Benzoic Acid Hydrazide Research Articles

Synthesis and analgesic activity of the products of the interaction between 3-aroylpyrrolo[1,2-a]-quinoxaline-1,2,4(5H)-triones with benzoic acid hydrazides

The synthesis, properties, structure, and analgesic activities of the products of the interaction of 3-aroylpyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones with benzoic acid hydrazides are described. The significance of the structure-function relationship is discussed.

Synthesis and Characterization of Group-6 Metal Carbonyl Complexes of Aroyl Hydrazone Derivatives

Carbonyl complexes of Chromium, molybdenum and tungsten of composition, [M(CO)4L-L], (where M= Cr, Mo or W and L-L= benzoic acid[1-(Furan-2-yl)methylene]hydrazide (BFMH), benzoic acid[(thiophene-2-yl)methylene]hydrazide (BTMH), benzoic acid[1-(thiophene-2-yl)ethylidene] hydrazide (BTEH), benzoic acid (phenylmethylene)hydrazide (BPMH) and benzoic acid[1-(anisol-3-yl)methylene] hydrazide (BAMH) are reported. These have been prepared by refluxing metal carbonyls and the ligands in 1:1molar ratio. The complexes were characterized by elemental analysis, IR spectra, UV-vis spectra,1H NMR, TGA/DTA, conductivity and magnetic susceptibility measurements. The IR bands suggest that in all the complexes the ligands behave as neutral bidentate chelating type coordinating metal through carbonyl oxygen and azomethine nitrogen. The CO force constants and CO-CO interaction constants for these derivatives have been calculated using Cotton-Kraihanzel secular equations, which indicate poorπ-bonding ability of the coordinated ligands.

Synthesis of Novel Tri-Arm Star Shaped 1,3,5-triazine Hydrazones from 2,4,6-tris(4-acetylphenoxy)-1,3,5-triazine Core

A series of novel symmetric triazine hydrazones [N3C3(-OC6H4-p-C(CH3)=N-NH-C(O)-C6H4-p-X)3] (X = H, Br, Cl, F, OH, OCH3, CH3, NO2, NH2) were prepared in excellent yields by a three-fold condensation reaction of 2,4,6- tris(4-acetylphenoxy)-1,3,5-triazine with p-substituted benzoic acid hydrazides [NH2-NH-C(O)-C6H4-p-X]. The structures were confirmed by FT-IR, 1H, 13C, 2D-HMQC NMR and mass spectrometry (MALDI-TOF).

Synthesis, characterization and anticancer evaluation of novel tri-arm star shaped 1,3,5-triazine hydrazones

A series of novel trisubstituted triazine hydrazones [N3C3(single bondOC6H4-p-CHdouble bond; length as m-dashNsingle bondNHsingle bondC(O)single bondC6H4-p-X)3] (X = H, Br, Cl, F, OH, OCH3, CH3, NO2, NH2) were prepared by a three-fold condensation reaction of 2,4,6-tris(4-formylphenoxy)-1,3,5-triazine with p-substituted benzoic acid hydrazides [NH2single bondNHsingle bondC(O)single bondC6H4-p-X] with excellent yields. The structures were confirmed by elemental analysis, FT-IR, 1H, 13C, 2D-HSQC NMR and mass spectrometry (MALDI-TOF). These derivatives bearing hydrolysable hydrazone linkages were evaluated for their invitro antiproliferative activity against the human liver carcinoma cell line (HepG2) and human cervix carcinoma cell line (HeLa).

Electrochemical and spectroscopic investigations of isoniazide and its analogs with ds.DNA at physiological pH: Evaluation of biological activities

Interaction and binding of isonicotinic acid hydrazide (INH) and its two analogs; pyrazine carboxylic acid hydrazide (PCH) and 2,4-dihydroxy benzoic acid hydrazide (2,4-DHBAH) with DNA has been investigated by UV-spectroscopy and cyclic voltammetry (CV) at physiological conditions of pH and temperature. Experimental results from both techniques were in good agreement and indicated stronger binding and formation of hydrazides–DNA complexes via intercalation. Among three hydrazides, 2,4-DHBAH showed greater interaction toward DNA at stomach pH (4.7) as evident from its comparatively greater binding constant, { K b ; 2.02 × 10 4 M −1 (UV), 3.13 × 10 4 M −1 (CV)}. The greater binding site size ( n = 3) for 2,4-DHBAH at stomach pH inferred 3:1 binding stoichiometry and possibility of electrostatic interactions or hydrogen bonding along with intercalative mode of interaction between 2,4-DHBAH and DNA. The free energies of hydrazides–DNA complexes indicated the spontaneity of their binding. 2,4-DHBAH has shown promising anti-bacterial activities while anti-oxidant and cytotoxic potentials were exhibited by all three hydrazides.

Synthesis and characterization of peroxo complexes of uranium(VI) with aroylhydrazone ligands

The uranium(VI) peroxo complexes containing aroylhydrazones ligands having composition [UO(O2)L-L(NO3)2]·H2O (where L-L=Benzoic acid[1-(Furan-2-yl)methylene] hydrazide, Benzoic acid[(thiophene-2-yl)methylene] hydrazide, Benzoic acid[1-(thiophene-2-yl)ethylidene] hydrazide, Benzoic acid(phenylmethylene) hydrazide, Benzoic acid[1-(anisol-3-yl)methylene] hydrazide and Benzoic acid[(p-chlorobenzyl)methylene] hydrazide are reported. The complexes were characterized by various physico-chemical techniques, viz. elemental analysis, molar conductivity, magnetic susceptibility measurements, infra red, electronic, mass spectral and TGA/DTA studies. These studies revealed that complexes are non-electrolytes and diamagnetic in nature. The ligands are bound to metal in a bidentate mode. Thermal analysis results provide conclusive evidence for the presence of water molecules in the complexes. Mass spectra confirm the molecular mass of the complexes. Antifungal activity of complexes revealed enhanced activity of complexes as compared to the corresponding ligands.

Synthesis, characterization and antibacterial activity of new salicylhydrazide containing azopyrazoles

Various ethyl-2-substituted phenyl hydrazono-3-oxobutyrate (2a-h) condensation with 2-hydroxy benzoic acid hydrazide (3) to afford 1-(2-hydroxybenzoyl)-3-methyl-4-(2- substituted phenyl hydrazono)-1H-pyrazol-5(4H)-one (4a-h). The structures of all these compounds (4a-h) were recognized on basis of analytical and spectral data. The newly synthesized compounds were evaluated for their antimicrobial activity against various bacteria and fungi.

Four-Component Reaction between Trimethyl Phosphite, Aroyl Chlorides and Dialkyl Acetylenedicarboxylate with Benzoic Acid Hydrazide

A four-component and one-pot reaction between trimethyl phosphite, a dialkyl acetylene dicarboxylate and an aroyl chloride with benzoic acid hydrazide is described as a simple and efficient route for the synthesis of functionalised pyrazoles in good yields.

The Uses of 2-Ethoxy-(4H)-3,1-benzoxazin-4-one in the Synthesis of Some Quinazolinone Derivatives of Antimicrobial Activity

The behavior of 2-ethoxy-(4H)-3,1-benzoxazin-4-one (1) towards nitrogen nucleophiles, e.g. ethanolamine, aromatic amines (namely: p-toluidine, p-anisidine, p-hydroxyaniline, o-hydroxyaniline, o-bromoaniline, o-phenylenediamine, p-phenylenediamine, o-tolidinediamine) p-aminobenzoic acid, glucosamine hydrochloride, 2-aminonicotinic acid, 1-naphthalenesulfonic acid hydrazide, n-decanoic acid hydrazide, benzoic acid hydrazide, semicarbazide, aminoacids (e.g. D,L-alanine, L-asparagine, L-arginine) and derivatives of 2-aminothiodiazole has been investigated. The behavior of the benzoxazinone towards a selected sulfur nucleophile, L-cysteine, has also been discussed. Formation of an amidine salt as a reaction intermediate has been assumed. The effect of solvent in some reactions has been elucidated. The structures of all the novel quinazoline and quinazolinone derivatives, obtained by heterocyclic ring opening and ring closure were inferred by the IR, MS as well as 1H-NMR spectral analysis. Moreover, the antimicrobial potential of some of the new synthesized derivatives has been evaluated.

Synthesis and antimicrobial and antioxidant activities of simple saccharin derivatives with N-basic side chains

A new class of N-basic side chains was obtained from 2,3-dihydro-2H-3-oxobenzo[d]isothiazole and aliphatic or aromatic aldehydes. Secondary amines (morpholine, N-methylpiperazine and ethyl isonipecotate) afforded tertiary N-basic side chains (4–6), while dibasic secondary amines (such as piperazine) gave bis-tertiary N-basic side chains (2). On the other hand, the use of mono- or dibasic primary amines namely; aniline, anisidine, phenyl hydrazine, o-hydroxy benzoic acid hydrazide, hydrazine hydrate, and ethylenediamine (instead of secondary amines) afforded secondary N-basic side chain as mono component or as bis component 7a-c, 9a-c, 11 and 12a-c. In addition, secondary Mannich base was synthesized via Michael addition to the corresponding aldimine. The new compounds were investigated for antioxidant and antimicrobial activities. Compounds 2, 7c and 12a exhibited significant antimicrobial activity, whereas compounds 7a, 7b, 9b, 9c and 11 exhibited high antioxidant activity as compared to ascorbic acid, These compounds showed the best protective effect against DNA damage induced by bleomycin.

Five-membered 2,3-dioxo heterocycles: LXXIV. Recyclization of 3-aroylpyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones by the action of benzohydrazides. Crystalline and molecular structure of N-[2,4-dihydroxy-5-oxo-3-(3-oxo-3,4-dihydroquinoxalin-2-yl)-2-phenyl-2,5-dihydro-1H-pyrrol-1-yl]benzamide

Recyclization of 3-aroyl-1H-pyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones by the action of benzoic acid hydrazides gave N-[2,4-dihydroxy-5-oxo-3-(3-oxo-3,4-dihydroquinoxalin-2-yl)-2-aryl-2,5-dihydro-1H-pyrrol-1-yl]benzamides whose structure was proved by X-ray analysis.

Reactions of 1-nitrocyclohexene with N,N-binucleophiles

A modification of 1-nitrocyclohexene synthesis is proposed; its reaction with phenylhydrazine and benzoic acid hydrazide is shown to afford monoadducts, and with hydrazine hydrate, bisaduct. With diphenylguanidine occurs heterocyclization to 1-phenyl-2-N-phenylamino-4,5,6,7-tetrahydrobenzimidazole, whose structure is confirmed by the X-ray diffraction data. The analysis performed for this compound of the electron density distribution function in the crystal made it possible to estimate the charge distribution, π-electrons delocalization nature, and the role of N-H…N, C-H…H-C and C-H…C interactions in the formation of the crystal packing.

Synthesis of 4-(1H-azol-1-ylmethyl)benzoic acid hydrazides and their effects on the leukocyte system in rats

The biological activities of 4-(1H-azol-1-ylmethyl)benzoic acid hydrazides were assessed by studying leukocyte responses to these compounds. The study compounds were found to have stimulatory actions on the body’s general resistance mechanisms.

Synthesis and Biological Activity of 2-Hydroxy-N(5-methylene-4-oxo-2-aryl-thiazolidin-3-yl)-benzamide

2-Hydroxy benzoic acid hydrazide (1) undergoes facile condensation with aromatic aldehydes to afford the corresponding 2-hydroxy benzoic acid arylidene hydrazides (2a–h) in good yields. Cyclocondensation of compounds 2a–h with thioglycolic acid yields 2-hydroxy-N(4-oxo-2-aryl-thiazolidin-3-yl)-benzamides (3a–h). These 3a–h compounds are for the reacted with benzaldehyde in the presence of sodium ethanolate affords, giving 2-hydroxy-N(5-methylene-4-oxo-2-aryl-thiazolidin-3-yl)-benzamides (4a–h). The structures of these compounds were established on the basis of analytical and spectral data. All the newly synthesized compounds were evaluated for their antibacterial and antifungal activities. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.

Novel 6,8-dibromo-4(3 H)quinazolinone derivatives of anti-bacterial and anti-fungal activities

Starting from 4-(6,8-dibromo-2-phenyl-4-oxo-(4 H)-quinazolin-3-yl)-benzoic acid ethyl ester ( II) and its acid hydrazide III, a new series of Schiff bases IV and their cyclized products, thiazolidinones V, oxadiazole VIII, pyrazoles X– XII, pyrroles XIII– XV and other related products were synthesized. These compounds were screened for their anti-bacterial activity against Gram-positive bacteria ( Staphylococcus aureus, Legionella monocytogenes and Bacillus cereus) and Gram-negative bacteria ( Escherichia coli, Pseudomonas aeruginosa and Salmonella typhimurium) and anti-fungal activity ( Candida albicans and Aspergillus flavus) using paper disc diffusion technique. The minimum inhibitory concentrations (MICs) of the compounds were also determined by agar streak dilution method. Among the synthesized compounds 2-(4-(2-phenyl-6,8-dibromo-4-oxo-(4 H)quinazolin-3-yl)- N-ethylamido benzoic acid hydrazide VIIa was found to exhibits the most potent in vitro anti-microbial activity with the MICs of 1.56, 3.125, 1.56, 25, 25 and 25 μg/ml against E. coli, S. typhimurium, L. monocytogenes, S. aureus, P. aeruginosa, and B. cereus respectively. Compound 2-(4-(2-phenyl-6,8-dibromo-4-oxo-(4 H)quinazolin-3-yl)- N-methyl thioamido benzoic acid hydrazide VIIc was found to exhibit the most potent in vitro anti-fungal activity with MICs 0.78 and 0.097 μg/ml against C. albicans and A. flavus.

Synthesis and cyclisation of 1,4-disubstituted semicarbazides

Semicarbazides, besides possessing medicinal properties, also find wide applications in agriculture and industry. We report in this article the synthesis of the four 1,4-disubstituted semicarbazides: 1-cinnamoyl-4-phenyl semicarbazide (1), 1-oleyl-4-phenyl semicarbazides (2), 1,1′,1″-tricitryl-4,4′,4″-triphenyl semicarbazide (3) and 1-benzoyl-4-phenyl semicarbazide (4), by the condensation of four different hydrazides: cinnamic acid hydrazide (5), oleic acid hydrazide (6), citric acid hydrazide (7) and benzoic acid hydrazide (8). The acid hydrazides were prepared by the condensation of four different acids with phenyl isocyanate. The semicarbazides were also subjected to acid catalysed intramolecular cyclisation. The cyclisation of (1) and (2) afforded substituted 1,3,4-oxadizoles: 2-cinnamoyl-5-aminophenyl 1,3,4-oxadizoles (9) and 2-oleyl-5-aminophenl 1,3,4-oxadizoles (10), respectively, in high yield, while no cyclisation occurred in the cases of (3) and (4). The products in each case have been identified on the basis of melting points and IR spectral studies.

Synthesis and characterization of some 1,2,4-triazole-3(4h)-thiones obtained from intramolecular cyclization of new 1-(4-(4-x-phenylsulfonyl)benzoyl)-4-(4-iodophenyl)- thiosemicarbazides

This paper presents new heterocyclic compounds from the class of 1,2,4-triazole-3(4H)-thione which were obtained by intramolecular cyclization, in basic media of the some acylthiosemicarbazides containing diphenylsulfone moieties. The new 1-(4-(4-X-phenylsulfonyl)benzoyl)-4- (4-iodophenyl)-thiosemicarbazides (7a-c) were obtained by the reaction of 4-(4-X-phenylsulfonyl)-benzoic acid hydrazides (6a-c) (X=H, Cl or Br) with 4-iodophenylisothiocyanate. The cyclization of the acylthiosemicarbazides 7a-c in the presence of an 8 % NaOH solution resulted in the formation of the new 5-(4-(4-X-phenylsulfonyl)phenyl)-4-(4-iodophenyl)-2H-1,2,4-triazole-3(4H)-thiones (8a-c). The structures of the newly synthesized compounds were elucidated by spectral methods (IR, UV-Vis, 1H-NMR, 13C-NMR and MS spectroscopy) and elemental analysis.

Cyano complexes of oxotungsten(IV) with aroyl hydrazone ligands

Reactions of K 3 Na[WO 2 (CN) 4 ].6H 2 O with aroyl hydrazone ligands namely benzoic acid[1-(furan-2-yl)methylene]hydrazide (BFMH), benzoic acid[(thiophene-2-yl)methylene]ttydrazide (BTMH), benzoic acid[1-(thiophene-2-yl)ethylidene]hydrazide (BTEH). benzoic acid(phenylmethytene)hydrazide (BPMH) and benzoic acid[1-(anisot-3-yl)methylene]hydrazide (BAMH)) in presence of acetic acid yield complexes of the type [wo(CN) 3 L.-L] - . The complexes have been characterized by conductivity, magnetic susceptibility, IR, 1 H NMR, UV-Vis and TGA/DTA studies. The ligands substitute one water and one cyanide group of the protonated K 3 N a [WO 2 (CN) 4 ].6H 2 O and bind in bidentate chelating mode. The mode of bonding of the ligands is confirmed by shifts observed in the 1 H NMR spectrum of the ligand after complexation.

Synthesis, characterization, catalytic and antimicrobial activities of RuII complexes of Schiff bases derived from 2-substituted benzoicacid (2-oxo-1 ,2-dihydro-indol-3-ylidene) hydrazides

A new ruthenium(II) Schiff base complexes of the type [RuX(CO)(EPh 3 )(B)(L)] (where X = H or CI; B = EPh 3, py; E = P/As; L = monobasic bidentate ligand) have been synthesized. All the complexes were characterized by physicochemical and spectroscopic methods. An octahedral geometry has been proposed for all the complexes. The new complexes have been tested to find out their catalytic activity for the oxidation of alcohols to corresponding carbonyl compounds. Further the ligands and complexes were subjected to antimicrobial activity studies.

Lipase-catalyzed hydrazinolysis of phenyl benzoate: Kinetic modeling approach

Immobilized lipase-catalyzed synthesis of benzoic acid hydrazide from hydrazine and phenyl benzoate is reported in this work. A series of immobilized lipases such as Candida antarctica lipase B, Mucor miehei lipase and Thermomyces lanuginosus lipase were screened to establish that C. antarctica lipase B was the best lipase for hydrazinolysis. When phenyl benzoate (0.01 mol) and hydrazine (0.02 mol) in toluene (15 ml) were reacted with C. antarctica lipase B (Novozym 435) at 50 °C, 95% of phenyl benzoate was converted to benzoic acid hydrazide after 2 h. The effects of various parameters such as speed of agitation, concentration of the substrates, temperature, enzyme concentration, and reusability of the enzyme were studied to deduce kinetics and mechanism of the reaction. A mechanism based on an ordered bi–bi dead end complex with hydrazine was found to fit the data. Systematic deactivation studies indicated that the enzyme was deactivated due to the hydrazine and phenol, enzyme deactivation obeys first-order series model. The kinetic parameters deduced from these models were used to simulate the lipase activity. There was a very good agreement between the simulated and experimental values.