80758-83-4Relevant articles and documents
Synthesis, biological activities, and quantitative structure-Activity relationship (QSAR) Study of novel camptothecin analogues
Wu, Dan,Zhang, Shao-Yong,Liu, Ying-Qian,Wu, Xiao-Bing,Zhu, Gao-Xiang,Zhang, Yan,Wei, Wei,Liu, Huan-Xiang,Chen, An-Liang
, p. 8634 - 8653 (2015)
In continuation of our program aimed at the development of natural product-based pesticidal agents, three series of novel camptothecin derivatives were designed, synthesized, and evaluated for their biological activities against T. Cinnabarinus, B. brassicae, and B. xylophilus. All of the derivatives showed good-To-excellent activity against three insect species tested, with LC50 values ranging from 0.00761 to 0.35496 mmol/L. Remarkably, all of the compounds were more potent than CPT against T. Cinnabarinus, and compounds 4d and 4c displayed superior activity (LC50 0.00761 mmol/L and 0.00942 mmol/L, respectively) compared with CPT (LC50 0.19719 mmol/L) against T. Cinnabarinus. Based on the observed bioactivities, preliminary structure activity relationship (SAR) correlations were also discussed. Furthermore, a three-dimensional quantitative structure activity relationship (3D-QSAR) model using comparative molecular field analysis (CoMFA) was built. The model gave statistically significant results with the cross-validated q2 values of 0.580 and correlation coefficient r2 of 0.991 and 2 pred r of 0.993. The QSAR analysis indicated that the size of the substituents play an important in the activity of 7-modified camptothecin derivatives. These findings will pave the way for further design, structural optimization, and development of camptothecin-derived compounds as pesticidal agents.
CRYSTALLINE FORM II OF 7-(DIMETHOXY-METHYL) CAMPTOTHECIN, ITS USE AS INTERMEDIATE AND PRODUCTS OBTAINED THEREFROM
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Page/Page column 8, (2009/03/07)
This invention relates to a process for preparing a crystalline form of (4S)-11-(dimethoxymethyl)-4-ethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]qui-no line-3,14(4H,12H)-dione (also named 7-(dimethoxy-methyl)camptothecin). With the provision of a particular crystallization step, in appropriate way, a new crystalline form of the above compound is obtained. The process for the preparation of the polymorph Form II comprises transforming camptothecin to the corresponding 7-(dimethoxy-methyl)-camptothecin, and crystallizing it from methanol.
CHEMICAL MODIFICATION OF ANTITUMOR ALKALOID CAMPTOTHECIN. ACID-CATALYZED CONVERSION OF 7-HYDROXYMETHYLCAMPTOTHECIN INTO THE ALDEHYDE AND ITS ACETALS
Miyasaka, Tadashi,Sawada, Seigo,Nokata, Ken-ichiro
, p. 1719 - 1721 (2007/10/02)
Camptothecin-7-carbaldehyde (3) was prepared from 7-hydroxymethylcamptothecin (2) by treatment with such cationoid agent as sulfuric acid, acetic acid, p-toluenesulfonyl chloride, phosphoryl chloride, thionyl chloride, or triphenylphosphinecarbon tetrachloride.On heating with sulfuric acid in an alcoholic solution, 2 afforded 7-alkoxymethylcamptothecin (4) and 7-dialkoxymethylcamptothecin (5), the product-ratio depending upon the acid-concentration.