Anthranilic Acid Hydrazide Research Articles

A New Domino Reaction under Microwave Irradiation for the Synthesis of Pyrazolo[5,1-b]quinazolinones

AbstractPyrazolo[5,1-b]quinazolinones were synthesized by consecutive pyrazole and quinazolinone ring closures in a new catalyst-free microwave-promoted domino reaction of hydrazine with 2-cyano-3-(methylthio)-3-(2-methoxycarbonylphenylamino)acrylates, which were prepared from methyl anthranilate and 2-cyano-3,3-bis(methylthio)acrylates. When 2-cyano-3,3-bis(methylthio)acrylates reacted directly with anthranilic acid hydrazide, the arylamino group remained intact, while the hydrazide moiety transformed into 1-acylpyrazoles and further to 2-(1,3,4-oxadiazolylidene)-2-cyanoacetates. The structures of representatives from each group of the prepared heterocyclic compounds were examined in detail by X-ray crystallography.

Synthesis, characterization and molecular docking studies of highly selective new hydrazone derivatives of anthranilic acid and their ring closure analogue Quinazolin-4(3H)-ones against lung cancer cells A549

In this study, new Schiff bases derived from anthranilic acid hydrazide (3a-j) and quinazolin-4(3H)-one (4a-j) were synthesized with high yields (99-90%) and characterized by FTIR, NMR (1H and 13C), and HRMS spectroscopic techniques. The effects of the synthesized compounds on the human lung adenocarcinoma cells (A549, CCL-185, ATCC) and the human bronchial epithelial cells (BEAS-2B, ECACC) were examined. IC50 values of the compounds were found in the range of 12.40 – 424.9 µM against A549 and 15.81 – 752.30 µM against BEAS-2B cell lines. Compounds 3i, 3j, 4b, and 4f are the most active compounds in the series, with low IC50 values against A549, high against BEAS-2B, and high selectivity. For the most active compounds in the series, molecular docking study was performed to understand ligand-protein interactions between the compounds and Epidermal Growth Factor Receptor (EGFR) and Vascular Endothelial Growth Factor Receptor (VEGFR1). The docking scores were calculated in the range of -5.870 – -6.711 kcal/mol for EGFR and -4.142 – -8.501 kcal/mol for VEGFR1.

Synthesis and structural characterization of N‐methylanthraniloyl‐ (4‐ethylthiosemicarbazide) and its Cu(II) trinuclear complex

AbstractThe new ligand N‐methylanthraniloyl(4‐ethylthiosemicarbazide) H2L was synthesized by the treatment of anthranilic acid hydrazide and ethyl isothiocyanate in absolute ethanol. The composition and structure of H2L were characterized by spectroscopic methods such as ESI MS, IR, 1H and 13C{1H} NMR spectroscopy as well as SCXRD. Reaction of H2L and mixture of [Cu(MeCN)4](PF6) and o‐phenanthroline in methanol gave rise to a cationic Cu(II) trinuclear complex, which could be separated as PF6– salt with the composition of [Cu3(L)2(o‐phen)2](PF6)2. The spectroscopic and X‐ray crystallographic data analyses demonstrated that H2L deprotonates hydrazide protons and the resulting dianion {L2–} acts as bridging ligand of which most potential donor atoms form stable chelates with Cu(II) ions. In particular, the central Cu(II) ion coordinates with two dianions {L2–} via (O, N2) donor sets, thereby adopting a distorted square planar coordination mode with trans configuration. While each of two terminal Cu(II) ions is five‐coordinate with the coordination sphere composed of (S, N1, Namine) and (N,N) donor sets belonging {L2–} and o‐phenanthroline, respectively.

Reactions of 3,4-dihydroxyhexa-2,4-diene-1,6-dioic acid esters with anthranilic acid hydrazide

Reactions of 3,4-dihydroxyhexa-2,4-diene-1,6-dioic acid esters with anthranilic acid hydrazide lead to the formation of 3,4-bis(2-aminobenzoylhydrazono)hexane-1,6-dioic acid esters. Structural features of the synthesized compounds are discussed.

Two directions of the reaction of 3,4-dihydroxy-6-oxoalka-2,4-dienoic acid esters with anthranilic acid hydrazide

Methyl 3,4-dihydroxy-6-oxoalka-2,4-dienoates reacted with anthranilic acid hydrazide to give methyl [5-alkyl-1-(2-aminobenzamido)-2-hydroxy-3-oxo-2,3-dihydro-1H-pyrrol-2-yl]acetates. The reaction of anthranilic acid hydrazide with ethyl 3,4-dihydroxy-6-oxohepta-2,4-dienoate afforded ethyl (2Z)-(3a-hydroxy-2-methyl-10-oxo-3,3a,5,10-tetrahydro-4H-pyrazolo[5,1-c][1,4]benzodiazepin-4-ylidene)acetate as solvate with one methanol molecule. The structure of the isolated compounds was determined on the basis of IR and NMR spectra and X-ray diffraction data.

Hyaluronic acid based hydroxamate and conjugates with biologically active amines: In vitro effect on matrix metalloproteinase-2

In this study, water soluble hyaluronic acid (HA) based hydroxamate and conjugates with biologically active amines and hydrazides such as p- and o-aminophenols, anthranilic, 4- and 5-aminosalicylic acids, nicotinic, N-benzylnicotinic and isonicotinic hydrazides, p-aminobenzenesulfonamide (Streptocide), p-aminobenzoic acid diethylaminoethyl ester (Procaine), and 4-amino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one (4-aminoantipyrene) were examined as matrix metalloproteinase-2 inhibitors (MMPIs). In a dose of 0.27–270μM, the most efficient MMPIs were HA conjugates with o-aminophenol=4-aminoantipyrine>4-aminosalicylic acid>5-aminosalicylic acid. Conjugates with Streptocide, Procaine and HA hydroxamate showed 40–50% inhibitory effect at all used concentrations. Conjugates with anthranilic acid and isonicotinic hydrazide (Isoniazid) in a dose of 0.27μM inhibited enzyme activity by ∼70%, but with the concentration increase their inhibitory effect was decreased.

Synthesis and biological evaluation of novel acylhydrazone derivatives as potential antitumor agents

We have designed, synthesized, and evaluated as potential antitumor agents a series of 2-hydroxybenzylidene derivatives of the N-(2-trifluoromethylpiridyn-4-yl)anthranilic acid hydrazide, and some analogues bearing a (2-trifluoromethyl)piridyn-4-ylamino group in 3- or 4-position of benzohydrazide or 4-position of phenylacetohydrazide. Compounds 12e, 13e, 15e, and 16e, bearing a 4-(diethylamino)salicylidene group exhibited potent cytotoxicity, with averaged GI50 values in sub-micromolar range, and a variety of cell selectivity at nanomolar concentrations. The determination of acute toxicity in athymic nudes mice proved some compounds to be non-toxic, making them good candidates for further study as antitumor agents.

ChemInform Abstract: Anthranilic Acid Hydrazide in the Synthesis of Fused Polycyclic Compounds with Quinazoline Moieties.

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Anthranilic acid hydrazide in the synthesis of fused polycyclic compounds with quinazoline moieties

A modified procedure was developed for the synthesis of 5,6,7,8,13,13a-hexahydrophthalazino[1,2-b]quinazoline-5,8-dione and 6-amino-5,6,6a,11-tetrahydroisoindolo[2,1-a]quinazoline-5,11-dione from o-formylbenzoic acid and anthranilic acid hydrazide. The mechanism of the transformation is suggested, some reactions were studied, and new derivatives of these compounds were synthesized. Anthranilic acid hydrazide was used in the novel synthesis of 5-substituted phthalazino[1,2-b]quinazolin-8-one derivatives. The possible reaction mechanism is discussed. 5,6,7,8-Tetrahydrophthalazino[1,2-b]quinazoline-5,8-dione and 5-phenylphthalazino[2,1-b]quinazolin-8-one were studied by X-ray diffraction.

ChemInform Abstract: Synthesis of 3‐Amino‐3,4‐dihydroquinazolin‐4‐one Derivatives from Anthranilic Acid Hydrazide and Dicarboxylic Acids.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Synthesis and properties of a new fused heterocyclic system 12H-benzo[5,6][1,2,4]triazepino[3,4-a]isoindol-5(6H)-one

12H-Benzo[5,6][1,2,4]triazepino[3,4-a]isoindol-5(6H)-one was synthesized by the condensation of anthranilic acid hydrazide with o-phthalaldehyde. The structure of this compound was established by the X-ray diffraction study of its isopropyl derivative. The mechanism of formation of this compound was suggested and its alkylation reactions were investigated.

Synthesis of 3-amino-3,4-dihydroquinazolin-4-one derivatives from anthranilic acid hydrazide and dicarboxylic acids

Treatment of anthranilic acid hydrazide with 2 equiv of ethoxalyl chloride gave the corresponding diester which underwent cyclization in acetic anhydride to produce ethyl 3-(ethoxalylamino)-4-oxo-3,4-dihydroquinazoline-2-carboxylate. Acylation of anthranilic acid hydrazide first with succinic anhydride and then with ethoxalyl chloride led to the formation of 4-[2-(2-{[ethoxy(oxo)acetyl]amino}benzoyl)hydrazino]-4-oxobutanoic acid whose cyclization in acetic acid afforded N-(2-ethoxycarbonyl-4-oxo-3,4-dihydroquinazolin-3-yl)succinamic acid, while in acetic anhydride ethyl 3-(2,5-dioxopyrrolidin-1-yl)-4-oxo-3,4-dihydroquinazoline-2-carboxylate was obtained. The latter was brought into reactions with amines and hydrazine hydrate and alkaline hydrolysis. Acylation of 2-[2-(2-aminobenzoyl)hydrazinocarbonyl]benzoic acid with ethoxalyl chloride gave ethyl N-[2-(phthalimidocarbamoyl)phenyl]oxamate, and with succinic anhydride, 3-[4-oxo-3-phthalimido-3,4-dihydroquinazolin-2-yl]propionic acid. 4-[2-(2-Aminobenzoyl)hydrazino]-4-oxobutanoic acid reacted with phthalic anhydride in boiling acetic acid to give phthalazino[1,2-b]quinazoline-5,8-dione via elimination of succinic acid residue.

Synthesis of N-(4-oxo-3,4-dihydroquinazolin-3-yl)succinimide and N-(4-oxoquinazolin-3-yl)succinamic acid derivatives based thereon

The reaction of anthranilic acid hydrazide with diethyl oxalate under microwave irradiation was accompanied by decarboxylation with formation of 3-amino-3,4-dihydroquinazolin-4-one, and acylation of the latter with succinic anhydride gave N-(4-oxo-3,4-dihydroquinazolin-3-yl)siccinimide which was converted into various N-(4-oxo-3,4-dihydroquinazolin-3-yl)succinamic acid derivatives.

Structure of the Reaction Product of Anthranilic Acid Hydrazide with Carbon Disulfide in Alkaline Medium

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Structure of the Reaction Product of Anthranilic Acid Hydrazide with Carbon Disulfide in Alkaline Medium

The reaction of anthranilic acid hydrazide with carbon disulfide in alkaline medium yields 5-(2-aminophenyl)-2,3-dihydro-1,3,4-oxadiazole-2-thione rather than 3-amino-2-thioxo-1,2,3,4-tetrahydroquinazolin-4-one. The structure of the product was proved by spectral methods and chemical transformations.

Synthesis and Reactions of Pyranoquinolines.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Corrosion inhibition of mild steel in hydrochloric acid by some aromatic hydrazides

Abstract The influence of some organic acid hydrazides, namely salicylic acid hydrazide (SAH), anthranilic acid hydrazide (AAH), benzoic acid hydrazide (BAH) and cinnamic acid hydrazide (CAH) on the corrosion inhibition of mild steel in the presence of 1 N HCl was studied. The adsorption of all the hydrazides on mild steel surface in the acid solution were found to obey Temkin’s adsorption isotherm. The values of activation energy and free energy of adsorption of all the hydrazides were also calculated. The potentiodynamic polarization studies indicated that all the hydrazides except SAH are mixed inhibitors.

Synthesis, Characterization, IR and Electronic Spectra, Magnetic Moments and Biological Activity of Trinuclear Nickel(II) TetrathiocyanatoBisArgentate(I) Complexes with Hydrazides and Hydrazones

Abstract Nickel (II) complexes of the type Ni[Ag(SCN)2]2.L [where L = benzoic acid hydrazide (BH), salicylic acid hydrazide (SH), anthranilic acid hydrazide (AH), isonicotinic acid hydrazide (INH), oxaldihydrazide (ODH), malondihydrazide (MDH) and their isopropanone derivatives, viz., isopropanone benzoyl hydrazone (IBH),-salicyl-hydrazone (ISH), -anthranoylhydrazone (IAH) and -isonicotinoyl hydrazone (IINH)] were synthesised and characterized with the help of elemental analyses, electronic, IR and magnetic moment data. The complexes are insoluble in common organic solvents, partially dissociate or dissolve in DMF and DMSO, have coordinated hydrazide or hydrazone ligands and bridging SCN groups. Nickel (II) in the complexes is spin free and has a pseudo-octahedral environment.

ChemInform Abstract: Another Rearrangement During the Photolysis of Lithium 3‐((p‐Tolylsulfonyl)amino)‐1,2,3‐benzotriazin‐4(3H)‐one.

AbstractThe benzotriazine (V) is prepared by two different methods from anthranilic acid hydrazide (I) or the benzotriazine (VI).

The reaction of 5‐aminoimidazole‐4‐carbohydrazides with orthoesters

AbstractThe reaction of 5‐aminoimidazole‐4‐carbohydrazides with orthoesters is shown to yield 1‐amino‐9‐alkyl‐hypoxanthines. Similar reaction of anthranilic acid hydrazide is shown to yield 3‐amino‐4‐quinazolone, and not 1,4‐dihydro‐5H‐1,3,4‐benzotriazepin‐5‐one as previously reported.