Anti-breast cancer activity of some novel quinoline derivatives release_2iyedderg5ctjgl7srg3hwbs2i

by Mostafa M. Ghorab, Mansour S. Alsaid

Published in Acta Pharmaceutica by Walter de Gruyter GmbH.

2015   Volume 65, p271-283

Abstract

<jats:title>Abstract</jats:title> To discover new bioactive lead compounds for medicinal purposes, 2-cyano-3-(4-substituted)-<jats:italic>N</jats:italic>-(quinolin-3-yl) acrylamide derivatives <jats:bold>2–24</jats:bold>, chromenes <jats:bold>25, 26</jats:bold> and benzochromenes <jats:bold>27, 28</jats:bold> were synthesized. The structures of the newly synthesized compounds were confirmed by elemental analyses, IR, <jats:sup>1</jats:sup>H NMR and <jats:sup>13</jats:sup>C NMR spectroscopies. In addition, the structure of compound <jats:bold>1</jats:bold> was confirmed through X-ray crystallography. All the newly synthesized compounds were evaluated for their cytotoxic activity against the breast cancer cell line MCF7. The corresponding 2-cyano-3-(4-hydroxy-3-methoxyphenyl)-<jats:italic>N</jats:italic>-(quinolin-3-yl) acrylamide (<jats:bold>15</jats:bold>), 3-oxo-<jats:italic>N</jats:italic>-(quinolin-3-yl)-3<jats:italic>H</jats:italic>-benzol[<jats:italic>f</jats:italic>] chromene-2-carboxamide (<jats:bold>27</jats:bold>), 2-cyano-3-(4-fluorophenyl-<jats:italic>N</jats:italic>-(quinolin-3-yl) acrylamide (<jats:bold>7</jats:bold>), 2-cyano-5-(4-(dimethyl-amino) phenyl)-<jats:italic>N</jats:italic>-(quinolin-3-yl) penta-2,4-dienamide (<jats:bold>19</jats:bold>) exhibited higher activity compared to doxorubicin (with <jats:italic>IC</jats:italic><jats:sub>50</jats:sub> value of 47.9 μmol L<jats:sup>−1</jats:sup>) as a reference drug, with <jats:italic>IC</jats:italic><jats:sub>50</jats:sub> values of 29.8, 39.0, 40.0, 40.4 μmol L<jats:sup>−1</jats:sup>, resp. Also, quinoline acrylamides containing 2,3,4-trimethoxyphenyl <jats:bold>17</jats:bold>, 2-chlorophenyl <jats:bold>10</jats:bold>, benzo[<jats:italic>d</jats:italic>][1,3]dioxol <jats:bold>12</jats:bold>, 2-methoxynaphthalen <jats:bold>22</jats:bold>, 2,4-dichlorophenyl <jats:bold>18</jats:bold> and quinoline carrying a chromene-3-carboxamide moiety <jats:bold>25</jats:bold> were nearly as active as doxorubicin, while quinoline acrylamides incorporating unsubstituted phenyl <jats:bold>2</jats:bold>, <jats:italic>p</jats:italic>-tolyl <jats:bold>3</jats:bold>, 2,4-dienamide <jats:bold>8</jats:bold>, 3-nitrophenyl <jats:bold>13</jats:bold>, 4-nitrophenyl <jats:bold>14</jats:bold>, 3,4-dimethoxyphenyl <jats:bold>16</jats:bold> and chromene <jats:bold>26</jats:bold> exhibited a moderate activity. In addition, quinoline with acetamide <jats:bold>1</jats:bold>, 4-hydroxyphenyl <jats:bold>4</jats:bold>, 4-dimethylaminophenyl <jats:bold>9</jats:bold>, 4-chlorophenyl <jats:bold>11</jats:bold>, 3-bromophenyl <jats:bold>20</jats:bold>, 4-bromophenyl <jats:bold>21</jats:bold> and 3-thienyl moiety <jats:bold>24</jats:bold> showed less activity than doxorubicin. On the other hand, quinoline having 2-methoxyphenyl <jats:bold>5</jats:bold>, 4-methoxyphenyl <jats:bold>6</jats:bold>, 4-metho xynaphthalene <jats:bold>23</jats:bold> and chromene-2-carboxamide <jats:bold>28</jats:bold> showed no activity.
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Type  article-journal
Stage   published
Date   2015-09-01
DOI  10.1515/acph-2015-0030
PubMed  26431105
Wikidata  Q38830774
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