The effects of some benzoic acid derivatives on polymorphonuclear leukocyte accumulation in vivo

Background: Protein Tyrosine Phosphatase 1B (PTP1B) is an attractive target for antidiabetic drug discovery owing to its pivotal role as a negative regulator of insulin and leptin signaling. Objective: The objective of this research is to design, synthesize, and evaluate some acetamido benzoic acid derivatives as a novel class of protein tyrosine phosphatase 1B inhibitors with therapeutic potential for Type II diabetes. Methods: 3-(2-(benzo[d]thiazol-2-ylthio)acetamido)benzoic acid derivatives 4(a-j) were synthesized and characterized by employing spectral studies. All the synthesized compounds were screened for in vitro PTP1B inhibitory activity and the most potent compound in the series was also evaluated for in vivo anti-hyperglycemic activity using STZ induced diabetic Wistar rat model. Molecular docking studies were also performed with the most potent analog using FlexX docking algorithm to delineate its binding mode to the active site of the PTP1B. Results and Discussion: Among all the synthesized compounds, 3-(2-(benzo[d]thiazol-2-ylthio)acetamido)-4- methylbenzoic acid (4f) displayed good PTP1B inhibitory activity with an IC50 value of 11.17 μM. The compound also exhibited good anti-hyperglycemic efficacy in streptozotocin induced diabetic Wistar rats. Docking studies with 4f revealed the compound bound in the catalytic and second aryl binding site of the PTP1B. Conclusion: Overall, compound 4f with good in vitro PTP1B inhibitory potency and in vivo antihyperglycemic efficacy would be a valuable lead molecule for the development of acetamido benzoic acid based PTP1B inhibitors with antidiabetic potential.

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Bjerkandera adusta as a source of benzoic acid derivatives targeting 26S proteasome and cathepsins B&L

10.1055/s-0039-3399861 ◽

2019 ◽

Author(s):

K Georgousaki ◽

N Tsafantakis ◽

S Gumeni ◽

V González-Menéndez ◽

G Lambrinidis ◽

...

Keyword(s):

Benzoic Acid ◽

26S Proteasome ◽

Bjerkandera Adusta ◽

Benzoic Acid Derivatives

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2,4-Dichloro-5-[(N-aryl/alkyl)sulfamoyl]benzoic Acid Derivatives: In Vitro Antidiabetic Activity, Molecular Modeling and In silico ADMET Screening

Medicinal Chemistry ◽

10.2174/1573406414666180924164327 ◽

2019 ◽

Vol 15 (2) ◽

pp. 186-195 ◽

Cited By ~ 3

Author(s):

Samridhi Thakral ◽

Vikramjeet Singh

Keyword(s):

Molecular Docking ◽

Benzoic Acid ◽

Inhibitory Activity ◽

In Silico ◽

Computational Study ◽

Antidiabetic Activity ◽

Standard Drug ◽

Benzoic Acid Derivatives ◽

In Silico Admet ◽

Inhibitory Potential

Background: Postprandial hyperglycemia can be reduced by inhibiting major carbohydrate hydrolyzing enzymes, such as α-glucosidase and α-amylase which is an effective approach in both preventing and treating diabetes. Objective: The aim of this study was to synthesize a series of 2,4-dichloro-5-[(N-aryl/alkyl)sulfamoyl] benzoic acid derivatives and evaluate α-glucosidase and α-amylase inhibitory activity along with molecular docking and in silico ADMET property analysis. Method: Chlorosulfonation of 2,4-dichloro benzoic acid followed by reaction with corresponding anilines/amines yielded 2,4-dichloro-5-[(N-aryl/alkyl)sulfamoyl]benzoic acid derivatives. For evaluating their antidiabetic potential α-glucosidase and α-amylase inhibitory assays were carried out. In silico molecular docking studies of these compounds were performed with respect to these enzymes and a computational study was also carried out to predict the drug-likeness and ADMET properties of the title compounds. Results: Compound 3c (2,4-dichloro-5-[(2-nitrophenyl)sulfamoyl]benzoic acid) was found to be highly active having 3 fold inhibitory potential against α-amylase and 5 times inhibitory activity against α-glucosidase in comparison to standard drug acarbose. Conclusion: Most of the synthesized compounds were highly potent or equipotent to standard drug acarbose for inhibitory potential against α-glucosidase and α-amylase enzyme and hence this may indicate their antidiabetic activity. The docking study revealed that these compounds interact with active site of enzyme through hydrogen bonding and different pi interactions.

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Investigation of 2-Fluoro Benzoic Acid Derivatives as Influenza A Viral Sialidase Selective Inhibitors

Anti-Infective Agents in Medicinal Chemistry ◽

10.2174/187152110794785077 ◽

2010 ◽

Vol 9 (4) ◽

pp. 198-204 ◽

Cited By ~ 2

Author(s):

Sadagopan Magesh ◽

Nongluk Sriwilaijaroen ◽

Vats Savita ◽

Hiromune Ando ◽

Taeko Miyagi ◽

...

Keyword(s):

Benzoic Acid ◽

Influenza A ◽

Selective Inhibitors ◽

Benzoic Acid Derivatives

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

Research on Chemical Intermediates ◽

10.1007/s11164-021-04555-y ◽

2021 ◽

Author(s):

Ganesh Prasad Mishra ◽

Rajesh Sharma ◽

Mukul Jain ◽

Debdutta Bandyopadhyay

Keyword(s):

Benzoic Acid ◽

Biological Evaluation ◽

Benzoic Acid Derivatives

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Hydrogenation of benzoic acid derivatives over Pt/TiO2 under mild conditions

Communications Chemistry ◽

10.1038/s42004-021-00489-z ◽

2021 ◽

Vol 4 (1) ◽

Author(s):

Miao Guo ◽

Xiangtao Kong ◽

Chunzhi Li ◽

Qihua Yang

Keyword(s):

Electron Transfer ◽

Benzoic Acid ◽

High Efficiency ◽

Carboxyl Groups ◽

Carboxyl Group ◽

Benzoic Acids ◽

Catalyst Poisoning ◽

Benzoic Acid Derivatives ◽

Mild Conditions ◽

Transfer Direction

AbstractHydrogenation of benzoic acid (BA) to cyclohexanecarboxylic acid (CCA) has important industrial and academic significance, however, the electron deficient aromatic ring and catalyst poisoning by carboxyl groups make BA hydrogenation a challenging transformation. Herein, we report that Pt/TiO2 is very effective for BA hydrogenation with, to our knowledge, a record TOF of 4490 h−1 at 80 °C and 50 bar H2, one order higher than previously reported results. Pt/TiO2 catalysts with electron-deficient and electron-enriched Pt sites are obtained by modifying the electron transfer direction between Pt and TiO2. Electron-deficient Pt sites interact with BA more strongly than electron-rich Pt sites, helping the dissociated H of the carboxyl group to participate in BA hydrogenation, thus enhancing its activity. The wide substrate scope, including bi- and tri-benzoic acids, further demonstrates the high efficiency of Pt/TiO2 for hydrogenation of BA derivatives.

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Antifungal Activity of Chemical Constituents from Piper pesaresanum C. DC. and Derivatives against Phytopathogen Fungi of Cocoa

Molecules ◽

10.3390/molecules26113256 ◽

2021 ◽

Vol 26 (11) ◽

pp. 3256

Author(s):

Luis C. Chitiva-Chitiva ◽

Cristóbal Ladino-Vargas ◽

Luis E. Cuca-Suárez ◽

Juliet A. Prieto-Rodríguez ◽

Oscar J. Patiño-Ladino

Keyword(s):

Antifungal Activity ◽

Benzoic Acid ◽

Chemical Constituents ◽

Chemical Study ◽

Positive Control ◽

Positive Influence ◽

Phytopathogenic Fungi ◽

Phytochemical Study ◽

Benzoic Acid Derivatives ◽

First Time

In this study, the antifungal potential of chemical constituents from Piper pesaresanum and some synthesized derivatives was determined against three phytopathogenic fungi associated with the cocoa crop. The methodology included the phytochemical study on the aerial part of P. pesaresanum, the synthesis of some derivatives and the evaluation of the antifungal activity against the fungi Moniliophthora roreri, Fusarium solani and Phytophthora sp. The chemical study allowed the isolation of three benzoic acid derivatives (1–3), one dihydrochalcone (4) and a mixture of sterols (5–7). Seven derivatives (8–14) were synthesized from the main constituents, of which compounds 9, 10, 12 and 14 are reported for the first time. Benzoic acid derivatives showed strong antifungal activity against M. roreri, of which 11 (3.0 ± 0.8 µM) was the most active compound with an IC50 lower compared with positive control Mancozeb® (4.9 ± 0.4 µM). Dihydrochalcones and acid derivatives were active against F. solani and Phytophthora sp., of which 3 (32.5 ± 3.3 µM) and 4 (26.7 ± 5.3 µM) were the most active compounds, respectively. The preliminary structure–activity relationship allowed us to establish that prenylated chains and the carboxyl group are important in the antifungal activity of benzoic acid derivatives. Likewise, a positive influence of the carbonyl group on the antifungal activity for dihydrochalcones was deduced.

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