Please use this identifier to cite or link to this item:

Authors: Teixeira, António P. S.
Teixeira, Fátima C.
Lucas, Carla
Duarte, M. Teresa
André, Vânia
Keywords: Pyrazolo[3,4-b]quinolines
Issue Date: Jul-2012
Publisher: Sociedade Portuguesa de Química
Citation: António P. S. Teixeira, Fátima C. Teixeira, Carla Lucas, M. Teresa Duarte, Vânia André, “ Unexpected intramolecular cyclization and phosphonation of a pyrazolo[3,4-b]quinoline”, 6th Spanish-Portuguese-Japanese Organic Chemistry Symposium , FCUL, Lisboa, 18-20 Julho, 2012
Abstract: The pyrazoloquinolines are an extensively studied group of compounds which present a large number of applications in medicinal chemistry, such as anticancer, antianxiety, anti-inflammatory, antiasthmatic and antiviral activities.[1,2] Also, they have been classified as a promising material for optoelectronics due to their highly fluorescent properties.[2] Bisphophonates (BPs) are potent antiresorptive agents used in the treatment of several bone diseases associated to bone resorption, such Paget’s disease, and osteoporosis. It has been also shown that these compounds were able to inhibit metastases proliferation in bone, prostate and breast cancers. In addition, functional BPs have been used as novel ligands for well-defined radioactive metal complexes for both imaging and radiotherapy applications and in the treatment of metal intoxications.[3] The aim of this work is to extend the previous studies on indazolebisphosphonates [4] to other condensed pyrazole derivatives. During these studies to achieve new BPs derived from pyrazolo[3,4-b]quinolines, a new and unexpected cyclization, followed by a phosphonation of C4 of pyrazolo[3,4-b]quinolines, were achieved, despite the different methods of synthesis used. The new compound shows a six-member lactone ring, formed from the reaction between the acyl chloride side chain and the aromatic N9 of pyrazolo[3,4-b]quinolines. It also shows an unexpected phosphonation of C4 position of pyrazolo[3,4-b]quinolines, with the change of the hybridization of this carbon atom from sp2 to sp3. Crystal structure of this compound (Figure 1) confirmed the proposed structure.
Type: article
Appears in Collections:CQE - Artigos em Livros de Actas/Proceedings
QUI - Artigos em Livros de Actas/Proceedings

Files in This Item:

File Description SizeFormat
ATeixeira_6spjocs_P14_2Versao.pdf347.01 kBAdobe PDFView/OpenRestrict Access. You can Request a copy!
FacebookTwitterDeliciousLinkedInDiggGoogle BookmarksMySpaceOrkut
Formato BibTex mendeley Endnote Logotipo do DeGóis 

Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.


Dspace Dspace
DSpace Software, version 1.6.2 Copyright © 2002-2008 MIT and Hewlett-Packard - Feedback
UEvora B-On Curriculum DeGois