SYNTHESIS, MOLECULAR DOCKING AND FLUORESCENT PROPERTIES OF NOVEL (E)-3-(9-ETHYL-9H-CARBAZOL-3YL)-1-PHENYLPROP-2-EN-1-ONES
Keywords:Carbazole, Fluorescence, Claisen-Schmidt condensation, Stockes shift, PBR, MDM2-bind p53 receptor cancer proteins
Objective: Synthesis of novel (E)-3-(9-ethyl-9H-carbazol-3yl)-1-phenylprop-2-en-1-ones 3a-i to evaluate for their fluorescence property and anticancer activity on Murine double minutes-2(MDM2) receptor bind p53 and Pheripheral benzodiazepine receptor (PBR) proteins.
Methods: A Claisen-Schmidt condensation of 9-ethyl-9H-carbazole-3-carbaldehyde 1 with substituted acetophenones 2a-i was carried out to obtain novel class of a series of (E)-3-(9-ethyl-9H-carbazol-3yl)-1-phenylprop-2-en-1-ones 3a-i. The fluorescent behavior in ethanol and acetone as solvents, in silico docking study against MDM2 receptor bind p53 and PBR proteins was investigated.
Results: The fluorescent spectrum of (E)-3-(9-ethyl-9H-carbazol-3yl)-1-phenylprop-2-en-1-ones 3a-i shows a large red shift in acetone and ethanol. The compounds 3a-i exhibits large Stoke's shifts value ranging from 135.5 to 160.0 nm in ethanol when compared to standard rhodamine B which was 32 nm. Similarly in acetone the compounds 3a-i exhibits large Stoke's shifts value ranging from 114.5 to 141.0 nm when compared to standard rhodamine B which was 40 nm. The docking study reveals that the (E)-3-(9-ethyl-9H-carbazol-3yl)-1-phenylprop-2-en-1-ones 3a-i were shown excellent interaction with PBR receptor protein with binding energy of -2.643050e+02 to -3.104552e+02 kcal/mol. However, the same target compounds exhibited poor interaction with MDM2-bind p53 receptor cancer protein.
Conclusion: The study could further widen the scope for the development of similar new structurally distinct (E)-3-(9-ethyl-9H-carbazol-3yl)-1-phenylprop-2-en-1-ones to identify potential anticancer agents. Also since the fluorescent spectrum of (E)-3-(9-ethyl-9H-carbazol-3yl)-1-phenylprop-2-en-1-ones 3a-i exhibits a large red shift with an increase in the polarity of the solvents, these can also serve as good candidates for biological probes in medicinal field.
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