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Issue 104, 2016, Issue in Progress
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Rational design, synthesis and 2D-QSAR studies of antiproliferative tropane-based compounds

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Abstract

3,4-Diaryl-11-methyl-7-[(aryl)methylidene]-4,5,11-triazatricyclo[6.2.1.0*2,6*]undec-5-enes 14a–s were synthesized through reaction of 2,4-bis[(aryl)methylidene]-8-methyl-8-azabicyclo[3.2.1]octan-3-ones 12a–f with aryl hydrazines in the presence of catalytic amount of thiamine hydrochloride. Meanwhile, the 4-acetyl analogs 16a,b were obtained through reaction of 12b,e and hydrazine hydrate in acetic acid. Good support for the structure was received from single crystal X-ray studies of 14a. Some of the synthesized tropane containing-compounds showed promising antitumor properties during the in vitro MTT bio-assay against HepG2 (hepatocellular) and MCF7 (breast) human tumor carcinoma cell lines, with potency higher than that of doxorubicin (DNA intercalating agent, standard reference). Statistically significant 2D-QSAR model describes the antitumor properties against MCF7.

Graphical abstract: Rational design, synthesis and 2D-QSAR studies of antiproliferative tropane-based compounds

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Publication details

The article was received on 26 Aug 2016, accepted on 05 Oct 2016 and first published on 14 Oct 2016


Article type: Paper
DOI: 10.1039/C6RA21486J
Citation: RSC Adv., 2016,6, 101911-101923
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    Rational design, synthesis and 2D-QSAR studies of antiproliferative tropane-based compounds

    N. S. M. Ismail, R. F. George, R. A. T. Serya, F. N. Baselious, M. El-Manawaty, E. M. Shalaby and A. S. Girgis, RSC Adv., 2016, 6, 101911
    DOI: 10.1039/C6RA21486J

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