Abstract
In this work, we synthesized two new s-triazine incorporates pyrazole/piperidine/aniline moieties. Molecular structure investigations in the light of X-ray crystallography combined with Hirshfeld and DFT calculations were presented. Intermolecular interactions controlling the molecular packing of 4-(3,5-dimethyl-1H-pyrazol-1-yl)-N-phenyl-6-(piperidin-1-yl)-1,3,5-triazin-2-amine; 5a and N-(4-bromophenyl)-4-(3,5-dimethyl-1H-pyrazol-1-yl)-6-(piperidin-1-yl)-1,3,5-triazin-2-amine; 5b were analyzed using Hirshfeld calculations. The most dominant interactions are the H...H, N...H and H...C contacts in both compounds. The N...H and H...C interactions in 5a and the N...H, Br...H and H...H interactions in 5b are the most important. In addition, DFT calculations were used to compute the molecular structures of 5a and 5b; then, their electronic properties, as well as the 1H- and 13C-NMR spectra, were predicted. Both compounds are polar where 5a (1.018 Debye) has lower dipole moment than 5b (4.249 Debye). The NMR chemical shifts were calculated and very good correlations between the calculated and experimental data were obtained (R2 = 0.938–0.997).
Highlights
Introduction s-Triazine scaffold has been extensively studied in the literature due to its wide applications in different fields, including coordination chemistry [1] and drug discovery development, such as Enasidenib (Idhifa), as a representative example, having the s-triazine privileged structure, which has been approved by FDA in 2017 for the IDH2-positive acute leukemia treatment [2,3]
A combination of the s-triazine privileged structure with other N-heterocycles such as pyrazoles [12,13,14] and quinazoline have raised a great of attention in cancer chemotherapeutics targeting enzyme inhibitors such as TK and EGFR inhibitors [15,16]
The results indicated the potential efficacy of compound IV against cancer via inhibition of EGFR-TK (Figure 1) [29]
Summary
3 and DMSO-d6 6on on aa Jeol chen, Germany). Infrared spectra recMHz and Infrared spectra werewere recorded orded on a Thermo. 2a,b and and 3a,b, 3a,b, which which were were required required for for this this study, study, were were prepared prepared acacCompounds cording to reported literature [[25]. The synthetic pathway for the desired compounds are depicted in Scheme 1
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