In this study, synthesis of novel isoindole-1,3-dione analogues bearig halo, hydroxy, and acetoxy groups at the position 4,5,6 of the bicyclic imide ring was performed to examine their potential anticancer effects against some cell lines. A multistep chemical pathway was used to synthesize the derivatives. The cytotoxic effect of trisubstituted isoindole derivatives were evaluated by determining cellular viability using the MTT assay against A549, PC-3, HeLa, Caco-2, and MCF-7 cell lines. The C-2 selective ring-opening products were obtained from the ring-opening reaction of 5-alkyl/aryl-2-hydroxyhexahydro-4H-oxireno[2,3-e]isoindole-4,6(5H)-diones with nucleophiles such as chloride (Cl⁻) and bromide (Br⁻) ions. In addition, the ring-opening products halodiols were converted to their related acetates. The anticancer activity of synthesized isoindole-1,3-dione derivatives was investigated against HeLa, A549, MCF-7, PC3, and Caco-2 cells in vitro and resulted in varies cytotoxic effect depend on the group attached to the isoindole molecule. Furthermore, the evaluation of the antimicrobial action of trisubstituted isoindole derivatives against Gram-positive (Staphylococcus aureus) and Gram-negative (Escherichia coli) bacteria was assessed and found out selective inhibition of the both bacterial growth via different trisubstituted isoindole derivatives. The results of this work encourage further research on the potential utilization of trisubstituted isoindole derivatives as cytotoxic and antimicrobial agents.

中文翻译：

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2,4,5,6-取代六氢-1H-异吲哚-1,3(2H)-二酮的合成、细胞毒性和抗菌研究

在这项研究中，合成了在双环酰亚胺环的4、5、6位上带有卤素、羟基和乙酰氧基的新型异吲哚-1,3-二酮类似物，以检查它们对某些细胞系的潜在抗癌作用。使用多步化学途径来合成衍生物。通过使用 MTT 测定针对 A549、PC-3、HeLa、Caco-2 和 MCF-7 细胞系的细胞活力来评估三取代异吲哚衍生物的细胞毒性作用。C-2选择性开环产物是由5-烷基/芳基-2-羟基六氢-4H-氧杂并[ 2,3-e]异吲哚-4,6(5H ) -二酮的开环反应得到与亲核试剂如氯离子 (Cl ^- ) 和溴离子 (Br ^- ) 发生反应。此外，开环产物卤代二醇被转化为其相关的乙酸酯。在体外研究了合成的异吲哚-1,3-二酮衍生物对 HeLa、A549、MCF-7、PC3 和 Caco-2 细胞的抗癌活性，并根据异吲哚分子上附着的基团产生不同的细胞毒性作用。此外，还评估了三取代异吲哚衍生物对革兰氏阳性菌（金黄色葡萄球菌）和革兰氏阴性菌（大肠杆菌）的抗菌作用，发现不同的三取代异吲哚衍生物对这两种细菌的​​生长具有选择性抑制作用。这项工作的结果鼓励进一步研究三取代异吲哚衍生物作为细胞毒性剂和抗菌剂的潜在用途。