- A practical regiospecific synthesis of 9-nitrocamptothecin
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9-Nitrocamptothecin has shown potent antitumor activity against many types of human cancers. A practical scale-up procedure for this compound is reported by selective reduction of corresponding sulfonate. Georg Thieme Verlag Stuttgart.
- Fu, Qingquan,Chen, Zhiyong
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p. 1940 - 1942
(2007/10/03)
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- Radiosynthesis of carbon-11-labeled camptothecin derivatives as potential positron emission tomography tracers for imaging of topoisomerase I in cancers
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Four carbon-11-labeled camptothecin derivatives, 9-[11C]methoxy- 20(S)-camptothecin ([11C]5), 10-[11C]methoxy-20(S)- camptothecin ([11C]7), 9-nitro-10-[11C]methoxy-20(S)- camptothecin ([11C]9), and 9-[([11C]trimethylamino)methyl] -10-hydroxy-20(S)-camptothecin ([11C]11), have been synthesized as potential positron emission tomography tracers for imaging of topoisomerase I in cancers.
- Gao, Mingzhang,Miller, Kathy D.,Sledge, George W.,Zheng, Qi-Huang
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p. 3865 - 3869
(2007/10/03)
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- Urea-mediated regioselective nitration of (20s)-camptothecin
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A facile and efficient procedure for the regioselective nitration of (20S) camptothecin, using urea mediated reagent system under relatively mild experimental conditions, yielding promising anticancer drug 9-nitro-(20S)- camptothecin in 40% yield with purity of 94.5% (on HPLC) is being reported.
- Puri,Handa,Suri,Qazi
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p. 3443 - 3448
(2007/10/03)
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- Antiangiogenic combination therapy for the treatment of cancer
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The present invention provides combinations of a DNA topoisomerase I inhibiting agent and a selective COX-2 inhibiting agent for preventing, treating, and/or reducing the risk of developing a neoplasia disorder in a mammal.
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- Aromatic esters of camptothecins and methods to treat cancers
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Aromatic camptothecin ester compounds having the formula: are described as well as formulations containing the compounds. Methods of treating cancer and/or tumors are also disclosed.
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- Polymeric derivatives of camptothecins
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The invention relates to polymeric conjugates of 20-O-[glycyl-aminoacyl-glycyl]-camptothecins and a process for producing the same.
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- Highly lipophilic camptothecin derivatives
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This invention relates to novel derivatives of camptothecin, and will, particularly to derivatives having a substitution at the C-7 position, or at one of the C-9, C-10, C-11 or C-12 positions, or to disubstituted derivatives having a first substitution at C-7 and a second at one of C-9, C-10, C-11 or C-12. The invention also includes methods of using the compounds as Topoisomerase I inhibitors to treat patients with cancer. The invention also includes pharmaceutical formulations which consist of the novel compounds in solution or suspension with one or more pharmaceutical excipients or dilutes.
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- PROCESS FOR THE PREPARATION OF 9-AMINO CAMPTOTHECIN
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A process for preparing the 9-amino camptothecin of formula (I) said process comprising: (1) reacting a compound of formula (III) wherein the hydroxy group on ring A is in the 10- or 12-position, with a nitrating agent, so obtaining a corresponding compound of formula (IV) (2) converting the compound of formula (IV) into a corresponding compound of formula (V) wherein XO is a group that can be removed reductively; and (3) reductively removing the said XO group and reducing the nitro group of the compound of formula (V), so obtaining the 9-amino camptothecin of formula (I), a known antitumor compound. The present invention includes also in its scope compounds having the above reported formula (V) and compound of formula (VII) which are endowed with antitumor activity.p
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- Methods of preparing and purifying 9-nitro-20-camptothecin
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A method is disclosed for the preparation of 9-nitrocamptothecin which involves reacting 20-camptothecin with at least one inorganic nitrate salt and at least one acid effective in catalyzing the formation of a nitronium ion, where the reaction occurs at a temperature and for a time sufficient to form the 9-nitrocamptothecin. Also, methods of further purifying the 9-nitrocamptothecin by column chromatography or by reprecipatation is also disclosed.
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- Nitration of camptothecin with various inorganic nitrate salts in concentrated sulfuric acid: A new preparation of anticancer drug 9- nitrocamptothecin
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The nitration reactions of camptothecin (1) with 19 commonly used inorganic nitrate salts and a combination of two or more different nitrate salts in concentrated sulfuric acid are discussed. A new preparation of a promising anticancer drug 9-nitro-camptothecin (4) with a combination of potassium nitrate and thallium(I) nitrate as the nitrating reagents in concentrated sulfuric acid is described.
- Cao, Zhisong,Armstrong, Kim,Shaw, Marcus,Petry, Eddie,Harris, Nick
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p. 1724 - 1730
(2007/10/03)
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- Process for the preparation of 9-amino camptothecin
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A process for preparing 9-amino camptothecin comprising the steps of: (1) reacting a compound of formula (III) STR1 wherein the hydroxy group on ring A is in the 10- or 12-position, with a nitrating agent, to form the corresponding 9-nitro compound; (2) converting the 9-nitro compound into a corresponding compound of formula (V) STR2 wherein XO is a group that can be removed reductively; and (3) reductively removing the XO group and reducing the nitro group of the compound of formula (V), to form the 9-amino camptothecin, a known antitumor compound. The present invention also includes compound having the above formula (V) and their 9-amino analogs, which have antitumor activity.
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- Plant Antitumor Agents. 30. Synthesis and Structure Activity of Novel Camptothecin Analogs
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A large number of camptothecin (CPT) analogs have been prepared in the 20S, 20RS, and 20R configurations with a number of ring A substituents.Topoisomerase I (T-I) inhibition data (IC50) have been obtained by standard procedures.In general, substitution at the 9 or 10 positions with amino, halogeno, or hydroxyl groups in compounds with 20S configuration results in compounds with enhanced T-1 inhibition.Compounds in the 20RS configuration were less active in vitro and in vivo and those in the 20R configuration were inactive.Compounds with 10,11-methylenedioxy substitution on ring A displayed a marked increase in potency in the T-I inhibition assay.The activities of some of the analogs as determined in a variety of in vivo assays including the L-1210 mouse leukemia assay were, in general, in accord with T-I inhibition.A number of water-soluble analogs such as 20-glycinate esters, 9-glycinamides, or hydrolyzed lactone salts were prepared and tested in in vitro and in vivo assays.In general, these compounds were less active than CPT both in terms of T-I inhibition and life prolongation in the L-1210 assay.However, certain 20-glycinate esters showed good in vivo activity after iv administration.
- Wall, Monroe E.,Wani, Mansukh C.,Nicholas, Allan W.,Manikumar, Govindarajan,Tele, Chhagan,et al.
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p. 2689 - 2700
(2007/10/02)
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- Synthesis and antitumor activity of 20(S)-camptothecin derivatives: A-ring modified and 7,10-disubstituted camptothecins
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20(S)-Camptothecin derivatives having nitro, amino, chloro, bromo, hydroxyl and methoxyl groups in the A-ring were synthesized. B-Ring hydrogenated camptothecin (2a) was converted into 10-hydroxycamptothecin (6e) by treatment with lead tetraacetate in trifluoroacetic acid. 10-Substituted derivatives (6) were obtained by a photoreaction of N-oxides (9). The cytotoxicity of the A-ring modified camptothecins was evaluated against KB cells in vitro and leukemia L1210 in mice. 7-Ethyl-10-hydroxycamptothecin (6i) was identified as a potential derivative for further modification.
- Sawada,Matsuoka,Nokata,Nagata,Furuta,Yokokura,Miyasaka
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p. 3183 - 3188
(2007/10/02)
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