Design, Synthesis and Antifungal Activity of New Schiff Bases Bearing 2-Aminothiophene Derivatives Obtained by Molecular Simplification

Design, Synthesis and Antifungal Activity of New Schiff Bases Bearing 2-Aminothiophene Derivatives Obtained by Molecular Simplification

Seventeen Schiff bases bearing 2-aminothiophene derivatives were designed and synthesized using molecular simplification. The resulting compounds (4a-4q) were evaluated for their in vitro antifungal activity against dermatophytes. Prediction of their druglikeness and pharmacokinetic properties, establishment of their structure-activity relationships (SAR), and cytotoxic evaluation of the most active compounds were performed. Using an eco-friendly procedure, microwave assisted synthesis resulted in compounds in good yields (35-85%). Compounds 4a-4q presented good druglikeness and pharmacokinetic profiles and no cytotoxicity for any cell line tested up to 100 µM. The compounds presenting the best antifungal profiles were 4e, 4f, 4g, 4k, 4l, 4m, 4o and 4p with more than one minimum inhibitory concentration (MIC) value occurring between 16-64 µg mL-1, thus, in some cases better than the reference drug (fluconazole). SAR testing indicated that the presence of halogens and nitro substituents increases antifungal activity. Taken together, the results demonstrate that 2-aminothiophene derivatives are promising lead compounds for the development of antifungal drugs.

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Main Authors: Luna,Isadora S., Neves,Wendell W., Lima-Neto,Reginaldo G. de, Albuquerque,Amanda P. B., Pitta,Maíra G. R., Rêgo,Moacyr J. B. M., Neves,Rejane P., Scotti,Marcus T., Mendonça-Junior,Francisco J. B.
Format: Digital revista
Language:English
Published: Sociedade Brasileira de Química 2021
Online Access:http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532021000501017
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spelling oai:scielo:S0103-505320210005010172021-04-28Design, Synthesis and Antifungal Activity of New Schiff Bases Bearing 2-Aminothiophene Derivatives Obtained by Molecular SimplificationLuna,Isadora S.Neves,Wendell W.Lima-Neto,Reginaldo G. deAlbuquerque,Amanda P. B.Pitta,Maíra G. R.Rêgo,Moacyr J. B. M.Neves,Rejane P.Scotti,Marcus T.Mendonça-Junior,Francisco J. B. 2-aminothiophene ADMET properties antifungal agents drug design Schiff base Seventeen Schiff bases bearing 2-aminothiophene derivatives were designed and synthesized using molecular simplification. The resulting compounds (4a-4q) were evaluated for their in vitro antifungal activity against dermatophytes. Prediction of their druglikeness and pharmacokinetic properties, establishment of their structure-activity relationships (SAR), and cytotoxic evaluation of the most active compounds were performed. Using an eco-friendly procedure, microwave assisted synthesis resulted in compounds in good yields (35-85%). Compounds 4a-4q presented good druglikeness and pharmacokinetic profiles and no cytotoxicity for any cell line tested up to 100 µM. The compounds presenting the best antifungal profiles were 4e, 4f, 4g, 4k, 4l, 4m, 4o and 4p with more than one minimum inhibitory concentration (MIC) value occurring between 16-64 µg mL-1, thus, in some cases better than the reference drug (fluconazole). SAR testing indicated that the presence of halogens and nitro substituents increases antifungal activity. Taken together, the results demonstrate that 2-aminothiophene derivatives are promising lead compounds for the development of antifungal drugs.info:eu-repo/semantics/openAccessSociedade Brasileira de QuímicaJournal of the Brazilian Chemical Society v.32 n.5 20212021-05-01info:eu-repo/semantics/articletext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532021000501017en10.21577/0103-5053.20210004
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language English
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author Luna,Isadora S.
Neves,Wendell W.
Lima-Neto,Reginaldo G. de
Albuquerque,Amanda P. B.
Pitta,Maíra G. R.
Rêgo,Moacyr J. B. M.
Neves,Rejane P.
Scotti,Marcus T.
Mendonça-Junior,Francisco J. B.
spellingShingle Luna,Isadora S.
Neves,Wendell W.
Lima-Neto,Reginaldo G. de
Albuquerque,Amanda P. B.
Pitta,Maíra G. R.
Rêgo,Moacyr J. B. M.
Neves,Rejane P.
Scotti,Marcus T.
Mendonça-Junior,Francisco J. B.
Design, Synthesis and Antifungal Activity of New Schiff Bases Bearing 2-Aminothiophene Derivatives Obtained by Molecular Simplification
author_facet Luna,Isadora S.
Neves,Wendell W.
Lima-Neto,Reginaldo G. de
Albuquerque,Amanda P. B.
Pitta,Maíra G. R.
Rêgo,Moacyr J. B. M.
Neves,Rejane P.
Scotti,Marcus T.
Mendonça-Junior,Francisco J. B.
author_sort Luna,Isadora S.
title Design, Synthesis and Antifungal Activity of New Schiff Bases Bearing 2-Aminothiophene Derivatives Obtained by Molecular Simplification
title_short Design, Synthesis and Antifungal Activity of New Schiff Bases Bearing 2-Aminothiophene Derivatives Obtained by Molecular Simplification
title_full Design, Synthesis and Antifungal Activity of New Schiff Bases Bearing 2-Aminothiophene Derivatives Obtained by Molecular Simplification
title_fullStr Design, Synthesis and Antifungal Activity of New Schiff Bases Bearing 2-Aminothiophene Derivatives Obtained by Molecular Simplification
title_full_unstemmed Design, Synthesis and Antifungal Activity of New Schiff Bases Bearing 2-Aminothiophene Derivatives Obtained by Molecular Simplification
title_sort design, synthesis and antifungal activity of new schiff bases bearing 2-aminothiophene derivatives obtained by molecular simplification
description Seventeen Schiff bases bearing 2-aminothiophene derivatives were designed and synthesized using molecular simplification. The resulting compounds (4a-4q) were evaluated for their in vitro antifungal activity against dermatophytes. Prediction of their druglikeness and pharmacokinetic properties, establishment of their structure-activity relationships (SAR), and cytotoxic evaluation of the most active compounds were performed. Using an eco-friendly procedure, microwave assisted synthesis resulted in compounds in good yields (35-85%). Compounds 4a-4q presented good druglikeness and pharmacokinetic profiles and no cytotoxicity for any cell line tested up to 100 µM. The compounds presenting the best antifungal profiles were 4e, 4f, 4g, 4k, 4l, 4m, 4o and 4p with more than one minimum inhibitory concentration (MIC) value occurring between 16-64 µg mL-1, thus, in some cases better than the reference drug (fluconazole). SAR testing indicated that the presence of halogens and nitro substituents increases antifungal activity. Taken together, the results demonstrate that 2-aminothiophene derivatives are promising lead compounds for the development of antifungal drugs.
publisher Sociedade Brasileira de Química
publishDate 2021
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532021000501017
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