Synthesis, anti-diabetic profiling and molecular docking studies of 2-(2-arylidenehydrazinyl)thiazol-4(5H)-ones.

Aim: To synthesize novel more potent anti-diabetic agents. Methodology: A simple cost effective Hantzsch's synthetic strategy was used to synthesize 2-(2-arylidenehydrazinyl)thiazol-4(5H)-ones. Results: Fifteen new 2-(2-arylidenehydrazinyl)thiazol-4(5H)-ones were established to check their anti-diabetic potential. From alpha(α)-amylase inhibition, anti-glycation and anti-oxidant activities it is revealed that most of the compounds possess good anti-diabetic potential. All tested compounds were found to be more potent anti-diabetic agents via anti-glycation mode. The results of α-amylase and anti-oxidant inhibition revealed that compounds are less active against α-amylase and anti-oxidant assays. Conclusion: This study concludes that introduction of various electron withdrawing groups at the aryl ring and substitution of different functionalities around thiazolone nucleus could help to find out better anti-diabetic drug.

Diabetes is a most spreading chronicle disease effecting millions of peoples across the globe every year and this number increases day by day. To cure the human population from this dilemma, we had synthesized, characterized and evaluated the anti-diabetic behavior of our synthesized compounds. α-Amylase, in vitro anti-glycation and anti-oxidant assays were performed to find out good lead for Diabetes Mellitus. All tested compounds were found to be excellent anti-glycating agents with IC₅₀ values far better than standard amino-guanidine (IC₅₀ = 3.582 ± 0.002 µM). Compound 4m was most efficient glycation inhibitor (IC₅₀ = 1.095 ± 0.002 µM). Cytotoxicity of all compounds was determined with in vitro hemolytic assay and found all compounds safe and bio-compatible to humans at all tested concentrations. The inhibition potential was also examined with theoretical docking studies to support our experimental results against human pancreatic alpha-amylase (HPA) and human serum albumin (HSA) proteins. All compounds showed excellent binding affinity with HSA active pockets however, only compound 4h and 4k binding affinity was good with HPA.

A first principles based prediction of electronic and nonlinear optical properties towards cyclopenta thiophene chromophores with benzothiophene acceptor moieties.

In the current work, organic cyclopenta-thiophene (CPT) based derivatives (FICR and FICD1-FICD5) were designed by the modulation of end-capped acceptor group of the reference molecule i.e., FICR, to explore their nonlinear optical (NLO) response. The effect of terminal acceptor and donor groups in the tailored compounds was explored by using DFT based quantum calculations. The UV-Vis analysis, frontier molecular orbitals (FMOs), transition density matrix (TDM), natural bond orbitals (NBOs), density of states (DOS), nonlinear optical (NLO) analyses were performed at M06/6-311G(d,p) functional. The LUMO-HOMO band gaps of FICD1-FICD5 were found to be smaller (1.75-1.92 eV) comparative to FICR (1.98 eV). Moreover, the global reactivity parameters (GRPs) were correlated with the results of other analyses. FICD2 and FICD5 with lowest band gap 1.73 and 1.75 eV showed less hardness (0.86 and 0.87 eV, respectively), high softness (0.58 and 0.57 eV-1), and larger absorption spectrum (815 and 813 nm) in gaseous phase and (889 and 880 nm) in solvent phase among all entitled compounds. All the designed chromophores (FICD1-FICD5) demonstrated a significant NLO response as compared to FICR. Particularly, FICD2 and FICD5 exhibited the highest average linear polarizability (<α>) [2.86 × 10-22 and 2.88 × 10-22 esu], first hyperpolarizability (ßtot) (8.43 × 10-27 and 8.35 × 10-27 esu) and second hyperpolarizability (γtot) (13.20 × 10-32 and 13.0 × 10-32 esu) values as compared to the other derivatives. In nutshell, structural modeling of CPT based chromophores with extended acceptors, can be significantly utilized to achieve potential NLO materials.

Influence of benzothiophene acceptor moieties on the non-linear optical properties of pyreno-based chromophores: first-principles DFT framework.

Herein, a series of heterocyclic organic compounds (PYFD1-PYFD7) are designed with different acceptor moieties at the terminal position of a reference compound (PYFR) for nonlinear optical (NLO) active materials. The optoelectronic characteristics of the designed chromophores were investigated using density functional theory (DFT) calculations with the M06/6-311G(d,p) functional. Frontier molecular orbital (FMO) analysis revealed a significant decrease in the energy of the band gaps (2.340-2.602 eV) for the derivatives as compared to the PYFR reference compound (3.12 eV). An efficient transfer of charge from the highest occupied molecular orbital (HOMO) to the lowest unoccupied molecular orbital (LUMO) was seen, which was further corroborated by the density of states (DOS) and transition density matrix (TDM) heat maps. The results of the global reactivity parameters (GRPs) indicated that all derivatives exhibited greater softness (σ = 0.384-0.427 eV) and lower hardness (η = 0.394-1.302 eV) as compared to PYFR, indicating a higher level of polarizability in the derivatives. Moreover, all of the derivatives showed significant findings in terms of nonlinear optical (NLO) results as compared to the reference chromophore. PYFD2 showed the most effective NLO response (α = 1.861 × 10-22 and ßtot = 2.376 × 10-28 esu), including a lowered band gap of 2.340 eV, the maximum softness value of 0.4273 eV, and the lowest hardness value of 1.170 eV as compared to other chromophores. The incorporation of different acceptors and thiophene as a π-spacer in this structural alteration significantly contributed to achieving remarkable NLO responses. Therefore, our findings may motivate experimentalists to synthesize these designed NLO active materials for the current advanced technological applications.

Synthesis, characterization and NLO properties of 1,4-phenylenediamine-based Schiff bases: a combined theoretical and experimental approach.

In the current study, three novel 1,4-phenylenediamine-based chromophores (3a-3c) were synthesized and characterized and then their nonlinear optical (NLO) characteristics were explored theoretically. The characterization was done by spectroscopic analysis, i.e. FT-IR, UV-Visible, and NMR spectroscopy, and elemental analysis. Notably, these chromophores exhibited UV-Visible absorption within the range of 378.635-384.757 nm in acetonitrile solvent. Additionally, the FMO findings for 3a-3c revealed the narrowest band gap (4.129 eV) for 3c. The GRPs for these chromophores were derived from HOMO-LUMO energy values, which showed correspondence with FMO results by depicting a minimum hardness (2.065 eV) for 3c. Among these compounds, 3c displayed the highest nonlinear behavior with maximum µtot, ßtot and γtot values of 4.79 D, 8.00 × 10-30 and 8.13 × 10-34 a.u., respectively. Our findings disclosed that the synthesized 1,4-phenylenediamine chromophores may be considered promising candidates for nonlinear optical materials, showing potential applications in the realm of optoelectronic devices.