Triazolo-tetrahydrofluorenones as selective estrogen receptor beta agonists

Pharmacophore and QSAR modeling of estrogen receptor β ligands and subsequent validation and in silico search for new hits

“…The literature was extensively surveyed to collect as many structurally diverse ERb ligands as possible (1-119, see Table A and Figure A in Supporting Information) [2,3,6,8,9,11,16,17,[39][40][41][42][43][44][45][46][47][48][49][50][51][52][53][54][55]. The collected compounds were carefully selected from around 800 reported inhibitors in such a way to guarantee dissimilar affinities to ERa and ERb, and therefore, to allow access to selective ERb pharmacophore models.…”

Selective estrogen receptor-beta (SERM-beta) compounds modulate raphe nuclei tryptophan hydroxylase-1 (TPH-1) mRNA expression and cause antidepressant-like effects in the forced swim test

“…Some of these include caffeic acid phenethyl ester (Jung et al, 2010), butyl 4-(butyryloxy) benzoate (Lin et al, 2008), the diarylpropionitriles (Meyers et al, 2001), the aryl diphenolic azoles and the benzoazole ERB-041 (Malamas et al, 2004;Follettie et al, 2006), genistein derivatives (Mewshaw et al, 2005), effusol derivatives (e.g., benzo[c]chromenone analogs) (Sun et al, 2006), salicylaldoximes (Bertini et al, 2011) and the tetrahydrofluorenones (Parker et al, 2006;Wilkening et al, 2006).…”

A facile and efficient method for the selective deacylation of N-arylacetamides and 2-chloro-N-arylacetamides catalyzed by SOCl2

“…This difference indicated that electrophilic substituents in the aromatic ring has a fundamental effect on the rate of deacylation. Compared with 2-chloro-N-arylacetamides bearing a benzene ring ( a The substrate(4 mmol) was treated with acetyl chloride (24 mmol) in the presence of 24 mmol K 2 CO 3 in acetone at room temperature b All products were identified by IR and 1 H NMR spectra c Yields refer to pure isolated products A facile and efficient method 81 [1][2][3][4][5][6][7][8][9][10][11][12], those with a aromatic heterocyclic ring (Table 8, entries 12-15) were, to some extent, less reactive and needed more than 3 h for completion of the reaction, but still afforded the corresponding products in excellent yields. We also found that both N-p-tolyl benzamide and N-benzyloxycarbonyl-benzamide could not be deacylated (not reported in this paper).…”

“…Alcoholysis of the acetyl amino group catalyzed by acid (HCl [10]) or alkali (CH 3 ONa [11]) in alcohol.…”