Research Article
Green Production of Indolylquinones, Derivatives of Perezone,
and Related Molecules, Promising Antineoplastic Compounds
René Gerardo Escobedo-González,
1
Héctor Pérez Martínez,
1
Ma. Inés Nicolás-Vázquez,
1
Joel Martínez,
2
Gabriela Gómez,
3
Juan Nava Serrano,
3
Vladimir Carranza Téllez,
4
C. L. Vargas-Requena,
5
and René Miranda Ruvalcaba
1
1
Departamento de Ciencias Qu´ ımicas, Facultad de Estudios Superiores Cuautitl´ an, Universidad Nacional Aut´ onoma de M´ exico,
54740 Cuautitl´ an Izcalli, MEX, Mexico
2
Facultad de Ciencias Qu´ ımicas, Posgrado en Ciencias en Ingenier´ ıa Qu´ ımica, Universidad Aut´ onoma de San Luis Potos´ ı,
78210 San Luis Potos´ ı, SLP, Mexico
3
Escuela Nacional de Ciencias Biol´ ogicas, Instituto Polit´ ecnico Nacional, Casco de Santo Tomas, 11340 Ciudad de M´ exico,
CDMX, Mexico
4
Laboratorio de Espectrometr´ ıa de Masas, Centro de Qu´ ımica, ICUAP, Benem´ erita Universidad Aut´ onoma de Puebla,
72570 Puebla, PUE, Mexico
5
Laboratorio de Biotecnolog´ ıa, Instituto de Ciencias Biom´ edicas, Universidad Aut´ onoma de Ciudad Ju´ arez,
Anillo Envolvente del Pronaf S/N, 32315 Ciudad Ju´ arez, CHIH, Mexico
Correspondence should be addressed to Ren´ e Miranda Ruvalcaba; mirruv@yahoo.com.mx
Received 4 May 2016; Accepted 14 June 2016
Academic Editor: Siva S. Panda
Copyright © 2016 Ren´ e Gerardo Escobedo-Gonz´ alez et al. Tis 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.
A green approach to produce the indolyl derivatives from four natural quinones (perezone, isoperezone, menadione, and
plumbagin) was performed; in this regard, a comparative study was accomplished among the typical mantle heating and three
nonconventional activating modes of reaction (microwave, near-infrared, and high speed ball milling or tribochemical), under
solventless conditions and using bentonitic clay as a catalyst. In addition, the tribochemical production of isoperezone from
perezone is also commented on. It is also worth noting that the cytotoxicity of the synthesized indolylquinones in human breast
cancer cell was tested by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay, with the 3-indolylisoperezone being
the most active. Te structural attribution of the target molecules was performed by typical spectroscopic procedures; moreover,
the experimental and computed
1
H and
13
C NMR chemical shifs data, with previous acquisition of the corresponding minimum
energetic structures, were in good agreement.
1. Introduction
Green Chemistry, with a protocol of a cohesive set of twelve
principles [1], is an actual discipline that encourages working
at the molecular level, in order to achieve sustainability; since
the early 1990s, this paradigm has acquired its up-to-date
position as a scientifc discipline, preventing pollution via the
implementation of reactions without damaging conditions to
the environment [2]. Under such a protocol, an ideal syn-
thesis would be that by which a target molecule is produced
quantitatively in one step from available and inexpensive
starting compounds in an ecologically sustainable process;
hence, the request of novel sustainable processes is among
the major challenges in organic synthesis. In this regard,
researchers at the vanguard of innovation must have the
knowledge to design chemicals processes with little or no risk
to the environment. However, no activity can be completely
risk-free or waste-free or have lower harmful emissions.
Consequently, the “Twelve Principles of Green Chemistry”
should be viewed and applied as a scientifc refection [3].
Many quinones are secondary metabolites generally
isolated from plants [4]. In particular, perezone or
Hindawi Publishing Corporation
Journal of Chemistry
Volume 2016, Article ID 3870529, 10 pages
http://dx.doi.org/10.1155/2016/3870529