36640-46-7Relevant academic research and scientific papers
Design, synthesis, biological evaluation, and molecular docking studies of some novel N,N-dimethylaminopropoxy-substituted aurones
Kumar, Gourav,Saroha, Bhavna,Kumar, Ramesh,Kumari, Meena,Dalal, Sunita,Kumar, Suresh
, p. 297 - 308 (2021/10/25)
In continuation of our ongoing research on the discovery of novel and potentially bioactive aurones, we have designed and synthesized some novel N,N-dimethylaminopropoxy-substituted pyrazole-based aurones 10(a-l). These pyrazole-benzofuranone hybrid compounds were characterized by using their IR, 1H-NMR, 13C-NMR, and mass spectrometry data. Compound 10c was used as a model to further explicate the structure of tilted compounds by means of 1H-1H COSY, 1H-13C HMQC, 1H-13C HMBC, 1H-1H TOCSY, 1H-1H NOSEY, DEPT-45°, DEPT-90°, and DEPT-135° NMR spectra. The comparative molecular docking study of N,N-dimethylaminopropoxy-substituted pyrazole-based aurones and standard drugs (Ampicillin and Chloramphenicol) against Bacillus subtilis (PDB: 6tzp) active site was performed to determine the binding interactions, binding energy, and orientation of the molecules at the active site of the target protein. Out of these synthesized compounds, five best analogs (10b, 10f, 10h, 10k, and 10l) of docking results were also evaluated for their in vitro antibacterial potential against Bacillus subtilis to validate the docking results.
Design and synthesis of novel quinazolinone-pyrazole derivatives as potential α-glucosidase inhibitors: Structure-activity relationship, molecular modeling and kinetic study
Azimi, Fateme,Azizian, Homa,Najafi, Mohammad,Hassanzadeh, Farshid,Sadeghi-aliabadi, Hojjat,Ghasemi, Jahan B.,Ali Faramarzi, Mohammad,Mojtabavi, Somayeh,Larijani, Bagher,Saghaei, Lotfollah,Mahdavi, Mohammad
, (2021/07/13)
In this study, a new series of quinazolinone-pyrazole hybrids were designed, synthesized and screened for their α-glucosidase inhibitory activity. The results of the in vitro screening indicated that all the molecular hybrids exhibited more inhibitory activity (IC50 values ranging from 60.5 ± 0.3 μM-186.6 ± 20 μM) in comparison to standard acarbose (IC50 = 750.0 ± 10.0 μM). Limited structure–activity relationship suggested that the variation in the inhibitory activities of the compounds affected by different substitutions on phenyl rings of diphenyl pyrazole moiety. The enzyme kinetic studies of the most potent compound 9i revealed that it inhibited α-glucosidase in a competitive mode with a Ki of 56 μM. Molecular docking study was performed to predict the putative binding interaction. As expected, all pharmacophoric moieties used in the initial structure design playing a pivotal role in the interaction with the binding site of the enzyme. In addition, by performing molecular dynamic investigation and MM-GBSA calculation, we investigated the difference in structural perturbation and dynamic behavior that is observed over α-glycosidase in complex with the most active compound and acarbose relative to unbound α-glycosidase enzyme.
Design and synthesis of novel pyrazole-phenyl semicarbazone derivatives as potential α-glucosidase inhibitor: Kinetics and molecular dynamics simulation study
Azimi, Fateme,Ghasemi, Jahan B.,Azizian, Homa,Najafi, Mohammad,Faramarzi, Mohammad Ali,Saghaei, Lotfollah,Sadeghi-aliabadi, Hojjat,Larijani, Bagher,Hassanzadeh, Farshid,Mahdavi, Mohammad
, p. 1082 - 1095 (2020/11/20)
A series of novel pyrazole-phenyl semicarbazone derivatives were designed, synthesized, and screened for in vitro α-glucosidase inhibitory activity. Given the importance of hydrogen bonding in promoting the α-glucosidase inhibitory activity, pharmacophore modification was established. The docking results rationalized the idea of the design. All newly synthesized compounds exhibited excellent in vitro yeast α-glucosidase inhibition (IC50 values in the range of 65.1–695.0 μM) even much more potent than standard drug acarbose (IC50 = 750.0 μM). Among them, compounds 8o displayed the most potent α-glucosidase inhibitory activity (IC50 = 65.1 ± 0.3 μM). Kinetic study of compound 8o revealed that it inhibited α-glucosidase in a competitive mode (Ki = 87.0 μM). Limited SAR suggested that electronic properties of substitutions have little effect on inhibitory potential of compounds. Cytotoxic studies demonstrated that the active compounds (8o, 8k, 8p, 8l, 8i, and 8a) compounds are also non-cytotoxic. The binding modes of the most potent compounds 8o, 8k, 8p, 8l and 8i was studied through in silico docking studies. Molecular dynamic simulations have been performed in order to explain the dynamic behavior and structural changes of the systems by the calculation of the root mean square deviation (RMSD) and root mean square fluctuation (RMSF).
Synthesis of some 2-({(2E)-3-(1,3-substituted diphenyl-1H-pyrazol-4-yl) prop-2-enoyl} amino) benzoic acids as antiinflammatory agents
Hari Priya,Madhava Reddy,Harinadha Babu
, p. 305 - 308 (2013/09/24)
Vilsmeier-Haack reaction of substituted phenyl hydrazone derivatives (1a-j) afforded 1,3-substituted diphenyl-1H-pyrazole-4-carbaldehydes (2a-j). Compounds (2a-j) on condensation with malonic acid gave (2E)-3-(1,3-substituted diphenyl-1H-pyrazol-4-yl) acrylic acids (3a-j) which on reaction with thionyl chloride afforded acryloyl chlorides. The reaction of acryloyl chlorides with anthranilic acid gave 2-({(2E)-3-(1,3-substituted diphenyl-1H-pyrazol-4-yl) prop-2-enoyl} amino) benzoic acids (4a-j) in good yields. The structures of the newly synthesized compounds have been confirmed on the basis of physical and spectral data. Some of the synthesized compounds have shown significant antiiflammatory actiivty.
