Research Article
Microwave-Assisted Synthesis and Antimicrobial
Activity of Some Novel Isatin Schiff Bases Linked to
Nicotinic Acid via Certain Amino Acid Bridge
Ahmed M. Naglah,
1,2
Hassan M. Awad,
3
Mashooq A. Bhat,
4
Mohamed A. Al-Omar,
1
and Abd El-Galil E. Amr
1,5
1
Department of Pharmaceutical Chemistry, Drug Exploration & Development Chair, College of Pharmacy,
King Saud University, Riyadh 11451, Saudi Arabia
2
Peptide Chemistry Department, Chemical Industries Research Division, National Research Centre, Dokki, Cairo 12622, Egypt
3
Chemistry of Natural and Microbial Products Department, Pharmaceutical Industries Division, National Research Centre,
Dokki, Cairo 12622, Egypt
4
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia
5
Applied Organic Chemistry Department, National Research Centre, Dokki, Cairo 12622, Egypt
Correspondence should be addressed to Ahmed M. Naglah; amnaglah@gmail.com
Received 1 October 2014; Revised 30 November 2014; Accepted 21 December 2014
Academic Editor: Rabah Boukherroub
Copyright © 2015 Ahmed M. Naglah 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.
Te coupling reaction of nicotinic acid with certain L-amino acid methyl esters including valine, leucine, and phenylalanine was
done by the use of acid chloride method. Te products were reacted with hydrazine hydrate 99% to give the corresponding
hydrazides that were reacted with indoline-2,3-dione (isatin) to get Schif bases under the application of microwave irradiation
technique. Tese novel compounds were characterized by means of their FT-IR,
1
H NMR, and mass spectral data. Additionally, the
specifc optical rotation and elemental analysis were measured. Te in vitro antimicrobial activity of the synthesized compounds was
evaluated by agar difusion method. Te compounds showed a strong antimicrobial inhibitory activity. Most of the test compounds
possessed a broad spectrum of activities having MIC values ranging from 50 g/mL to 500 g/mL.
1. Introduction
Nicotinic acid (pyridine-3-carboxylic acid), also known as
niacin and vitamin B3, is found in various plants and
animals; also, it has vital roles in such biological processes as
production of energy [1]. Nicotinic acid derivatives and its
isomers have antibacterial, antioxidant, anti-infammatory,
anticarcinogenic, and antitubercular activities [2], signal
transduction, regulation of gene expression [3], and involve-
ment in the synthetic pathway of lipids [4]. On the other
hand, some of new heterocyclic and peptide derivatives have
been studied with respect to antivirus [5], anti-infammatory
[6], enzymatic peptide [7], and antimicrobial activities [8, 9].
Also, there are several successful publications of microwave-
assisted solid phase peptide synthesis of various unnatural
biopolymers such as peptoids, pseudopeptides, small pep-
tides [10], phosphopeptides [11], difcult peptides [12], -
peptide libraries [13], and glycopeptides [14].
It is as well known that isatin is an endogenous compound
identifed in humans and that its biological properties include
a range of actions in the brain; it ofers protection against
certain types of infections [15]. Isatin constitutes an important
class of bioactive compounds exhibiting caspase inhibitor
[16, 17], antiproliferative [18], and antibacterial activities [19].
Furthermore, novel inhibitors of mycobacterium tubercu-
losis, prepared from indoline-2,3-dione (isatin) derivatives
by the use of microwave irradiation technique, have been
reported [20].
Due to the importance of nicotinic acid derivatives,
amino acids, peptides, and isatin as bioactive compounds and
Hindawi Publishing Corporation
Journal of Chemistry
Volume 2015, Article ID 364841, 8 pages
http://dx.doi.org/10.1155/2015/364841