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

被引：11

作者：

Shaik, Mahammad Sadik ^{[1
]}

Nadiveedhi, Maheshwara Reddy ^{[1
]}

Gundluru, Mohan ^{[1
,2
]}

Poola, Sreelakshmi ^{[1
]}

Allagadda, Rajasekhar ^{[3
]}

Chippada, Appa Rao ^{[3
]}

Cirandur, Suresh Reddy ^{[1
,4
]}

机构：

[1] Sri Venkateswara Univ, Dept Chem, Tirupati 517502, Andhra Pradesh, India

[2] Sri Venkateswara Univ, DST PURSE Ctr, Tirupati, Andhra Pradesh, India

[3] Sri Venkateswara Univ, Dept Biochem, Tirupati, Andhra Pradesh, India

[4] Univ Malaysia Kelantan, Inst Food Secur & Sustainable Agr, Kampus Jeli, Jeli, Kelantan, Malaysia

来源：

SYNTHETIC COMMUNICATIONS | 2020年 / 50卷 / 04期

关键词：

Acarbose; anatase TiO2 nanoparticles; alpha-glucosidase inhibitory activity; Kabachnik-fields reaction; molecular docking; KABACHNIK-FIELDS REACTION; AMINO PHOSPHONIC-ACIDS; ASYMMETRIC-SYNTHESIS; ANTIVIRAL ACTIVITIES; MEDIATED SYNTHESIS; AMINOPHOSPHONATES; DERIVATIVES; PHOSPHITES; PROTOCOL; DESIGN;

D O I：

10.1080/00397911.2019.1709208

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 TiO2 nanoparticles as catalyst under solvent free conditions. The molecular docking studies of synthesized compounds with alpha-glucosidase enzyme revealed that these compounds have strong alpha-glucosidase inhibitory activity. The synthesized compounds (4a-j) are also screened for in vitro alpha-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.

引用

页码：587 / 601

页数：15

共 43 条

[1] Bronsted acid-mediated synthesis of α-amino phosphonates under solvent-free conditions [J].

Akiyama, T ;

Sanada, M ;

Fuchibe, K .

SYNLETT, 2003, (10) :1463-1464

[2] PHOSPHONOPEPTIDES, A NEW CLASS OF SYNTHETIC ANTIBACTERIAL AGENTS [J].

ALLEN, JG ;

ATHERTON, FR ;

HALL, MJ ;

HASSALL, CH ;

HOLMES, SW ;

LAMBERT, RW ;

NISBET, LJ ;

RINGROSE, PS .

NATURE, 1978, 272 (5648) :56-58

[3] One-pot synthesis of α-aminophosphonates catalyzed by antimony trichloride adsorbed on alumina [J].

Ambica ;

Kumar, Satish ;

Taneja, Subhash C. ;

Hundal, Maninder S. ;

Kapoor, Kamal K. .

TETRAHEDRON LETTERS, 2008, 49 (14) :2208-2212

[4] A mild and highly efficient protocol for the one-pot synthesis of primary α-amino phosphonates under solvent-free conditions [J].

Azizi, N ;

Rajabi, F ;

Saidi, MR .

TETRAHEDRON LETTERS, 2004, 45 (50) :9233-9236

[5] Zirconium(IV) compounds as efficient catalysts for synthesis of α-aminophosphonates [J].

Bhagat, Srikant ;

Chakraborti, Asit K. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (15) :6029-6032

[6] An extremely efficient three-component reaction of aldehydes/ketones, amines, and phosphites (Kabachnik-Fields reaction) for the synthesis of α-aminophosphonates catalyzed by magnesium perchlorate [J].

Bhagat, Srikant ;

Chakraborti, Asit K. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (04) :1263-1270

[7] SYNTHESIS OF NOVEL N-PHOSPHONOALKYL DIPEPTIDE INHIBITORS OF HUMAN COLLAGENASE [J].

BIRD, J ;

DEMELLO, RC ;

HARPER, GP ;

HUNTER, DJ ;

KARRAN, EH ;

MARKWELL, RE ;

MILESWILLIAMS, AJ ;

RAHMAN, SS ;

WARD, RW .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (01) :158-169

[8] Increasing permeability of phospholipid bilayer membranes to alanine with synthetic α-aminophosphonate carriers [J].

Danila, Delia C. ;

Wang, Xinyan ;

Hubble, Heather ;

Antipin, Igor S. ;

Pinkhassik, Eugene .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (07) :2320-2323

[9] RCM-mediated synthesis of trifluoromethyl-containing nitrogen heterocycles [J].

De Matteis, Valeria ;

van Delft, Floris L. ;

Jakobi, Harald ;

Lindell, Stephen ;

Tiebes, Jorgg ;

Rutjes, Floris P. J. T. .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (20) :7527-7532

[10] OPTICALLY-ACTIVE 1-AMINOALKYLPHOSPHONIC ACIDS [J].

DHAWAN, B ;

REDMORE, D .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1987, 32 (3-4) :119-144

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