Experimental and DFT study of pyrazinamide

Chiş, Vasile; Pîrnaˇu, A.; Jurca, Tünde; Vasilescu, Marius; Simon, S.; Cozar, O.; David, L.

doi:10.1016/j.chemphys.2005.05.004

Cited by 49 publications

(34 citation statements)

References 41 publications

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“…In a recent study, Castro et al 31 reported the infrared spectra of the different polymorphs of PZA, thus filling an important gap on the available knowledge about this compound. Taking the conclusions of that study into account, it can now be stated beyond doubt that Gunasekaran and Sailatha, 3 Akyuz and Akyuz, 8 Favila et al, 28 Cozar et al, 29 and Chiş et al 30 investigated the R polymorph, whereas Kalkar et al 6 studied R-PZA in nujol mull but the γ polymorph in KBr pellet; Wang et al 11 presented data of poor quality, but probably all corresponding to the γ polymorph. According to Castro et al, 31 all polymorphs are kinetically stable at room temperature, with the γ form being the stable polymorph above 180°C and the δ one being the most stable polymorph at low temperature.…”

Section: Introductionmentioning

confidence: 99%

“…According to the theoretical predictions, 29,30 conformer E has a planar structure, while in the second conformer the plane containing the C 2 , C 10 , N 11 , and O 14 atoms remains 33.8°out of the pyrazinic ring and the H 12 and H 13 atoms are twisted 25.6°a nd 6.5°in relation to the C 2 C 10 N 11 O 14 plane. The E conformer was predicted to be 34.9 kJ mol -1 more stable than the Z form.…”

Section: Introductionmentioning

confidence: 99%

“…The E conformer was predicted to be 34.9 kJ mol -1 more stable than the Z form. 29,30 The isolated centrosymmetric dimer based on the E monomer that constitutes the main structural motif of the R, , and δ crystalline modifications of PZA has also been studied theoretically. 29,30 It was suggested that the two N-H · · · Od intermolecular H-bonds in this dimer are moderately strong and predominately electrostatic in nature, following the general pattern found for dimers of other compounds formed by N-H · · · Od bonds.…”

Section: Introductionmentioning

confidence: 99%

“…For example, infrared or Raman data for the compound have been discussed in several of those studies 3,6,8,10,11,[28][29][30] without specification of which polymorph was under investigation. In a recent study, Castro et al 31 reported the infrared spectra of the different polymorphs of PZA, thus filling an important gap on the available knowledge about this compound.…”

Section: Introductionmentioning

confidence: 99%

“…In contrast with the substantial number of studies previously reported on the crystalline states of PZA, no experimental data ontheisolatedmoleculehavebeenreportedhitherto.Theoretically, [28][29][30] two possible conformers of PZA have been predicted to exist, one with the NH 2 group in the cis position to the ring nitrogen atom ortho to the amide substituent (E conformer) and the other one with the NH 2 group in the trans position (Z conformer). According to the theoretical predictions, 29,30 conformer E has a planar structure, while in the second conformer the plane containing the C 2 , C 10 , N 11 , and O 14 atoms remains 33.8°out of the pyrazinic ring and the H 12 and H 13 atoms are twisted 25.6°a nd 6.5°in relation to the C 2 C 10 N 11 O 14 plane.…”

Section: Introductionmentioning

confidence: 99%

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Low Temperature Infrared Spectroscopy Study of Pyrazinamide: From the Isolated Monomer to the Stable Low Temperature Crystalline Phase

et al. 2009

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A structural and spectroscopic analysis of the anti-tuberculosis drug pyrazinamide (PZA) was carried out. The PZA molecule was predicted theoretically to possess two conformers differing by internal rotation around the C-C(dO) bond, with the E conformer (C s symmetry point group; N-C-CdO dihedral: 180°) being ca. 30 kJ mol -1 more stable than the Z form (C 1 point group; N-C-CdO dihedral: ca. ( 42°). In consonance with both the large energy difference and low energy barrier between the Z and E conformers, upon isolation in low temperature argon and xenon matrices, only the E form could be observed and characterized spectroscopically. In the argon matrix, this conformer was found to exist in at least three matrix sites, of different stability. In a supersonic jet, besides the monomer (E), the most stable dimer of PZA with two equivalent NH · · · Od hydrogen bonds could also be identified. Its spectrum reveals rapid energy flow out of the excited NH stretching mode mediated by one of the heteroatoms in the ring. Finally, the IR spectra of the amorphous solid resulting from fast cooling of the vapor of the compound (initially in the R crystalline phase) onto the cold substrate of the cryostat (10 K) and of the crystalline phase resulting from warming the amorphous solid were also recorded and interpreted. The obtained crystalline phase was found to be the thermodynamically most stable δ polymorph of PZA.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Low Temperature Infrared Spectroscopy Study of Pyrazinamide: From the Isolated Monomer to the Stable Low Temperature Crystalline Phase

et al. 2009

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Computational investigation of pyrazinamide drugs and its transition metal complexes using aDFTapproach

Khan,

Maha,

Riaz

et al. 2023

J Comput Chem

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Pyrazinamide, an antituberculosis but documented toxic drug, is subjected to computational investigation along with the metal complexes via a DFT approach to predict the structure–activity and structure‐toxicity relationship. 6‐31G(d,p) basis set was used for Zn, Ni, Mn, Fe, and Co, while the SDD basis set was applied to Cu, Cr, Cd, and Hg. Several reactivity parameters and charge distribution were calculated and the reactivity profile was estimated. The complexes were found to be soft and polarizable which could be responsible for their binding with bacterial targets to inhibit their growth. In contrast, pyrazinamide which is found to be hard among all is susceptible to being toxic. Moreover, the electronegative nature of the complexes can endow them with a better antibacterial effect. Since metal complexes have been found to be less toxic and more biologically interactive by computational methods, they can be employed as potent drugs for the cure of tuberculosis.

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CHIH-DFT determination of the molecular structure infrared spectra, UV spectra and chemical reactivity of three antitubercular compounds: Rifampicin, Isoniazid and Pyrazinamide

2007

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Three of the most frequent antitubercular agents employed against Mycobacterium tuberculosis are: Rifampicin, Isoniazid and Pyrazinamide. It has been proven that the use of these antitubercular agents together, shortens the treatment period from 12-18 months to 6 months [1]. In this work we use a new Density Functional Theory chemistry model called CHIH-DFT (Chihuahua-Heterocycles-Density Functional Theory) that reflects the mixture of Hartree Fock exchange and DFT exchange, according to a mixing parameter based on empirical rules suited for heterocyclic systems. This new chemistry model was used to calculate the molecular structure of these antitubercular compounds, as well as their infrared, UV spectra, chemical reactivity and electronic properties. The UV and infrared spectra were obtained by experimental techniques. The calculated molecular structure, UV and IR spectra values from CHIH-DFT were compared with experimentally obtained values and theoretical studies. These results are in good agreement with experimental and theoretical studies. We also predicted using the relative electrophilicity and relative nucleophilicity concepts as defined by Roy et al. [2] the chemical active sites for the three antitubercular compounds as well as their electronegativity, ionization potential, electron affinity, hardness, dipole moment, E(HOMO)-E(LUMO) gap energy, etc.

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Experimental and DFT study of pyrazinamide

Cited by 49 publications

References 41 publications

Low Temperature Infrared Spectroscopy Study of Pyrazinamide: From the Isolated Monomer to the Stable Low Temperature Crystalline Phase

Low Temperature Infrared Spectroscopy Study of Pyrazinamide: From the Isolated Monomer to the Stable Low Temperature Crystalline Phase

Computational investigation of pyrazinamide drugs and its transition metal complexes using aDFTapproach

CHIH-DFT determination of the molecular structure infrared spectra, UV spectra and chemical reactivity of three antitubercular compounds: Rifampicin, Isoniazid and Pyrazinamide

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