Syntheses, biological evaluation of some novel substituted benzoic acid derivatives bearing hydrazone as linker

Mishra, Ganesh Prasad; Sharma, Rajesh; Jain, Mukul; Bandyopadhyay, Debdutta

doi:10.1007/s11164-021-04555-y

Cited by 5 publications

(5 citation statements)

References 23 publications

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“…PABA and its derivatives exhibit a wide range of biological activities such as, antioxidant, [21,22] antibacterial, [23] anticancer, [24] antitumor, [25] anticholinergic, [22] antiphospholipaz and antiprotease, [26] antiplatelet, [27] and hypoglycemic activity. [28] Combining the molecules from two or more compound classes into a single molecule by chemical reactions is known as molecular hybridization. Molecular hybridization is a good drug design strategy.…”

Section: Introductionmentioning

confidence: 99%

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Novel Benzoic Acid Derivatives Bearing Quinazolin‐4(3H)‐one Ring: Synthesis, Characterization, and Inhibition Effects on α‐Glucosidase and α‐Amylase

Tokalı

2022

ChemistrySelect

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In this study, new benzoic acid derivatives of the quinazolinone ring, which is one of the biologically active members of nitrogen-containing heterocyclic compounds, were synthesized with excellent yields (98-90 %). The structures of the novel compounds (1-12) were characterized with Fourier-transform Infrared (FTIR), Nuclear Magnetic Resonance ( 1 H NMR-13 C NMR), and High-Resolution Mass Spectroscopy (HRMS). α-Glucosidase and α-Amylase inhibition properties were examined to evaluate the anti-diabetic properties of the synthesized compounds. For α-Glucosidase, molecules showed IC 50 in ranging of > 100-3.468 � 0.270 μM and K i s in ranging of > 100-3.310 � 0.326 μM. For α-Amylase, molecules showed IC 50 in ranging of > 100-1.215 � 0.225 μM. 4-[(2-[(4-phenylpiperazin-1-yl)methyl]-4-oxoquinazolin-3(4H)-ylimino)methyl]benzoicacid (10) has the strongest inhibitory effect for both enzymes. It is 5.4 times more potent inhibitor for α-Glucosidase and 34.9 times more potent for α-Amylase than the standard inhibitor Acarbose. Also, the molecular docking study was carried out for the most active compound for the determination of ligand-enzyme interactions. Binding affinities of the most active compound were calculated as À 5.978 kcal/mol and À 5.548 kcal/mol for α-Glucosidase and α-Amylase, respectively. The aromatic ring and the aminomethyl group of the quinazoline and the carboxyl group moieties have played a critical role in the inhibition.

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Section: Introductionmentioning

confidence: 99%

“…PABA plays important roles in a wide variety of metabolic processes. PABA and its derivatives exhibit a wide range of biological activities such as, antioxidant, [21,22] antibacterial, [23] anticancer, [24] antitumor, [25] anticholinergic, [22] antiphospholipaz and antiprotease, [26] antiplatelet, [27] and hypoglycemic activity [28] …”

Section: Introductionmentioning

confidence: 99%

Novel Benzoic Acid Derivatives Bearing Quinazolin‐4(3H)‐one Ring: Synthesis, Characterization, and Inhibition Effects on α‐Glucosidase and α‐Amylase

Tokalı

2022

ChemistrySelect

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“…Arm I polar residues interact with the carboxylate group: His323 and His449 are involved in salt-bridges interactions, while Ser289 and Tyr473 stabilize the ligand through hydrogen bonds. Arm II residues stabilize the hydrophobic fatty acids tail via van der Waals interactions (Figure 2A) [27,28].…”

Section: Pparγ Ligand Binding Modementioning

confidence: 99%

A Combined Molecular Dynamics and Hydropathic INTeraction (HINT) Approach to Investigate Protein Flexibility: The PPARγ Case Study

Agosta,

Cozzini

2024

Molecules

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Molecular Dynamics (MD) is a computational technique widely used to evaluate a molecular system’s thermodynamic properties and conformational behavior over time. In particular, the energy analysis of a protein conformation ensemble produced though MD simulations plays a crucial role in explaining the relationship between protein dynamics and its mechanism of action. In this research work, the HINT (Hydropathic INTeractions) LogP-based scoring function was first used to handle MD trajectories and investigate the molecular basis behind the intricate PPARγ mechanism of activation. The Peroxisome Proliferator-Activated Receptor γ (PPARγ) is an emblematic example of a highly flexible protein due to the extended ω-loop delimiting the active site, and it is responsible for the receptor’s ability to bind chemically different compounds. In this work, we focused on the PPARγ complex with Rosiglitazone, a common anti-diabetic compound and analyzed the molecular basis of the flexible ω-loop stabilization effect produced by the Oleic Acid co-binding. The HINT-based analysis of the produced MD trajectories allowed us to account for all of the energetic contributions involved in interconverting between conformational states and describe the intramolecular interactions between the flexible ω-loop and the helix H3 triggered by the allosteric binding mechanism.

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“…Long-term human use of plant extracts provides reliable evidence for diabetes treatment in traditional medicine system. The plant extract contains a variety of phytochemicals that contain many primary and secondary metabolites that can enhance the efficacy of plant-related drugs in treating disease [6].…”

Section: Medicinal Plantsmentioning

confidence: 99%

“…Injections of hypoglycaemic agents are used in Western medical treatment for diabetes (insulin, insulin analogs, etc. ), the pharmacotherapy suggests that the biguanides, glinides, sulfonylureas and glycosidase inhibitors, thiazolidinedione used as hypoglycaemic medications in oral formulations [5,6]. These medications have some adverse effects such as severe hypoglycaemia, weight gain, gastrointestinal discomfort, and nausea [7].…”

Section: Introductionmentioning

confidence: 99%

Plant bioactive compounds and their mechanistic approaches in the treatment of diabetes: a review

et al. 2022

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Background Diabetes mellitus (DM) is a growing disease across the world; diabetes is a complex metabolic disorder in which blood glucose concentration level increases and continue for a prolonged period due to a decrease secretion of insulin or action, resulting in the disorder of carbohydrate, lipid, and protein metabolism. The plant-related bioactive compounds have proven their efficacy with least toxicities and can be utilized for the disease treatment. Our objective is to elucidate the mechanism of action of plant bioactive compounds which can give future direction in diabetes treatment. Main body In this review paper, we briefly study more than 200 research papers related to disease and bioactive compounds that have therapeutic applicability in treatment. The plant contains many bio-active compounds which possess in vitro and in vivo anti-diabetic effect which may be responsible for the hypoglycaemic property by inhibiting the digestive enzyme i.e. alpha-amylase and alpha-glucosidase, by producing mimetic action of insulin, by reducing the oxidative stress, by showing antihyperglycemic activity and hypolipidemic activity, by inhibition of aldose reductase, and by increasing or enhancing glucose uptake and insulin secretion. Conclusion Our study revealed that terpenes, tannin, flavonoids, saponin, and alkaloids are important bioactive constituents for anti-diabetic activity. The mechanistic approach on alpha-glucosidase and alpha-amylase, hypolipidemic activity, and AR inhibitory action clear-cut explain the therapeutic applicability of these bioactive compounds in disease. Plants that contain these bioactive compounds can be good drug candidates for future research on diabetes treatment.

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Syntheses, biological evaluation of some novel substituted benzoic acid derivatives bearing hydrazone as linker

Cited by 5 publications

References 23 publications

Novel Benzoic Acid Derivatives Bearing Quinazolin‐4(3H)‐one Ring: Synthesis, Characterization, and Inhibition Effects on α‐Glucosidase and α‐Amylase

Novel Benzoic Acid Derivatives Bearing Quinazolin‐4(3H)‐one Ring: Synthesis, Characterization, and Inhibition Effects on α‐Glucosidase and α‐Amylase

A Combined Molecular Dynamics and Hydropathic INTeraction (HINT) Approach to Investigate Protein Flexibility: The PPARγ Case Study

Plant bioactive compounds and their mechanistic approaches in the treatment of diabetes: a review

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