131811-95-5

Basic information

• Product Name: N-n-butyl-N-methyl-11-(3'-(benzoyloxy)-17'-oxoestra-1',3',5'(10')-trien-7'α-yl)undecanamide
• Synonyms: N-n-butyl-N-methyl-11-(3'-(benzoyloxy)-17'-oxoestra-1',3',5'(10')-trien-7'α-yl)undecanamide
• CAS NO: 131811-95-5
• Molecular Weight: 627.908
• Mol File: 131811-95-5.mol

Chemical Properties

• CAS DataBase Reference: N-n-butyl-N-methyl-11-(3'-(benzoyloxy)-17'-oxoestra-1',3',5'(10')-trien-7'α-yl)undecanamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-n-butyl-N-methyl-11-(3'-(benzoyloxy)-17'-oxoestra-1',3',5'(10')-trien-7'α-yl)undecanamide(131811-95-5)
• EPA Substance Registry System: N-n-butyl-N-methyl-11-(3'-(benzoyloxy)-17'-oxoestra-1',3',5'(10')-trien-7'α-yl)undecanamide(131811-95-5)

Safety Data

• Hazardous Substances Data: 131811-95-5(Hazardous Substances Data)

Upstream product

• 55592-11-5 11-<3'-(benzoyloxy)-17'-oxoestra-1',3',5'(10')-trien-7'α-yl>undecanoic acid 
• 98008-28-7 11-(3,17β-dihydroxy-estra-1,3,5(10)-triene-7a-yl)-undecanoic acid n-butyl-methyl-amide 3-O-benzoate 
• 55592-10-4 3-benzoyloxy 7α-(11'-hydroxy undecyl) estra-1,3,5(10)-trien-17β-ol 
• 110-68-9 N-n-butyl-N-methylamine 

Downstream Products

• 131811-54-6 EM-139 

Relevant articles and documents

STEROIDS FOR CANCER TREATMENT

The present invention relates to novel compounds which are 7α-substituted 17-alkylene-16α-hydroxy steroidal estrogens. This invention specifically relates to estrogen derivatives which contain 7α-substituents and which exhibit anti-estrogenic properties. The present invention also relates to use of said compounds as a medicament, and for the treatment of estrogen dependent disorders, a pharmaceutical composition comprising one or more of said compounds and a method of treatment.

N-butyl-N-methyl-11-(3'-hydroxy-21',17'-carbolactone-19'-nor-17'α- pregna-1',3',5'(10')-trien-7'α-yl)-undecanamide: An inhibitor of type 2 17β-hydroxysteroid dehydrogenase that does not have oestrogenic or androgenic activity

It is well known that 17β-hydroxysteroid dehydrogenases (17β-HSDs) play a key role in the formation and inactivation, from circulating precursors, of several active androgens and oestrogens. These enzymes can thus regulate tumoural cell proliferation in androgen- and oestrogen- dependent cancers. Recently, we discovered that adding a spiro-γ-lactone to the oestradiol nucleus results in a novel inhibitor of type 2 17β-HSD, an enzyme that catalyses the interconversions between 4-androstene-3,17-dione and testosterone, and between oestrone and oestradiol. This finding motivated our introducing the spiro-γ-lactone moiety onto an anti-oestrogenic nucleus. The N-butyl-N-methyll-1-(3'-hydroxy-21',7'-carbolactone-19'-nor-17'α-pregna- 1',3',5'(10')-trien-7'α-yl)-undecanamide (4) was then efficiently synthesized and its biological activity was assessed in vitro. Despite the presence of a bulky alkylamide side chain, the spiro-γ-lactone function conserved its ability to inhibit type 2 17β-HSD (IC50 = 0.35 and 0.25 μM, with and without side chain, respectively). Furthermore, the selective inhibition by lactone 4 toward type 2 17β-HSD (microsomal fraction of human placenta) was demonstrated by the absence of inhibitory activity toward type 1 17β-HSD (cytosolic fraction of human placenta). Cell proliferation assays indicated that compound 4 had no oestrogenic activity but did show anti- oestrogenic activity on ER+ cell line ZR-75-1. No androgenic activity could be detected when assayed on the AR+ cell line Shionogi either. Based on these facts, we report the synthesis of a new steroidal derivative, one that inhibits type 2 17β-HSD while possessing anti-oestrogenic activity. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

Synthesis and biological activity of new halo-steroidal antiestrogens

Antiestrogen therapy is the most widely used endocrine manipulation for the treatment of breast cancer, especially in postmenopausal women. Unfortunately, the compounds presently available possess mixed agonistic/antagonistic activity, thus potentially li