Nitro-Substituted Azo Dyes as Anti-Prostate Cancer Candidates and Nonlinear Optical Properties: Synthesis and In Silico Studies.

Azo dye derivatives are prepared using the diazotation reaction of (o-,m-, and p-) nitroaniline, followed by coupling with 2-naphthaleneol under low-temperature conditions. The prepared azo dyes (1-3) are characterized via FTIR, 1HNMR, 13CNMR, and mass spectroscopy. DFT calculations via B3LYP/6-311 + + G (d,p) provided understanding of the electronic structures, revealing narrow gaps between the HOMO and LUMO at 3.1368 and 3.2713 and 3.2100 eV. Molecular docking studies demonstrated strong affinity of the prepared azo dyes with selected androgen receptor 1E3G. The azo dye substituted with a nitro group showed a low affinity energy at - 8.7, - 7.7, and - 8 kcal/mol and is associated with hydrogen bonds, hydrophobic, and Van der Waals interactions. The nonlinear optical (NLO) properties of azo dyes 1-3 are investigated using the diffraction patterns (DPs) method with 473 nm continuous wave (CW) laser beam. Azo dyes 1 and 2 produced diffraction patterns when the laser beam traversed both separated, whereas no DPs resulted from the third one. The nonlinear refractive index (NL RI) values for azo dyes 1 and 2 are found to be 10.123 × 10-7 and 7.23 × 10-7 cm2/W, respectively. These high NLRI, n2, values make azo dyes 1 and 2 promising candidates for use in optical devices.