Synthesis of C3/C1-Substituted Tetrahydroisoquinolines

Publikationstyp:
Zeitschriftenaufsatz
Metadaten:
Autoren
  • Mohamed Mihoubi
  • Nicola Micale
  • Angela Scala
  • Raoudha Mezghani Jarraya
  • Amira Bouaziz
  • Tanja Schirmeister
  • Francesco Risitano
  • Anna Piperno
  • Giovanni Grassi
Autoren-URL
https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000361375400083&DestLinkType=FullRecord&DestApp=WOS_CPL
DOI
10.3390/molecules200814902
Externe Identifier
  • Clarivate Analytics Document Solution ID: CR5IU
  • PubMed Identifier: 26287146
ISSN
1420-3049
Ausgabe der Veröffentlichung
8
Zeitschrift
MOLECULES
Schlüsselwörter
  • Bischler-Napieralski condensation
  • N-methylisosalsoline
  • nitroalkene
  • proteasome
  • tetrahydroisoquinoline
Paginierung
14902 - 14914
Datum der Veröffentlichung
2015
Status
Published
Titel
Synthesis of C3/C1-Substituted Tetrahydroisoquinolines
Sub types
  • Article
Ausgabe der Zeitschrift
20

Datenquelle: Web of Science (Lite)

Andere Metadatenquellen:
Autoren
  • Mohamed Mihoubi
  • Nicola Micale
  • Angela Scala
  • Raoudha Jarraya
  • Amira Bouaziz
  • Tanja Schirmeister
  • Francesco Risitano
  • Anna Piperno
  • Giovanni Grassi
DOI
10.3390/molecules200814902
eISSN
1420-3049
Ausgabe der Veröffentlichung
8
Zeitschrift
Molecules
Sprache
en
Online publication date
2015
Paginierung
14902 - 14914
Status
Published online
Herausgeber
MDPI AG
Herausgeber URL
http://dx.doi.org/10.3390/molecules200814902
Datum der Datenerfassung
2018
Titel
Synthesis of C3/C1-Substituted Tetrahydroisoquinolines
Ausgabe der Zeitschrift
20

Datenquelle: Crossref

Abstract
A broad biological screening of the natural alkaloid N-methylisosalsoline (2) extracted from Hammada scoparia leaves against a panel of human and parasitic proteases revealed an interesting activity profile of 2 towards human 20S proteasome. This outcome suggests that the 1,2,3,4-tetrahydroisoquinoline skeleton may be exploited as a template for the development of novel anticancer agents. In this article, we report the synthesis and chemical characterization of a new series of isosalsoline-type alkaloids (10-11) with variations at N2 and C3 positions with respect to the natural Compound 2, obtained by a synthetic strategy that involves the Bischler-Napieralski cyclization. The substrate for the condensation to the tetrahydroisoquinoline system, i.e., a functionalized β-arylethyl amine, was obtained through an original double reduction of nitroalkene. The synthetic strategy can be directed to the construction of highly substituted and functionalized 1,2,3,4-tetrahydroisoquinolines.
Addresses
  • Laboratoire de Chimie des Substances Naturelles UR/11-ES-74, Faculté des Sciences de Sfax, Université de Sfax, Route de l'aeroport, BP 1171, 3000 Sfax, Tunisia. mohamed.mihoubi@hotmail.fr.
Autoren
  • Mohamed Mihoubi
  • Nicola Micale
  • Angela Scala
  • Raoudha Mezghani Jarraya
  • Amira Bouaziz
  • Tanja Schirmeister
  • Francesco Risitano
  • Anna Piperno
  • Giovanni Grassi
DOI
10.3390/molecules200814902
eISSN
1420-3049
Externe Identifier
  • PubMed Identifier: 26287146
  • PubMed Central ID: PMC6332194
Open access
true
ISSN
1420-3049
Ausgabe der Veröffentlichung
8
Zeitschrift
Molecules (Basel, Switzerland)
Schlüsselwörter
  • Animals
  • Cattle
  • Humans
  • Parasites
  • Tetrahydroisoquinolines
  • Peptide Hydrolases
  • Cell Proliferation
Sprache
eng
Medium
Electronic
Online publication date
2015
Open access status
Open Access
Paginierung
14902 - 14914
Datum der Veröffentlichung
2015
Status
Published
Publisher licence
CC BY
Datum der Datenerfassung
2015
Titel
Synthesis of C3/C1-Substituted Tetrahydroisoquinolines.
Sub types
  • Research Support, Non-U.S. Gov't
  • research-article
  • Journal Article
Ausgabe der Zeitschrift
20

Files

https://www.mdpi.com/1420-3049/20/8/14902/pdf https://europepmc.org/articles/PMC6332194?pdf=render

Datenquelle: Europe PubMed Central

Abstract
A broad biological screening of the natural alkaloid N-methylisosalsoline (2) extracted from Hammada scoparia leaves against a panel of human and parasitic proteases revealed an interesting activity profile of 2 towards human 20S proteasome. This outcome suggests that the 1,2,3,4-tetrahydroisoquinoline skeleton may be exploited as a template for the development of novel anticancer agents. In this article, we report the synthesis and chemical characterization of a new series of isosalsoline-type alkaloids (10-11) with variations at N2 and C3 positions with respect to the natural Compound 2, obtained by a synthetic strategy that involves the Bischler-Napieralski cyclization. The substrate for the condensation to the tetrahydroisoquinoline system, i.e., a functionalized β-arylethyl amine, was obtained through an original double reduction of nitroalkene. The synthetic strategy can be directed to the construction of highly substituted and functionalized 1,2,3,4-tetrahydroisoquinolines.
Date of acceptance
2015
Autoren
  • Mohamed Mihoubi
  • Nicola Micale
  • Angela Scala
  • Raoudha Mezghani Jarraya
  • Amira Bouaziz
  • Tanja Schirmeister
  • Francesco Risitano
  • Anna Piperno
  • Giovanni Grassi
Autoren-URL
https://www.ncbi.nlm.nih.gov/pubmed/26287146
DOI
10.3390/molecules200814902
eISSN
1420-3049
Externe Identifier
  • PubMed Central ID: PMC6332194
Ausgabe der Veröffentlichung
8
Zeitschrift
Molecules
Schlüsselwörter
  • Bischler-Napieralski condensation
  • N-methylisosalsoline
  • nitroalkene
  • proteasome
  • tetrahydroisoquinoline
  • Animals
  • Cattle
  • Cell Proliferation
  • Humans
  • Parasites
  • Peptide Hydrolases
  • Tetrahydroisoquinolines
Sprache
eng
Country
Switzerland
Paginierung
14902 - 14914
PII
molecules200814902
Datum der Veröffentlichung
2015
Status
Published online
Datum, an dem der Datensatz öffentlich gemacht wurde
2016
Titel
Synthesis of C3/C1-Substituted Tetrahydroisoquinolines.
Sub types
  • Journal Article
  • Research Support, Non-U.S. Gov't
Ausgabe der Zeitschrift
20

Datenquelle: PubMed

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