Herein, we report an efficient and eco-friendly, ultrasound assisted synthetic strategy for the construction of diversified pyrrolobenzodiazepine-triazole hybrids, which are potentially pharmaceutically important scaffolds, via a domino reaction involving intermolecular electrophilic substitution followed by intramolecular Huisgen 1,3-dipolar azide-alkyne cycloaddition. The USP of the reported protocol is the use of benign and inexpensive, recyclable molecular iodine-ionic liquid synergistic catalytic system cum reaction media for achieving the synthesis. The other salient features of this method are the use of mild reaction conditions, high yield and atom economy, operational simplicity, broad substrate scope and easy workup and purification. All the synthesized compounds were evaluated for in vitro anti-proliferative activity against various cancer cell lines. From among the synthesized title compounds, 9,9-dimethyl-8-phenyl-9H-benzo [b]pyrrolo [1,2-d][1,2,3]triazolo[5,1-g][1,4]diazepine (7) was found most to be the most active compound exhibiting IC50 value of 6.60, 5.45, 7.85, 11.21, 12.24, 10.12, and 11.32 µM against MCF-7, MDA-MB-231, HeLa, SKOV-3, A549, HCT-116 and DLD-1 cell lines, respectively. Further the compounds were found to be non-toxic against normal human embryonic kidney (HEK-293) cell line.

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An ultrasound assisted, ionic liquid-molecular iodine synergy driven efficient green synthesis of pyrrolobenzodiazepine-triazole hybrids as potential anticancer agents

The first electrochemical molecular iodine promoted, domino reactions for the green synthesis of biologically relevant dicyano 2-(2-oxoindolin-3-ylidene) malononitriles (11 examples, up to 94% yield) from readily available isatin derivatives, malononitrile, and iodine at room temperature have been presented. This synthesis method showed tolerance towards various EDG and EWG and was completed in a short reaction time at the constant low current density of 5 mA cm−2 in the low redox potential range of −0.14 to 0.07 V. The present study exhibited by-product-free formation, easy operation, and product isolation. In particular the formation of a C 
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 C bond was observed at room temperature with a high atom economy. Furthermore, in the present study, the electrochemical behavior of dicyano 2-(2-oxoindolin-3-ylidene) malononitrile derivatives using a cyclic voltammetry (CV) technique in 0.1 M NaClO4 in acetonitrile solution was studied. All the chosen substituted isatin exhibited well-defined diffusion-controlled quasi-reversible redox peaks except 5-substituted derivatives. This synthesis could serve as an alternative strategy to synthesize other biologically important oxoindolin-3-ylidene malononitrile derivatives.

https://pubs.rsc.org/en/content/articlepdf/2023/ra/d3ra02152a

Yin Cao

Papers

A Review on Molecular Iodine Catalyzed/Mediated Multicomponent Reactions