Cargando…
Structural Characterization and Antimicrobial Activities of 7H-Benzo[h]chromeno[2,3-d]pyrimidine and 14H-Benzo[h]chromeno[3,2-e][1,2,4]triazolo[1,5-c] pyrimidine Derivatives
Three new series of chromene molecules have been synthesized in order to explore their antimicrobial activity. The series encompass 2-substituted 14-(4-halophenyl)-12-methoxy-14H-benzo[h]chromeno[3,2-e][1,2,4]-triazolo[1,5-c]pyrimidines 7a–o, 9-benzylideneamino-7-(4-halo-phenyl)-5-methoxy-8-imino-7H...
Autores principales: | , , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2016
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273467/ https://www.ncbi.nlm.nih.gov/pubmed/27809292 http://dx.doi.org/10.3390/molecules21111450 |
_version_ | 1783377391142305792 |
---|---|
author | Okasha, Rawda M. Albalawi, Fawzia F. Afifi, Tarek H. Fouda, Ahmed M. Al-Dies, Al-Anood M. El-Agrody, Ahmed M. |
author_facet | Okasha, Rawda M. Albalawi, Fawzia F. Afifi, Tarek H. Fouda, Ahmed M. Al-Dies, Al-Anood M. El-Agrody, Ahmed M. |
author_sort | Okasha, Rawda M. |
collection | PubMed |
description | Three new series of chromene molecules have been synthesized in order to explore their antimicrobial activity. The series encompass 2-substituted 14-(4-halophenyl)-12-methoxy-14H-benzo[h]chromeno[3,2-e][1,2,4]-triazolo[1,5-c]pyrimidines 7a–o, 9-benzylideneamino-7-(4-halo-phenyl)-5-methoxy-8-imino-7H-benzo-[h]chromeno[2,3-d]pyrimidines 8a–b and 3-ethoxycarbonyl-14-(4-halophenyl)-12-methoxy-14H-benzo-[h]chromeno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine-2-one derivatives 12a–b. The structure of these novel compounds were confirmed using IR, (1)H- and (13)C-NMR as well as MS spectroscopy. The new compounds were evaluated in vitro for their antimicrobial activity and it was demonstrated that 7H-benzochromenopyrimidine and derivatives of 14H-benzochromenotriazolopyrimidine exhibited the most promising antibacterial activities compared to the reference antimicrobial agents. The structure activity relationship (SAR) studies of the target compounds agreed with the in vitro essays and confirmed higher potent antimicrobial activity against some of the tested microorganisms. |
format | Online Article Text |
id | pubmed-6273467 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-62734672018-12-28 Structural Characterization and Antimicrobial Activities of 7H-Benzo[h]chromeno[2,3-d]pyrimidine and 14H-Benzo[h]chromeno[3,2-e][1,2,4]triazolo[1,5-c] pyrimidine Derivatives Okasha, Rawda M. Albalawi, Fawzia F. Afifi, Tarek H. Fouda, Ahmed M. Al-Dies, Al-Anood M. El-Agrody, Ahmed M. Molecules Article Three new series of chromene molecules have been synthesized in order to explore their antimicrobial activity. The series encompass 2-substituted 14-(4-halophenyl)-12-methoxy-14H-benzo[h]chromeno[3,2-e][1,2,4]-triazolo[1,5-c]pyrimidines 7a–o, 9-benzylideneamino-7-(4-halo-phenyl)-5-methoxy-8-imino-7H-benzo-[h]chromeno[2,3-d]pyrimidines 8a–b and 3-ethoxycarbonyl-14-(4-halophenyl)-12-methoxy-14H-benzo-[h]chromeno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine-2-one derivatives 12a–b. The structure of these novel compounds were confirmed using IR, (1)H- and (13)C-NMR as well as MS spectroscopy. The new compounds were evaluated in vitro for their antimicrobial activity and it was demonstrated that 7H-benzochromenopyrimidine and derivatives of 14H-benzochromenotriazolopyrimidine exhibited the most promising antibacterial activities compared to the reference antimicrobial agents. The structure activity relationship (SAR) studies of the target compounds agreed with the in vitro essays and confirmed higher potent antimicrobial activity against some of the tested microorganisms. MDPI 2016-11-01 /pmc/articles/PMC6273467/ /pubmed/27809292 http://dx.doi.org/10.3390/molecules21111450 Text en © 2016 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Okasha, Rawda M. Albalawi, Fawzia F. Afifi, Tarek H. Fouda, Ahmed M. Al-Dies, Al-Anood M. El-Agrody, Ahmed M. Structural Characterization and Antimicrobial Activities of 7H-Benzo[h]chromeno[2,3-d]pyrimidine and 14H-Benzo[h]chromeno[3,2-e][1,2,4]triazolo[1,5-c] pyrimidine Derivatives |
title | Structural Characterization and Antimicrobial Activities of 7H-Benzo[h]chromeno[2,3-d]pyrimidine and 14H-Benzo[h]chromeno[3,2-e][1,2,4]triazolo[1,5-c] pyrimidine Derivatives |
title_full | Structural Characterization and Antimicrobial Activities of 7H-Benzo[h]chromeno[2,3-d]pyrimidine and 14H-Benzo[h]chromeno[3,2-e][1,2,4]triazolo[1,5-c] pyrimidine Derivatives |
title_fullStr | Structural Characterization and Antimicrobial Activities of 7H-Benzo[h]chromeno[2,3-d]pyrimidine and 14H-Benzo[h]chromeno[3,2-e][1,2,4]triazolo[1,5-c] pyrimidine Derivatives |
title_full_unstemmed | Structural Characterization and Antimicrobial Activities of 7H-Benzo[h]chromeno[2,3-d]pyrimidine and 14H-Benzo[h]chromeno[3,2-e][1,2,4]triazolo[1,5-c] pyrimidine Derivatives |
title_short | Structural Characterization and Antimicrobial Activities of 7H-Benzo[h]chromeno[2,3-d]pyrimidine and 14H-Benzo[h]chromeno[3,2-e][1,2,4]triazolo[1,5-c] pyrimidine Derivatives |
title_sort | structural characterization and antimicrobial activities of 7h-benzo[h]chromeno[2,3-d]pyrimidine and 14h-benzo[h]chromeno[3,2-e][1,2,4]triazolo[1,5-c] pyrimidine derivatives |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273467/ https://www.ncbi.nlm.nih.gov/pubmed/27809292 http://dx.doi.org/10.3390/molecules21111450 |
work_keys_str_mv | AT okasharawdam structuralcharacterizationandantimicrobialactivitiesof7hbenzohchromeno23dpyrimidineand14hbenzohchromeno32e124triazolo15cpyrimidinederivatives AT albalawifawziaf structuralcharacterizationandantimicrobialactivitiesof7hbenzohchromeno23dpyrimidineand14hbenzohchromeno32e124triazolo15cpyrimidinederivatives AT afifitarekh structuralcharacterizationandantimicrobialactivitiesof7hbenzohchromeno23dpyrimidineand14hbenzohchromeno32e124triazolo15cpyrimidinederivatives AT foudaahmedm structuralcharacterizationandantimicrobialactivitiesof7hbenzohchromeno23dpyrimidineand14hbenzohchromeno32e124triazolo15cpyrimidinederivatives AT aldiesalanoodm structuralcharacterizationandantimicrobialactivitiesof7hbenzohchromeno23dpyrimidineand14hbenzohchromeno32e124triazolo15cpyrimidinederivatives AT elagrodyahmedm structuralcharacterizationandantimicrobialactivitiesof7hbenzohchromeno23dpyrimidineand14hbenzohchromeno32e124triazolo15cpyrimidinederivatives |