Synthesis and Cytotoxic and Antitumor Activity of 1,2-Dihydroxy-1,2-dihydrobenzo[b]acronycine Diacid Hemiesters and Carbamates
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- Doan Thi Mai Huong
- Laboratoire de Pharmacognosie de l'Université René Descartes, U.M.R./C.N.R.S. n°8638, Faculté des Sciences Pharmaceutiques et Biologiques
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- Gaslonde Thomas
- Laboratoire de Pharmacognosie de l'Université René Descartes, U.M.R./C.N.R.S. n°8638, Faculté des Sciences Pharmaceutiques et Biologiques
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- Michel Sylvie
- Laboratoire de Pharmacognosie de l'Université René Descartes, U.M.R./C.N.R.S. n°8638, Faculté des Sciences Pharmaceutiques et Biologiques
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- Koch Michel
- Laboratoire de Pharmacognosie de l'Université René Descartes, U.M.R./C.N.R.S. n°8638, Faculté des Sciences Pharmaceutiques et Biologiques
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- Tillequin François
- Laboratoire de Pharmacognosie de l'Université René Descartes, U.M.R./C.N.R.S. n°8638, Faculté des Sciences Pharmaceutiques et Biologiques
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- Pfeiffer Bruno
- Les Laboratoires Servier
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- Renard Pierre
- Les Laboratoires Servier
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- Kraus-Berthier Laurence
- Institut de Recherches Servier, Division Recherche Cancérologie
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- Léonce Stéphane
- Institut de Recherches Servier, Division Recherche Cancérologie
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- Pierré Alain
- Institut de Recherches Servier, Division Recherche Cancérologie
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Abstract
A series of cis-1,2-dihydroxy-1,2-dihydrobenzo[b]acronycine diacid hemiesters and dicarbamates were prepared by acylation of cis-1,2-dihydroxy-6-methoxy-3,3,14-trimethyl-1,2,3,14-tetrahydro-7H-benzo[b]pyrano[3,2-h]acridin-7-one. The cytotoxicity of the dicarbamates depended on the steric hindrance of the esterifying groups at positions 1 and 2. Diacid hemiesters displayed significant in vitro cytotoxic activities and induced cell cycle perturbations similar to those obtained with cis-1,2-diacetoxy-1,2-dihydrobenzo[b]acronycine (S23906-1) currently under preclinical development. cis-1-Acetoxy-2-hemiglutaryloxy-1,2-dihydrobenzo[b]acronycine was the most promizing compound of the series, inducing complete inhibition of tumor growth when tested against C38 colon adenocarcinoma implanted in mice.
Journal
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- Chemical and Pharmaceutical Bulletin
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Chemical and Pharmaceutical Bulletin 52 (3), 293-297, 2004
The Pharmaceutical Society of Japan
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Details 詳細情報について
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- CRID
- 1390001204171340800
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- NII Article ID
- 110003615552
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- NII Book ID
- AA00602100
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- ISSN
- 13475223
- 00092363
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- NDL BIB ID
- 6866909
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- PubMed
- 14993749
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- Text Lang
- en
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- Data Source
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- JaLC
- NDL
- Crossref
- PubMed
- CiNii Articles
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- Abstract License Flag
- Disallowed