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11. LIST OF CONTRIBUTORS

Author

Alazard, J.P., primary, Amin, S.G., additional, Andrus, A., additional, ApSimon, J.W., additional, Armstrong, V.W., additional, Au-Yeung, B.-W., additional, Avram, M., additional, Ayer, W.A., additional, Babin, D., additional, Backinowsky, L.V., additional, Baldwin, J.E., additional, Bally, I., additional, Balsetan, A.T., additional, Bamezai, S., additional, Bandara, B.M.R., additional, Barth, G., additional, Barton, D.H.R., additional, Beaujean, M., additional, Beeley, N.R.A., additional, Berke, C.M., additional, Besselièvre, R., additional, Betaneli, V.I., additional, Beugelmans, R., additional, Birch, A.J., additional, Bose, A.K., additional, Brambilla, R., additional, Braun-Keller, E., additional, Brown, E., additional, Brownbridge, P., additional, Caspi, E., additional, Chamberlain, K., additional, Chan, T.H., additional, Chauncy, B., additional, Chottard, J.C., additional, Clardy, J., additional, Clark, B.C., additional, Collins, J.B., additional, Coulton, S., additional, Crouse, G.D., additional, Dadoun, H., additional, Dahler, P., additional, Day, A.I., additional, De Ville, G., additional, Dinulescu, I.G., additional, Djerassi, C., additional, von E. Doering, W., additional, Drâghici, C., additional, Elian, M., additional, Factor, R.E., additional, Faulkner, D.J., additional, Fernandez, I.F., additional, Finer-Moore, J., additional, Fleming, I., additional, Florent, J.-C., additional, Fourneron, J.-D., additional, Friary, R., additional, Fuhrer, H., additional, Fukuyama, T., additional, Funke, P.T., additional, Furmanova, N.G., additional, Fürst, A., additional, Furuhata, K., additional, Gala, K., additional, Ganguly, A., additional, Georgescu, E.G., additional, Gheorghiu, M.D., additional, Girard, P., additional, Gneuss, K.D., additional, Greaves, A.M., additional, Grier, D., additional, Gruska, R., additional, Guilhem, J., additional, Hangauer, D.G., additional, Hendrickson, J.B., additional, Hillenbrand, G.F., additional, Holohan, J.J., additional, Huber, C.P., additional, Huffman, J.W., additional, Husson, H.-P., additional, Iacobucci, G.A., additional, Ireland, C., additional, Irwin, A.J., additional, Janousek, Z., additional, Jenkins, I.D., additional, Johnson, M.A., additional, Jones, B.B., additional, Julia, M., additional, Kagan, H.B., additional, Kägi, D., additional, Kalvoda, J., additional, Kapur, J.C., additional, Katritzky, A.R., additional, Kaufmann, H., additional, Kelly, L.P., additional, Khajavi, M.S., additional, Khor, T.-C., additional, Kishi, Y., additional, Kitchin, J.P., additional, Kochetkov, N.K., additional, Kreder, J., additional, Kretschmer, G., additional, Kriemler, H.-P., additional, Ksander, G.M., additional, Kuwano, H., additional, Lansbury, P.T., additional, Lester, D.J., additional, Lewis, M., additional, Ley, S.V., additional, Liepa, A.J., additional, Lindley, M., additional, Lusinchi, X., additional, Mahanty, M.K., additional, Mallion, K.B., additional, Manhas, M.S., additional, Mansuy, D., additional, Mastrocola, A.R., additional, McMurry, J.E., additional, McPhail, A.T., additional, Meerholz, C.A., additional, Merenyi, R., additional, Metlushenko, V.P., additional, Mignani, S., additional, Minkin, V.I., additional, Mohr, P., additional, Monneret, C., additional, Motherwell, W.B., additional, Mukkavilli, L., additional, Müller, G., additional, Müller, M., additional, Mulliez, E., additional, Musser, J.H., additional, Naegeli, P., additional, Nakatsuka, S.-I., additional, Namy, J.L., additional, Narula, A.S., additional, Ogura, H., additional, Olekhnovich, L.P., additional, Onan, K.D., additional, Ovchinnikov, M.V., additional, Papoula, M.T.B., additional, Paquette, L.A., additional, Parker, W.L., additional, Pârvulescu, L., additional, Patel, R.C., additional, Peel, R., additional, Pickett, J.E., additional, Piper, J.U., additional, Puar, M.S., additional, Ragault, M., additional, Ram, B., additional, Ramachandran, P.V., additional, Ramage, R., additional, Ranganathan, D., additional, Ranganathan, S., additional, Rathnum, M.L., additional, Raverty, W.D., additional, Reed, N.V., additional, Rizzardo, E., additional, Roussi, G., additional, Saeedi-Ghomi, M.H., additional, Saito, I., additional, Scheuer, P.J., additional, Schriver, G.W., additional, Schwartz, R.E., additional, Scott, A.I., additional, Sell, C., additional, Sependa, G.J., additional, Shapiro, S., additional, Sing, L.Y., additional, Smith, K.M., additional, Sondheimer, F., additional, Soulié, J., additional, Stanescu, L., additional, Stephenson, G.R., additional, Stiller, K., additional, Streitwieser, A., additional, Sugiura, M., additional, Sum, F.W., additional, Sundararaman, P., additional, Sunday, B.R., additional, Sutherland, J.K., additional, Suzuki, M., additional, Tagle, B., additional, Tamm, Ch., additional, Tho, N.-D., additional, Thomas, E.J., additional, Thompson, D.J., additional, Toczko, G.A., additional, Van Engen, D., additional, van der Veen, J.M., additional, Viehe, H.G., additional, Vincent, J.E., additional, Wasserman, H.H., additional, Watson, W.H., additional, Weiler, L., additional, Wetli, M., additional, Wiley, D.C., additional, Williamson, D.H., additional, Wolff, M.S., additional, Wong, H.N.C., additional, Wright, J.J., additional, Zabel, V., additional, and Zimmerman, H.E., additional

Published
1982
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12. Domino aza-Claisen/Mannich cyclization reaction from a chiral α-alkoxy enamine or sequential alkylation of an α-alkoxy ester enolate or nitrile anion, followed by an intramolecular Wittig reaction: Two (3+2) annulation routes to homochiral 4-alkyl-4-hydroxy-2-cyclopentenone synthesis

Author

Kuhn, C. Skaltsounis, L. Monneret, C. Florent, J.-C.

Abstract

A study on the enantioselective synthesis of 4-alkyl-4-hydroxyalkylidene-cyclopentenone prostaglandins is reported. Two (3+2) annulation processes allow the synthesis of homochiral 4-alkyl-4-hydroxy-2-cyclopentenones 4-5, 10-11, and 17. The first process involves a domino aza-Claisen/Mannich cyclization reaction, resulting from the alkylation of an α-alkoxy-enamine, derived from chiral α-alkoxy aldehydes 1, 9, or 16 with 3-iodo-2-(methoxymethoxy)prop-1-ene (3) as the acetonyl equivalent. The second process is based on the sequential alkylation of esters 21, 39, or nitrile 20 with acetonyl equivalents 3 or 25, followed by an intramolecular Wittig reaction. As an application, the synthesis of the naturally occurring alkylidene-cyclopentenone prostaglandin clavulone II from the spiro[cyclopentene-furan]one 5 and the formal total synthesis of (+/-)-untenone 19 has been carried out. © Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Published
2003

14. Synthesis of self-immolative glucuronide-based prodrugs of a phenol mustard

Author

Lougerstay-Madec R, jean-claude florent, Monneret C, Nemati F, and Mf, Poupon

Subjects
Mustard Compounds, Drug Stability, Phenols, Drug Design, Hydrolysis, Tumor Cells, Cultured, Humans, Antineoplastic Agents, Glucuronates, Prodrugs, Drug Screening Assays, Antitumor, Chromatography, High Pressure Liquid, Glucuronidase
Abstract

The design and synthesis of the mustard pro-prodrugs which can be used in ADEPT is reported. Prodrugs 1 and 2 include a glucuronide group which is connected to the drug via an aromatic and/or aliphatic bis-carbamate spacer. The design of these new prodrugs takes advantage of a spontaneous 1,6-elimination and/or an intramolecular cyclization reaction after enzymatic cleavage. Thus, enzymatic-catalyzed hydrolysis of the glucuronyl moiety of 1 by Escherichia coli beta-glucuronidase results in the liberation of the parent mustard drug 20 with formation of CO2, 2-nitro-4-hydroxymethylphenol 19 and dimethylimidazolidinone 21. Surprisingly, prodrug 2 was not cleaved under the same conditions. According to in vitro experiments, prodrugs 1 and 2 were approximately 50- and 80-fold less cytotoxic than the parent drug and, when treated with beta-glucuronidase, the level of cytotoxic activity of 1 became comparable to that of the drug. Stability of 1 in phosphate buffer was satisfactory. These results demonstrate that 1 is a prodrug that can be specifically activated to release the cytotoxic agent.

Published
1999

15. Application of the ADEPT strategy to the MDR resistance in cancer chemotherapy

Author

Desbene, S., Van, HDT, Sylvie MICHEL, Tillequin, F., Koch, M., Schmidt, F., Florent, Jc, Monneret, C., Straub, R., Czech, J., Gerken, M., Bosslet, K., Chimie biologique des membranes et ciblage thérapeutique (CBMCT - UMR 3666 / U1143), Centre National de la Recherche Scientifique (CNRS)-Institut Curie [Paris]-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC), and SCHMIDT, Frédéric

Subjects
MESH: Quinine, [SDV]Life Sciences [q-bio], Antineoplastic Agents, Glucuronates, MESH: Drug Resistance, Multiple, Structure-Activity Relationship, MESH: Doxorubicin, MESH: Structure-Activity Relationship, Drug Stability, Glucuronic Acid, MESH: Spectrophotometry, Ultraviolet, MESH: Drug Stability, [CHIM] Chemical Sciences, Escherichia coli, Tumor Cells, Cultured, MESH: Glucuronidase, Animals, Humans, [CHIM]Chemical Sciences, Prodrugs, MESH: Animals, MESH: Tumor Cells, Cultured, Leukemia L1210, MESH: Chromatography, High Pressure Liquid, Chromatography, High Pressure Liquid, Glucuronidase, MESH: Leukemia L1210, MESH: Humans, Quinine, MESH: Escherichia coli, Hydrolysis, Dipyridamole, Drug Resistance, Multiple, MESH: Drug Resistance, Neoplasm, MESH: Glucuronates, [SDV] Life Sciences [q-bio], Verapamil, MESH: Glucuronic Acid, Doxorubicin, Drug Resistance, Neoplasm, MESH: Antineoplastic Agents, Spectrophotometry, Ultraviolet, MESH: Dipyridamole, MESH: Verapamil, MESH: Prodrugs, MESH: Hydrolysis
Abstract

International audience; New prodrugs consisting of a beta-D-glucuronic acid linked to a MDR reversal agent (verapamil, quinine or dipyridamole) through a self-immolative spacer were synthesized. Four of them were selected for their reduced cytoxicity and beta-glucuronidase enzymatic efficient hydrolysis. Combined use of these prodrugs with a beta-D-glucuronyl-spacer-doxorubicin (HMR1826) according to an ADEPT strategy restored in vitro the sensibility of a MDR resistant strain.

Published
1999

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