Increasing interests have been invested in the development of synthetic strategies toward the construction of spiro[pyrrolidine-2,3′-oxindole], which is the core structural skeleton in some compounds with diverse biological activities. In this work, an efficient diastereoselective 1,3-dipolar cycloaddition reaction of azomethine ylides generated in situ from 3-amino oxindoles and aldehydes with maleimides has been described. The protocol provides a facile and efficient access to structurally diverse succinimide-fused spiro[pyrrolidine-2,3′-oxindole] compounds in good to high yields (up to 93%) with moderate to excellent diastereoselectivities (up to >95:5). The relative stereochemistry of cycloaddition products has been assigned by X-ray diffraction analysis.Keywords:1,3-dipolar cycloaddition;azomethine ylide;one pot synthesis;maleimide;succinimide-fused spiro[pyrrolidine-2,3′-oxindole]
Jiqing Dong,Ran Ping,Xun Dai,Dongchao Wang,Fusheng Liu,Shanshan Du,Mengshuai Liu
The combination of pyrrolidine-2,5-dione-derived ionic liquids with silver acetate (AgOAc) were developed as binary catalysts for conversion of simulated flue gas CO 2 and propargylic alcohols to α-alkylidene cyclic carbonates . By tuning different catalyst components, the [HTMG][Pyrro]/AgOAc system was confirmed to be the most efficient and exhibited an excellent synergistic action in facilitating the carboxylic cyclization under room temperature and solvent-free conditions. The influence of reaction parameters on carboxylic cyclization of CO 2 with 2-methylbut-3-yn-2-ol were optimized. Under the determined conditions, the [HTMG][Pyrro]/AgOAc system was stable enough to show durable high activity in eight recycles, and also versatile in carboxylic cyclization of flue gas CO 2 with other propargylic alcohols. Moreover, a thorough comparison of [HTMG][Pyrro]/AgOAc with the reported catalysts was provided and evaluated, the results suggested that the developed catalytic system has significant advantages in practical application. Finally, the mechanistic details for the conversion of CO 2 into α-alkylidene cyclic carbonates catalyzed by [HTMG][Pyrro]/AgOAc was also elucidated on the basis of reactants activation.
We have synthesized Rhopaladins’ analog (2E,4E)-4-chlorobenzylidene-2-(4-chlorostyryl)-N-cyclohexyl-1-(4-fluorophenyl)-5-oxopyrrolidine-2-carboxamide (RPDPRH) via a highly facile, inexpensive and green approach and verified the structural superiority of compound RPDPRH through molecular docking. Moreover, we further detected the anti-proliferation, apoptosis and HPV E6/E7 effects of RPDPRH on CaSki cells. Finally, we confirmed that compared with the previous compound (E)-N-(tert-butyl)-2-(4-chlorobenzoyl)-4-(4-fluorobenzylidene)-1-isopropyl-5-oxopyrrolidine-2-carboxamide (RPDPB), RPDPRH could better inhibit proliferation, induce apoptosis, and down-regulate HPV E6/E7 mRNA expression on Caski cells. And preliminary RT-PCR experiments have demonstrated that RPDPRH also could affect the expression of Bcl-2, Bax and Caspase-3 mRNA in Caski cells. In summary, RPDPRH has potential as an effective agent against cervical cancer and will play an important role in our subsequent research.Keywords: 4-arylidene-5-oxopyrrolidine, green synthesis, molecular docking, anti-tumor activity, apoptosis
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