A Solution- and Solid-Phase Approach to Tetrahydroquinoline-Derived Polycyclics Having a 10-Membered Ring

Abstract

Access and use of this website and the material on it are subject to the Terms and Conditions set forth at A solution-and solid-phase approach to tetrahydroquinoline-derived polycyclics having a 10-membered ring Khadem, Shahriar; Joseph, Reni; Rastegar, Majid; Leek, Donald M.; Oudatchin, Kostantin A.; Arya, Prabhat http://nparc.cisti-icist.nrc-cnrc.gc.ca/npsi/jsp/nparc_cp.jsp?lang=fr L'accès à ce site Web et l'utilisation de son contenu sont assujettis aux conditions présentées dans le site LISEZ CES CONDITIONS ATTENTIVEMENT AVANT D'UTILISER CE SITE WEB. NRC Publications Record / Notice d'Archives des publications de CNRC:http://nparc.cisti-icist.nrc-cnrc.gc.ca/npsi/ctrl?action=rtdoc&an=12340957&lang=en http://nparc.cisti-icist.nrc-cnrc.gc.ca/npsi/ctrl?action=rtdoc&an=12340957&lang=fr READ THESE TERMS AND CONDITIONS CAREFULLY BEFORE USING THIS WEBSITE.http://nparc.cisti-icist.nrc-cnrc.gc.ca/npsi/jsp/nparc_cp.jsp?lang=en Vous avez des questions? Nous pouvons vous aider. Pour communiquer directement avec un auteur, consultez la première page de la revue dans laquelle son article a été publié afin de trouver ses coordonnées. Si vous n'arrivez pas à les repérer, communiquez avec nous à PublicationsArchive-ArchivesPublications@nrc-cnrc.gc.ca. Questions? Contact the NRC Publications Archive team atPublicationsArchive-ArchivesPublications@nrc-cnrc.gc.ca. If you wish to email the authors directly, please see the first page of the publication for their contact information. NRC Publications Archive Archives des publications du CNRCThis publication could be one of several versions: author's original, accepted manuscript or the publisher's version. / La version de cette publication peut être l'une des suivantes : la version prépublication de l'auteur, la version acceptée du manuscrit ou la version de l'éditeur. For the publisher's version, please access the DOI link below./ Pour consulter la version de l'éditeur, utilisez le lien DOI ci-dessous.http://doi.org/10.1021/cc049941oJournal of Combinatorial Chemistry, 6, 5, pp. 724-734, 2004-07-23 A Solution-and Solid-Phase Approach to Tetrahydroquinoline-Derived Polycyclics Having a 10-Membered Ring Sciences, National Research Council of Canada, 100 Sussex DriVe, Ottawa, Ontario, Canada K1A 0R6 ReceiVed March 6, 2004 With the goal of library generation using a polycyclic derivative 5 having an enamide functional group, a simple and practical, enantioselective synthesis of tetrahydroquinoline derivative 2 was achieved. The phenolic hydroxyl group in compound 2 was utilized as an anchoring site for solid-phase synthesis. The ring closing metathesis approach yielded the desired polycyclic product 5 on solid phase in five steps (overall 40% yield). Compound 5 is a novel scaffold for the library generation of natural product-like polycyclics having a functionalized medium ring for obtaining a new class of small molecules to be utilized as chemical probes.

Synthesis of Nine Safrole Derivatives and Their Antiproliferative Activity Towards Human Cancer Cells

“…Synthesis Nitrosafrol (2) obtained under standard conditions [7][8][9][10] (HNO 3 / H 2 SO 4 /HAc) afforded the nitro compound 2 and aldehyde 3 with 75.0% and 5.2% yields respectively (scheme 1). Oxidative hydroboration of the side chain of nitrosafrol led to an alcohol at C-3'.…”

“…Safrole (1) and its synthetic derivatives (2)(3)(4)(5)(6)(7)(8) were tested in vitro for antiproliferative effect on two human tumor breast cancer cell lines (MDA-MB-231, MCF-7), one human colorectal cancer cell line (DLD-1) and one dermal human fibroblast cell line (DHF). The in vitro growth inhibition assay used was based on sulphorhodamine dye, widely used to quantify cell viability.…”

Advances in Solution- and Solid-Phase Synthesis toward the Generation of Natural Product-like Libraries

“…446 The enantiopure tetrahydroquinoline scaffold 82.2 (Scheme 82) was obtained in several steps from compound 82.1. Further functional group manipulations were performed on 82.2 that included the reduction of the carboxyl ester with lithium borohydride, a selective N-alloc protection, Osilylation of the primary hydroxyl, the protection of the secondary hydroxyl group, the removal of the O-Alloc group using mild base, acylation with pentenoic acid, N-Alloc removal, and N-acylation using acryloyl chloride, giving compound 82.3.…”

Metathesis Reactions in Solid‐Phase Organic Synthesis

“…They have prepared a wide variety of tetrahydroquinoline derivatives and polycyclic compounds including 6-, 8-, and 10-membered rings as shown in Figure 13.6. The phenolic hydroxyl group was utilized as an anchorage point to a Wang resin which can be conveniently cleaved with triflouroacetic acid (TFA) [33][34][35]. An extension of this work was published more recently in which an aminoindoline-based library was prepared.…”