91799-73-4Relevant articles and documents
Total Synthesis of (-)-Aristoquinoline via an Intramolecular Nitrilium Ion Cyclization
Gujarati, Priyansh D.,Reber, Keith P.
, p. 1404 - 1412 (2021/12/02)
The enantioselective total synthesis of the alkaloid aristoquinoline has been achieved in seven steps and 26% overall yield. A new preparation of the useful synthetic building block (-)-α -terpinyl amine was also developed in order to avoid stoichiometric mercury reagents or azide-containing intermediates. Key steps in the optimized synthetic route include an intramolecular nitrilium ion cyclization to form the characteristic azabicyclo[3.3.1]nonane ring system and a diastereoselective reduction of the resulting imine mixture to afford the natural product. An isomer of aristoquinoline containing an exocyclic alkene was also obtained and found to exhibit unusual chromatographic and spectroscopic properties.
Synthesis and aldose reductase inhibitory activity of N-(quinolinyl thiocarbonyl) glycine derivatives
Nicolaie, E,Guengoer, T,Goyard, J,Cure, G,Fouquet, A,et al.
, p. 977 - 984 (2007/10/02)
The onset of diabetic complications may be prevented by the inhibition of aldose reductase.Derivatives of N-(quinolinyl thiocarbonyl) glycine were prepared and their in vitro and ex vivo aldose reductase inhibitory activities were tested on rat lens.The cincophen derivatives were the most potent in vitro with an enzyme inhibition value of 29percent at 10-8 M and 91percent at 10-7 for the N--N-methylglycine compound 10a.This activity was shown to be dependent on the nature of the substituents and seems to be optimal for the acids; esterswerefound to be inactive.No compound have shown ex vivo inhibitory activity.It is concluded that the lack of ex vivo activity is likely due to a poor bioavailability or a bad penetration of the compounds in target tissue (lens). aldose reductase inhibitors / diabetic complications / N-(quinolinyl thiocarbonyl) glycine
