313468-78-9

Downstream Products

• 313468-79-0 (4aS,4bR,10bS,12aS)-8-Benzyloxy-3-iodomethyl-12a-methyl-3,4,4a,4b,5,6,10b,11,12,12a-decahydro-1H-2-oxa-chrysene 
• 1620902-34-2 3-benzyloxy-13α-(p-tolylsulfonyloxymethyl)-14β-(prop-2-en-yl)-des-D-estra-1,3,5(10)-triene 
• 1620902-26-2 3-benzyloxy-16α-phenylselenylmethyl-17-oxa-D-homoestra-1,3,5(10)-triene 
• 1620902-25-1 3-Benzyloxy-16β-phenylselenylmethyl-17-oxa-D-homoestra-1,3,5(10)-triene 
• 1620902-32-0 13α-acetoxymethyl-3-benzyloxy-14β-(prop-2-en-yl)-des-D-estra-1,3,5(10)-triene 
• 1620902-22-8 3-benzyloxy-16β-bromomethyl-17-oxa-D-homoestra-1,3,5(10)-triene 
• 313468-81-4 C₃₉H₄₂O₇ 
• 313468-82-5 C₃₀H₃₆O₅ 
• 313468-83-6 C₃₀H₃₈O₅ 
• 313468-80-3 (4aS,4bR,10bS,12aS)-8-Benzyloxy-12a-methyl-3-methylene-3,4,4a,4b,5,6,10b,11,12,12a-decahydro-1H-2-oxa-chrysene 

Relevant academic research and scientific papers

Synthesis and in Vitro antiproliferative evaluation of C-13 epimers of triazolyl-D-secoestrone alcohols: The first potent 13α-D-secoestrone derivative

The syntheses of C-13 epimeric 3-[(1-benzyl-1,2,3-triazol-4-yl)methoxy]-D-secoestrones are reported. Triazoles were prepared from 3-(prop-2-inyloxy)-D-secoalcohols and p-substituted benzyl azides via Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC). The antiproliferative activities of the products and their precursors were determined in vitro against a panel of human adherent cervical (HeLa, SiHa and C33A), breast (MCF-7, MDA-MB-231, MDA-MB-361 and T47D) and ovarian (A2780) cell lines by means of MTT assays. The orientation of the angular methyl group and the substitution pattern of the benzyl group of the azide greatly influenced the cell growth-inhibitory potential of the compounds. The 13β derivatives generally proved to be more potent than their 13α counterparts. Introduction of a benzyltriazolylmethyl group onto the 3-OH position seemed to be advantageous. One 13α compound containing an unsubstituted benzyltriazolyl function displayed outstanding antiproliferative activities against three cell lines.

Syntheses and antiproliferative effects of d-homo- and d-secoestrones

Substituted and/or heterocyclic d-homoestrone derivatives were synthetized via the intramolecular cyclization of a δ-alkenyl-d-secoaldehyde, -d-secoalcohol or -d-secocarboxylic acid of estrone 3-benzyl ether. The d-secoalcohol was modified at three sites in the molecule. The in vitro antiproliferative activities of the new d-homo- and d-secoestrone derivatives were determined on HeLa, MCF-7, A431 and A2780 cells through use of MTT assay. d-Homoalcohols 3 and 5 displayed cell line-selective cytostatic effects against ovarian and cervical cell lines, respectively. Two d-secoestrones (6 and 12c) proved to be effective, with IC50 values comparable with those of the reference agent cisplatin. A selected compound (6) was tested by tubulin polymerization assay and its cancer specificity was additionally determined by using noncancerous human fibroblast cells.

A novel approach in drug discovery: Synthesis of estrone-talaromycin natural product hybrids

Hetero-Diels - Alder reaction of the steroidal exocyclic enol ethers 14 and 15, obtained from the secoestrones 8 and 9 by reduction, iodoetherification, and elimination, with ethyl O-benzoyldiformylacetate (16) leads to the spiroacetals 17 and 18 as a mixture of four diastereomers. Reduction of the major diastereomers 17a and 18 a with DIBAH and subsequent hydrogenation yields the novel natural product hybrids 21, 23, 24, and 25, which possess the structural features of the steroid estrone (7) and the mycotoxin talaromycin 6.