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  • C6-(N,N-butyl-methyl-heptanamide) derivatives of estrone and estradiol as inhibitors of type 1 17beta-hydroxysteroid dehydrogenase: Chemical synthesis and biological evaluation.

C6-(N,N-butyl-methyl-heptanamide) derivatives of estrone and estradiol as inhibitors of type 1 17beta-hydroxysteroid dehydrogenase: Chemical synthesis and biological evaluation.

Bioorganic & medicinal chemistry (2006-11-18)
Christine Cadot, Yannick Laplante, Fatima Kamal, Van Luu-The, Donald Poirier
ABSTRACT

A series of estrone and estradiol derivatives having an N-butyl,methyl heptanamide side chain at C6-position were synthesized, tested as inhibitors of type 1 17beta-HSD and assessed for their possible estrogenic activity. A better type 1 17beta-HSD inhibition was obtained for the 6beta-side chain orientation over 6alpha; the C17-alcohols are more potent inhibitors than the corresponding ketones; introducing a 2-methoxy group decreased the inhibitory potency; and the replacement of a C-S bond by a C-C bond in the C6beta-side chain is not detrimental to inhibition. Interestingly, the new inhibitors were also found less estrogenic than the lead compound in two breast cancer cell lines, T-47D and MCF-7.

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Sigma-Aldrich
β-Estradiol, BioReagent, powder, suitable for cell culture
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80 units
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$364.00
Sigma-Aldrich
β-Estradiol, analytical standard
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80 units
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$364.00
Sigma-Aldrich
β-Estradiol-6-one
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80 units
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$364.00
Sigma-Aldrich
β-Estradiol, powder, γ-irradiated, suitable for cell culture
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80 units
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$364.00
Sigma-Aldrich
Estrone, ≥99%
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80 units
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$364.00
Sigma-Aldrich
β-Estradiol, ≥98%
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SKUPack SizeAvailabilityPriceQuantity
80 units
Estimated to ship on March 23, 2025
$364.00
Sigma-Aldrich
Estradiol, meets USP testing specifications
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SKUPack SizeAvailabilityPriceQuantity
80 units
Estimated to ship on March 23, 2025
$364.00