Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Download PDF
Synthesis 2012; 44(24): 3757-3764
DOI: 10.1055/s-0032-1316810
DOI: 10.1055/s-0032-1316810
paper
Stereospecific Synthesis and Biological Evaluation of Monodesmethyl Metabolites of (+)-13a-(S)-Deoxytylophorinine as Potential Antitumor Agents
Authors
Further Information
Publication History
Received: 09 September 2012
Accepted after revision: 24 October 2012
Publication Date:
09 November 2012 (online)
Abstract
Three major monodesmethyl metabolites of (+)-13a-(S)-deoxytylophorinine were synthesized stereospecifically and their configurations at C-13a were determined. Biological assays revealed that one of the metabolites, 3-O-desmethyl-13a-(S)-deoxytylophorinine, had a higher cytotoxic potency than the parent compound or the positive controls doxorubicin (Adriamycin) and paclitaxel (Taxol).
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information (PDF) (opens in new window)
-
References
- 1 These authors contributed equally to this study.
- 2 Cordell GA, Colvard MD. J. Nat. Prod. 2012; 75: 514
- 3 McChesney JD, Venkataraman SK, Henri JT. Phytochemistry 2007; 68: 2015
- 4 Newman DJ, Cragg GM. J. Nat. Prod. 2007; 70: 461
- 5 Govindachari TR, Viswanathan N. Heterocycles 1978; 11: 587
- 6 Mulchandani NB, Venkatachalam SR. Phytochemistry 1984; 23: 1206
- 7 Huang XS, Gao S, Fan LH, Yu SS, Liang XT. Planta Med. 2004; 70: 441
- 8 Tanner U, Wiegrebe W. Arch. Pharm. (Weinheim, Ger.) 1993; 326: 67
- 9 Stærk D, Lykkeberg AK, Christensen J, Budnik BA, Abe F, Jaroszewski JW. J. Nat. Prod. 2002; 65: 1299
- 10 Komatsu H, Watanabe M, Ohyama M, Enya T, Koyama K, Kanazawa T, Kawahara N, Sugimura T, Wakabayashi K. J. Med. Chem. 2001; 44: 1833
- 11 Gao WL, Bussom S, Grill SP, Gullen EA, Hu YC, Huang XS, Zhong SB, Kaczmarek C, Gutierrez J, Francis S, Baker DC, Yu S, Cheng YC. Bioorg. Med. Chem. Lett. 2007; 17: 4338
- 12 Chuang TH, Lee SJ, Yang CW, Wu PL. Org. Biomol. Chem. 2006; 4: 860
- 13 Suffness M, Douros J In Anticancer Agents Based on Natural Product Models . Cassady JM, Douros JD. Academic Press; New York: 1980: 465
- 14 Liu ZJ, Lv HN, Li HY, Zhang Y, Zhang HJ, Su FQ, Xu S, Li Y, Si YK, Yu SS, Chen XG. Chemotherapy (Basel, Switz.) 2011; 57: 310
- 15 Liu ZJ, Lv HN, Li HY, Zhang Y, Zhang HJ, Su FQ, Si YK, Yu SS, Chen XG. J. Asian Nat. Prod. Res. 2011; 13: 400
- 16 Lv HN, Ren JH, Ma SG, Xu S, Qu J, Liu ZJ, Zhou Q, Chen XG, Yu SS. PLoS ONE 2012; 7: e30342 ; doi: 10.1371/journal.pone.0030342
- 17 Tian YP, He JM, Zhang RP, Lv HN, Ma SG, Chen YH, Yu SS, Chen XG, Wu Y, He WY, Abliz Z. Anal. Chim. Acta 2012; 731: 60
- 18 Bao K, Fan AX, Dai Y, Zhang L, Zhang WG, Cheng MS, Yao XS. Org. Biomol. Chem. 2009; 7: 5084
- 19 Ikeda T, Yaegashi T, Matsuzaki T, Yamazaki R, Hashimoto S, Sawada S. Bioorg. Med. Chem. Lett. 2011; 21: 5978
- 20 Banwell MG, Flynn BL, Stewart SG. J. Org. Chem. 1998; 63: 9139
- 21 Buckley TF, Rapoport H. J. Org. Chem. 1983; 48: 4222
- 22 Ikeda T, Yaegashi T, Matsuzaki T, Hashimoto S, Sawada S. Bioorg. Med. Chem. Lett. 2011; 21: 342
- 23 Wu M, Li L, Su B, Liu ZH, Wang QM. Org. Biomol. Chem. 2011; 9: 141
- 24 Wang ZW, Wu M, Wang Y, Li Z, Wang L, Han GF, Chen FZ, Liu YX, Wang KL, Zhang A, Meng LH, Wang QM. Eur. J. Med. Chem. 2012; 51: 250