644-62-2Relevant academic research and scientific papers
Synthesis, crystal structures and spectroscopy of meclofenamic acid and its metal complexes with manganese(II), copper(II), zinc(II) and cadmium(II). Antiproliferative and superoxide dismutase activity
Kovala-Demertzi, Dimitra,Staninska, Malgorzata,Garcia-Santos, Isabel,Castineiras, Alfonso,Demertzis, Mavroudis A.
, p. 1187 - 1195 (2011)
Some new complexes of meclofenamic acid (N-(2,6-dichloro-m-tolyl) anthranilic acid), Hmeclo (1), with potentially interesting biological activities are described. Complexes [Mn(meclo)2] (2), [Cu(meclo) 2(H2O)2] (3), [Zn(meclo)2(H 2O)2] (4) and [Cd(meclo)2(H2O) 2] (5) were prepared and structurally characterized by means of vibrational, electronic and 1H and 13C NMR spectroscopies. The crystal structure of complexes [Cu4(meclo)6(OH) 2(DMSO)2]2DMSO (3a) and [Cd(meclo)2(DMSO) 3] (5a) have been determined by X-ray crystallography. Complex (3a) is a centrosymmetric tetramer built up around the planar cyclic Cu 2(OH)2 unit. Complex 5a is mononuclear seven-coordinated complex with the meclofenamato ligand behaving as a bidentate deprotonated chelating ligand. Intra and intermolecular hydrogen bonds stabilize these two structures, while the crystal packing is determined by π-π and C-H - π interactions. Meclofenamic acid and its metal complexes have been evaluated for antiproliferative activity in vitro against the cells of three human cancer cell lines, MCF-7 (breast cancer cell line), T24 (bladder cancer cell line), and A-549 (non-small cell lung carcinoma), and a mouse fibroblast L-929 cell line. Complex 5 exhibits the highest selectivity against MCF-7 and 4 shows the highest selectivity against T-24. Complexes 2-5 were found to be more potent cytotoxic agents against T-24 and complex 5 against MCF-7 cancer cell lines than the prevalent benchmark metallodrug, cis-platin. The superoxide dismutase activity was measured by the Fridovich test which showed that complex [Cu(meclo) 2(H2O)2] is a good superoxide scavenger.
COMPOSITIONS AND METHODS TO MODULATE CHLORIDE ION CHANNEL ACTIVITY
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Paragraph 0208, (2020/02/05)
Provided herein are small-molecules for use in modulating chloride ion channel (CLC) activity, particularly the activity of CLC-2, to elucidate the role of CLC-2 in disorders associated with CLC-2 malfunction, and to identify therapeutic leads for their treatment. Compositions and methods for modulating CLC activity are also provided. In certain aspects, the subject compounds and compositions are useful for imaging or channel pull-down studies.
High solubility piperazine salts of the nonsteroidal anti-inflammatory drug (NSAID) meclofenamic acid
Sanphui, Palash,Bolla, Geetha,Nangia, Ashwini
body text, p. 2023 - 2036 (2012/06/30)
Meclofenamic acid (MFA) is the most potent anti-inflammatory drug among the fenamic acids. We report (1) two cocrystals of MFA with isonicotinamide (INA) and 4,4′-bipyridine (BPY); (2) polymorphs of MFA and piperazine (PPZ) 1:1 salt (orthorhombic P212121 O and monoclinic P21/c M), MFA-PPZ-H2O 1:1:1 salt hydrate, MFA-PPZ 2:1 salt; and (3) MFA and 2-aminopyridine (2-APY) 1:1 salt, MFA and 4-aminopyridine (4-APY) 1:1:1 salt hydrate. Sublimation of MFA gave single crystals for X-ray diffraction which provided good quality data for refinement and all atomic coordinates. The cocrystal and salt structures are assembled via neutral O-H???O, O-H???N, N-H???O, N-H???N, and ionic O-H???O-, N +-H???O- hydrogen bonds. The disorder of the methyl group in the MFA crystal structure is absent in the cocrystal and salt structures, which contain different conformers (A or B) of methyl group orientation. The solubility of MFA-INA (1:1) and MFA-BPY (1:0.5) cocrystals is 2.9 and 7.6 times higher than that of MFA at 37 °C in 50% EtOH-water. Interestingly, MFA-PPZ-M 1:1 salt and its 1:1:1 hydrate are 2724- and 1334-fold more soluble than MFA. Both of these salts transformed in 50% EtOH-water slurry at 37 °C to MFA-PPZ 2:1 salt after 24 h, which in turn transformed to MFA after another 24 h of slurry stirring. Remarkably, the dissolution rate of MFA-PPZ-M (1:1) salt in water is just slightly lower than that of the marketed sodium meclofenamate.
Process for making n-aryl-anthranilic acids and their derivatives
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, (2008/06/13)
The present invention relates to a process for the preparation of N-arylanthranilic acids, and a process for the preparation of N-aryl anthranilic esters, amides, and hydroxamic esters.
Use of N,N-dimethylformamide as solvent in the synthesis of N-phenylanthranilic acids
Pellon, Rolando F.,Carrasco, Ramon,Marquez, Tania,Mamposo, Taimirys
, p. 5107 - 5110 (2007/10/03)
It is known that N-phenylanthranilic acids can be synthesized by Ullmann-Goldberg condensation in different conditions. This paper reports some parameters which influence the condensation and reports a general procedure for this reaction using N,N-Dimethylformamide as solvent.
Methods for use of GABAa receptor GABAergic compounds
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, (2008/06/13)
A method is disclosed for potentiating mammalian GABA A receptor responses to GABA. The receptor responses are potentiated according to the invention by contacting GABA A receptors with GABA and an effective amount of non-steroidal anti-inflammatory agents, in particular, fenamates and structurally related compounds.
FENAMATE 1,3,4-THIADIAZOLES AND 1,3,4-OXADIAZOLES AS ANTIINFLAMMATORY AGENTS
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, (2008/06/13)
The present invention is novel compounds which are 1,3,4-thiadiazoles and 1,3,4-oxadiazoles, and pharamaceutically acceptable acid addition or base salts thereof having activity as inhibitors of singly or together 5-lipoxygenase and cyclooxygenase, and pharmaceutical compositions or methods of use therefor.
TRIAZOLE DERIVATIVES OF FENAMATES AS ANTIINFLAMMATORY AGENTS
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, (2008/06/13)
The present invention is novel compounds which are 1,2,4-triazoles, derivatives of fenamates and pharmaceutically acceptable additions and base salts thereof, pharmaceutical compositions and methods of use thereof. The invention compounds are now found to have activity as inhibitors of 5-lipoxygenase and/or cyclooxygenase providing treatment of conditions advantageously affected by such inhibition including inflammation, arthritis, pain, fever, and the like
High molecular weight prodrug derivatives of antiinflammatory drugs
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, (2008/06/13)
Compounds of the formula 1, PS - O - A - (CH2)n- B - D (1), wherein PS-O represents an alkoxide residue of any of the free hydroxy groups of a polysaccharide (PS-OH) compound with molecular weight (Mw) of from 40,000 to 5,000,000 selected from dextran, carboxymethyl dextran, diethylaminoethyl dextran, starch, hydroxyet-hyl starch, alginates, glycogen, pullullan, agarose, cellulose, chitosan, chitin and carrageenan,A is a carbonyl group or absent,n is zero or a positive integer from 1 to 14,B is oxygen, a carbonyl group, NR wherein R is hydrogen or lower alkyl, or B is absent, and, D is (i) a group of the formula:, R1 - CO - (11), wherein R1-CO- represents the acyl residue of a carboxylic acid drug (R1-COOH) used in the treatment of inflammatory disorders; or (ii) a group of the formula:, R2 - O - (12), wherein R2-O- refers to the C-21 alkoxide residue of a known antiinflammatory steroid (R2-OH) or an alkoxide residue of any other drug or medicament containing a hydroxy functional group used in the treatment of inflammatory disorders; with the proviso that when A is absent, n is 0, and B is absent, then R1-CO- is different from the acyl residue of acetylsalicylic acid;, and non-toxic pharmaceutically acceptable acid addition salts thereof;, and non-toxic pharmaceutically acceptable cation salts thereof. Such compounds are biolabile prodrugs providing controlled release and prolonged duration of action of the parent active antiinflamma-tory agents locally at the administration site after intra-articular, intra-muscular, subcutaneous or extra-dural application while at the same time being highly stable in aqueous solution in the pH range 3--5. After oral administration of such prodrugs the parent drug is liberated selectively in the terminal ileum and the colon over an extended period of time.
Structure-activity relationships in a series of anti-inflammatory N-arylanthranilic acids
Kaltenbronn,Scherrer,Short,Jones,Beatty,Saka,Winder,Wax,Williamson
, p. 621 - 627 (2007/10/02)
A large series of N-arylanthranilic acids has been prepared. Many of these compounds show high anti-inflammatory activity as measured by the anti-UV-erythema test. From this series have come the clinically useful nonsteroidal anti-inflammatory agents, flufenamic acid (Arlef), mefenamic acid (Ponstel), and the latest and most potent agent, N-(2,6-dichloro-m-tolyl)anthranilic acid (meclofenamic acid, Meclomen = the sodium salt). The structure-activity relationships of this series is discussed and a graphical representation is presented which allows the prediction of activity of new agents.
