35376-44-4

Upstream product

• 1071-46-1 hydrogen ethyl malonate 
• 122-57-6 1-Phenylbut-1-en-3-one 
• 100-52-7 benzaldehyde 
• 17488-65-2 4-phenylbut-3-en-2-ol 
• 105-53-3 diethyl malonate 
• 1896-62-4 (E)-benzalacetone 
• 108-59-8 malonic acid dimethyl ester 

Downstream Products

• 70336-36-6 2-bromo-3-hydroxy-5-phenylcyclohex-2-enone 
• 38765-89-8 2-acetyl-5-phenyl-1,3-cyclohexanedione 
• 95331-96-7 2,2-Dimethyl-7-phenyl-2,3,7,8-tetrahydro-6H-chromene-4,5-dione 
• 55815-00-4 3-methoxy-5-phenylcyclohex-2-ene-1-one 
• 157495-70-0 2--5-phenylcyclohexane-1,3-dione 
• 36646-70-5 3-amino-5-phenylcyclohex-2-en-1-one 
• 400873-45-2 3-(2-hydroxy-ethylamino)-5-phenyl-cyclohex-2-enone 
• 34192-25-1 2-methyl-7-phenyl-5,6,7,8-tetrahydroquinolin-5-one 
• 239131-16-9 7-phenyl-2,4-dimethyl-5,6,7,8-tetrahydroquinolin-5-one 
• 851935-77-8 {2-[(2-hydroxy-6-oxo-4-phenyl-cyclohex-1-enyl)-(6-nitro-benzo[1,3]dioxol-5-yl)-methylsulfanyl]-ethyl}-carbamic acid 9H-fluoren-9-ylmethyl ester 
• 851935-79-0 {2-[(4,5-dimethoxy-2-nitro-phenyl)-(2-hydroxy-6-oxo-4-phenyl-cyclohex-1-enyl)-methylsulfanyl]-ethyl}-carbamic acid 9H-fluoren-9-ylmethyl ester 
• 851935-81-4 {2-[(2-hydroxy-6-oxo-4-phenyl-cyclohex-1-enyl)-(2-nitro-phenyl)-methylsulfanyl]-ethyl}-carbamic acid 9H-fluoren-9-ylmethyl ester 
• 239130-24-6 6-phenyl-1,5,6,7-tetrahydro-4H-indol-4-one 
• 444814-12-4 4-methyl-7-phenyl-7,8-dihydro-6H-quinolin-5-one 

Relevant academic research and scientific papers

Identification of substituted 3-hydroxy-2-mercaptocyclohex-2-enones as potent inhibitors of human lactate dehydrogenase

A novel class of 3-hydroxy-2-mercaptocyclohex-2-enone-containing inhibitors of human lactate dehydrogenase (LDH) was identified through a high-throughput screening approach. Biochemical and surface plasmon resonance experiments performed with a screening hit (LDHA IC50 = 1.7 μM) indicated that the compound specifically associated with human LDHA in a manner that required simultaneous binding of the NADH co-factor. Structural variation of this screening hit resulted in significant improvements in LDHA biochemical inhibition activity (best IC50 = 0.18 μM). Two crystal structures of optimized compounds bound to human LDHA were obtained and explained many of the observed structure-activity relationships. In addition, an optimized inhibitor exhibited good pharmacokinetic properties after oral administration to rats (F = 45%).

Enantiomer and Diastereoisomer Resolution, Rotational Barriers, and CD and UV Spectra of Some Twisted Push-Pull Ethylenes

Suitably substituted twisted push-pull ethylenes capable of existing either as mixtures of achiral diastereoisomers or as pairs of enantiomers have been resolved, in the first case into diastereoisomers by HPLC on silica, in the second case into enantiome

Cyclization reactions leading to β-hydroxyketo esters

The purpose of the research was to synthesize β-diketo esters and to evaluate them for anticonvulsant activity. The reaction of methyl vinyl ketone with dimethyl malonate in the presence of potassium carbonate gave an uncyclized product that underwent a Claisen condensation to yield methyl 2- hydroxy-4-oxocyclohex-2-en-1-oate (5a). Similarly, other cyclized β- hydroxyketo esters were prepared, and their spectrometric data confirmed that the enol tautomers were preferred to the β-diketo tautomers. The synthetic work clarified the reaction pathway for the Michael addition of malonate esters to enones. Of the intermediates and products tested for anticonvulsant activity, dimethyl 2,2-bis-(3-oxobutyl)malonate (9a) was found to possess anticonvulsant property. However, it is emphasized that the β-hydroxyketo esters could be useful intermediates in the synthesis of enaminone anticonvulsants.

SYNTHESIS OF CYCLOHEXYLALIPHATIC ACIDS AND THEIR PHARMACOLOGICAL PROPERTIES

A series of substituted cyclohexylacetic acids I has been obtained by hydrogenation of the unsaturated analogues II and III.Esters of these analogues were prepared by the Horner-Wittig reaction of the corresponding cyclohexanones IV and/or 2-cyclohexenones V with triethyl phosphonoacetate.These esters were obtained in two isomeric forms (Z and E), differing in the double bond in the exo-position.The derivatives with a substituent in the 2-position exhibited a partial shift of the double bond to the cyclohexane ring; this shift was especially marked in the 2-phenyl derivative.With the acids I-III, activation of fibrinolysis was assessed by the hanging clot method; the anti-inflammatory effect was assessed by inhibition of two experimental model inflammations.The regression equation relating fibrinolytic capacity to lipophilicity was a quadratic one, the logarithm of optimum lipophilicity being log Popt = 5.55.A qualitative assessment of the anti-inflammatory effect in relation to lipophilicity suggests that log Popt is probably higher than with arylaliphatic acids.These acids seem to have an active site different from that of the acids I-III.