Synthesis of Some Novel Substituted Nicotines and Evaluation of Their Antimicrobial Activity
Masoud, D., Azzam, R., Hussein, H., Mekawey, A., Abdel-Aziz, H. (2020). Synthesis of Some Novel Substituted Nicotines and Evaluation of Their Antimicrobial Activity. EKB Journal Management System, 63(3), 791-803. doi: 10.21608/ejchem.2019.13805.1853
Doaa M. Masoud; Rasha Azzam; Hussein S. Hussein; Aml A.I. Mekawey; Hatem A. Abdel-Aziz. "Synthesis of Some Novel Substituted Nicotines and Evaluation of Their Antimicrobial Activity". EKB Journal Management System, 63, 3, 2020, 791-803. doi: 10.21608/ejchem.2019.13805.1853
Masoud, D., Azzam, R., Hussein, H., Mekawey, A., Abdel-Aziz, H. (2020). 'Synthesis of Some Novel Substituted Nicotines and Evaluation of Their Antimicrobial Activity', EKB Journal Management System, 63(3), pp. 791-803. doi: 10.21608/ejchem.2019.13805.1853
Masoud, D., Azzam, R., Hussein, H., Mekawey, A., Abdel-Aziz, H. Synthesis of Some Novel Substituted Nicotines and Evaluation of Their Antimicrobial Activity. EKB Journal Management System, 2020; 63(3): 791-803. doi: 10.21608/ejchem.2019.13805.1853

Synthesis of Some Novel Substituted Nicotines and Evaluation of Their Antimicrobial Activity

Egyptian Journal of Chemistry
Article 67, Volume 63, Issue 3, March 2020, Page 791-803  XML PDF (1.27 MB)
Document Type: Original Article
DOI: 10.21608/ejchem.2019.13805.1853
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Authors
Doaa M. Masoud1; Rasha Azzam email orcid 2; Hussein S. Hussein1; Aml A.I. Mekawey3; Hatem A. Abdel-Azizorcid 4
1Chemistry Department, Faculty of Science, Helwan University, Ain-Helwan, Cairo11795, Egypt
2Chemistry department, Faculty of Science, Helwan University, Ain-Helwan, Cairo 11795, Egypt
3Regional Center of Mycology and Biotechnology, Al-Azhar University, Cairo, Egypt
4Department of Applied Organic Chemistry, National Research Centre, Dokki, Giza, P.O. Box 12622, Egypt.
Abstract
A VARIETY of some novel substituted nicotines were synthesized and characterized by spectroscopic means where nicotinic acid hydrazide (6a) and/or (6b) are used as a key intermediate in the synthesis of hydrazones (8a-l) and (10a-f) by the reaction with different aromatic aldehydes (7a-f) and isatines (9a-e), respectively. Moreover, nicotinic acid hydrazide reacted with pentane-2,4-dione (11), 2-ethoxymethylene-malononitrile (13) and thiosemicarbazone (15) generating pyrazoles (12), (14) and 1,2,4-triazole (16), respectively. The newly synthesized compounds were tested against nine microbial strains. Some of these compounds showed a significant activity against several of the microorganisms. Compounds (8d), (10b) and (10c) were determined to be the most active compounds. Compound (8d) showed activity against S. aureus, B. subtilis and A. flavus with IZ = 2.4, 3.2 and 2.6 mm, respectively when compared with reference drugs (Amoxicillin, IZ = 2.3, 3.5 and Griseofulvin, IZ = 2.4 mm). Additionally, compound (10b) showed potent activity against P. aeruginosa and P. expansum with IZ = 2.6 and 2.8, respectively when compared with reference drugs (Amoxicillin, IZ = 2.2 mm and Griseofulvin, IZ = 2.8 mm), respectively, while (10c) showed the same activity as Griseofulvin against P. expansum with IZ = 2.8 mm. The biological activity (SAR) of the evaluated compounds and the relationship between the functional group variations are discussed.
Keywords
antimicrobial activity; Enaminone; Isatin; Nicotines; Pyridine
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