22086-89-1Relevant academic research and scientific papers
Acetic acid aldose reductase inhibitors bearing a five-membered heterocyclic core with potent topical activity in a visual impairment rat model
La Motta, Concettina,Sartini, Stefania,Salerno, Silvia,Simorini, Francesca,Taliani, Sabrina,Marini, Anna Maria,Da Settimo, Federico,Marinelli, Luciana,Limongelli, Vittorio,Novellino, Ettore
supporting information; experimental part, p. 3182 - 3193 (2009/04/06)
A number of 1,2,4-oxadiazol-5-yl-acetic acids and oxazol-4-yl-acetic acids were synthesized and tested for their ability to inhibit aldose reductase (ALR2). The oxadiazole derivatives, 7c, 7f, 7i, and 8h, 8i, proved to be the most active compounds, exhibiting inhibitory levels in the submicromolar range. In this series, the phenyl group turned out to be the preferred substitution pattern, as its lengthening to a benzyl moiety determined a general reduction of the inhibitory potency. The lead compound, 2-[3-(4-methoxyphenyl)-1,2,4- oxadiazol-5-yl]acetic acid, 7c, showed an excellent in vivo activity, proving to prevent cataract development in severely galactosemic rats when administered as an eye-drop solution in the precorneal region of the animals. Computational studies on the ALR2 inhibitors were performed to rationalize the structure-activity relationships observed and to provide the basis for further structure-guided design of novel ALR2 inhibitors.
Ramoplanin derivatives possessing antibacterial activity
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Page/Page column 38; 70, (2010/11/23)
Novel ramoplanin derivatives are disclosed. These ramoplanin derivatives exhibit antibacterial activity. As the compounds of the subject invention exhibit potent activities against gram positive bacteria, they are useful antimicrobial agents. Methods of synthesis and of use of the compounds are also disclosed.
Synthesis of 2-phenyloxazole derivatives containing amino acids as insulin sensitivity enhancers for treatment of type II diabetes
Faul, Margaret M.,Winneroski, Leonard L.,York, Jeremy S.,Reinhard, Matt R.,Hoying, Richard C.,Gritton, William H.,Dominianni, Samuel J.
, p. 689 - 704 (2007/10/03)
The search for Insulin Sensitivity Enhancers (ISE) for use in the treatment of Non-Insulin Dependent Diabetes Mellitus (NIDDM) has led to the preparation of N-[(phenylmethoxy)carbonyl]-O-[[4-[2-(2-phenyl-4-oxazolyl)-ethoxy]phenyl] methyl]-L-serine (1) and 7-[2-(2-phenyl-4-oxazolyl)ethoxyl]-L-1,2,3,4-tetrahydro-N-Cbz- isoquinoline-3-carboxylic acid (2), that contain a 2-phenyloxazole moiety linked to an amino acid in place of the 2,4-thiazolidinedione pharmacophore. The 2-phenyloxazole was incorporated into 1 and 2 in high yield by alkylation of 4-hydroxybenzaldehyde or methyl 7-1,2,3,4-tetrahydro-N-benzyloxycarbonyl-hydroxyisoquinoline-3-carboxylate with 2-(2-phenyl-4-oxazolyl)ethyl p-toluenesulfonate (16). Successful incorporation of serine into 1 required use of an N-trityl protecting group to minimize β-elimination and epimerization at the α-center.
