Synthesis of new 7-benzothiazol-2-yl quinolone derivatives as antitumor agents
Journal of Chemical and Pharmaceutical Research, 2016, 8(1):503-509 • 2016
Publication Information
Authors
S. A. Hussein, H. Abd El Maksoud, K. A. Moustafa, M. M. Afify, Mohamed Sadek
Abdel-Bakky3,4 and Mohamed A. Abdelgawad
Keywords
quinolone, Benzothiazole, MCF7, Breast cancer
Journal
Journal of Chemical and Pharmaceutical Research, 2016, 8(1):503-509
Publisher
Journal of Chemical and Pharmaceutical Research,
Volume
8
Issue
1
Pages
503-509
publication.type
International
Paper Link
Not Available
Supplementary Materials
Not Available
Abstract
In this work, 3-benzothazol-2-yl-phenylamine(1)was synthesized through the reaction of 2-aminothiophenol and 3-
aminobenzoic acid using polyphosphoric acid as dehydrating agent, and used as start for the preparation of the
target compounds IV and V. Benzothiazolyl-phenylamine1was reacted with ethoxymethylene diethyl malonate ester
(EMME) to afford compound II which was thermally cyclized in diphenyl ether to give 7-benzothizol-2-ylquinolone
III. Benzaothiazolylquinolone IV was synthesized from the reflux of 7-benzothizol-2-ylquinolone III with POCl5. The
nucleophillic substitution of chloride anion of 7-benzothizol-2-ylchloroquinolone IVwith p-toluidine was preceded
by using anhydrous potassium carbonate in DMF. Compounds IV and V were screened for antitumor activity
against breast carcinoma cell line (MCF-7). The IC 50% of compounds IV and V were 0.066 and 0.056 umol/mL
respectively and showed high activity in comparison to 0.065 umol/mL standard A . The structure of the compounds
IV and V was confirmed using IR, NMR, mass spectroscopy and elemental analysis.
aminobenzoic acid using polyphosphoric acid as dehydrating agent, and used as start for the preparation of the
target compounds IV and V. Benzothiazolyl-phenylamine1was reacted with ethoxymethylene diethyl malonate ester
(EMME) to afford compound II which was thermally cyclized in diphenyl ether to give 7-benzothizol-2-ylquinolone
III. Benzaothiazolylquinolone IV was synthesized from the reflux of 7-benzothizol-2-ylquinolone III with POCl5. The
nucleophillic substitution of chloride anion of 7-benzothizol-2-ylchloroquinolone IVwith p-toluidine was preceded
by using anhydrous potassium carbonate in DMF. Compounds IV and V were screened for antitumor activity
against breast carcinoma cell line (MCF-7). The IC 50% of compounds IV and V were 0.066 and 0.056 umol/mL
respectively and showed high activity in comparison to 0.065 umol/mL standard A . The structure of the compounds
IV and V was confirmed using IR, NMR, mass spectroscopy and elemental analysis.
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