© 2017 Asmaa M. Fahim. This open access article is distributed under a Creative Commons Attribution (CC-BY)
3.0 license.
OnLine Journal of Biological Sciences
Original Research Paper
Microwave Assisted Regioselective Synthesis and Biological
Evaluation of Pyrano[2,3-c]Pyridine Derivatives Utilizing
DMAP as a Catalyst
Asmaa M. Fahim
Department of Green Chemistry, National Research Center, Dokki, P.O. Box.12622 Cairo, Egypt
Article history
Received: 02-10-2017
Revised: 06-12-2017
Accepted: 14-12-2017
E-mail: asmaamahmoud8521@hotmail.com
asmaamahmoud8521@gmail.com
Abstract: Regioselective facile production of pyrano[2,3-c]pyridine
through multicomponent reaction of aromatic aldehydes, ethyl cyano
acetate or malononitrile and C-H activated compound of 3-hydroxy
picolinic acid in the occurrence of smaller amount of DMAP catalyst
utilizing microwave apparatus, which is green and simple environmentally
with high yield, recyclability catalyst. Totally the products were partitioned
for antimicrobiogical action; it was detected that were active in contrast to
S. pneumonia, E. coli and Candida albicans such as equated to typical
drugs. Compounds of pyrano[2,3-c]pyridine-8-carboxylic acid derivatives
4i, 4e, 4p and 4p demonstrated effective development inhibitory activities.
Additionally, the manufactured products were partitioned for in vitro-
antioxidant action by DPPH analysis. Products of pyrano[2,3-c]pyridine 4o
and 4p were worthy free radical scavenging action through IC
50
values of
252.52 and 223.2 µM; respectively.
Keywords: Multicomponent Reactions (MCR), 4-Dimethylaminopyridine
(DMAP), Pyrano[2,3-c]Pyridine, Antimicrobial and Antioxidant Activity
Introduction
Multicomponent Reactions (MCR) have attempted
extensive thought in combinatorial and biological
chemistry (Thomas, 2017; Zhu, 2003; Zhu and Bienayme,
2005; Dömling, 2006; Dömling and Ugi, 2000). We
established successfully numerous catalytic agent in organic
synthesis exhausting MCR approach (Karnakar et al.,
2015). The catalyst attractiveness is decrease of solvents
ratios (Khan et al., 2008; 2010a; Khan 2010b and Khan,
2011) and furthermore performance role in the yield of the
product. This would be inexpensive, mild and
environmentally friendly for attention to the synthetic
organic researcher. Dimethyl Amino Pyridine (DMAP) is
a catalyst of outstanding effectiveness in a variation
group-transfer reactions and considered for applications in
stereo selective catalysis (Armand et al., 2014).
Pyrane and fused 4H-pyrane derivatives have
concerned of interest (Dean, 1963) outstanding to their
varied physiological activities. (Feuer, 1974) Earlier
studies have presented that pyran derivatives possess
pronounced chemical and biological activities, such
antimicrobial activity, (Bonsignore et al., 1993; Ashraf,
2012) anti-coagulant, (Akbar et al., 2015; Dinesh et al.,
2017) anti-tumor and anti-HIV. Additionally, their besides
valuable for the neurodegenerative disorder behavior, for
instance Alzheimer, lateral amyotrophic sclerosis,
Huntington's and Parkinson diseases (Fan et al., 2010)
Moreover, they are similarly used as cosmetics, (Vyas
et al., 2009) pigments, doze and useful as
photoactive fabric (Nandakumar et al., 2010). In
recent times, a limited approaches have been informed by
hiring three-constituent responses exhausting different
catalyst like as DBU (1,8-Diazabicyclo[5.4.0]undec-7-
ene) (Wen et al., 2001), TBAB(Tetra-n-butylammonium
bromide) (Yusuke et al., 2016), ammonium phosphate
(Saeed et al., 2015; 2007; Jitender and Ankita, 2012)
hetero-poly supermans (Brahmachari et al., 2014).
However, these procedures informed through, others are
relatively beneficial, stable, there is auxiliary opportunity
to improve innovative approach exhausting inexpensive
catalyst above mild reaction stipulation and appropriate to
a widespread variety of substrates.
Materials and Methods
General Instruments
Gallenkamp melting point apparatus were used for
measuring the melting points. Furthermore the instrument