Synthesis, characterization and antimicrobial activity of a 7-chloro-4- aminoquinolinesemicarbazone derivative

Síntesis, caracterización y actividad antimicrobiana de un derivado 7-cloro-4-aminoquinolinsemicarbazona

  • Yonathan de J. Parra Universidad Central del Ecuador
  • Rosa E. Ferrer Universidad del Zulia
  • Jaime Charris Universidad Central de Venezuela
Keywords: semicarbazone, 7-chloro-4-aminoquinoline, antimicrobial activity, molecular hybridization

Abstract

This study describes the synthesis, characterization and antimicrobial activity evaluation of 2-(1-{3-[(7-chloroquinolin-4-yl)amino]phenyl}ethylidene)hydrazinecarboxamide (5), which was designed and synthesized applying a molecular hybridization strategy, considering two pharmacophoric portions: 7-chloro-4-aminoquinoline and semicarbazone; both fractions have been related to antimicrobial activity exhibited by a series of derivatives synthesized. Compound 5 was characterized using 1H NMR, 13C NMR and Electrospray Ionization Mass Spectrometry (ESI-MS) studies. Biological evaluation showed that compound 5 exhibited antimicrobial activity against bacteria Gram (-) Pseudomona aeruginosa, comparable with the activities corresponding to Amikacin, Ampicillin/Sulbactam and Ofloxacin.

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Author Biographies

Yonathan de J. Parra, Universidad Central del Ecuador

Escuela de Ingeniería Ambiental, Facultad de Ingeniería en Geología, Minas, Petróleos y Ambiental, Universidad Central del Ecuador, Quito, Ecuador.

Rosa E. Ferrer, Universidad del Zulia

Departamento de Química, Facultad de Humanidades y Educación, Universidad del Zulia, Maracaibo, Venezuela.

Jaime Charris, Universidad Central de Venezuela

Laboratorio de Síntesis Orgánica, Facultad de Farmacia, Universidad Central de Venezuela, Caracas, Venezuela.

References

BERALDO H. Quim Nova 27(3): 461-471. 2004.

IBRAHIM MN., AL-DIFAR HA. Der Chemica Sinica 2(1): 171-173. 2011.

VIJAYA S., RAJITHA B. Med Chem Res 21: 85–90. 2012.

AHSAN MJ., AMIR M., BAKHT MA., SAMY JG., HASAN MZ., NOMANI MS. Arab J Chem 9(S1): S861-S866. 2016.

SINGH V., MISHRA A., KHALID M., SINGH S. J Pharm Chem Biol Sci 4: 350-358.2016.

SALES PA., MOLINA I., FONSECA SM., SÁNCHEZ-MONTALVÁ A., SALVADOR F., CORRÊA-OLIVEIRA R., CARNEIRO CM. Am J Trop Med Hyg 97(5): 1289–1303. 2017.

PANDEYA SN. Acta Pharm 62(3): 263-286. 2012.

LIU Z., WU S., WANG Y., LI R., WANG J., WANG L., ZHAO Y., GONG P. Eur J Med Chem 87: 782-793. 2014.

SHAABANI B., KHANDAR AA., MAHMOUDI F., MAESTRO MA., BALULA SS., CUNHA-SILVA L. Polyhedron 57: 118-126. 2013.

SHAABANI B., KHANDAR AA., DUSEK M., POJAROVA M., MAHMOUDI F. Inorg Chim Acta 394: 563-568. 2013.

EL-GAMAL KMA., SHERBINY FF., EL-MORSI AM., EL KHAIR HEA., EISSA IH., EL SEBAEI MM. Pharm Pharmacol Int J 2(5):165-177. 2015.

EL-GAMAL KM., HAGRS MS., ABULKHAIR HS. Bull Fac Pharm Cairo Univ 54(2): 263-273. 2016.

DESAI NC., PATEL BY., DAVE BP. Med Chem Res 26: 109–119. 2017.

ABOELNAGA A., EL-SAYED TH. Green Chem Lett Rev 11(3): 254–263. 2018.

RUDRAPAL M., CHETIA D. Int. J Chemtech Res 2(3): 1606-1611. 2010.

BISPO M., LIMA C., CARDOSO L., CANDÉA A., BEZERRA F., LOURENÇO M., HENRIQUES M., ALENCASTRO RB., KAISER CR., SOUZA M., ALBUQUERQUE MG. Pharmaceuticals (Basel, Switzerland) 10(2): 52-67. 2017.

VIEGAS-JUNIOR C., DANUELLO A., DA SILVA- BOLZANI V., BARREIRO EJ., MANSSOUR- FRAGA CA. Curr Med Chem 14(17):1829-1852. 2007.

FERRER R., LOBO G., GAMBOA N., RODRIGUES J., ABRAMJUK C., JUNG K., LEIN M., CHARRIS J. Sci Pharm 77: 725-741. 2009.

JANSSEN AM, SCHEFFER JJ, BAERHEIM, A. 1987. Planta Med 53(5):395-398. 1987.

SAMBROOK J., FRITSCH EF., MANIATIS T. Molecular cloning: A laboratory manual. Cold Spring Harbor Laboratory Press. New York (USA). Appendix A, pp A.1. 1989.

CHAUHAN P., PRATAP R., SHARMA S. Indian J Chem 24B: 1154-1157. 1985.

GOTO H., KUMADA Y., ASHIDA H., YOSHIDA K. Biosci Biotech Bioch 73(1): 124-128. 2009.

SANTANDER J., OTTO C., LOWRY D., CUELLAR M., MELLADO M., SALAS C., ROTHHAMMER F., ECHIBURU-CHAU C. Microbiol Res J 5(2): 94-106. 2014.

KALLEN A., HIDRON A., PATEL J., SRINIVASAN Infect Control Hosp Epidemiol 31(5): 528- 531. 2010.

KEEN EF., ROBINSON BJ., HOSPENTHAL DR., ALDOUS WK., WOLF SE., CHUNG KK., MURRAY CK. Burns 36: 819–825. 2010.
Published
2018-12-20
How to Cite
Parra, Y. de J., Ferrer, R. E., & Charris, J. (2018). Synthesis, characterization and antimicrobial activity of a 7-chloro-4- aminoquinolinesemicarbazone derivative: Síntesis, caracterización y actividad antimicrobiana de un derivado 7-cloro-4-aminoquinolinsemicarbazona . Ciencia, 26(3-4), 89-94. https://doi.org/10.5281/zenodo.5590947
Section
Química/Chemistry