制剂的合成：体外和计算机研究

目的：合成新型 4-溴苯甲酸基腙-席夫碱衍生物并筛选其 α-淀粉酶抑制活性。目的:: 腙-希夫碱化合物的生物活性促使我们评估合成的衍生物 (4-32) 对 α-淀粉酶的体外抑制活性。方法:: 在目前的研究工作中，通过在催化量的乙酸中使用甲醇溶剂用4-溴苯甲酰肼处理各种取代的醛，以有价值的产率合成了29种4-溴苯甲酸的席夫碱衍生物(4-32)。通过多种光谱方法（EI-MS 和 1HNMR）的支持对产品进行结构描述，并最终针对 α-淀粉酶进行评估。结果:: 当相当于通常的阿卡波糖药物的 IC50 = 1.34 ± 0.01 μM 时，所有制备的衍生物都表现出有价值的抑制潜力，从 IC50 = 0.21 ± 0.01 到 5.50 ± 0.01 μM。化合物 21 (IC50 = 0.21 ± 0.01 μM) 被确定为该系列中活性最强的抑制剂，优于标准品。构效关系研究表明，所产生的产物活性的改变可能是由于取代基的连接位置和性质造成的。此外，计算机模拟研究支持了附着基团对与 α-淀粉酶结合相互作用的影响。结论：制备了一系列基于4-溴苯甲酸的取代腙席夫碱，通过EI-MS和1H-NMR光谱方法确认了其结构，最后测试了其体外α-淀粉酶抑制潜力。在该系列中，24 种产品表现出出色的抑制潜力，IC50 值范围为 0.21 ± 0.01 至 1.30 ± 0.01 μM。构效关系研究表明，合成产物活性的改变可能是由于取代基的连接位置和性质造成的。另一方面，计算机研究表明，合成的席夫碱衍生物在α-淀粉酶的活性位点内具有普遍的结合相互作用，并且由于它们具有各种附着的取代基，它们的构象在酶的活性位点发生改变。目前的研究发现了许多源自 4-溴苯甲酸的主要候选物。对合成衍生物进行进一步研究，以用于后续研究以获得新型 α-淀粉酶抑制剂。