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Design, Synthesis, and In Vitro Antileishmanial and Antitumor Activities of New Tetrahydroquinolines
Author(s) -
Madkour Hassan Mohamed Fawzy,
ElHashash Maher Abd ElAziz Mahmoud,
Salem Marwa Sayed,
Mahmoud AlShimaa Omar Ali,
Al kahraman Yasser M. S. A.
Publication year - 2018
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3046
Subject(s) - chemistry , cytotoxicity , in vitro , stereochemistry , pyrazole , combinatorial chemistry , pharmacology , biochemistry , medicine
A novel series of tetrahydroquinolines containing acetohydrazide, oxopyrazole, oxothioxodihydropyrazole, and thioxotriazole have been synthesized. Antileishmanial, antitumor, and cytotoxicity activities of synthesized compounds were evaluated in vitro . Antileishmanial activity of the most synthesized compounds showed tremendous activity towards Leishmania major . Most of the test compounds exhibited significant level of tumor inhibition. The tetrahydropyrano[2,3‐ b ]quinolin‐2‐one 6 and 4‐oxo‐4 H ‐pyrazol‐3‐yloxytetrahydroquinoline‐3‐carbonitrile derivatives 18 showed 100% tumor inhibition comparable with standard drug vincristine (100% tumor inhibition). Tetrahydroquinolines under investigation showed cytotoxicity with LD 50 values in the range 0.56–3.01 μg/mL compared with standard drug MS‐222 with LD 50 value of 4.30 μg/mL. The presence of a pyrazole ring markedly improved the activity profiles of tetrahydroquinoline. All newly synthesized compounds were characterized by IR, 1 H NMR, and MS.