Total synthesis and biological evaluation of fluorinated cryptophycins

Weiß C, Bogner T, Sammet B, Sewald N (2012)
Beilstein Journal Of Organic Chemistry 8: 2060-2066.

Journal Article | Published | English

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Abstract
Cryptophycins are cytotoxic natural products that exhibit considerable activities even against multi-drug-resistant tumor cell lines. As fluorinated pharmaceuticals have become more and more important during the past decades, fluorine-functionalized cryptophycins were synthesized and evaluated in cell-based cytotoxicity assays. The unit A trifluoromethyl-modified cryptophycin proved to be highly active against KB-3-1 cells and exhibited an IC50 value in the low picomolar range. However, the replacement of the 3-chloro-4-methoxyphenyl-substituent in unit B by a pentafluorophenyl moiety resulted in a significant loss of activity.
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Weiß C, Bogner T, Sammet B, Sewald N. Total synthesis and biological evaluation of fluorinated cryptophycins. Beilstein Journal Of Organic Chemistry. 2012;8:2060-2066.
Weiß, C., Bogner, T., Sammet, B., & Sewald, N. (2012). Total synthesis and biological evaluation of fluorinated cryptophycins. Beilstein Journal Of Organic Chemistry, 8, 2060-2066.
Weiß, C., Bogner, T., Sammet, B., and Sewald, N. (2012). Total synthesis and biological evaluation of fluorinated cryptophycins. Beilstein Journal Of Organic Chemistry 8, 2060-2066.
Weiß, C., et al., 2012. Total synthesis and biological evaluation of fluorinated cryptophycins. Beilstein Journal Of Organic Chemistry, 8, p 2060-2066.
C. Weiß, et al., “Total synthesis and biological evaluation of fluorinated cryptophycins”, Beilstein Journal Of Organic Chemistry, vol. 8, 2012, pp. 2060-2066.
Weiß, C., Bogner, T., Sammet, B., Sewald, N.: Total synthesis and biological evaluation of fluorinated cryptophycins. Beilstein Journal Of Organic Chemistry. 8, 2060-2066 (2012).
Weiß, Christine, Bogner, Tobias, Sammet, Benedikt, and Sewald, Norbert. “Total synthesis and biological evaluation of fluorinated cryptophycins”. Beilstein Journal Of Organic Chemistry 8 (2012): 2060-2066.
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4 Citations in Europe PMC

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Design and synthesis of a new class of cryptophycins based tubulin inhibitors.
Kumar A, Kumar M, Sharma S, Guru SK, Bhushan S, Shah BA., Eur J Med Chem 93(), 2015
PMID: 25647428
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Weiss C, Sammet B, Sewald N., Nat Prod Rep 30(7), 2013
PMID: 23732943
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Dixit RB, Suseela MR., Antonie Van Leeuwenhoek 103(5), 2013
PMID: 23532410

2 References

Data provided by Europe PubMed Central.

A two step synthesis of a key unit B precursor of cryptophycins by asymmetric hydrogenation.
Sammet B, Brax M, Sewald N., Beilstein J Org Chem 7(), 2011
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