Synthesis and Biological Evaluation of Indoloquinolines and Pyridocarbazoles: A New Example of Unexpected Photoreduction Accompanying Photocyclization
Indoloquinoline alkaloid cryptolepine and pyridocarbazole alkaloid ellipticine are of great interest because in vitro and in vivo studies revealed their good cytotoxic properties. In order to obtain some biologically active analogs of these compounds, we developed a synthesis based on the photocycli...
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| Veröffentlicht in: | Chemical & Pharmaceutical Bulletin 2007/09/01, Vol.55(9), pp.1349-1355 |
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| creator | Aragon, Pierre-Jean Yapi, Ange-Désiré Pinguet, Frédéric Chezal, Jean-Michel Teulade, Jean-Claude Blache, Yves |
| description | Indoloquinoline alkaloid cryptolepine and pyridocarbazole alkaloid ellipticine are of great interest because in vitro and in vivo studies revealed their good cytotoxic properties. In order to obtain some biologically active analogs of these compounds, we developed a synthesis based on the photocyclization of tertiary N-substituted enaminones derived from 1,3-cyclohexandione and 3 or 6-aminoquinoline. The angular cyclized compounds thus obtained were tested in vitro on K 562 cells and A 2780 doxorubicin sensitive and resistant cells. All compounds were less effective than doxorubicin in sensitive cells but their activity wasn't decreased by MDR resistance. |
| doi_str_mv | 10.1248/cpb.55.1349 |
| format | Article |
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Pharm. Bull.</addtitle><description>Indoloquinoline alkaloid cryptolepine and pyridocarbazole alkaloid ellipticine are of great interest because in vitro and in vivo studies revealed their good cytotoxic properties. In order to obtain some biologically active analogs of these compounds, we developed a synthesis based on the photocyclization of tertiary N-substituted enaminones derived from 1,3-cyclohexandione and 3 or 6-aminoquinoline. The angular cyclized compounds thus obtained were tested in vitro on K 562 cells and A 2780 doxorubicin sensitive and resistant cells. All compounds were less effective than doxorubicin in sensitive cells but their activity wasn't decreased by MDR resistance.</description><subject>Alkaloids - chemical synthesis</subject><subject>Alkaloids - pharmacology</subject><subject>Antibiotics, Antineoplastic - pharmacology</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Cell Line, Tumor</subject><subject>Chemical Sciences</subject><subject>Cyclization</subject><subject>cytotoxicity</subject><subject>Doxorubicin - pharmacology</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Ellipticines - chemical synthesis</subject><subject>Ellipticines - pharmacology</subject><subject>Humans</subject><subject>Indicators and Reagents</subject><subject>indoloquinoline</subject><subject>K562 Cells</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Medicinal Chemistry</subject><subject>Organic chemistry</subject><subject>Oxidation-Reduction</subject><subject>Photochemistry</subject><subject>pyridocarbazole</subject><subject>Ultraviolet Rays</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkU-P0zAQxSMEYsvCiTvKCQmhFv-J44QTZdVlV6oACfZsOc64deXYIU6WzX4QPi9OU8plRvL7zRtrXpK8xmiFSVZ8UG21YmyFaVY-SRax8SUjhD5NFgihckloTi-SFyEcECIMcfo8ucC8IJznaJH8-TG6fg_BhFS6Ov1svPU7o6RNN_fSDrI33qVep7eujsqvwThvjYOZ_j52pvZKdpV89BbCx3SdfoXf6eZBNq2Fae7OwUMLqodI733vO6gHdTRdK-WbVrrRuN2sqVFZ83hc-TJ5pqUN8OrUL5O7683Pq5vl9tuX26v1dqlyjvqlrrmqixIqCarWRV5yXCmd1ZgTkgPTpKCqkDrTwHMiaQWKIqKrqqIYSY05vUzezb57aUXbmUZ2o_DSiJv1VkxviNAiy8ryHkf27cy2XTwEhF40JiiwVjrwQxB5QRhmBYvg-xlUnQ-hA312xkhMkYkYmWBMTJFF-s3JdqgaqP-zp4wicD0DUZ2S8W5KQBz80Ll4G6ECV3tojCAIcYEQY6gUCJOjfSyM0YJhPhl9mo0OoZc7OG-SXW-UhX-_KudynD5Le9kJcPQvQqDDiw</recordid><startdate>2007</startdate><enddate>2007</enddate><creator>Aragon, Pierre-Jean</creator><creator>Yapi, Ange-Désiré</creator><creator>Pinguet, Frédéric</creator><creator>Chezal, Jean-Michel</creator><creator>Teulade, Jean-Claude</creator><creator>Blache, Yves</creator><general>The Pharmaceutical Society of Japan</general><general>Pharmaceutical Society of Japan</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>1XC</scope><scope>VOOES</scope><orcidid>https://orcid.org/0000-0001-7162-8450</orcidid></search><sort><creationdate>2007</creationdate><title>Synthesis and Biological Evaluation of Indoloquinolines and Pyridocarbazoles: A New Example of Unexpected Photoreduction Accompanying Photocyclization</title><author>Aragon, Pierre-Jean ; 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| source | J-STAGE Free; MEDLINE; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| subjects | Alkaloids - chemical synthesis Alkaloids - pharmacology Antibiotics, Antineoplastic - pharmacology Antineoplastic Agents - chemical synthesis Antineoplastic Agents - pharmacology Cell Line, Tumor Chemical Sciences Cyclization cytotoxicity Doxorubicin - pharmacology Drug Screening Assays, Antitumor Ellipticines - chemical synthesis Ellipticines - pharmacology Humans Indicators and Reagents indoloquinoline K562 Cells Magnetic Resonance Spectroscopy Medicinal Chemistry Organic chemistry Oxidation-Reduction Photochemistry pyridocarbazole Ultraviolet Rays |
| title | Synthesis and Biological Evaluation of Indoloquinolines and Pyridocarbazoles: A New Example of Unexpected Photoreduction Accompanying Photocyclization |
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