Cargando…

Synthesis of novel Schiff bases using 2-Amino-5-(3-fluoro-4-methoxyphenyl)thiophene-3-carbonitrile and 1,3-Disubstituted pyrazole-4-carboxaldehydes derivatives and their antimicrobial activity

2-Amino-5-(3-fluoro-4-methoxyphenyl)thiophene-3-carbonitrile have been synthesized from 1-(3-fluoro-4-methoxyphenyl)ethanone, malononitrile, a mild base and sulfur powder using Gewald synthesis technique and the intermediate was treated with 1,3-disubstituted pyrazole-4-carboxaldehyde to obtain the...

Descripción completa

Detalles Bibliográficos
Autores principales: Puthran, Divyaraj, Poojary, Boja, Purushotham, Nikil, Harikrishna, Nandam, Nayak, Soukhyarani Gopal, Kamat, Vinuta
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Elsevier 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6717141/
https://www.ncbi.nlm.nih.gov/pubmed/31485504
http://dx.doi.org/10.1016/j.heliyon.2019.e02233
_version_ 1783447504255188992
author Puthran, Divyaraj
Poojary, Boja
Purushotham, Nikil
Harikrishna, Nandam
Nayak, Soukhyarani Gopal
Kamat, Vinuta
author_facet Puthran, Divyaraj
Poojary, Boja
Purushotham, Nikil
Harikrishna, Nandam
Nayak, Soukhyarani Gopal
Kamat, Vinuta
author_sort Puthran, Divyaraj
collection PubMed
description 2-Amino-5-(3-fluoro-4-methoxyphenyl)thiophene-3-carbonitrile have been synthesized from 1-(3-fluoro-4-methoxyphenyl)ethanone, malononitrile, a mild base and sulfur powder using Gewald synthesis technique and the intermediate was treated with 1,3-disubstituted pyrazole-4-carboxaldehyde to obtain the novel Schiff bases. 1,3-disubstituted pyrazole-4-carboxaldehyde derivatives have been synthesized by Vilsmeier-Haack reaction in the course of a multi-step reaction. The structure of novel compounds were established on the basis of their elemental analyses IR, (1)H NMR, (13)C NMR, and mass spectral data and then screened for their in vitro antimicrobial activity. Among them 5a, 5c, 5f and 5h showed excellent activity when compared to other derivatives. Remaining derivatives showed moderate activity.
format Online
Article
Text
id pubmed-6717141
institution National Center for Biotechnology Information
language English
publishDate 2019
publisher Elsevier
record_format MEDLINE/PubMed
spelling pubmed-67171412019-09-04 Synthesis of novel Schiff bases using 2-Amino-5-(3-fluoro-4-methoxyphenyl)thiophene-3-carbonitrile and 1,3-Disubstituted pyrazole-4-carboxaldehydes derivatives and their antimicrobial activity Puthran, Divyaraj Poojary, Boja Purushotham, Nikil Harikrishna, Nandam Nayak, Soukhyarani Gopal Kamat, Vinuta Heliyon Article 2-Amino-5-(3-fluoro-4-methoxyphenyl)thiophene-3-carbonitrile have been synthesized from 1-(3-fluoro-4-methoxyphenyl)ethanone, malononitrile, a mild base and sulfur powder using Gewald synthesis technique and the intermediate was treated with 1,3-disubstituted pyrazole-4-carboxaldehyde to obtain the novel Schiff bases. 1,3-disubstituted pyrazole-4-carboxaldehyde derivatives have been synthesized by Vilsmeier-Haack reaction in the course of a multi-step reaction. The structure of novel compounds were established on the basis of their elemental analyses IR, (1)H NMR, (13)C NMR, and mass spectral data and then screened for their in vitro antimicrobial activity. Among them 5a, 5c, 5f and 5h showed excellent activity when compared to other derivatives. Remaining derivatives showed moderate activity. Elsevier 2019-08-26 /pmc/articles/PMC6717141/ /pubmed/31485504 http://dx.doi.org/10.1016/j.heliyon.2019.e02233 Text en © 2019 Published by Elsevier Ltd. http://creativecommons.org/licenses/by-nc-nd/4.0/ This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Article
Puthran, Divyaraj
Poojary, Boja
Purushotham, Nikil
Harikrishna, Nandam
Nayak, Soukhyarani Gopal
Kamat, Vinuta
Synthesis of novel Schiff bases using 2-Amino-5-(3-fluoro-4-methoxyphenyl)thiophene-3-carbonitrile and 1,3-Disubstituted pyrazole-4-carboxaldehydes derivatives and their antimicrobial activity
title Synthesis of novel Schiff bases using 2-Amino-5-(3-fluoro-4-methoxyphenyl)thiophene-3-carbonitrile and 1,3-Disubstituted pyrazole-4-carboxaldehydes derivatives and their antimicrobial activity
title_full Synthesis of novel Schiff bases using 2-Amino-5-(3-fluoro-4-methoxyphenyl)thiophene-3-carbonitrile and 1,3-Disubstituted pyrazole-4-carboxaldehydes derivatives and their antimicrobial activity
title_fullStr Synthesis of novel Schiff bases using 2-Amino-5-(3-fluoro-4-methoxyphenyl)thiophene-3-carbonitrile and 1,3-Disubstituted pyrazole-4-carboxaldehydes derivatives and their antimicrobial activity
title_full_unstemmed Synthesis of novel Schiff bases using 2-Amino-5-(3-fluoro-4-methoxyphenyl)thiophene-3-carbonitrile and 1,3-Disubstituted pyrazole-4-carboxaldehydes derivatives and their antimicrobial activity
title_short Synthesis of novel Schiff bases using 2-Amino-5-(3-fluoro-4-methoxyphenyl)thiophene-3-carbonitrile and 1,3-Disubstituted pyrazole-4-carboxaldehydes derivatives and their antimicrobial activity
title_sort synthesis of novel schiff bases using 2-amino-5-(3-fluoro-4-methoxyphenyl)thiophene-3-carbonitrile and 1,3-disubstituted pyrazole-4-carboxaldehydes derivatives and their antimicrobial activity
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6717141/
https://www.ncbi.nlm.nih.gov/pubmed/31485504
http://dx.doi.org/10.1016/j.heliyon.2019.e02233
work_keys_str_mv AT puthrandivyaraj synthesisofnovelschiffbasesusing2amino53fluoro4methoxyphenylthiophene3carbonitrileand13disubstitutedpyrazole4carboxaldehydesderivativesandtheirantimicrobialactivity
AT poojaryboja synthesisofnovelschiffbasesusing2amino53fluoro4methoxyphenylthiophene3carbonitrileand13disubstitutedpyrazole4carboxaldehydesderivativesandtheirantimicrobialactivity
AT purushothamnikil synthesisofnovelschiffbasesusing2amino53fluoro4methoxyphenylthiophene3carbonitrileand13disubstitutedpyrazole4carboxaldehydesderivativesandtheirantimicrobialactivity
AT harikrishnanandam synthesisofnovelschiffbasesusing2amino53fluoro4methoxyphenylthiophene3carbonitrileand13disubstitutedpyrazole4carboxaldehydesderivativesandtheirantimicrobialactivity
AT nayaksoukhyaranigopal synthesisofnovelschiffbasesusing2amino53fluoro4methoxyphenylthiophene3carbonitrileand13disubstitutedpyrazole4carboxaldehydesderivativesandtheirantimicrobialactivity
AT kamatvinuta synthesisofnovelschiffbasesusing2amino53fluoro4methoxyphenylthiophene3carbonitrileand13disubstitutedpyrazole4carboxaldehydesderivativesandtheirantimicrobialactivity