The relationship between Hirshfeld potential and cytotoxic activity: a study along a series of flavonoid and chromanone derivatives

Abstract

<jats:p>The present study examines a series of six biologically-active flavonoid and chromanone derivatives by X-ray crystal structure analysis: (<jats:italic>E</jats:italic>)-3-benzylidene-2-phenylchroman-4-one, C<jats:sub>22</jats:sub>H<jats:sub>16</jats:sub>O<jats:sub>2</jats:sub>, <jats:bold>I</jats:bold>, (<jats:italic>E</jats:italic>)-3-(4-methylbenzylidene)-2-phenylchroman-4-one, C<jats:sub>23</jats:sub>H<jats:sub>18</jats:sub>O<jats:sub>2</jats:sub>, <jats:bold>II</jats:bold>, (<jats:italic>E</jats:italic>)-3-(3-methylbenzylidene)-2-phenylchroman-4-one, C<jats:sub>23</jats:sub>H<jats:sub>18</jats:sub>O<jats:sub>2</jats:sub>, <jats:bold>III</jats:bold>, (<jats:italic>E</jats:italic>)-3-(4-methoxybenzylidene)-2-phenylchroman-4-one, C<jats:sub>23</jats:sub>H<jats:sub>18</jats:sub>O<jats:sub>3</jats:sub>, <jats:bold>IV</jats:bold>, (<jats:italic>E</jats:italic>)-3-benzylidenechroman-4-one, C<jats:sub>16</jats:sub>H<jats:sub>12</jats:sub>O<jats:sub>2</jats:sub>, <jats:bold>V</jats:bold>, and (<jats:italic>E</jats:italic>)-3-(4-methoxybenzylidene)chroman-4-one, C<jats:sub>17</jats:sub>H<jats:sub>14</jats:sub>O<jats:sub>3</jats:sub>, <jats:bold>VI</jats:bold>. The cytotoxic activities of the presented crystal structures have been determined, together with their intermolecular interaction preferences and Hirshfeld surface characteristics. An inverse relationship was found between the contribution of C...C close contacts to the Hirshfeld surface and cytotoxic activity against the WM-115 cancer line. Dependence was also observed between the log<jats:italic>P</jats:italic> value and the percentage contribution of C...H contacts to the Hirshfeld surface.</jats:p>

Cytotoxicity of piano‐stool ruthenium cyclopentadienyl complexes bearing different imidato ligands

“…For instance, recently it was reported that the presence of this kind interactions (reflected as C˙˙˙C contacts in crystal packing) is in line with the cytotoxic activity of some flavonoids and chromanones. [53] 4 | CONCLUSION Our results showed that complex 1 (η 5 -cyclopentadienyl) Ru (CO) 2 (η 1 -N-maleimidato) has anticancer potential. It should be emphasized that this complex was about 10 times more cytotoxic to leukemic HL-60 cells compared with normal cells, which indicates its selective action.…”

“…For instance, recently it was reported that the presence of this kind interactions (reflected as C˙˙˙C contacts in crystal packing) is in line with the cytotoxic activity of some flavonoids and chromanones. [ 53 ]…”