Cargando…
Synthesis and Antimicrobial Activity of Novel Piperidinyl Tetrahydrothieno[2,3-c]isoquinolines and Related Heterocycles
[Image: see text] A novel series of 1-amino-2-substituted-5-piperidinyl-6,7,8,9-tertahydrothieno[2,3-c]isoquinolines (4a–e) was synthesized upon treatment of 4-cyano-1-piperidinyl-5,6,7,8-tetrahydroisoquinline-3(2H)-thione (2) with α-halo carbonyl compounds such as chloroacetone, ethyl chloroacetate...
Autores principales: | , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical
Society
2019
|
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6964266/ https://www.ncbi.nlm.nih.gov/pubmed/31956772 http://dx.doi.org/10.1021/acsomega.9b02604 |
_version_ | 1783488452772233216 |
---|---|
author | Zaki, Remon M. Kamal El-Dean, Adel M. Radwan, Shaban M. Sayed, Asmaa S. A. |
author_facet | Zaki, Remon M. Kamal El-Dean, Adel M. Radwan, Shaban M. Sayed, Asmaa S. A. |
author_sort | Zaki, Remon M. |
collection | PubMed |
description | [Image: see text] A novel series of 1-amino-2-substituted-5-piperidinyl-6,7,8,9-tertahydrothieno[2,3-c]isoquinolines (4a–e) was synthesized upon treatment of 4-cyano-1-piperidinyl-5,6,7,8-tetrahydroisoquinline-3(2H)-thione (2) with α-halo carbonyl compounds such as chloroacetone, ethyl chloroacetate, 2-bromoacetophenone, chloroacetamide, and chloroacetanilide. Construction the pyrrolyl ring associated with the thienotetrahydroisoquinoline moiety was achieved by treatment of compounds 4a, b with 2,5-dimethoxytertahydrofuran in acetic acid. 1-Pyrrolyl-2-substituted-thieno[2,3-c]isoquinolines 5a and 5b which in turn were used as multipurpose precursors for synthesis of other new heterocycles. Assignments of the chemical structures of the respectively synthesized thienotetrahydroisoquinolines and their derivatives were established on the bases of elemental and spectral techniques (Fourier transform infrared, (1)H NMR, (13)C NMR, and mass spectroscopy). Furthermore, certain compounds were screened for their antimicrobial activity which revealed promising activities against various pathogenic strains of bacteria and fungi. |
format | Online Article Text |
id | pubmed-6964266 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | American Chemical
Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-69642662020-01-17 Synthesis and Antimicrobial Activity of Novel Piperidinyl Tetrahydrothieno[2,3-c]isoquinolines and Related Heterocycles Zaki, Remon M. Kamal El-Dean, Adel M. Radwan, Shaban M. Sayed, Asmaa S. A. ACS Omega [Image: see text] A novel series of 1-amino-2-substituted-5-piperidinyl-6,7,8,9-tertahydrothieno[2,3-c]isoquinolines (4a–e) was synthesized upon treatment of 4-cyano-1-piperidinyl-5,6,7,8-tetrahydroisoquinline-3(2H)-thione (2) with α-halo carbonyl compounds such as chloroacetone, ethyl chloroacetate, 2-bromoacetophenone, chloroacetamide, and chloroacetanilide. Construction the pyrrolyl ring associated with the thienotetrahydroisoquinoline moiety was achieved by treatment of compounds 4a, b with 2,5-dimethoxytertahydrofuran in acetic acid. 1-Pyrrolyl-2-substituted-thieno[2,3-c]isoquinolines 5a and 5b which in turn were used as multipurpose precursors for synthesis of other new heterocycles. Assignments of the chemical structures of the respectively synthesized thienotetrahydroisoquinolines and their derivatives were established on the bases of elemental and spectral techniques (Fourier transform infrared, (1)H NMR, (13)C NMR, and mass spectroscopy). Furthermore, certain compounds were screened for their antimicrobial activity which revealed promising activities against various pathogenic strains of bacteria and fungi. American Chemical Society 2019-12-30 /pmc/articles/PMC6964266/ /pubmed/31956772 http://dx.doi.org/10.1021/acsomega.9b02604 Text en Copyright © 2019 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes. |
spellingShingle | Zaki, Remon M. Kamal El-Dean, Adel M. Radwan, Shaban M. Sayed, Asmaa S. A. Synthesis and Antimicrobial Activity of Novel Piperidinyl Tetrahydrothieno[2,3-c]isoquinolines and Related Heterocycles |
title | Synthesis and Antimicrobial
Activity of Novel Piperidinyl
Tetrahydrothieno[2,3-c]isoquinolines and Related
Heterocycles |
title_full | Synthesis and Antimicrobial
Activity of Novel Piperidinyl
Tetrahydrothieno[2,3-c]isoquinolines and Related
Heterocycles |
title_fullStr | Synthesis and Antimicrobial
Activity of Novel Piperidinyl
Tetrahydrothieno[2,3-c]isoquinolines and Related
Heterocycles |
title_full_unstemmed | Synthesis and Antimicrobial
Activity of Novel Piperidinyl
Tetrahydrothieno[2,3-c]isoquinolines and Related
Heterocycles |
title_short | Synthesis and Antimicrobial
Activity of Novel Piperidinyl
Tetrahydrothieno[2,3-c]isoquinolines and Related
Heterocycles |
title_sort | synthesis and antimicrobial
activity of novel piperidinyl
tetrahydrothieno[2,3-c]isoquinolines and related
heterocycles |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6964266/ https://www.ncbi.nlm.nih.gov/pubmed/31956772 http://dx.doi.org/10.1021/acsomega.9b02604 |
work_keys_str_mv | AT zakiremonm synthesisandantimicrobialactivityofnovelpiperidinyltetrahydrothieno23cisoquinolinesandrelatedheterocycles AT kamaleldeanadelm synthesisandantimicrobialactivityofnovelpiperidinyltetrahydrothieno23cisoquinolinesandrelatedheterocycles AT radwanshabanm synthesisandantimicrobialactivityofnovelpiperidinyltetrahydrothieno23cisoquinolinesandrelatedheterocycles AT sayedasmaasa synthesisandantimicrobialactivityofnovelpiperidinyltetrahydrothieno23cisoquinolinesandrelatedheterocycles |