117601-28-2Relevant academic research and scientific papers
Design, Synthesis, and In Vitro Antileishmanial and Antitumor Activities of New Tetrahydroquinolines
Madkour, Hassan Mohamed Fawzy,El-Hashash, Maher Abd El-Aziz Mahmoud,Salem, Marwa Sayed,Mahmoud, Al-Shimaa Omar Ali,Al kahraman, Yasser M. S. A.
, p. 391 - 401 (2018)
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-4H-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 LD50 values in the range 0.56–3.01?μg/mL compared with standard drug MS-222 with LD50 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, 1H NMR, and MS.
Convenient Heterocyclization Reactions with 2-Functionalized-3-amino-4-aryl-5,6,7,8-tetrahydrothieno[2,3-b]quinolines; Synthesis of new Thienoquinolines, Pyridothienoquinolines, Pyranothienoquinolines and Pyrimidothienoquinolines
Bakhite, Etify A.
, p. 1201 - 1220 (2007/10/03)
The condensation of 2-acetyl-3-amino-4-aryl-5,6,7,8-tetrahydrothieno[2,3-b]quinolines (3a-c) with aromatic aldehydes afforded the corresponding chalcones 4a-e. Treatment of 4a-c with hydrazine hydrate gave pyrazolinyl derivatives 5a-c. Heating of 4a-c with orthophosphoric acid resulted in the formation of hexahydropyridothienoquinolinones 6a-c. Saponification of ethyl 3-amino-4-(p-methoxyphenyl)-5,6,7,8-tetrahydrothieno[2,3-b]quinioline-2-carboxylate (3d) gave the corresponding carboxylic acid 7 which was decarboxylated upon treatment with orthophosphoric acid at room temperature to give 3-amino-4-(p-methoxyphenyl)-5,6,7,8-tetrahydrothieno[2,3-b]quinoline (8). When the latter reaction was performed at 100 deg C, 4-(p-methoxyphenyl)-5,6,7,8-tetrahydrothieno[2,3-b]quinolin-3(2H)-one (9) was obtained. Compounds 8,9 and 3-amino-4-(p-methoxyphenyl)-5,6,7,8-tetrahydrothieno[2,3-b]quinoline-2-carboxamide (3e) were transformed into novel thieno[2,3-b]quinolines and their pyrido-, pyrano- and pyrimido-fused derivatives.
