Synthesis Under Green Chemistry Context of Novel Molecules with Both Biginelli and Diindolylmethane Moieties

PENIERES CARRILLO, GUILLERMO; CEBALLOS NOELIA M.; ELIZABETH L. MOYANO; EUGENIA RAMIREZ GUIDO; JOSÉ VALDEZ ROJAS

ROSARIO

Workshop; 1st Argentinean Workshop in Environmental Science; 2009

A number of heterocyclic compounds containing Biginelli esters (3,4-dihydro-2(1H)-pyrimidones) are known to have important and interesting pharmacological activity, including calcium channel modulation, antiviral and antibacterial activity. The recent discovery of dihydropyrimidine biological activity has led to a renewed exploration of the reaction conditions, revealing a variety of compatible solvents, acid catalysts and an expanded substrate scope. In the same way, compounds containing diindolylalkane moiety that present anticancer activity are well-known. The simplest diindolyalkane (bis(indol-3-yl)methane), named DIM, has an important breast, prostate and cervical anticancer activity. Related to the above-mentioned, there is an on-going need for the development of new structures to assist in the drug discovery process. As a part of our program to develop simple and efficient methods, according with the Green Chemistry context, for the preparation of heterocyclic compounds with biological activity, we planned to synthesize novel compounds with both 3,4-dihydropyrimidin-2-one and diindolylmethane structural fragments (I) in order to later on they carry out studies of pharmacological activity. We would like to report herein the followed synthetic methodologies with the aim to obtain the title compounds, employing microwave, infrared or thermal energies, with or without the use of bentonitic clay as catalyst.