4350-74-7Relevant academic research and scientific papers
COMPOUNDS AND METHODS OF TREATING OCULAR DISORDERS
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, (2016/06/14)
A method of treating an ocular disorder in a subject associated with increased all-trans-retinal in an ocular tissue includes administering to the subject a therapeutically effective amount of a primary amine compound of formula (I); and pharmaceutically acceptable salts thereof.
Expansion of first-in-class drug candidates that sequester toxic all-trans-retinal and prevent light-induced retinal degeneration
Zhang, Jianye,Dong, Zhiqian,Mundla, Sreenivasa Reddy,Hu, X. Eric,Seibel, William,Papoian, Ruben,Palczewski, Krzysztof,Golczak, Marcin
supporting information, p. 477 - 491 (2015/01/30)
All-trans-retinal, a retinoid metabolite naturally produced upon photoreceptor light activation, is cytotoxic when present at elevated levels in the retina. To lower its toxicity, two experimentally validated methods have been developed involving inhibition of the retinoid cycle and sequestration of excess of all-trans-retinal by drugs containing a primary amine group. We identified the first-in-class drug candidates that transiently sequester this metabolite or slow down its production by inhibiting regeneration of the visual chromophore, 11-cis-retinal. Two enzymes are critical for retinoid recycling in the eye. Lecithin:retinol acyltransferase (LRAT) is the enzyme that traps vitamin A (all-trans-retinol) from the circulation and photoreceptor cells to produce the esterified substrate for retinoid isomerase (RPE65), which converts all-trans-retinyl ester into 11-cis-retinol. Here we investigated retinylamine and its derivatives to assess their inhibitor/substrate specificities for RPE65 and LRAT, mechanisms of action, potency, retention in the eye, and protection against acute light-induced retinal degeneration in mice. We correlated levels of visual cycle inhibition with retinal protective effects and outlined chemical boundaries for LRAT substrates and RPE65 inhibitors to obtain critical insights into therapeutic properties needed for retinal preservation.
Fast preparation of dihydrocyclocitral from citronellal under solventless microwave irradiation
Nhuan, Ngoc Doan,Thach, Ngoc Le,Poul, Erik Hansen,Duus, Fritz
, p. 6749 - 6751 (2007/10/03)
Dihydrocyclocitral, a useful reagent in organic synthesis, has been synthesized in high yield and with high stereoselectivity from citronellal under microwave irradiation in two steps, involving acetic anhydride under base catalysis, then p-toluenesulfonic acid adsorbed on silica gel under solventless conditions (80% yield, reaction time 22 min).
Ethyl (1R,6S)-2,2,6-trimethylcyclohexanecarboxylate, aroma chemical composition containing the same and process of producing the same
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, (2008/06/13)
Ethyl (1R,6S)-2,2,6-trimethylcyclohexanecarboxylate represented by formula (1) STR1 is disclosed. Also, an aroma chemical composition containing the same and a process of the production of the same are disclosed.
Aldehyde Enol Esters as Novel Chain Terminators in Cationic Olefin Cyclizations
Simmons, Dana P.,Reichlin, Daniel,Skuy, David
, p. 1000 - 1004 (2007/10/02)
Citronellal (1) has been transformed into enol acetates 2 which have been cyclized with various Lewis and Broensted acids to dihydrocyclocitral (4).Application of this methodology to the synthesis of mono- and bicyclic ring systems has been examined.
1-diphenylphosphonio-1-methoxymethyllithium, a useful reagent for the synthesis of aldehydes from hindered ketones
Corey,Tius, Marcus A.
, p. 3535 - 3538 (2007/10/02)
A new reagent, 1-diphenylphosphonio-1-methoxymethyllithium, has been found to be highly effective for the transformation R2CO → R2CHCHO with sterically hindered, enolizable ketones.
