Synthesis, Single Crystal Study, in silico Analysis, in vitro Antiinflammatory and Anticancer Activities of 7-hydroxy-14H-naphtho[2,3- a]phenothiazine-8,13-dione

Background: 7–hydroxy–14H–naphtho[2,3–a]phenothiazine–8,13–dione (AQATP) was synthesized by using iodobenzenediacetate as catalyst from 1,4–dihydroxyanthraquinone (1,4–AQ) which was isolated from Cassia tora seeds. Methods: They were then characterized by various spectral techniques. Single crystal X-ray diffraction studies revealed that AQATP crystallizes in orthorhombic space group. ADME Test was performed to determine pharmacokinetic parameter using MedChem designer software. The In silico docking studies were performed to find out the anticancer effect of 1,4–AQ and AQATP using iGEMDOCK software taking CK2 protein as the target. In silico anti-inflammatory study was also carried out by means of the same software taking COX–2 and LOX–5 enzymes as the targets. Results: It was found that the derivative exhibited more binding affinity than the parent compound for both anticancer and anti-inflammatory activities. In vitro anticancer activity in colon cancer cell lines, anti-inflammatory activity by denaturation, COX and LOX assay were performed on AQATP. Conclusion: Results from both computational and in vitro analysis suggest that structural modification of 1,4–AQ could be considered as a good strategy to obtain a lead molecule for drug discovery.