We report a convenient and efficient synthesis of indeno[1,2-c]pyrazol-4(1H)-ones (4a‒o) by the reaction of a variety of 2-acyl-(1H)-indene-1,3(2H)-diones (1) and 2-hydrazinylbenzo[d]thiazole/2-hydrazinyl-6-substitutedbenzo[d]thiazoles (2) in the presence of glacial acetic acid in good yields. The structure of the compounds thus prepared were confirmed by analytical and spectral (FT-IR, ¹H NMR, ¹³C NMR, and HRMS) techniques. All the synthesized indeno[1,2-c]pyrazol-4(1H)-ones (4a‒o) were assayed for their in vitro Type II diabetes inhibitory activity by using Acarbose as standard drug and in vitro antimicrobial activity utilizing Streptomycin and Fluconazole as reference drugs. Among the synthesized derivatives, 4e (IC₅₀ = 6.71 μg/mL) was found to be more potent against α-glucosidase enzyme as compared with the standard Acarbose (IC₅₀ = 9.35 μg/mL) and 4i (IC₅₀ = 11.90 μg/mL) exhibited good inhibitory activity against α-amylase enzyme as compared with the standard Acarbose (IC₅₀ = 22.87 μg/mL). Also, all the titled compounds showed good antimicrobial activity. In addition, in vitro α-glucosidase and α-amylase inhibition were supported by docking studies performed on the derivatives 4e and 4o, respectively.

中文翻译：

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茚并[1,2-c]吡唑-4（1 H）-ones的合成，II型糖尿病抑制活性，抗菌评价和对接研究

我们报告了通过各种2-酰基-（1 H）-茚-1的反应，方便高效地合成茚并[1,2 - c ]吡唑-4（1 H）-ones（4a‒o），在冰乙酸存在下，以高收率得到3（2 H）-二酮（1）和2-肼基苯并[ d ]噻唑/ 2-肼基-6-取代的苯并[ d ]噻唑（2）。通过分析和光谱（FT-IR，¹ H NMR，¹³ C NMR和HRMS）技术确认了由此制备的化合物的结构。所有合成的茚并[1,2 - c ]吡唑-4（1 H）-ones（4a‒o通过使用阿卡波糖（Acarbose）作为标准药物测定其体外II型糖尿病抑制活性，并以链霉素和氟康唑为参考药物测定其体外抗菌活性。在合成的衍生物中，发现4e（IC ₅₀  = 6.71μg/ mL）与标准阿卡波糖（IC ₅₀  = 9.35μg/ mL）和4i（IC ₅₀  = 11.90μg / mL）相比，对α-葡萄糖苷酶的抑制作用更强。与标准阿卡波糖（IC ₅₀  = 22.87μg/ mL）相比，mL）表现出对α-淀粉酶的良好抑制活性。同样，所有标题化合物均显示出良好的抗菌活性。此外，体外α-葡萄糖苷酶和分别对衍生物4e和4o进行的对接研究支持了α-淀粉酶的抑制作用。