Res Chem Intermed
https://doi.org/10.1007/s11164-018-3311-6
1 3
Synthesis, antileishmanial and cytotoxicity activities
of fused and nonfused tetrahydroquinoline derivatives
Hassan Mohamed Fawzy Madkour
1
·
Maher Abd El‑Aziz Mahmoud El‑Hashash
1
· Marwa Sayed Salem
1
·
Al‑Shimaa Omar Ali Mahmoud
1
Received: 23 December 2017 / Accepted: 23 January 2018
© Springer Science+Business Media B.V., part of Springer Nature 2018
Abstract Developing novel antileishmanial, and cytotoxic drugs has been a sig-
nifcant area in modern pharmaceutical research. A series of novel triazolo[4,3-a]
quinoline, triazino[4,3-a]quinoline, thiadiazepino[5,6-b]quinoline and pyrazolqui-
noline have been synthesized from the reaction of 2-hydrazinyltetrahydroquinoline-
3-carbonitrile with formamide, formic acid, ethyl chloroacetate, carbon disulphide
in an alcoholic solution of potassium hydroxide acetyl acetone and/or ethyl cyanoac-
etate, respectively. These compounds were evaluated for their in vitro studies against
L. major leishmanial. The brine shrimp bioassay was also conducted to study their
in vitro cytotoxic properties which displayed potent cytotoxic activity against Vin-
cristine. The newly synthesized compounds were all characterized through IR,
1
H-
NMR, and MS.
Keywords Tetrahydroquinolines · Triazolo[4,3-a]quinoline · Triazino[4,3-a]
quinoline · Thiadiazepino[5,6-b]quinoline · Antileishmanial · Cytotoxicity
Introduction
Tetrahydroquinolines are one of the important structural subunits of various natu-
rally occurring compounds and numerous recent reports have proved that com-
pounds containing the tetrahydroquinoline moiety elicit potent biological responses
leading to anti-infammatory [1], antinephritic [2], treatment of Alzheimer’s disease
[3], antitumor [4, 5] and antiallergenic [6] activities. In addition, many tetrahydro-
quinoline derivatives appeared as anti-HIV [7, 8], antimalarial [9, 10] cholesteryl
* Marwa Sayed Salem
marwa_k@sci.asu.edu.eg
1
Synthetic Organic Chemistry Laboratory, Chemistry Department, Faculty of Science, Ain
Shams University, Abbassia, Cairo 11566, Egypt