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

Abstract

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.

Ionic liquids for the green synthesis of 1,2,3-triazoles: a systematic review

“…Saquib and co-workers developed an eco-friendly synthetic stratagem for the synthesis of various pyrrolobenzodiazepine-fused 1,2,3-triazole hybrids ( 47a–47l ) via an intramolecular 1,3-dipolar cycloaddition reaction (Scheme 50). 128 This reaction involved use of inexpensive, benign, recyclable molecular iodine-IL, i.e. , iodine-[Bmim][BF 4 ], as a catalyst and reaction medium.…”

Dietary isothiocyanates and anticancer agents: exploring synergism for improved cancer management

“…Combinational therapy marks a significant advancement in cancer treatment and prevention by harnessing the synergistic effects of multiple therapeutic agents to boost efficacy, reduce side effects, and counteract drug resistance ( 65 ). The integration of dietary ITCs, especially SFN, with both conventional and non-conventional anticancer agents has paved new pathways for enhancing the effectiveness of cancer management.…”

Advances in the use of green and sustainable synthesis to obtain nanomaterials

“…• Safer Solvents and Auxiliaries: It is about substituting conventional organic solvents with other less dangerous/contaminants. Green nanomaterial synthesis usually can use aqueous plant extracts [18][19][20] and ionic liquids [21][22][23][24][25] for this substitution with more benefits to desired products.…”