197796-01-3

Upstream product

• 4654-08-4 5-(4'-hydroxyphenyl)pentanoic acid 
• 100-39-0 benzyl bromide 
• 19578-68-8 4-(4-benzyloxyphenyl) iodide 
• 591-80-0 pent-4-enoic acid 
• 100-44-7 benzyl chloride 

Downstream Products

• 204589-93-5 5-(4-Benzyloxy-phenyl)-pentanoyl chloride 
• 197796-04-6 25,27-bis(5-(4-benzyloxyphenyl)pentoxy)-26,28-dihydroxy-p-tert-butylcalix[4]arene 
• 197796-06-8 25,27-bis(5-(4-hydroxyphenyl)pentoxy)-26,28-dihydroxy-p-tert-butylcalix[4]arene 
• 154044-14-1 5-(4-benzyloxyphenyl)pentyl tosylate 
• 199444-26-3 5-(4-Hydroxy-phenyl)-pentanoic acid pentachlorophenyl ester 
• 142516-74-3 5-(4-benzyloxyphenyl)pentanol 

Relevant academic research and scientific papers

Discovery of 1-(4-fluorophenyl)-(3R)-[3-(4-fluorophenyl)-(3S)- hydroxypropyl]-(4S)-(4-hydroxyphenyl)-2-azetidinone (SCH 58235): A designed, potent, orally active inhibitor of cholesterol absorption

(3R)-(3-Phenylpropyl)-1,(4S)-bis(4-methoxyphenyl)-2-azetidinone (2, SCH 48461), a novel inhibitor of intestinal cholesterol absorption, has recently been described by Burnett et al. and has been demonstrated to lower total plasma cholesterol in man. The potential sites of metabolism of 2 were considered, and the most probable metabolites were prepared. The oral cholesterol-lowering efficacy of the putative metabolites was evaluated in a 7-day cholesterol-fed hamster model for the reduction of serum total cholesterol and liver cholesteryl esters versus control. On the basis of our analysis of the putative metabolite structure-activity relationship (SAR), SCH 58235 (1, 1-4-fluorophenyl)-(3R)-[3-(4-fluorophenyl)-(3S)-hydroxypropyl]- (4S)-(4-hydroxyphenyl)-2-azetidinone) was designed to exploit activity enhancing oxidation and to block sites of potential detrimental metabolic oxidation. Additionally, a series of congeners of 2 were prepared incorporating strategically placed hydroxyl groups and fluorine atoms to further probe the SAR of 2-azetidinone cholesterol absorption inhibitors. Through the SAR analysis of a series of putative metabolites of 2, compound 1 was targeted and found to exhibit remarkable efficacy with an ED50 of 0.04 mg/kg/day for the reduction of liver cholesteryl esters in a 7-day cholesterol-fed hamster model.

Head-to-Tail Connected Double Calix[4]arenes

New macrotricyclic compounds consisting of two calix[4]arene substructures connected by aliphatic chains of various length (three to five carbon atoms) between two opposite p-positions and two distal phenolic oxygens have been synthesized. Starting with p-tert-butyl-calix[4]arene, two O-protected phenolic units are attached via ether links in 1,3-position by reaction with the corresponding tosylates. After deprotection, the new calix[4]arene is formed by fragment condensation with 2,6-tobromomethylated 4-alkylphenols. The structure of one example (8c) has been confirmed by single crystal X-ray analysis. Both calixarene parts assume the cone conformation, a molecule of acetonitrile being included in both cavities.

Kinetics and Mechanism of the Alkaline Hydrolysis of Pentachlorophenyl ω-(p-Hydroxyphenyl)alkanoates

A kinetic study of the alkaline hydrolysis of pentachlorophenyl esters of ω-(p-hydroxyphenyl)alkanoic acids 3 shows that the dissociative route involving a spirodienone intermediate is not a feasible alternative to the normal associative BAC2 pathway.