Synthesis and antimicrobial activities of hydrazones derived from 4-hydroxy-3-nitrobenzaldehyde

Nguyen Thi Ngoc Mai, Trinh Thi Huan, Le Thanh Van, Nguyen Vu Huan, Duong Quoc Hoan
Author affiliations

Authors

  • Nguyen Thi Ngoc Mai Department of Science, Hong Duc University, 565 Quang Trung Str., Dong Ve Ward, Thanh Hoa City, Viet Nam https://orcid.org/0000-0002-9639-1696
  • Trinh Thi Huan Department of Science, Hong Duc University, 565 Quang Trung, Dong Ve, Thanh Hoa City, Viet Nam https://orcid.org/0000-0002-4584-822X
  • Le Thanh Van Yen Dinh 1 High School, 05, Quan Lao, Yen Dinh, Thanh Hoa, Viet Nam
  • Nguyen Vu Huan Department of Chemistry, Hanoi National University of Education, 136 Xuan Thuy Str., Cau Giay Dist., Ha Noi, Viet Nam
  • Duong Quoc Hoan Department of Chemistry, Hanoi National University of Education, 136 Xuan Thuy Str., Cau Giay Dist., Ha Noi, Viet Nam https://orcid.org/0000-0001-7540-6142

DOI:

https://doi.org/10.15625/2525-2518/17073

Keywords:

4-hydroxy-3-nitrobenzaldehyde, benzo[d]thiazole, hydrazone, microwave

Abstract

A method using transistors based on semiconducting carbon nanotubes were developed for the real-time monitoring of the electrophysiological responses of individual cells to histamine stimulation. Transistors with one or three floating electrodes were utilized to evaluate histamine-induced Ca2+ influx into Hela cells via recording the conductance changes of the transistors. The Hela cells were directly cultured on the semiconducting carbon nanotube junction area of the transistors. The Ca2+ influx resulted from the activation of histamine H1 receptors embedded on the cell membranes by histamine, which generated a temporary negative potential at the gap between the cell and the transistor. The addition of histamine therefore increased the conductance of the p-type transistors. Moreover, the antihistamine effects of chlorpheniramine on histamine-induced Ca2+ influx were also investigated using a transistor including three floating electrodes. The data showed that chlorpheniramine partial reduced the increase in the conductance of the transistor during the addition of histamine, indicating the antihistamine activity of chlorpheniramine. Especially, only a single transistor was applied to repeat the measurements of the responses of multiple Hela cells pretreated with chlorpheniramine to histamine stimulation. This allows us to acquire data without being suffered from device-to-device variations, implying that our method would be a simple yet powerful one for applications of nanoscale biosensors for electrophysiological studies.

Downloads

Download data is not yet available.

References

Mohareb, R.M., EL-Sharkawy K. A, Farouk F. O. A. Synthesis, cytotoxicity against cancer and normal cell lines of novel hydrazide–hydrazone derivatives bearing 5H-chromen-5-one. Med. Chem. Res. 28 (2019), 1885–1900. doi.org/10.1007/S00044-019-02421-6. DOI: https://doi.org/10.1007/s00044-019-02421-6

Kumar D., Kumar N. M., Ghosh S., Shah K., Novel bis(indolyl)hydrazide-hydrazones as potent cytotoxic agents. Bioorganic Med. Chem. Lett. 22(2012), 212–215. doi.org/10.1016 / j.bmcl.2011.11.031. DOI: https://doi.org/10.1016/j.bmcl.2011.11.031

John S. F., Aniemeke E., Ngan P. H., Chong C. R., Gu P., Zhou J., Zhang Y., Graviss E., Liu J. O., Olaleye O. A., Characterization of 2-hydroxy-1-naphthaldehyde isonicotinoyl hydrazone as a novel inhibitor of methionine aminopeptidases from Mycobacterium tuberculosis, Tuberculosis, 101 (2016) S73-S77. doi.org/10.1016/j.tube.2016.09.025. DOI: https://doi.org/10.1016/j.tube.2016.09.025

Bonnett S.A., Dennison D., Files M., Bajpai A., Parish T. A class of hydrazones are active against nonreplicating Mycobacterium tuberculosis. PLoS One. 13 (2018), 1-11. doi.org/10.1371/journal.pone.0198059. DOI: https://doi.org/10.1371/journal.pone.0198059

De Miranda A. S., Júnior W. B., Da Silva Y. K. C., Alexandre-Moreira M. S., Castro R. P., Sabino J. R., Lião L. M., Lima L. M., Barreiro E. J. Design, synthesis, antinociceptive and anti-inflammatory activities of novel piroxicam analogues. Molecules. 17(2012), 14126–14145. doi.org/10.3390%2Fmolecules171214126. DOI: https://doi.org/10.3390/molecules171214126

Nikiforchin. R. N. Comparative evaluation of antimicrobial properties of actinomyces isolated from the patients with pulmonary tuberculosis, treated with phthivazid and streptomycin. Probl Tuberk. 49(1971), 66-71.

Meyer-Rohn J. S. P. Experimental and clinical experiences with isonicotinoylhydrazone-D-glucuronic-acid-lactone (Gluronazid). Der Hautarzt. 22 (1971). 105-110.

Chatterjee S. N., Ghosh S. Mechanism of action of furazolidone: inter-stand cross-linkage in DNA & liquid holding recovery of Vibrio cholerae cells. Indian J. Biochem. Biophys. 16 (1979),125-130.

McCalla D.R., Reuvers A. and Kaiser C. Mode of action of nitro-furazone. J. Bacteriol. 104 (1970), 1126-1134. doi.org/ 10.1128/jb.104.3.1126-1134.1970 DOI: https://doi.org/10.1128/jb.104.3.1126-1134.1970

Munoz-Davila M.J. Role of old antibiotics in the Era of antibiotic resistance. Highlighted nitrofuranation for the treatment of lower urinary tract infections. Antibiotics, 3(2014), 39-48. doi.org/ 10.3390/antibiotics3010039 DOI: https://doi.org/10.3390/antibiotics3010039

Hoan D. Q., Tuyet V. T. A., Duong L. T., Hien N., Preparation of some new benzo[d]thiazole derivatives, Vietnam J. Chem. Int. Ed. 55 (2017), 433–437. doi.org/10.15625/2525-2321.2017-00487 DOI: https://doi.org/10.15625/2525-2321.2017-00487

Mai N. T. N., Anh T. T. P., May P. T. T., Thao P. P., Trang N. V., Hoan D. Q., Preparation of some benzo[d]thiazole-containing acetohydrazide derivatives, J. Sci. HNUE, 64(2019), 3–10. doi.org/10.18173/2354-1059.2019-0039. DOI: https://doi.org/10.18173/2354-1059.2019-0039

Siddiqui N., Sarafroz M., Alam M. M., Ahsan W. Synthesis, anticonvulsant and neurotoxicity evaluation of 5-carbomethoxybenzoxazole derivatives. Acta Pol. Pharm. 65(2008), 449–455.

Robert, D.J.K., Silverstein M., Webster F.X., Spectrometric Identification of Organic Compounds. John Wiley & Sons (2005).

Nguyen T. N. M., Duong Q. H., Vu T. A. T., Tran T. T. T., Duong K. L. and Trinh T. H.. An effective assembling of novel derivatives containing both benzo[d]thiazole and benzo[d]oxazole rings, Letter in Organic Chemistry, 17 (2020), 815 – 822. doi.org/10.2174/1570178617666200207104912. DOI: https://doi.org/10.2174/1570178617666200207104912

Palla, G.; Pelizzi, G.; Predieri, G.; Vignali, C. Conformational study on N-acylhydrazones of aromatic aldehydes by NMR spectroscopy. Gazz. Chim. Ital., 112 (1982), 339.

Syakaev V. V., Podyachev S. N., Habicher W. D, Buzykin B. I., Latypov S. K., Konovalov A. I. NMR study of conformation and isomerization of aryl- and heteroarylaldehyde 4-tert-butylphenoxyacetylhydrazones, J. Mol. Struct. 788 (2006) 55–62. doi.org/10.1016/j.molstruc.2005.11.018. DOI: https://doi.org/10.1016/j.molstruc.2005.11.018

Himmerlreich, U.; Tschwatschal, F.; Borsdorf, R. NMR-spektroskopische Untersuchungen an Derivaten des 2,4-Dichlorphenoxyessigsäurehydrazids. Monatsh. Chem. 124 (1993), 1041-1051. doi.org/10.1007/BF00814150. DOI: https://doi.org/10.1007/BF00814150

Downloads

Published

05-04-2023

How to Cite

[1]
Nguyen Thi Ngoc Mai, Trinh Thi Huan, Le Thanh Van, Nguyen Vu Huan, and Duong Quoc Hoan, “Synthesis and antimicrobial activities of hydrazones derived from 4-hydroxy-3-nitrobenzaldehyde”, Vietnam J. Sci. Technol., vol. 61, no. 3, pp. 373–381, Apr. 2023.

Issue

Section

Natural Products