102254-58-0

Upstream product

• 2525-16-8 O-methylcaprolactim 
• 40106-13-6 2-amino-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxylic acid ethyl ester 
• 105-60-2 caprolactam 
• 502-42-1 cycloheptanone 

Relevant academic research and scientific papers

Synthesis and biological evaluation of 17β-hydroxysteroid dehydrogenase type 1 (17β-HSD1) inhibitors based on a thieno[2,3-d] pyrimidin-4(3H)-one core

Many breast tumors are hormone-dependent, and estrogens, especially estradiol (E2), have a pivotal role in their growth and development. 17β-Hydroxysteroid dehydrogenase type 1 (17β-HSD1) is a key enzyme in the biosynthesis of female sex steroids, catalyzing the NADPH-dependent reduction of estrone into biologically active estradiol. In this study, a library of fused (di)cycloalkeno thieno[2,3-d]pyrimidin-4(3H)-one based compounds was synthesized, and the biological activities against 17β-HSD1 in a cell-free and in a cell-based assay were evaluated. Several thieno[2,3-d]pyrimidin-4(3H)-one based compounds, at 0.1 and 1 μM test concentrations, were found to be potent 17β-HSD1 inhibitors. For example, 4-(3-hydroxyphenylthio)-1,2,7,8,9,10,11,13-octahydro-13-oxo-[1] benzothieno[2′,3′:4,5]-pyrimido[1,2-a]azepine-3-carboxaldehyde (7f) is one of the most potent nonsteroidal 17β-HSD1 inhibitors reported to date with 94% inhibition of the recombinant enzyme at 0.1 μM test concentration. Importantly, the majority of these compounds exhibited excellent selectivity over the oxidative isoform 17β-HSD2 and lacked estrogenic effects in an estrogen receptor (ER) binding assay.

Saturated Heterocycles, 75 - Preparation of Tetracyclic Thiophene Derivatives with Bridgehead Nitrogen. Synthesis of Polymethylenethienodihydropyrrolo-, tetrahydropyrido- and tetrahydroazepinopyrimidin-4-ones and -4-thiones

The following tetracyclic ring systems and their derivatives have been synthesized for pharmacological investigations: Trimethylenethienodihydropyrrolopyrimidin-4-one and -4-thione (1a, 5a); Tetramethylenethienodihydropyrrolopyrimidin-4-one and -4-thione (1b, 1j, 5b); Pentamethylenethienodihydropyrrolopyrimidin-4-one and-4-thione (1c, 5c); Trimethylenethienotetrahydropyridopyrimidin-4-one and -4-thione (1d, 5d); Tetramethylenethienotetrahydropyridopyrimidin-4-one and -4-thione (1e, 5e);Pentamethylenethienotetrahydropyridopyrimidin-4-one and -4-thione (1f, 5f); Trimethylenethienotetrahydroazepinopyrimidin-4-one and -4-thione (1g,5g); Tetramethylenethienopyrimidin-4-one and -4-thione (1h, 5h); Pentamethylenethienotetrahydroazepinopyrimidin-4-one and -4-thione (1i, 5i); Tetramethylenethienotetrahydroazepinopyrimidin-4-one (7b); Pentamethylenethieno-tetrahydropyridopyrimidin-4-one (7c).Compounds 1a-i were synthesized from 2-amino-3-ethoxycarbonyl-4,5-polymethylenethiophene 2a-c with the corresponding lactim ethers (3a-c) in chlorobenzene in the presence of polyphosphoric acid (PPA).Compounds 7b and 7c were obtained in the reaction ob β-amino acid esters 2a and 2c with 2-bromopyridine (6).The thione derivatives (5a-i) were prepared from compounds 1a-i with phosphorus(V) sulphide. - Keywords: Condensation of 2-amino-3-ethoxycarbonyl-4,5-polymethylenethiophene with lactim ethers and 2-bromopyridine; Oxo-thio exchange