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Merck

SAR and pH stability of cyano-substituted epothilones.

Organic letters (2003-02-26)
Alicia Regueiro-Ren, Kenneth Leavitt, Soong-Hoon Kim, Gerhard Höfle, Michael Kiffe, Jack Z Gougoutas, John D DiMarco, Francis Y F Lee, Craig R Fairchild, Byron H Long, Gregory D Vite
ABSTRACT

[formula: see text] 3-Cyano epothilones 15-18 are the only examples of non-hydroxy C-3-substituted analogues. Their tubulin binding affinity and cytotoxicity provide meaningful structure-activity relationship information on the dependence of C-1/C-3 conformation upon activity. 12-Cyano epothilone 24 has improved pH stability over epothilone B, and its activity further supports the hypothesis that C-12 stereochemistry is not critical for tubulin affinity.

MATERIALS
Product Number
Brand
Product Description

Supelco
Discovery® Cyano Supelguard Cartridge, 5 μm particle size, L × I.D. 2 cm × 4 mm
Supelco
Discovery® Cyano HPLC Column, 5 μm particle size, L × I.D. 25 cm × 4.6 mm
Supelco
Discovery® Cyano HPLC Column, 5 μm particle size, L × I.D. 15 cm × 4.6 mm
Supelco
Discovery® Cyano HPLC Column, 5 μm particle size, L × I.D. 25 cm × 4 mm