Abstract
The designed target compound of N-acetyl indole linked to a fused triazolo/thiadiazole scaffold was synthesized via the reaction of 4-amino-5-(1H-indol-2-yl)-1,2,4-triazol-3(2H)-thione as the starting material with acetic anhydride under reflux conditions for 6 h, resulting in an excellent and pure chemical yield. The structural features of the designed compound were confirmed using spectroscopic tools including single crystal X-ray diffraction analysis along with 1H-NMR, 13C-NMR, 2D-NMR, and high resolution mass spectrometry. Using Hirshfeld analysis, we determined the molecular packing depends on strong interactions (O···H and N···H) along with weak interactions (S···H, C···H and H···H). The shortest contacts corresponding to the N3···H12 (2.490 Å), N2···H5 (2.503 Å), and O1···H2 (2.490 Å) interactions were confirmed based on the Hirshfeld analysis. The calculated dipole moment was 6.6557 Debye. The atomic charge distribution, molecular electrostatic potential map, and reactivity descriptors are also discussed. The computed NMR spectra of the requisite compound correlated well with the results obtained experimentally. The UV-Vis electronic spectra of the requisite compound were simulated using the TD-DFT method and compared with the experimental data. The different σ→σ*, π→π*, n→σ*, and n→π* donor–acceptor interactions and their interaction energies stabilized the studied system to 9.84, 20.65, 29.33, and 45.82 kcal/mol, respectively.
Highlights
Heterocyclic compounds are of great importance in our daily life
In continuation of our research program [22,23,24,25,26] to design a new scaffold that may be useful for material science, we have reported here a new motif-attributed indole synthon linked with a fused triazolo/thiadiazole scaffold at position 2 of the indole nucleus
The at δ 7.34 ppm displayed a 3JC,H coupling correlation with carbon at δ 140.47 was synthesized from the reaction
Summary
Heterocyclic compounds are of great importance in our daily life. Almost all basic biochemical processes of living cells are mediated by biomolecules that contain these ring systems, such as enzymes, coenzymes, heme, hormones, vitamins, chlorophyll, amino acids, carbohydrates (in cyclic forms), and nucleic acids. Heterocyclic frameworks, notably those containing nitrogen and/or oxygen atoms, are considered as valuable sources for new synthetic drug candidates of high functional specialization and are targeted by drug discovery and development research programs to fight diseases. They are Crystals 2020, 10, 600; doi:10.3390/cryst10070600 www.mdpi.com/journal/crystals. Indole is a privileged core structure embedded in a very interesting group of polycyclic alkaloids that exhibit a wide spectrum of important biological activities including anti-human immunodeficiency virus (anti-HIV) [11], anti-inflammatory [12], anti-malarial [13], anti-microbial [14], anti-vascular [15], anti-convulsant [16], and α-glucosidase inhibiting [17] properties; ischemia/reperfusion injury [18]; and anti-proliferative activity for EGFR and PARP-1 potential inhibitors [19,20,21]. The molecular insight of the target molecule was explored
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