Synthesis of N-(3-picolyl)-based 1,3,2λ5-benzoxazaphosphinamides as potential 11β-HSD1 enzyme inhibitors

Balam, Satheesh Krishna; Krishnammagari, Suresh Kumar; Harinath, Jayaprakash Soora; Sthanikam, Siva Prasad; Chereddy, Syama Sundar; Yellapu, Nanda Kumar; Peddiahgari, Vasu Govardhana Reddy; Cirandur, Suresh Reddy

doi:10.1007/s00044-014-1194-7

Cited by 18 publications

(13 citation statements)

References 22 publications

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“…blood) and Pgp inhibition [ 55 ]. Bioactivity of synthesized compounds was predicted by Molinspiration ( http://www.molinspiration.com/ ) online tool kit [ 56 ] and toxicity parameters like mutagenicity, tumorigenicity irritating effects and reproductive effects were computed by OSIRIS property explorer [ 57 ].…”

Section: Methodsmentioning

confidence: 99%

Synthesis, molecular docking and molecular dynamic simulation studies of 2-chloro-5-[(4-chlorophenyl)sulfamoyl]-N-(alkyl/aryl)-4-nitrobenzamide derivatives as antidiabetic agents

et al. 2020

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A series of 2-chloro-5-[(4-chlorophenyl)sulfamoyl]-N-(alkyl/aryl)-4-nitrobenzamide derivatives (5a-5v) has been synthesized and confirmed by physicochemical(R f , melting point) and spectral means (IR, 1 HNMR, 13 CNMR). The results of in vitro antidiabetic study against α-glucosidase indicated that compound 5o bearing 2-CH 3-5-NO 2 substituent on phenyl ring was found to be the most active compound against both enzymes. The electron donating (CH 3) group and electron withdrawing (NO 2) group on a phenyl ring highly favoured the inhibitory activity against these enzymes. The docking simulations study revealed that these synthesized compounds displayed hydrogen bonding, electrostatic and hydrophobic interactions with active site residues. The structure activity relationship studies of these compounds were also corroborated with the help of molecular modeling studies. Molecular dynamic simulations have been done for top most active compound for validating its α-glucosidase and α-amylase inhibitory potential, RMSD analysis of ligand protein complex suggested the stability of top most active compound 5o in binding site of target proteins. In silico ADMET results showed that synthesized compounds were found to have negligible toxicity, good solubility and absorption profile as the synthesized compounds fulfilled Lipinski's rule of 5 and Veber's rule.

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Section: Methodsmentioning

confidence: 99%

Synthesis, molecular docking and molecular dynamic simulation studies of 2-chloro-5-[(4-chlorophenyl)sulfamoyl]-N-(alkyl/aryl)-4-nitrobenzamide derivatives as antidiabetic agents

et al. 2020

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“…The compound's capacity to cross the blood‐brain barrier in vivo ranged from 0.10 to 2.43, indicating moderate to the good ability for penetration and aiding in their distribution in vivo . (See Table 7 for details) [70] …”

Section: In Vitro Biological Evaluationmentioning

confidence: 99%

Exploration of N‐(6‐Indazolyl) benzenesulfonamide Derivatives as Potential Antioxidants and Antimicrobial Agents: Integrating Synthesis, In Silico Docking, and Bioactivity Profiling

Yadav,

Rao,

Kumar

et al. 2023

ChemistrySelect

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A new series of N‐(1‐(2‐chloropyrimidin‐4‐yl)‐1H‐indazol‐5‐yl) benzenesulfonamide derivatives (4 a–i) and N‐(1‐(2‐chloropyrimidin‐4‐yl)‐6‐ethoxy‐1H‐indazol‐5‐yl) benzenesulfonamide derivatives (5 a–i) was synthesized via reduction of 1‐(2‐halopyrimidin‐4‐yl)‐5‐nitro‐1H‐indazole (3) with SnCl2 followed by reaction with various aryl sulphonyl chlorides in pyridine. The structures were confirmed using IR, 1H‐NMR, 13C‐NMR, and mass spectral methods. Compounds 4 a–i and 5 a–i were evaluated for antifungal and antibacterial activities against Gram‐negative and Gram‐positive bacteria. They also exhibited antioxidant potential in DPPH (IC50=0.094‐0.467 μmol/ml) and ABTS assays (IC50=0.101–0.496 μmol/ml). Remarkably, N‐(1‐(2‐chloropyrimidin‐4‐yl)‐1H‐indazol‐5‐yl)‐2‐nitrobenzenesulfonamide displayed the highest antibacterial activity, while N‐(1‐(2‐chloropyrimidin‐4‐yl)‐1H‐indazol‐5‐yl)‐4‐methoxybenzenesulfonamide showed excellent antifungal potential. Compound N‐(1‐(2‐chloropyrimidin‐4‐yl)‐1H‐indazol‐5‐yl)‐2‐nitrobenzenesulfonamide exhibited the most significant antioxidant activity. In this study, molecular dynamics simulations were utilized to rigorously examine the stability of ligand‐protein complexes, demonstrating a consistent and robust binding of the most potent compound within the target proteins′ binding sites. Computational assessments were further employed to predict the drug‐likeness and ADMET properties of the synthesized compounds. The results unequivocally confirmed the remarkable antioxidant and antimicrobial potential of all derivatives, a finding substantiated by comprehensive molecular docking analyses that revealed intricate interactions involving hydrogen bonds, electrostatic forces, and hydrophobic contacts. These findings collectively provide invaluable insights into the complex molecular structure and receptor target site dynamics, laying a strong foundation for the development of novel active antioxidant and antimicrobial agents with promising pharmaceutical implications.

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“…Organophosphorus chemistry research bestowed an elegant locus to α-aminophosphonates as they have exhilarated with potential antioxidant, antifungal, antibacterial, antidiabetic, anticancer, antiviral, antitumor, cytotoxic, antiproliferative, antibiotic, antithrombotic, peptidomimetic, catalytic antibodies hapten, neuroactive enzyme inhibiting, and anti-bone resorption activities. As they are tetrahedral transition-state mimics, they are identified as HIV protease, synthase, serine hydrolase, and UDP-galactopyranose mutase inhibitors.…”

Section: Introductionmentioning

confidence: 99%

Green Synthesis, Antioxidant, and Plant Growth Regulatory Activities of Novel α-Furfuryl-2-alkylaminophosphonates

et al. 2021

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A series of novel α-furfuryl-2-alkylaminophosphonates have been efficiently synthesized from the one-pot threecomponent classical Kabachnik−Fields reaction in a green chemical approach by addition of an in situ generated dialkylphosphite to Schiff's base of aldehydes and amines by using environmental and eco-friendly silica gel supported iodine as a catalyst by microwave irradiation. The advantage of this protocol is simplicity in experimental procedures and products were resulted in high isolated yields. The synthesized α-furfuryl-2alkylaminophosphonates were screened to in vitro antioxidant and plant growth regulatory activities and some are found to be potent with antioxidant and plant growth regulatory activities. These in vitro studies have been further supported by ADMET (absorption, distribution, metabolism, excretion, and toxicity), quantitative structure−activity relationship, molecular docking, and bioactivity studies and identified that they were potentially bound to the GLN340 amino acid residue in chain C of 1DNU protein and TYR597 amino acid residue in chain A of 4M7E protein, causing potential exhibition of antioxidant and plant growth regulatory activities. Eventually, title compounds are identified as good blood− brain barrier (BBB)-penetrable compounds and are considered as proficient central nervous system active and neuroprotective antioxidant agents as the neuroprotective property is determined with BBB penetration thresholds.

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Synthesis of N-(3-picolyl)-based 1,3,2λ5-benzoxazaphosphinamides as potential 11β-HSD1 enzyme inhibitors

Cited by 18 publications

References 22 publications

Synthesis, molecular docking and molecular dynamic simulation studies of 2-chloro-5-[(4-chlorophenyl)sulfamoyl]-N-(alkyl/aryl)-4-nitrobenzamide derivatives as antidiabetic agents

Synthesis, molecular docking and molecular dynamic simulation studies of 2-chloro-5-[(4-chlorophenyl)sulfamoyl]-N-(alkyl/aryl)-4-nitrobenzamide derivatives as antidiabetic agents

Exploration of N‐(6‐Indazolyl) benzenesulfonamide Derivatives as Potential Antioxidants and Antimicrobial Agents: Integrating Synthesis, In Silico Docking, and Bioactivity Profiling

Green Synthesis, Antioxidant, and Plant Growth Regulatory Activities of Novel α-Furfuryl-2-alkylaminophosphonates

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