In silico??????? molecular docking study and nano TiO2-SiO2 catalyzed microwave facilitated synthesis of new bis(a-aminophosphonates) as potential anti-diabetic agents

被引:3
作者
Kumar, Mahankali Pavan Phani [1 ]
Vejendla, Anuradha [1 ]
Malar, C. Gladis Raja [2 ]
Chennamsetty, Subramanyam [3 ]
Talari, Subrahmanyam [4 ,5 ]
Vedula, Nagalakshmi [6 ]
机构
[1] Vignan Degree Coll, Dept Chem, Guntur 522005, Andhra Pradesh, India
[2] Vel Tech Multi Tech Dr RR & Dr SR Engn Coll, Dept Chem, Chennai, Tamil Nadu, India
[3] Bapatla Engn Coll Autonomous, Dept Chem Engn & PG Studies, Bapatla, India
[4] SIR CR Reddy Coll, Dept Chem, Eluru, India
[5] Acharya Nagarjuna Univ, Dept Chem, Guntur, India
[6] Ch SD St Theresas Coll Women Autonomous, Dept Chem, Eluru, Andhra Pradesh, India
关键词
Bis(alpha-aminophosphonates); nano TiO2; SiO2; microwave; Kabachnik-Fields reaction; alpha-amylase; alpha-glucosidase enzyme; ONE-POT SYNTHESIS; KABACHNIK-FIELDS REACTION; SOLVENT-FREE SYNTHESIS; ALPHA-AMINOPHOSPHONATES; 3-COMPONENT CONDENSATION; MACROCYCLIC INHIBITORS; EFFICIENT CATALYST; REUSABLE CATALYST; GREEN PROCEDURE; ACID;
D O I
10.1080/10426507.2023.2198715
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
In the present work, we have developed a greener approach to synthesize a series of novel bis(a- aminophosphonates) (bis(a-Aps)) via a microwave-mediated nano TiO2-SiO2 catalyzed KabachnikFields (K-F) reaction under solvent-free conditions. An in silico molecular docking analysis was performed on all the designed molecules prior to their synthesis to get insight into their capacity to block the enzymes, a-amylase (PDB ID:3IJ8) and a-glucosidase (PDB ID:1OBB). The molecules with significant binding affinity were synthesized and spectroscopically analyzed to confirm their structure. They were screened further in vitro for their inhibitory activity on the target enzymes. When compared with the reference drug, the compounds diethyl[(2H-1,3-benzodioxol-5-yl)[(6-{[(2H-1,3-benzo-dioxol-5-yl)(diethoxyphosphoryl)-methyl]amino}-10,10-dioxo-9H-10?(6)-thioxanthen-3-yl)amino]-methyl] phosphonate (4h), diethyl [(anthracen-9-yl)[(6-{[(anthracen-9-yl)(diethoxyphosphoryl)methyl]amino}- 10,10-dioxo-9H-10?(6)-thioxanthen-3-yl)amino]-methyl]phosphonate (4i) have shown greater inhibition, and diethyl{[(6-{[(diethoxyphosphoryl)(phenyl)methyl]amino}-10,10-dioxo-9H-10?(6)-thioxanthen-3-yl)ami-no](phenyl)methyl}phosphonate (4a), diethyl {[(6-{[(diethoxyphosphoryl)(4-hydroxy-3-nitrophenyl) methyl]amino}-10,10-dioxo-9H-10?(6)-thioxanthen-3-yl)amino](4-hydroxy-3-nitrophenyl)methyl}phosph-onate (4e) have shown equal inhibition against the a-amylase enzyme. Compounds diethyl{[(6-{[(diethoxyphosphoryl)(phenyl)methyl]amino}-10,10-dioxo-9H-10?(6)-thioxanthen-3-yl)-amino](phenyl) methyl}phosphonate (4a), diethyl[(2H-1,3-benzodioxol-5-yl)[(6-{[(2H-1,3-benzodioxol-5-yl)(diethoxyphos-phoryl) methyl]amino}-10,10-dioxo-9H-10?(6)-thioxanthen-3-yl)amino]methyl]phosphonate (4h), and diethyl [(anthracen-9-yl)[(6-{[(anthracen-9-yl)(diethoxyphosphoryl)methyl]amino}-10,10-dioxo-9H-10?(6)-thioxanthen-3-yl)amino]-methyl]phosphonate (4i) have shown superior inhibition and dieth yl{[(6-{[(diethoxyphosphoryl)(naphthalen-1-yl)methyl]amino}-10,10-dioxo-9H-10?(6)-thioxanthen-3-yl) amino](naphthalen-1-yl)methyl}phosphonate (4 g) has shown equal inhibition against the a-glucosidase enzyme. All the remaining compounds displayed modest to good inhibition when compared with the reference drug, Acarbose.
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页码:808 / 821
页数:14
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