Green synthesis of diethyl((2-iodo-4-(trifluoromethyl)phenyl)amino)(aryl)methyl)phosphonates as potent α-glucosidase inhibitors

• Published in: Synthetic communications Vol. 50; no. 4; pp. 587 - 601
• Main Authors: Shaik, Mahammad Sadik, Nadiveedhi, Maheshwara Reddy, Gundluru, Mohan, Poola, Sreelakshmi, Allagadda, Rajasekhar, Chippada, Appa Rao, Cirandur, Suresh Reddy
• Format: Journal Article
• Language: English
• Published: Philadelphia Taylor & Francis 16-02-2020; Taylor & Francis Ltd
• Subjects: Acarbose; Aldehydes; Anatase; anatase TiO; Aniline; Aromatic compounds; Chemical synthesis; Glucosidase; Inhibitors; Kabachnik-fields reaction; Molecular docking; Nanoparticles; Phosphonates; Titanium dioxide; α-glucosidase inhibitory activity
• ISSN: 0039-7911; 1532-2432
• DOI: 10.1080/00397911.2019.1709208

Novel diethyl((2-iodo-4-(trifluoromethyl)phenyl)amino)(aryl)methyl)phosphonates (4a-j) were synthesized via a simple and efficient one pot by three-component condensation reaction (Kabachnik-Fields reaction) of 2-iodo-4-trifluoromethyl aniline, aromatic aldehydes and diethyl phosphite in presence of anatase TiO
2
nanoparticles as catalyst under solvent free conditions. The molecular docking studies of synthesized compounds with α-glucosidase enzyme revealed that these compounds have strong α-glucosidase inhibitory activity. The synthesized compounds (4a-j) are also screened for in vitro α-glucosidase inhibitory activity and the results showed compound 4i as the strongest inhibitor and compounds 4a, 4b, 4f and 4g as stronger inhibitors even better than the reference standard acarbose.