International Journal of Organic Chemistry, 2015, 5, 37-47
Published Online March 2015 in SciRes. http://www.scirp.org/journal/ijoc
http://dx.doi.org/10.4236/ijoc.2015.51005
How to cite this paper: Mousa, B.A., Bayoumi, A.H., Korraa, M.M., Assy, M.G. and El-Kalyoubi, S.A. (2015) A Novel One-Pot
and Efficient Procedure for Synthesis of New Fused Uracil Derivatives for DNA Binding. International Journal of Organic
Chemistry, 5, 37-47. http://dx.doi.org/10.4236/ijoc.2015.51005
A Novel One-Pot and Efficient Procedure for
Synthesis of New Fused Uracil Derivatives
for DNA Binding
Bothaina A. Mousa
1
, Ashraf H. Bayoumi
2*
, Makarem M. Korraa
1
, Mohamed G. Assy
3
,
Samar A. El-Kalyoubi
4
1
Department of Organic Chemistry, Faculty of Pharmacy, Cairo University, Giza, Egypt
2
Department of Organic Chemistry, Faculty of Pharmacy (Boys), Al-Azhar University, Cairo, Egypt
3
Department of Organic Chemistry, Faculty of Science, Zagazig University, Zagazig, Egypt
4
Department of Organic Chemistry, Faculty of Pharmacy (Girls), Al-Azhar University, Cairo, Egypt
Email: s.elkalyoubi@hotmail.com
Received 22 December 2014; accepted 25 March 2015, published 27 March 2015
Copyright © 2015 by authors and Scientific Research Publishing Inc.
This work is licensed under the Creative Commons Attribution International License (CC BY).
http://creativecommons.org/licenses/by/4.0/
Abstract
Hydrazinolysis of 6-chloro-1-methyluracil followed by condensation of the product with different
aromatic aldehyde gives the respective hydrazones which undergoes oxidative cyclization using
thionyl chloride to obtain pyrazolo[3,4-d]pyrimidines in good yields. On the other hand, nitrosa-
tion of 6-aminouracils followed by the reaction with different arylidineanilines gives new xan-
thine derivatives. Finally, indenopyrrolopyrimidine and indenopteridine are obtained in good
yields via the reaction of 6-aminouracils and 5,6-diaminouracil with ninhydrin respectively. The
newly synthesized compounds show binding, chelation and fragmentation of the nucleic acid DNA.
Keywords
6-Chloro-1-methyluracil, Pyrazolo[3,4-d]pyrimidines, 6-Aminouracils, Xanthine,
Indenopyrrolopyrimidine and Indenopteridine
1. Introduction
The importance of fused pyrimidines, common source for the development of new potential therapeutic agents
[1] [2], is well known.
Fused pyrimidines continue to attract considerable attention because of their great practical usefulness, pri-
marily due to very wide spectrum of biological activities. This is evident especially from publications of regular