110351-94-5Relevant articles and documents
Synthetic studies on camptothecins. Part 3
Kuang, Yun-Yan,Niu, Jing-Ze,Chen, Fen-Er
, p. 2094 - 2099 (2010)
A concise and efficient asymmetric process for the total synthesis of (20S)-7-ethyl-10-hydroxycamptothecin (=SN-38; 1f), an active metabolic form of the prodrug irinotecan, is described. This approach features the enantioselective cyanosilylation of indolizinone 4 into the corresponding cyanohydrin 5, mediated by a bifunctional thiourea-based cinchona alkaloid under mild conditions, and I2-catalyzed Friedlnder condensation of the tricyclic lactone 6 and 2-amino-5-hydroxy propiophenone (=1-(2-amino-5- hydroxyphenyl)propan-1-one). Copyright
Enantioselective synthesis of 20(S)-camptothecin using Sharpless catalytic asymmetric dihydroxylation
Jew,Ok,Kim,Kim,Kim,Hah,Cho
, p. 1245 - 1248 (1995)
The homochiral key intermediate 2 of 20(S)-camptothecin was prepared enantioselectively by using catalytic asymmetric dihydroxylation as the key reaction.
Enantioselective synthesis of 20(S)-camptothecin using an enzyme- catalyzed resolution
Imura, Akihiro,Itoh, Motohiro,Miyadera, Akihiko
, p. 2285 - 2291 (1998)
The important key intermediate of a 20(S)-camptothecin synthesis was prepared enantioselectively using an enzyme-catalyzed resolution. A commercially available papain was found to exhibit the highest enantioselectivity with moderate activity, and the (S)-enantiomer of 99% ee was obtained as the remaining substrate.
Rigid Analogs of Camptothecin as DNA Topoisomerase I Inhibitors
Lackey, Karen,Besterman, Jeffrey M.,Fletcher, Wade,Leitner, Peter,Morton, Bradley,Sternbach, Daniel D.
, p. 906 - 911 (1995)
Substituted 8-ethyl-2-(2-oxo-1,2-dihydroindol-3-ylidene)-8-hydroxy-2,3,5,8-tetrahydro-6-oxa-3a-azacyclopentanaphthalene-1,4,7-triones were synthesized and evaluated as topoisomerase I inhibitors in an in vitro cleavable complex assay.The activity of these compounds may be attributed to their rigid, planar geometry, and an attempt was made to correlate the SAR in this series to known attributes of camptothecin.
Camptothecin derivative and preparation method and application thereof
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, (2020/01/03)
The invention relates to a compound with a structure shown in a formula (I), a stereoisomer of the compound and a pharmaceutically acceptable salt form of the compound, and further relates to a preparation method of the compound, a pharmaceutical composition containing therapeutically effective dose of the compound, and application of the pharmaceutical composition in the preparation for the prevention and/or treatment of cancer. The compound is a camptothecin derivative with a novel structure with 10 site and 11 site of a stem nucleus introduced with methylene dioxy groups and 7-site introduced with different substituted groups. The raw materials of the preparation method can be obtained easily, a synthetic method is simple, a purification method is simple and fast, the compound has excellent cytotoxic activity in vitro and excellent antitumor effect in vivo, and the compound has broad medicinal prospects.(Please see the specification for the formula).
An improved synthesis of (20S)-camptothecin and its analogue via an asymmetric α-hydroxylation with a chiral organocatalyst
Wang, Xinlong,Xu, Lingjun,Xiong, Fangjun,Wu, Yan,Chen, Fener
, p. 843 - 848 (2017/06/13)
An efficient and stereocontrolled synthesis of (20S)-camptothecin and an analogue has been developed. The key feature of this synthesis is the organocatalyzed asymmetric α-hydroxylation of the lactone precursor 4 to construct its stereocenter, providing tricyclic hydroxylactone 2 in 90% yield and with 88% enantioselectivity. The precursor 4 was efficiently synthesized from the known pyridine 5 in three steps.
COMPOUND OF CAMPTOTHECIN AND PREPARATION AND USE THEREOF
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Paragraph 0097, (2015/05/05)
The present disclosure relates to a compound of formula I, a pharmaceutical composition thereof and the use thereof as an anti-tumor drug.
COMPOUND OF CAMPTOTHECIN AND PREPARATION AND USE THEREOF
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Paragraph 0145; 0146, (2015/06/24)
The present disclosure relates to a compound of formula I, a pharmaceutical composition thereof and the use thereof as an anti-tumor drug.
METHOD OF SYNTHESIZING CAMPTOTHECIN-RELATING COMPOUNDS
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Page 40, (2010/02/05)
The present invention is to prepare efficiently 2'-amino-5'-hydroxypropiophenone corresponding to the AB-ring part of camptothecin (CPT) skeleton and a tricyclic ketone corresponding to the CDE-ring part in order to provide efficiently CPT by the total synthesis, which is a starting material for irinotecan hydrochloride and various kinds of camptothecin derivatives, and to provide stably CPT and its derivatives.
Condensed-hexacyclic compounds and a process therefor
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, (2008/06/13)
Disclosed are a process for the preparation of a compound represented by the formula (1), which comprises treating a compound represented by the formula (2) with methanesulfonic acid and then subjecting the thus-treated compound to recrystallization; and Compound (1) so obtained. This Compound (1) is free of hygroscopicity, excellent in filterability and solubility and easy in handling. Furthermore, according to the preparation process of the present invention, an unnecessary isomer can be converted into the target one and separation of the target isomer can be conducted easily.
