Synthesis and evaluation of 2-phenylamino-1,4-naphthoquinones derivatives as potential hypoglycaemic agents

Detalhes bibliográficos
Autor(a) principal: Razaque,R.
Data de Publicação: 2024
Outros Autores: Raza,A. R., Irshad,M., Rubab,S. L., Batool,S., Nisar,B., Akram,Z., Akhtar,M. T., Qadir,R., Siddique,Abu Bakar, Siddique,Farzana, Saadia,M.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Brazilian Journal of Biology
Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S1519-69842024000100242
Resumo: Abstract Due to the severe side effects revealed by most of the currently used antidiabetic medicines, search for finding new and safe drugs to manage diabetes is continued. Naphthoquinones possessing strong antioxidant properties have been employed as candidates for diabetes therapy. Present study is aimed at finding the antioxidant and hypoglycaemic potential of some novel derivatives of 2-phenylamino-1,4-naphthoquinones (PAN) including chloro, nitro, methyl and bromo (5a-d) derivatives synthesized by single pot experiment. Product crystals were purified by TLC and characterized by FT-IR. The antioxidant potential of the compounds was assayed through DPPH radical scavenging and reducing power activities noted as UV-vis. absorbance. The DPPH assay has showed the powerful antioxidant activity of nitro and bromo derivatives, while the nitro derivative showed the significant reduction potential towards FRAP assay. Hypoglycaemic potential of the compounds was studied in rat animal model. All synthesized compounds revealed better hypoglycaemic activity; however, the chloro-derivative exhibited the more potent hypoglycaemic activity showing about 43% reduction in the mean blood glucose levels of the treated animals. As the bioreduction of naphthoquinones may be influenced by changing its redox properties, it has been noticed that the e-donating resonance effect (+R) of ‘chloro’ group has shown the significant effects on biological activity through stabalization of its imine form which limits the potential of generation of free radicals during bioreduction of quinones and thus has been proposed as the reason of its hypoglycaemic activity. Future studies employing the properties of e-donating groups of PAN may optimize the drug-receptor interaction for better drug designing and drug development strategies against diabetes and also for the clinical trials.
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spelling Synthesis and evaluation of 2-phenylamino-1,4-naphthoquinones derivatives as potential hypoglycaemic agentsdiabetesnaphthoquinone derivatives2-phenylamino-1,4-naphthoquinoneshypoglycaemic agentsantioxidantsAbstract Due to the severe side effects revealed by most of the currently used antidiabetic medicines, search for finding new and safe drugs to manage diabetes is continued. Naphthoquinones possessing strong antioxidant properties have been employed as candidates for diabetes therapy. Present study is aimed at finding the antioxidant and hypoglycaemic potential of some novel derivatives of 2-phenylamino-1,4-naphthoquinones (PAN) including chloro, nitro, methyl and bromo (5a-d) derivatives synthesized by single pot experiment. Product crystals were purified by TLC and characterized by FT-IR. The antioxidant potential of the compounds was assayed through DPPH radical scavenging and reducing power activities noted as UV-vis. absorbance. The DPPH assay has showed the powerful antioxidant activity of nitro and bromo derivatives, while the nitro derivative showed the significant reduction potential towards FRAP assay. Hypoglycaemic potential of the compounds was studied in rat animal model. All synthesized compounds revealed better hypoglycaemic activity; however, the chloro-derivative exhibited the more potent hypoglycaemic activity showing about 43% reduction in the mean blood glucose levels of the treated animals. As the bioreduction of naphthoquinones may be influenced by changing its redox properties, it has been noticed that the e-donating resonance effect (+R) of ‘chloro’ group has shown the significant effects on biological activity through stabalization of its imine form which limits the potential of generation of free radicals during bioreduction of quinones and thus has been proposed as the reason of its hypoglycaemic activity. Future studies employing the properties of e-donating groups of PAN may optimize the drug-receptor interaction for better drug designing and drug development strategies against diabetes and also for the clinical trials.Instituto Internacional de Ecologia2024-01-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S1519-69842024000100242Brazilian Journal of Biology v.84 2024reponame:Brazilian Journal of Biologyinstname:Instituto Internacional de Ecologia (IIE)instacron:IIE10.1590/1519-6984.254234info:eu-repo/semantics/openAccessRazaque,R.Raza,A. R.Irshad,M.Rubab,S. L.Batool,S.Nisar,B.Akram,Z.Akhtar,M. T.Qadir,R.Siddique,Abu BakarSiddique,FarzanaSaadia,M.eng2022-03-09T00:00:00Zoai:scielo:S1519-69842024000100242Revistahttps://www.scielo.br/j/bjb/https://old.scielo.br/oai/scielo-oai.phpbjb@bjb.com.br||bjb@bjb.com.br1678-43751519-6984opendoar:2022-03-09T00:00Brazilian Journal of Biology - Instituto Internacional de Ecologia (IIE)false
dc.title.none.fl_str_mv Synthesis and evaluation of 2-phenylamino-1,4-naphthoquinones derivatives as potential hypoglycaemic agents
title Synthesis and evaluation of 2-phenylamino-1,4-naphthoquinones derivatives as potential hypoglycaemic agents
spellingShingle Synthesis and evaluation of 2-phenylamino-1,4-naphthoquinones derivatives as potential hypoglycaemic agents
Razaque,R.
diabetes
naphthoquinone derivatives
2-phenylamino-1,4-naphthoquinones
hypoglycaemic agents
antioxidants
title_short Synthesis and evaluation of 2-phenylamino-1,4-naphthoquinones derivatives as potential hypoglycaemic agents
title_full Synthesis and evaluation of 2-phenylamino-1,4-naphthoquinones derivatives as potential hypoglycaemic agents
title_fullStr Synthesis and evaluation of 2-phenylamino-1,4-naphthoquinones derivatives as potential hypoglycaemic agents
title_full_unstemmed Synthesis and evaluation of 2-phenylamino-1,4-naphthoquinones derivatives as potential hypoglycaemic agents
title_sort Synthesis and evaluation of 2-phenylamino-1,4-naphthoquinones derivatives as potential hypoglycaemic agents
author Razaque,R.
author_facet Razaque,R.
Raza,A. R.
Irshad,M.
Rubab,S. L.
Batool,S.
Nisar,B.
Akram,Z.
Akhtar,M. T.
Qadir,R.
Siddique,Abu Bakar
Siddique,Farzana
Saadia,M.
author_role author
author2 Raza,A. R.
Irshad,M.
Rubab,S. L.
Batool,S.
Nisar,B.
Akram,Z.
Akhtar,M. T.
Qadir,R.
Siddique,Abu Bakar
Siddique,Farzana
Saadia,M.
author2_role author
author
author
author
author
author
author
author
author
author
author
dc.contributor.author.fl_str_mv Razaque,R.
Raza,A. R.
Irshad,M.
Rubab,S. L.
Batool,S.
Nisar,B.
Akram,Z.
Akhtar,M. T.
Qadir,R.
Siddique,Abu Bakar
Siddique,Farzana
Saadia,M.
dc.subject.por.fl_str_mv diabetes
naphthoquinone derivatives
2-phenylamino-1,4-naphthoquinones
hypoglycaemic agents
antioxidants
topic diabetes
naphthoquinone derivatives
2-phenylamino-1,4-naphthoquinones
hypoglycaemic agents
antioxidants
description Abstract Due to the severe side effects revealed by most of the currently used antidiabetic medicines, search for finding new and safe drugs to manage diabetes is continued. Naphthoquinones possessing strong antioxidant properties have been employed as candidates for diabetes therapy. Present study is aimed at finding the antioxidant and hypoglycaemic potential of some novel derivatives of 2-phenylamino-1,4-naphthoquinones (PAN) including chloro, nitro, methyl and bromo (5a-d) derivatives synthesized by single pot experiment. Product crystals were purified by TLC and characterized by FT-IR. The antioxidant potential of the compounds was assayed through DPPH radical scavenging and reducing power activities noted as UV-vis. absorbance. The DPPH assay has showed the powerful antioxidant activity of nitro and bromo derivatives, while the nitro derivative showed the significant reduction potential towards FRAP assay. Hypoglycaemic potential of the compounds was studied in rat animal model. All synthesized compounds revealed better hypoglycaemic activity; however, the chloro-derivative exhibited the more potent hypoglycaemic activity showing about 43% reduction in the mean blood glucose levels of the treated animals. As the bioreduction of naphthoquinones may be influenced by changing its redox properties, it has been noticed that the e-donating resonance effect (+R) of ‘chloro’ group has shown the significant effects on biological activity through stabalization of its imine form which limits the potential of generation of free radicals during bioreduction of quinones and thus has been proposed as the reason of its hypoglycaemic activity. Future studies employing the properties of e-donating groups of PAN may optimize the drug-receptor interaction for better drug designing and drug development strategies against diabetes and also for the clinical trials.
publishDate 2024
dc.date.none.fl_str_mv 2024-01-01
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
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dc.identifier.uri.fl_str_mv http://old.scielo.br/scielo.php?script=sci_arttext&pid=S1519-69842024000100242
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S1519-69842024000100242
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.1590/1519-6984.254234
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv text/html
dc.publisher.none.fl_str_mv Instituto Internacional de Ecologia
publisher.none.fl_str_mv Instituto Internacional de Ecologia
dc.source.none.fl_str_mv Brazilian Journal of Biology v.84 2024
reponame:Brazilian Journal of Biology
instname:Instituto Internacional de Ecologia (IIE)
instacron:IIE
instname_str Instituto Internacional de Ecologia (IIE)
instacron_str IIE
institution IIE
reponame_str Brazilian Journal of Biology
collection Brazilian Journal of Biology
repository.name.fl_str_mv Brazilian Journal of Biology - Instituto Internacional de Ecologia (IIE)
repository.mail.fl_str_mv bjb@bjb.com.br||bjb@bjb.com.br
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