Cyclic amide derivatives as potential prodrugs. Synthesis and evaluation of N-hydroxymethylphthalimide esters of some non-steroidal anti-inflammatory carboxylic acid drugs

1998 ◽  
Vol 33 (2) ◽  
pp. 123-131 ◽  
Author(s):  
Farghaly A. Omar
Keyword(s):  
Carboxylic Acid ◽  
Amide Derivatives ◽  
Cyclic Amide ◽  
Anti Inflammatory

Design and Synthesis of Novel Ibuprofen Derivatives as Selective COX-2 inhibitors and potential anti-inflammatory agents: Evaluation of PGE2, TNF-α, IL-6 and histopathological study

2021 ◽  
Vol 17 ◽  
Author(s):  
Peter Amir Halim ◽  
Hala Bakr El-Nassan ◽  
Yara Sayed El-Dash
Keyword(s):  
Carboxylic Acid ◽  
Gastric Mucosa ◽  
Docking Simulation ◽  
Histopathological Study ◽  
Acid Moiety ◽  
Rat Serum ◽  
Tnf Α ◽  
Cox 2 ◽  
Anti Inflammatory

Background: The reported binding mode of ibuprofen in the COX-2 binding site indicated that the carboxylic group binds with Arg-120 and Tyr-355 at the entrance of the cyclooxygenase channel and does not extend into the pocket. This accounted for the non-selectivity of ibuprofen. Based on this fact, we assumed that extending the length of the carboxylic acid moiety in ibuprofen and adding more bulky rigid groups as well as bulky groups carrying H-bonding functions might increase the selectivity and reduce the side effects of ibuprofen while maintaining its analgesic and anti-inflammatory activities. Objective: In this work, four series of ibuprofen derivatives were designed and prepared. The compounds were designed by increasing the length of the carboxylate group along with the incorporation of large hydrophobic groups. Method: Four series of ibuprofen derivatives were synthesized starting from ibuprofen. Their chemical structure was confirmed by spectral data. All the compounds were tested for their COX inhibitory activity. Results : The best COX-2 activity and selectivity were obtained with compounds 5c and 5d, which were subjected to further in vivo testing (carrageenan-induced paw edema, rat serum PGE2, TNF- α and IL-6, hot plate latency test) to investigate their anti-inflammatory and analgesic activities as well as their effects on the gastric mucosa. The anti-inflammatory activity of both compounds was comparable to that of ibuprofen, diclofenac, and indomethacin. Both compounds suppressed the production of PGE2 as well as the rat serum concentrations of both TNF-α and IL-6. This potent anti-inflammatory and analgesic behavior was not accompanied by any effect on the gastric mucosa. Docking simulation studies of the two compounds explained the higher selectivity for the COX-2 enzyme. Conclusion: Potent and selective ibuprofen derivatives can be successively obtained by extending the length of the carboxylic acid moiety in ibuprofen and adding more bulky rigid groups as well as bulky groups with H-bonding functions.

Synthesis and evaluation of a novel series of 6-bromo-1-cyclopentyl-1H-indazole-4-carboxylic acid-substituted amide derivatives as anticancer, antiangiogenic, and antioxidant agents

2019 ◽  
Vol 29 (1) ◽  
pp. 17-32
Author(s):  
Ajay S. Sawant ◽  
Sonali S. Kamble ◽  
Parshuram M. Pisal ◽  
Rohan J. Meshram ◽  
Sanjay S. Sawant ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Antioxidant Agents ◽  
Amide Derivatives

scholarly journals Synthesis and Biological Evaluation of New Heteroaryl Carboxylic Acid Derivatives as Anti-inflammatory-Analgesic Agents

2013 ◽  
Vol 61 (2) ◽  
pp. 222-228 ◽  
Author(s):  
Khaled Abouzid Mohamed Abouzid ◽  
Nadia Abdalla Khalil ◽  
Eman Mohamed Ahmed ◽  
Sawsan Abo-Bakr Zaitone
Keyword(s):  
Carboxylic Acid ◽  
Biological Evaluation ◽  
Analgesic Agents ◽  
Anti Inflammatory ◽  
Synthesis And Biological Evaluation

Co-crystallization of anti-inflammatory pharmaceutical contaminants and rare carboxylic acid–pyridine supramolecular synthon breakdown

CrystEngComm ◽  
2018 ◽  
Vol 20 (41) ◽  
pp. 6377-6381 ◽  
Author(s):  
Qixuan Zheng ◽  
Samantha L. Rood ◽  
Daniel K. Unruh ◽  
Kristin M. Hutchins
Keyword(s):  
Carboxylic Acid ◽  
Mefenamic Acid ◽  
Supramolecular Synthon ◽  
Pharmaceutical Contaminants ◽  
Anti Inflammatory

Co-crystallization of the pharmaceutical contaminants mefenamic acid and naproxen is reported; one co-crystal exhibits a rare carboxylic acid–pyridine synthon breakdown.

scholarly journals A New Bithiophene from the Root of Echinops grijsii

2015 ◽  
Vol 10 (12) ◽  
pp. 1934578X1501001 ◽  
Author(s):  
Fang-Pin Chang ◽  
Chien-Chih Chen ◽  
Hui-Chi Huang ◽  
Sheng-Yang Wang ◽  
Jih-Jung Chen ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Cell Line ◽  
Natural Source ◽  
Inflammatory Activity ◽  
Raw 264.7 ◽  
Raw 264.7 Cell ◽  
Anti Inflammatory ◽  
First Time ◽  
Raw 264.7 Cell Line

A new bithiophene, 5-(4-hydroxy-3-methoxy-1-butyny)-2,2′-bithiophene (1), and sixteen known thiophenes: 2-(3,4-dihydroxybut-1-ynyl)-5-(penta-1,3-diynyl)thiophene (2), α-terthienyl (3), 5-(3,4-dihydroxybut-1-ynyl)-2,2′-bithiophene (4), 5-acetyl-2,2′-bithiophene (5), 5-formyl-2,2′-bithiophene (6), methyl 2,2′-bithiophene-5-carboxylate (7), 5-(but-3-en-1-ynyl)-2,2′-bithiophene (8), 5-(4-isovaleroyloxybut-1-ynyl)-2,2′-bithiophene (9), cardopatine (10), isocardopatine (11), 5-(3-hydroxy-4-isovaleroyloxybut-1-ynyl)-2,2′-bithiophene (12), 5-(3-hydroxymethyl-3-isovaleroyloxyprop-1-ynyl)-2,2′-bithiophene (13), 5-(4-hydroxy-1-butynyl)-2,2′-bithiophene (14), 5-(4-acetoxy-1-butynl)-2,2′-bithiophene (15), 2,2′-bithiophene-5-carboxylic acid (16) and 2-(4-hydroxybut-1-ynyl)-5-(penta-1,3-diynyl)thiophene (17) were isolated from the roots of Echinops grijisii Hance. Among them, compounds 6, 7 and 16 were isolated from a natural source for the first time. Compounds 2, 4 and 14 exhibited significant anti-inflammatory activity against nitrite of LPS-stimulated production in the RAW 264.7 cell line.

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