Efficient Method for Removal of a Carboxylic Acid Moiety from Sterically Crowded Cyclopropanedicarboxylic Acid Derivatives

1996 ◽  
Vol 26 (11) ◽  
pp. 2127-2133 ◽  
Author(s):  
Zoltán Hell ◽  
László TŌke
Keyword(s):  
Carboxylic Acid ◽  
Efficient Method ◽  
Acid Moiety

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.

THE APPLICATION OF THE ARNDT–EISTERT REACTION TO THE SYNTHESIS OF FATTY ACIDS OF HIGH MOLECULAR WEIGHT

1950 ◽  
Vol 28b (9) ◽  
pp. 556-560 ◽  
Author(s):  
F. A. Vandenheuvel ◽  
P. Yates
Keyword(s):  
Fatty Acids ◽  
Molecular Weight ◽  
Carboxylic Acid ◽  
Stearic Acid ◽  
High Molecular Weight ◽  
Efficient Method ◽  
Convenient Method ◽  
Ultraviolet Absorption ◽  
Aliphatic Carboxylic Acid ◽  
Eicosanoic Acid

The Arndt–Eistert reaction offers a convenient method for the synthesis of the higher members of the aliphatic carboxylic acid series. Nonadecanoic acid, eicosanoic acid, and heneicosanoic acid have been prepared successively from stearic acid in good yields. An efficient method of purification of the synthetic products is described. The ultraviolet absorption maxima for some diazoketones derived from the higher members of the aliphatic carboxylic acid series are recorded.

scholarly journals A new solvate of epalerstat, a drug for diabetic neuropathy

2017 ◽  
Vol 73 (8) ◽  
pp. 1264-1267 ◽  
Author(s):  
Okky Dwichandra Putra ◽  
Daiki Umeda ◽  
Kaori Fukuzawa ◽  
Mihoko Gunji ◽  
Etsuo Yonemochi
Keyword(s):  
Hydrogen Bond ◽  
Acetic Acid ◽  
Carboxylic Acid ◽  
Hydrogen Bonds ◽  
Diabetic Neuropathy ◽  
Dihedral Angle ◽  
Phenyl Ring ◽  
Acid Moiety ◽  
Acta Cryst ◽  
Carboxylic Acid Groups

Epalerstat {systematic name: (5Z)-5-[(2E)-2-methyl-3-phenylprop-2-en-1-ylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidine-3-acetic acid} crystallized as an acetone monosolvate, C15H13NO3S2·C3H6O. In the epalerstat molecule, the methylpropylenediene moiety is inclined to the phenyl ring and the five-membered rhodamine ring by 21.4 (4) and 4.7 (4)°, respectively. In addition, the acetic acid moiety is found to be almost normal to the rhodamine ring, making a dihedral angle of 85.1 (2)°. In the crystal, a pair of O—H...O hydrogen bonds between the carboxylic acid groups of epalerstat molecules form inversion dimers with an R 2 2(8) loop. The dimers are linked by pairs of C—H...O hydrogen bonds, enclosing R 2 2(20) loops, forming chains propagating along the [101] direction. In addition, the acetone molecules are linked to the chain by a C—H...O hydrogen bond. Epalerstat acetone monosolvate was found to be isotypic with epalerstat tertrahydrofuran solvate [Umeda et al. (2017). Acta Cryst. E73, 941–944].

scholarly journals Molecular insight into carboxylic acid–alkali metal cations interactions: reversed affinities and ion-pair formation revealed by non-linear optics and simulations

2019 ◽  
Vol 21 (21) ◽  
pp. 11329-11344 ◽  
Author(s):  
Adrien Sthoer ◽  
Jana Hladílková ◽  
Mikael Lund ◽  
Eric Tyrode
Keyword(s):  
Carboxylic Acid ◽  
Alkali Metal ◽  
Metal Cations ◽  
Pair Formation ◽  
Alkali Metal Cations ◽  
Linear Optics ◽  
Acid Moiety ◽  
Non Linear Optics ◽  
Relative Affinity ◽  
Insight Into

Alkali metal cations’ relative affinity to the carboxylic acid moiety is pH dependent, and typically remain hydrated.

Preparation of sulfonic acid functional proton conducting phosphazenes by covalent protection

2017 ◽  
Vol 8 (19) ◽  
pp. 3022-3033 ◽  
Author(s):  
Elif Büşra Çelebi ◽  
Ferda Hacıvelioğlu
Keyword(s):  
Efficient Method ◽  
Sulfonic Acid ◽  
Acid Moiety ◽  
Proton Conducting

An easy and efficient method has been developed for preparation of sulfonic acid functional cyclic and polymeric phosphazenes by selective covalent protection of the sulfonic acid moiety.

Synthesis of Hippospongic Acid A Analogues Designed for Investigating the Structure-Activity Relationship of its Biological Activity

2000 ◽  
Vol 53 (12) ◽  
pp. 909 ◽  
Author(s):  
Yoshikazu Hiraga ◽  
Mariko Ago ◽  
Munetaka Tokumasu ◽  
Ken Kaku ◽  
Katsuo Ohkata
Keyword(s):  
Biological Activity ◽  
Carboxylic Acid ◽  
Sea Urchin ◽  
Essential Feature ◽  
Structure Activity Relationship ◽  
Activity Relationship ◽  
Acid Moiety ◽  
Sea Urchin Embryos ◽  
Structure Activity ◽  
Relationship Of

Analogues of hippospongic acid A, which inhibit the gastrulation of sea urchin embryos, were synthesized. From a study on structure—activity relationships, the conjugated carboxylic acid moiety was found to be an essential feature for biological activity.

Direct C(sp3)–H Activation of Carboxylic Acids

Synthesis ◽  
2019 ◽  
Vol 52 (04) ◽  
pp. 479-488 ◽  
Author(s):  
Alexander Uttry ◽  
Manuel van Gemmeren
Keyword(s):  
Carboxylic Acid ◽  
General Solution ◽  
Carboxylic Acids ◽  
Bond Activation ◽  
Acid Moiety ◽  
Group Approach ◽  
Research Fields ◽  
Directing Group ◽  
Aliphatic Carboxylic Acids

Carboxylic acids are important in a variety of research fields and applications. As a result, substantial efforts have been directed towards the C–H functionalization of such compounds. While the use of the carboxylic acid moiety as a native directing group for C(sp2)–H functionalization reactions is well established, as yet there is no general solution for the C(sp3)–H activation of aliphatic carboxylic acids and most endeavors have instead relied on the introduction of stronger directing groups. Recently however, novel ligands, tools, and strategies have emerged, which enable the use of free aliphatic carboxylic acids in C–H-activation-based transformations.1 Introduction2 Challenges in the C(sp3)–H Bond Activation of Carboxylic Acids3 The Lactonization of Aliphatic Carboxylic Acids4 The Directing Group Approach5 The Direct C–H Arylation of Aliphatic Carboxylic Acids6 The Direct C–H Olefination of Aliphatic Carboxylic Acids7 The Direct C–H Acetoxylation of Aliphatic Carboxylic Acids8 Summary

scholarly journals The Synthesis of 2, 2-Dimethyl-3, 3-dichlorocyclopropane Carboxylic Acid, a Novel Active Acid Moiety of Pyrethroids

1974 ◽  
Vol 38 (8) ◽  
pp. 1511-1514 ◽  
Author(s):  
Takeshi KITAHARA ◽  
Keimei FUJIMOTO ◽  
Masanao MATSUI
Keyword(s):  
Carboxylic Acid ◽  
Acid Moiety
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