Synthesis, Characterization, Antimicrobial and Antioxidant Activities of The Homocyclotrimer Of 4-Oxo-4h-Thieno[3,4-C]Chromene-3-Diazonium Sulfate

Sopbue Fondjo, Emmanuel; Sorel, Djeukoua Dimo Kamal; Jean-de-Dieu, Tamokou; Joseph, Tsemeugne; Sylvian, Kouamo; Doriane, Ngouanet; Rodolphe, Chouna Jean; Pepin, Nkeng-Efouet-Alango; Jules-Roger, Kuiate; Arnaud, Ngongang Ndjintchui; Lucas, Sondengam Beibam

Synthesis, Characterization, Antimicrobial and Antioxidant Activities of The Homocyclotrimer Of 4-Oxo-4h-Thieno[3,4-C]Chromene-3-Diazonium Sulfate

Emmanuel Sopbue Fondjo^{*, a}, Djeukoua Dimo Kamal Sorel^a, Tamokou Jean-de-Dieu^b, Tsemeugne Joseph^a, Kouamo Sylvian^a, Ngouanet Doriane^a, Chouna Jean Rodolphe^a, Nkeng-Efouet-Alango Pepin^a, Kuiate Jules-Roger^b, Ngongang Ndjintchui Arnaud^c, Sondengam Beibam Lucas^d

^a Laboratory of Applied Synthetic Organic Chemistry, Department of Chemistry, Faculty of Science, University of Dschang, P.O. Box 67 Dschang, Republic of Cameroon

^b Laboratory of Microbiology and antimicrobial Substances, Department of Biochemistry, Faculty of Science, University of Dschang, PO Box 067 Dschang, Republic of Cameroon

^c Technical University of Munich, Department of Chemistry Lichtenbergstrasse 4, D-85747 Garching, Germany

^d Department of Organic Chemistry, University of Yaounde I, P.O. Box 812 Yaounde, Republic of Cameroon

Article Information

Identifiers and Pagination:

Year: 2016
Volume: 10
First Page: 21
Last Page: 32
Publisher ID: TOMCJ-10-21
DOI: 10.2174/1874104501610010021

Article History:

Received Date: 02/10/2015
Revision Received Date: 09/05/2016
Acceptance Date: 12/5/2016
Electronic publication date: 30/06/2016
Collection year: 2016

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© Sopbue Fondjo et al.; Licensee Bentham Open.

open-access license: This is an open access article licensed under the terms of the Creative Commons Attribution-Non-Commercial 4.0 International Public License (CC BY-NC 4.0) (https://creativecommons.org/licenses/by-nc/4.0/legalcode), which permits unrestricted, non-commercial use, distribution and reproduction in any medium, provided the work is properly cited.

^* Address correspondence to this author at the Laboratory of Applied Synthetic Organic Chemistry, Department of Chemistry, Faculty of Science, University of Dschang, P.O. Box 67 Dschang, Republic of Cameroon; Tel: +237 677822491; E-mail: sopbue@yahoo.fr

The in situ formed 4-oxo-4H-thieno[3,4-c]chromene-3-diazonium sulfate (5) in the coupling reactions involving the parent 2-aminothiophene (4) and various phenolic and arylamines’ couplers, readily undergoes homocyclotrimerization at low temperature to afford in fairly good yield the first ever reported eighteen member ring heteroaromatic holigomer 6. Compound 6 was fully characterized by its elemental analysis, IR, UV-Vis, ¹H-NMR, ¹³C-NMR and HRMS spectral data. The HMBC and HSQC techniques were used to ascertain the structural assignments. A comparative study on the antimicrobial and antioxidant activities of compounds 3, 4 and 6 was carried out to assess the SAR due to the transformations (from 3 to 6 via 4) on the tested compounds. It was found that compounds 6 and 4 were respectively the most active compounds against bacteria (MIC = 32-64 μg/ml) and yeasts (MIC = 16–64 μg/ml). Compound 6 also showed high radical-scavenging activities and ferric reducing power when compared with vitamin C and BHT used as reference antioxidants.

Keywords: 2-aminothiophene, Azo compounds, Antimicrobial, Antioxidant, Coumarin, Homocyclotrimerization, Holigomer, SAR.

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RESEARCH ARTICLE

Synthesis, Characterization, Antimicrobial and Antioxidant Activities of The Homocyclotrimer Of 4-Oxo-4h-Thieno[3,4-C]Chromene-3-Diazonium Sulfate

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