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Applied Chemistry, Vol. 1, Issue 1, Jun  2018, Pages 1-12; DOI: 10.31058/j.ac.2018.11001 10.31058/j.ac.2018.11001

Functionalization and Antimicrobial Evaluation of New Linear Azo-Phenothiazine Derivatives

Applied Chemistry, Vol. 1, Issue 1, Jun  2018, Pages 1-12.

DOI: 10.31058/j.ac.2018.11001

Ayuk, Eugene L. 1* , Eze Boniface. 1 , Njokunwogbu 1 , Ambrose N. 1 , Aronimo, Samuel B. 2

1 Department of Chemical Sciences, Faculty of Natural and Applied Sciences, Godfrey Okoye University, Ugeuomu-Nike, Enugu, Nigeria

2 Department of Chemistry, Kogi State College of Education (Technical), Kabba, Kogi State, Nigeria

Received: 1 December 2017; Accepted: 21 December 2017; Published: 12 February 2018

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Abstract

Phenothiazine and its derivatives are very important compounds that have many biological and industrial applications. Azo-compounds on the other hand have also been identified to possess good dyeing and biological properties as well. This work is focused on the synthesis of new linear phenothiazine azo-dye compounds via diazotization reaction as well as the determination of their biological activity against some microogrganisms. The above was achieved by the condensation reaction of 3-nitoaniline and phenol in presence of potassium hydroxide and DMF (solvent) to furnished 3-nitrodiphenylamine. Sulphonation of this compound in presence of molecular iodine gave 4-nitro-[10H]-phenothiazine. The conversion of nitro group in 4-nitro-[10H]-phenothiazine to an amino group was achieved by treating it with dilute hydrochloric acid and iron (III) chloride. The amino compound formed, (4-amino-[10H]-phenothiazine) was thereafter converted to an unstable diazonium ion in the presence of sodium nitrite and concentrated hydrochloric. The ion formed above was immediately coupled with the following compounds; 3-nitroaniline, 4-nitroaniline and phenol respectively to furnish four new azophenothiazine compounds namely; 4-azo-(4-amino-2-nitroanilino)-[10H]-phenothiazine, 4-azo-(2-amino-5-nitroanilino)-[10H]-phenothiazine and 4-azo-(4-hydroxyphenyl)-[10H]-phenothiazine with good percentage yields. The synthesized compounds were tested for activity against some microorganisms and they showed some level of inhibition.

Keywords

Antimicrobial Screening, Microorganisms, Diazotization, Diazonium Ion, Inhibition, Sulphonation, Condensation

Copyright

© 2017 by the authors. Licensee International Technology and Science Press Limited. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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