Table of Contents Author Guidelines Submit a Manuscript
Journal of Chemistry
Volume 2013, Article ID 531208, 9 pages
http://dx.doi.org/10.1155/2013/531208
Research Article

A Green Approach to the Production of Hybrid Diindolylmethane-Phenylboronic Acids via a 3MCR: Promising Antineoplasic Molecules

1Departamento de Química, Facultad de Estudios Superiores Cuautitlán-Campus 1, Universidad Nacional Autónoma de México, Cuautitlán Izcalli, Estado de México, 54740 México DF, Mexico
2Instituto de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, Coyoacán, 04510 México DF, Mexico

Received 8 March 2013; Revised 13 June 2013; Accepted 24 June 2013

Academic Editor: Sedat Yaşar

Copyright © 2013 Mónica Zarco Juarez et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

The current role of the “Green Chemistry Protocol” in multicomponent reactions is first highlighted. Then, the green approach to the production of three novel hybrid diindolylmethanes-phenylboronic acids via a 3MCR is discussed, which features the following: solventless conditions, the use of microwave irradiation to activate the reactions, the absence of catalyst, and an efficient atom economy. The products were achieved with moderate yields (41–61%) within a short time frame (5 min) and appropriately characterized by elemental analysis and spectroscopic methods (NMR: 1H, 13C, 11B; MS: EI, CI, FAB+, HRMS). During the FAB+ MS determinations, various artifacts that are associated with the boron atom via an interaction with thioglycerol from the matrix were noted in the corresponding FAB+ mass spectra; in addition, the accurate mass determination of these adducts unequivocally confirmed the presence of the target molecules. Moreover, the activity of these target molecules was evaluated in the presence of six cancer cell lines (U251 = glia of the central nerve system, PC-3 = prostate, K562 = leukemia, HCT-15 = colon, MCF-7 = breast, and SKLU-1 = lung), which resulted in the meta-regioisomer being the most active. Finally, the products were also analyzed using computational chemistry in order to determine their most stable geometries and reactivities by computing the respective molecular electrostatic potentials.