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

Fernando Carlos Carrasco Solis; Wilfredo Román Hernandez Gorritti; Oscar Chupayo; Patricia Sheen; Mirko Zimic; Jorge Coronel; Celedonio M. Álvarez; Sergio Ferrero; Sandra Oramas-Royo; Evgenia Spodine; Jesus M. Rodilla; Juan Z. Dávalos

doi:10.1155/2021/6014093

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

Fernando Carlos Carrasco Solis, Wilfredo Román Hernandez Gorritti, Oscar Chupayo, Patricia Sheen, Mirko Zimic, Jorge Coronel, Celedonio M. Álvarez, Sergio Ferrero, Sandra Oramas-Royo, Evgenia Spodine, Jesus M. Rodilla, Juan Z. Dávalos

Research output: Contribution to journal › Article (Contribution to Journal) › peer-review

5 Scopus citations

Abstract

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.

Translated title of the contribution	Derivados del fenilisoxazol-3/5-carbaldehído isonicotinilhidrazona: Síntesis, caracterización, y actividad antitubercular
Original language	English
Article number	ID 6014093
Number of pages	14
Journal	journal of chemistry
Volume	2021
Issue number	ID 6014093
Early online date	31 Oct 2021
DOIs	https://doi.org/10.1155/2021/6014093
State	Published - 31 Oct 2021

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Carrasco Solis, F. C., Hernandez Gorritti, W. R., Chupayo, O., Sheen, P., Zimic, M., Coronel, J., Álvarez, C. M., Ferrero, S., Oramas-Royo, S., Spodine, E., Rodilla, J. M., & Dávalos, J. Z. (2021). Phenylisoxazole-3/5-Carbaldehyde Isonicotinylhydrazone Derivatives: Synthesis, Characterization, and Antitubercular Activity: Synthesis, Characterization, and Antitubercular Activity. journal of chemistry, 2021(ID 6014093), Article ID 6014093. https://doi.org/10.1155/2021/6014093

@article{cdf3058838724639a066f97a8cc261ba,

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

abstract = "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-carbaldehydeisonicotinylhydrazone (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 2DNMR (1H-1H NOESY) analysis of 1 and 2 confirmed that these compounds in acetone-d6 are in the trans(E) isomeric form. Thisevidence 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 Mycobacteriumtuberculosis standard strains: sensitive H37Rv (ATCC-27294) and resistant TB DM97. All the compounds exhibitedmoderate 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 morecytotoxic, compared with isoniazid, against the resistant strain TB DM97.",

author = "{Carrasco Solis}, {Fernando Carlos} and {Hernandez Gorritti}, {Wilfredo Rom{\'a}n} and Oscar Chupayo and Patricia Sheen and Mirko Zimic and Jorge Coronel and {\'A}lvarez, {Celedonio M.} and Sergio Ferrero and Sandra Oramas-Royo and Evgenia Spodine and Rodilla, {Jesus M.} and D{\'a}valos, {Juan Z.}",

note = "Publisher Copyright: {\textcopyright} 2021 Fernando Carrasco et al.",

year = "2021",

month = oct,

day = "31",

doi = "10.1155/2021/6014093",

language = "Ingl{\'e}s",

volume = "2021",

journal = "journal of chemistry",

issn = "2090-9071",

number = "ID 6014093",

}

Carrasco Solis, FC , Hernandez Gorritti, WR, Chupayo, O, Sheen, P, Zimic, M, Coronel, J, Álvarez, CM, Ferrero, S, Oramas-Royo, S, Spodine, E, Rodilla, JM & Dávalos, JZ 2021, 'Phenylisoxazole-3/5-Carbaldehyde Isonicotinylhydrazone Derivatives: Synthesis, Characterization, and Antitubercular Activity: Synthesis, Characterization, and Antitubercular Activity', journal of chemistry, vol. 2021, no. ID 6014093, ID 6014093. https://doi.org/10.1155/2021/6014093

Phenylisoxazole-3/5-Carbaldehyde Isonicotinylhydrazone Derivatives: Synthesis, Characterization, and Antitubercular Activity: Synthesis, Characterization, and Antitubercular Activity. / Carrasco Solis, Fernando Carlos ; Hernandez Gorritti, Wilfredo Román; Chupayo, Oscar et al.
In: journal of chemistry, Vol. 2021, No. ID 6014093, ID 6014093, 31.10.2021.

Research output: Contribution to journal › Article (Contribution to Journal) › peer-review

TY - JOUR

T1 - Phenylisoxazole-3/5-Carbaldehyde Isonicotinylhydrazone Derivatives: Synthesis, Characterization, and Antitubercular Activity

T2 - Synthesis, Characterization, and Antitubercular Activity

AU - Carrasco Solis, Fernando Carlos

AU - Hernandez Gorritti, Wilfredo Román

AU - Chupayo, Oscar

AU - Sheen, Patricia

AU - Zimic, Mirko

AU - Coronel, Jorge

AU - Álvarez, Celedonio M.

AU - Ferrero, Sergio

AU - Oramas-Royo, Sandra

AU - Spodine, Evgenia

AU - Rodilla, Jesus M.

AU - Dávalos, Juan Z.

PY - 2021/10/31

Y1 - 2021/10/31

N2 - 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-carbaldehydeisonicotinylhydrazone (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 2DNMR (1H-1H NOESY) analysis of 1 and 2 confirmed that these compounds in acetone-d6 are in the trans(E) isomeric form. Thisevidence 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 Mycobacteriumtuberculosis standard strains: sensitive H37Rv (ATCC-27294) and resistant TB DM97. All the compounds exhibitedmoderate 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 morecytotoxic, compared with isoniazid, against the resistant strain TB DM97.

AB - 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-carbaldehydeisonicotinylhydrazone (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 2DNMR (1H-1H NOESY) analysis of 1 and 2 confirmed that these compounds in acetone-d6 are in the trans(E) isomeric form. Thisevidence 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 Mycobacteriumtuberculosis standard strains: sensitive H37Rv (ATCC-27294) and resistant TB DM97. All the compounds exhibitedmoderate 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 morecytotoxic, compared with isoniazid, against the resistant strain TB DM97.

UR - http://www.scopus.com/inward/record.url?scp=85118949427&partnerID=8YFLogxK

U2 - 10.1155/2021/6014093

DO - 10.1155/2021/6014093

M3 - Artículo (Contribución a Revista)

AN - SCOPUS:85118949427

SN - 2090-9071

VL - 2021

JO - journal of chemistry

JF - journal of chemistry

IS - ID 6014093

M1 - ID 6014093

ER -

Carrasco Solis FC , Hernandez Gorritti WR, Chupayo O, Sheen P, Zimic M, Coronel J et al. Phenylisoxazole-3/5-Carbaldehyde Isonicotinylhydrazone Derivatives: Synthesis, Characterization, and Antitubercular Activity: Synthesis, Characterization, and Antitubercular Activity. journal of chemistry. 2021 Oct 31;2021(ID 6014093):ID 6014093. Epub 2021 Oct 31. doi: 10.1155/2021/6014093

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

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