Novel pyridine-2,4,6-tricarbohydrazide derivatives: Design, synthesis, characterization and in vitro biological evaluation as α- and β-glucosidase inhibitors

Riaz, Sadaf; Khan, Islam Ullah; Yar, Muhammad; Ashraf, Muhammad; Rehman, Tanzeel U.; Shaukat, Ayesha; Jamal, Syed Babar; Duarte, Vera C. M.; Alves, M. I. Caetano

doi:10.1016/j.bioorg.2014.10.007

Cited by 13 publications

(11 citation statements)

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“…The desired 2,4,6‐trisubstituted pyridine tricarbohydrazides ( 4a–i ) were prepared in good to excellent yields (59–92%) as shown in Table . The preparation of pyridine‐2,4,6‐tricarbohydrazide followed the reported method by our research group . The synthesis of the thiourea was carried out by the reaction of pyridine‐2,4,6‐tricarbohydrazide ( 2 ) with various substituted phenyl isothiocyanates ( 3a–i ) (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

“…Melting points were measured on a Buchi 434 melting point apparatus and are uncorrected. For the detailed synthesis of compounds 1 and 2 please see our previous paper …”

Section: Methodsmentioning

confidence: 99%

“…Docking studies aims: (1) specific structural modeling, (2) the accurate prediction of the activity. MOE‐Dock was selected because it allows ligands to be flexible during docking so that they can adjust their conformations in the binding pocket of the receptor.…”

Section: Introductionmentioning

confidence: 99%

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Novel pyridine‐2,4,6‐tricarbohydrazide thiourea compounds as small key organic molecules for the potential treatment of type‐2 diabetes mellitus: In vitro studies against yeast α‐ and β‐glucosidase and in silico molecular modeling

Rehman

Riaz

Khan

et al. 2017

Archiv der Pharmazie

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A range of novel pyridine-2,4,6-tricarbohydrazide thiourea compounds (4a-i) were synthesized in good to excellent yields (63-92%). The enzyme inhibitory potentials of these compounds were investigated against α-and β-glucosidases because these enzymes play a crucial role in treating type-2 diabetes mellitus (T2DM). As compared to the reference compound acarbose (IC 50 38.22 ± 0.12 μM), compounds 4i (IC 50 25.49 ± 0.67 μM), 4f (IC 50 28.91 ± 0.43 μM), 4h (IC 50 30.66 ± 0.52 μM), and 4e (IC 50 35.01 ± 0.45 μM) delivered better inhibition against α-glucosidase and were quite inactive/completely inactive against β-glucosidase. The structure-activity relationship of these compounds was developed and elaborated with the help of molecular docking studies. K E Y W O R D S2,4,6-tricarbohydrazide, α-glucosidase, acarbose, diabetes mellitus type-2, pyridine derivatives, thiourea

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Section: Resultsmentioning

confidence: 99%

“…Melting points were measured on a Buchi 434 melting point apparatus and are uncorrected. For the detailed synthesis of compounds 1 and 2 please see our previous paper …”

Section: Methodsmentioning

confidence: 99%

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Novel pyridine‐2,4,6‐tricarbohydrazide thiourea compounds as small key organic molecules for the potential treatment of type‐2 diabetes mellitus: In vitro studies against yeast α‐ and β‐glucosidase and in silico molecular modeling

Rehman

Riaz

Khan

et al. 2017

Archiv der Pharmazie

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“…In current studies, we selected pyridine-2,4,6-tricarbohydrazide 3 [26] as starting material to prepare a range of compounds 4a-4i (Scheme 1). Pyridine-2,4,6-tricarbohydrazide 3 was reacted with a number of selected commercially available sulfonyl chlorides in the presence of aqueous Na 2 CO 3 solution (basic pH) [30].…”

Section: Chemistrymentioning

confidence: 99%

“…The high desire and need for the development of potent dual inhibitors for the treatment of both AD and DM [12,27], and our continued research efforts for the synthesis and evaluation of AChE, BChE and α-glucosidase inhibitors [22][23][24][25][26]. In this paper, we report the synthesis of a series of new pyridine sulfonamide derivatives and their in vitro AChE, BChE and α-glucosidase inhibition activities and in silico molecular modeling studies to uncover the binding patterns of these compounds with respective targeted proteins.…”

Section: Introductionmentioning

confidence: 99%

Pyridine sulfonamide as a small key organic molecule for the potential treatment of type-II diabetes mellitus and Alzheimer’s disease: In vitro studies against yeast α-glucosidase, acetylcholinesterase and butyrylcholinesterase

Riaz

Khan

Bajda

et al. 2015

Bioorganic Chemistry

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Synthesis, density functional theory calculations and luminescence of lanthanide complexes with 2,6‐bis[(3‐methoxybenzylidene)hydrazinocarbonyl] pyridine Schiff base ligand

et al. 2017

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A pyridine-diacylhydrazone Schiff base ligand, L = 2,6-bis [(3-methoxy benzylidene) hydrazinocarbonyl]pyridine was prepared and characterized by single crystal X-ray diffraction. homogeneous and heterogeneous catalysis. [16][17][18] Following our recently published work towards the complexation of lanthanide(III) nitrate salts with dimethyl pyridine-2,6-dicarboxylate, we were interested in the synthesis of a 2,6-bis [(3-methoxybenzylidene)hydrazine carbonyl]pyridine L ligand derived from dimethyl pyridine-2,6-dicarboxylate ligand. [19] In comparison with dimethyl pyridine-2,6-dicarboxylate ligand, the L ligand possesses more coordination sites that can bind and stabilize different lanthanide metal ions with high coordination numbers. Moreover it has flexible groups that can accommodate and protect lanthanide metal atoms from solvent molecules, which avoid non-radiative deactivation processes. [20] Moreover, L is efficient in the displacement of water molecules present in the coordination sphere of lanthanide ions that quenches the luminescence by absorption of the emitted radiation in the vibrational excitation processes via the vibrational levels of the O-H of water molecules. [21] This work reports the synthesis of the L ligand by a condensation reaction between 2-methoxybenzaldehyde and 2,6-bis(hydrazinocarbonyl)pyridine in ethanol and describes its crystal structure. Additionally the coordinating behavior of L with lanthanide metals (Ln = La, Pr, Nd, Sm, Eu, Gd, Tb, Dy and Er) has been investigated by elemental analysis, conductivity measurements, spectral analysis (IR, NMR, UV-Vis and mass) and thermal studies.The antioxidant activity and photoluminescence properties of L and Ln-L have been investigated.

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Novel pyridine-2,4,6-tricarbohydrazide derivatives: Design, synthesis, characterization and in vitro biological evaluation as α- and β-glucosidase inhibitors

Cited by 13 publications

References 50 publications

Novel pyridine‐2,4,6‐tricarbohydrazide thiourea compounds as small key organic molecules for the potential treatment of type‐2 diabetes mellitus: In vitro studies against yeast α‐ and β‐glucosidase and in silico molecular modeling

Novel pyridine‐2,4,6‐tricarbohydrazide thiourea compounds as small key organic molecules for the potential treatment of type‐2 diabetes mellitus: In vitro studies against yeast α‐ and β‐glucosidase and in silico molecular modeling

Pyridine sulfonamide as a small key organic molecule for the potential treatment of type-II diabetes mellitus and Alzheimer’s disease: In vitro studies against yeast α-glucosidase, acetylcholinesterase and butyrylcholinesterase

Synthesis, density functional theory calculations and luminescence of lanthanide complexes with 2,6‐bis[(3‐methoxybenzylidene)hydrazinocarbonyl] pyridine Schiff base ligand

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