Cytotoxicity and Leishmanicidal Activity of Isoniazid-Derived Hydrazones and 2-Pyrazineformamide Thiosemicarbazones

Amim, Raquel S.; Firmino, Gisele S. S.; Rego, Ana C. P. D.; Nery, Adriane L.; Da-Silva, Silvia A. G.; Souza, Marcus V. N. de; Pessoa, Cláudia; Resende, Jackson A. L. C.; Figueroa‐Villar, José Daniel; Lessa, Josane A.

doi:10.5935/0103-5053.20150330

Cited by 4 publications

(4 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…7,8 Furthermore, some hydrazones are used as quantitative analytical reagents, especially in the colorimetric and fluorimetric determination of metal ions. [4][5][6] The ubiquity and versatility of hydrazones can be attributed to the ease of their synthesis [9][10][11][12] and, most importantly, unique structural properties, which enable their existence in different isomeric forms. [13][14][15][16][17] Isomerism involving this functional group has been extensively investigated in recent years.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and computationally assisted spectroscopic study of tautomerism in 3-(phenyl(2-arylhydrazineylidene)methyl)quinoxalin-2(1H)-ones

et al. 2022

View full text Add to dashboard Cite

show abstract

Section: Introductionmentioning

confidence: 99%

Synthesis and computationally assisted spectroscopic study of tautomerism in 3-(phenyl(2-arylhydrazineylidene)methyl)quinoxalin-2(1H)-ones

et al. 2022

View full text Add to dashboard Cite

show abstract

“… Overlay of molecules for analog structures from CSD (zwitterion form (YACFOY [ 39 ], WEXSUO [ 11 ], WEXSOI [ 11 ], SUZGUP [ 40 ], PASZEP [ 12 ], MEVNIK [ 41 ], BEWLOH [ 7 ], ADABIQ [ 42 ])—blue, neutral form (YAPJUV [ 43 ], XOTWUY01 [ 44 ], WOGGAC [ 44 ], WOGFUV [ 44 ], UYOSIM [ 45 ], MEMWUW [ 46 ], DIFROZ01 [ 47 ])—red). …”

Section: Figures Scheme and Tablesmentioning

confidence: 99%

Relationship between the Crystal Structure and Tuberculostatic Activity of Some 2-Amidinothiosemicarbazone Derivatives of Pyridine

et al. 2022

View full text Add to dashboard Cite

Tuberculosis remains one of the most common diseases affecting developing countries due to difficult living conditions, the rapidly increasing resistance of M. tuberculosis strains and the small number of effective anti-tuberculosis drugs. This study concerns the relationship between molecular structure observed in a solid-state by X-ray diffraction and the 15N NMR of a group of pyridine derivatives, from which promising activity against M. tuberculosis was reported earlier. It was found that the compounds exist in two tautomeric forms: neutral and zwitterionic. The latter form forced the molecules to adopt a stable, unique, flat frame due to conjugation and the intramolecular hydrogen bond system. As the compounds exist in a zwitterionic form in the crystal state generally showing higher activity against tuberculosis, it may indicate that this geometry of molecules is the “active” form.

show abstract

“…e characterization of a novel series of the phenylisoxazole-3/5-carbaldehyde isonicotinylhydrazone derivatives 1-8 was performed by using the 1D NMR ( 1 H-and 13 C-NMR) and 2D ( 1 H-1 H COSY, 1 H-1 H NOESY, 1 H- 13 C HSQC, and 1 H- 13 C HMBC) spectra, recorded in acetone-d 6 / DMSO-d 6 (see Supplementary [11][12][13][14][15]18,19,22,23,26,[28][29][30][31][32][34][35][36][37][38]41,and 42 in Supplementary Materials).…”

Section: Nmr Spectramentioning

confidence: 99%

“…In recent years, the isoniazid derivatives with phenyl, pyridyl, amidoether, dibenzofuran, and carvone fragments have been investigated since they exhibit wide spectrum of pharmacological applications, such us antitubercular [17][18][19][20], antimicrobial [21,22], antileishmanial [23], antifungal [24], and anticancer [23,[25][26][27] activities.…”

Section: Introductionmentioning

confidence: 99%

Phenylisoxazole-3/5-Carbaldehyde Isonicotinylhydrazone Derivatives: Synthesis, Characterization, and Antitubercular Activity

Carrasco

Hernández

Chupayo

et al. 2021

Journal of Chemistry

View full text Add to dashboard Cite

Eight new phenylisoxazole isoniazid derivatives, 3-(2′-fluorophenyl)isoxazole-5-carbaldehyde isonicotinylhydrazone (1), 3-(2′-methoxyphenyl)isoxazole-5-carbaldehyde isonicotinylhydrazone (2), 3-(2′-chlorophenyl)isoxazole-5-carbaldehyde isonicotinylhydrazone (3), 3-(3′-clorophenyl)isoxazole-5-carbaldehyde isonicotinylhydrazone (4), 3-(4′-bromophenyl)isoxazole-5-carbaldehyde isonicotinylhydrazone (5), 5-(4′-methoxiphenyl)isoxazole-3-carbaldehyde isonicotinylhydrazone (6), 5-(4′-methylphenyl)isoxazole-3-carbaldehyde isonicotinylhydrazone (7), and 5-(4′-clorophenyl)isoxazole-3-carbaldehyde isonicotinylhydrazone (8), have been synthesized and characterized by FT-IR, 1H-NMR, 13C-NMR, and mass spectral data. The 2D NMR (1H-1H NOESY) analysis of 1 and 2 confirmed that these compounds in acetone-d6 are in the trans(E) isomeric form. This evidence is supported by computational calculations which were performed for compounds 1–8, using DFT/B3LYP level with the 6-311++G(d,p) basis set. The in vitro antituberculous activity of all the synthesized compounds was determined against the Mycobacterium tuberculosis standard strains: sensitive H37Rv (ATCC-27294) and resistant TB DM97. All the compounds exhibited moderate bioactivity (MIC = 0.34–0.41 μM) with respect to the isoniazid drug (MIC = 0.91 μM) against the H37Rv sensitive strain. Compounds 6 (X = 4′-OCH3) and 7 (X = 4′-CH3) with MIC values of 12.41 and 13.06 μM, respectively, were about two times more cytotoxic, compared with isoniazid, against the resistant strain TB DM97.

show abstract

Cytotoxicity and Leishmanicidal Activity of Isoniazid-Derived Hydrazones and 2-Pyrazineformamide Thiosemicarbazones

Cited by 4 publications

References 1 publication

Synthesis and computationally assisted spectroscopic study of tautomerism in 3-(phenyl(2-arylhydrazineylidene)methyl)quinoxalin-2(1H)-ones

Synthesis and computationally assisted spectroscopic study of tautomerism in 3-(phenyl(2-arylhydrazineylidene)methyl)quinoxalin-2(1H)-ones

Relationship between the Crystal Structure and Tuberculostatic Activity of Some 2-Amidinothiosemicarbazone Derivatives of Pyridine

Phenylisoxazole-3/5-Carbaldehyde Isonicotinylhydrazone Derivatives: Synthesis, Characterization, and Antitubercular Activity

Contact Info

Product

Resources

About