Synthesis, antiplatelet and in silico evaluations of novel N-substituted-phenylamino-5-methyl-1H-1,2,3-triazole-4-carbohydrazides

Jordão, Alessandro K.; Ferreira, Vı́tor F.; Lima, Emerson Silva; Souza, Maria C. B. V. de; Carlos, Eduardo C.L.; Castro, Helena C.; Geraldo, Reinaldo Barros; Rodrigues, Carlos Rangel; Almeida, Maria C.B.; Cunha, Anna C.

doi:10.1016/j.bmc.2009.03.053

Cited by 73 publications

(22 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The 13 C-NMR spectrum of the ligand showed a signal at 169.5 ppm which could be assigned to carbonyl carbon C 9 =O. The chemical shift appeared at 153.27 and 150 ppm is assignable to azomethine carbon atoms(C 13,15 ) [41,42,46]. While the chemical shifts of the methane carbon (C 8 ) were observed at δ = 77.…”

Section: Nmr Spectramentioning

confidence: 99%

“…Hydrazone ligands represent a class of Schiff base with an extra function group characterized by a nitrogen-nitrogen covalent bond that enhances their capability to form more stable metal complexes via reaction with most of the transition metal ions [6,7]. Both hydrazide and hydrazone compounds have drawn much concern in order to investigate their structures as well as their enormous biomedical activities as: antioxidant [8,9], analgesic, anti-inflammatory [10], antimalarial, anti-leishmanial and anti-trypanosomal [11], anti-convulsant [(12)], antibacterial [13,14], antiplatelet [15], antitumor [16] and antiviral [17,18] activities. The presence of active azomethine NHN=CH-protons in these compounds imparts them a major importance as good candidates for the development of new drugs [19][20][21].…”

mentioning

confidence: 99%

See 1 more Smart Citation

Preparation, characterization and Microbicide activities of N'-((3-(hydroxyimino)butan-2-ylidene)-2-(phenylamino)acetohydrazide and its complexes

et al. 2017

View full text Add to dashboard Cite

, UO 2 2+ and VO 3 -). The ligand, N'-((3-(hydroxyimino) butan-2-ylidene)-2-(phenylamino)acetohydrazide was prepared by refluxing an equimolar amount of phenyl amino acetohydrazide with 2,3-butanedione monoxime. The synthesized compounds were characterized using elemental and thermal analyses, NMR, IR, U.V spectroscopy, magnetic and conductance measurements. The results demonstrated that complexes (2), (3), (5-7), (10) and (12) were formed in 1L:1M molar ratio. Complexes (4), (8), (9), (13) and (14) were found to afford M 2 L formulae while complex (11) adopted ML 2 formulae. The ligand acted as a neutral (bidentate [11], tridentate [6,7], monobasic (tridentate [2,3,5,12]), dibasic (tridentate [10], tetradentate [4,8,9,13,14]) chelating to the metal ions via nitrogen atoms of aceto-amino and azomethine groups, carbonyl oxygen atom in its enolic or ketonic form and/or protonated or deprotonated oximino nitrogen atom, adopting an octahedral, tetrahedral or square planar geometry around metal ions. The antimicrobial activity of the ligand, as well as the metal complexes, was examined using Amphotericin B and Amoxicillin as drugstandards against Aspergillus niger (A.niger) and Escherichia coli (E. coli) ,respectively. The ligand demonstrates a high cytotoxicity against A.niger whereas it recorded a moderate activity against E. coli. It is interestingly found that zinc(II) complex (6), copper(II) complexes (8) and (10) recorded higher activities than the Amphotericin B drug with 122%, 116% and 111.1% percentages respectively against A.niger. Zinc(II) complex (6) was also the most sensitive complex against E. coli with (94.1 %) comparable to Amoxicillin.

show abstract

Section: Nmr Spectramentioning

confidence: 99%

mentioning

confidence: 99%

Preparation, characterization and Microbicide activities of N'-((3-(hydroxyimino)butan-2-ylidene)-2-(phenylamino)acetohydrazide and its complexes

et al. 2017

View full text Add to dashboard Cite

show abstract

“…A large number of 1,2,3-triazoles exhibit various biological effects [3], e.g., antiviral ( 1 ), antibacterial ( 2 ), antifungal ( 3 ) and anticancer ( 4 ) activities [4–7] (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Efficient continuous-flow synthesis of novel 1,2,3-triazole-substituted β-aminocyclohexanecarboxylic acid derivatives with gram-scale production

Ötvös¹,

Georgiádes²,

Mándity³

et al. 2013

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

SummaryThe preparation of novel multi-substituted 1,2,3-triazole-modified β-aminocyclohexanecarboxylic acid derivatives in a simple and efficient continuous-flow procedure is reported. The 1,3-dipolar cycloaddition reactions were performed with copper powder as a readily accessible Cu(I) source. Initially, high reaction rates were achieved under high-pressure/high-temperature conditions. Subsequently, the reaction temperature was lowered to room temperature by the joint use of both basic and acidic additives to improve the safety of the synthesis, as azides were to be handled as unstable reactants. Scale-up experiments were also performed, which led to the achievement of gram-scale production in a safe and straightforward way. The obtained 1,2,3-triazole-substituted β-aminocyclohexanecarboxylates can be regarded as interesting precursors for drugs with possible biological effects.

show abstract

“…However, in connection with this, it should be noted that as yet the biological effects of molecules derived from organic synthesis have not been well explored. Literature has described 1,2,3-triazole compound as an important class of five-member nitrogen heterocyclic system which exhibits different pharmacological profiles, such as antiplatelet activity [15], anticlotting [16], antiviral [17], trypanocidal [18], antimicrobial [19], and/or their use in treating schizophrenia [20] and leishmaniasis [21]. Two general methods are available for the construction of 1,2,3-triazole rings: Huisgen 1,3-dipolar cycloaddition reactions [22], in particular the copper(I)-catalyzed cycloaddition [23], and the intramolecular 1,5-electrocyclization of β -substituted- α -diazocarbonyl compounds [24].…”

Section: Introductionmentioning

confidence: 99%

Antivenom Effects of 1,2,3-Triazoles againstBothrops jararacaandLachesis mutaSnakes

Domingos

Moura

Campos

et al. 2013

BioMed Research International

Self Cite

View full text Add to dashboard Cite

Snake venoms are complex mixtures of proteins of both enzymes and nonenzymes, which are responsible for producing several biological effects. Human envenomation by snake bites particularly those of the viperid family induces a complex pathophysiological picture characterized by spectacular changes in hemostasis and frequently hemorrhage is also seen. The present work reports the ability of six of a series of 1,2,3-triazole derivatives to inhibit some pharmacological effects caused by the venoms of Bothrops jararaca and Lachesis muta. In vitro assays showed that these compounds were impaired in a concentration-dependent manner, the fibrinogen or plasma clotting, hemolysis, and proteolysis produced by both venoms. Moreover, these compounds inhibited biological effects in vivo as well. Mice treated with these compounds were fully protected from hemorrhagic lesions caused by such venoms. But, only the B. jararaca edema-inducing activity was neutralized by the triazoles. So the inhibitory effect of triazoles derivatives against some in vitro and in vivo biological assays of snake venoms points to promising aspects that may indicate them as molecular models to improve the production of effective antivenom or to complement antivenom neutralization, especially the local pathological effects, which are partially neutralized by antivenoms.

show abstract

Synthesis, antiplatelet and in silico evaluations of novel N-substituted-phenylamino-5-methyl-1H-1,2,3-triazole-4-carbohydrazides

Cited by 73 publications

References 20 publications

Preparation, characterization and Microbicide activities of N'-((3-(hydroxyimino)butan-2-ylidene)-2-(phenylamino)acetohydrazide and its complexes

Preparation, characterization and Microbicide activities of N'-((3-(hydroxyimino)butan-2-ylidene)-2-(phenylamino)acetohydrazide and its complexes

Efficient continuous-flow synthesis of novel 1,2,3-triazole-substituted β-aminocyclohexanecarboxylic acid derivatives with gram-scale production

Antivenom Effects of 1,2,3-Triazoles againstBothrops jararacaandLachesis mutaSnakes

Contact Info

Product

Resources

About