137567-91-0Relevant academic research and scientific papers
C-3 SUBSTITUTED BICYCLOOCTANE BASED HIV PROTEASE INHIBITORS
-
Page/Page column 36, (2013/03/26)
C3-functionalized-cyclopentanyltetrahydrofuranyl carbamates that inhibit HIV proteolytic enzymes and processes for preparing the compounds are described. Compositions comprising the disclosed compound and methods of using the compounds and/or compositions for treating patients infected with HIV are also described.
Design of HIV-1 protease inhibitors with C3-substituted hexahydrocyclopentafuranyl urethanes as P2-ligands: Synthesis, biological evaluation, and protein-ligand X-ray crystal structure
Ghosh, Arun K.,Chapsal, Bruno D.,Parham, Garth L.,Steffey, Melinda,Agniswamy, Johnson,Wang, Yuan-Fang,Amano, Masayuki,Weber, Irene T.,Mitsuya, Hiroaki
experimental part, p. 5890 - 5901 (2011/10/08)
We report the design, synthesis, biological evaluation, and the X-ray crystal structure of a novel inhibitor bound to the HIV-1 protease. Various C3-functionalized cyclopentanyltetrahydrofurans (Cp-THF) were designed to interact with the flap Gly48 carbonyl or amide NH in the S2-subsite of the HIV-1 protease. We investigated the potential of those functionalized ligands in combination with hydroxyethylsulfonamide isosteres. Inhibitor 26 containing a 3-(R)-hydroxyl group on the Cp-THF core displayed the most potent enzyme inhibitory and antiviral activity. Our studies revealed a preference for the 3-(R)-configuration over the corresponding 3-(S)-derivative. Inhibitor 26 exhibited potent activity against a panel of multidrug-resistant HIV-1 variants. A high resolution X-ray structure of 26-bound HIV-1 protease revealed important molecular insight into the ligand-binding site interactions.
Synthesis of the C1-C9 fragment of callipeltoside-A
Velázquez, Francisco,Olivo, Horacio F.
, p. 1931 - 1933 (2007/10/03)
(Equation presented) The C1-C9 fragment of callipeltoside (17) was prepared in 12 steps and 7.2% overall yield from bicyclic lactone (+)-4. Key steps include a stereoselective epoxidation and further regiocontrolled nucleophilic opening of the oxirane ring to install two vicinal stereocenters (C5 and C6), and the use of bis(trimethylsilyl) peroxide and a catalytic amount of Sn(IV) chloride for the chemoselective Baeyer-Villiger oxidation of unsaturated cyclopentanone 15.
SYNTHESIS OF NOVEL BICYCLIC ALCOHOLS AND THEIR NITRATES
Gombos, Zsuzsanna,Nyitrai, J.,Nagy, J.,Sohar, P.,Balogh, Gy.,Brlik, J.
, p. 327 - 336 (2007/10/02)
1(R),5(S)-2-oxa-bicyclooct-6-en-3-one (2), a chiral by-product of the manufacture of prostaglandin derivatives, is easily converted into the alcohols (5a), (6a), (6c) and nitrates (5b), (6b), and (6d).Regio- and stereoisomers were identified on the basis of their NMR spectra.
Microbial Oxidation of 7endo-Methylbicyclohept-2-en-6-one, 7,7-Dimethylbicyclohept-2-en-6-one and 2exo-Bromo-3endo-hydroxy-7,7-dimethylbicycloheptan-6-one using Acinetobacter NCIMB 9871
Carnell, Andrew J.,Roberts, Stanley M.,Sik, Vladimir,Willetts, Andrew J.
, p. 2385 - 2390 (2007/10/02)
A bio-Bayer-Villiger reaction using Acinetobacter NCIMB 9871 and the bicycloheptanone 2 provided the corresponding substituted oxabicyclooctanones 6 and 7.Similarly the ketones 3 and 9 furnished the lactones 8 and 10 respectively: the lactones 6, 7 and 10 were obtained in states of high optical purity.
TOTAL SYNTHESIS AND PROPERTIES OF PROSTAGLANDINS. 30. MODIFICATION OF (1S,5R)-2-OXABICYCLO-6-OCTEN-3-ONE AT THE α-CARBON ATOM
Dikovskaya, K. I.,Mazur, T. V.,Turovskii, I. V.,Gavars, M. P.,Freimanis, Ya. F.
, p. 1300 - 1308 (2007/10/02)
Derivatives of α-alkyl-, α-alkylidene-, and α-hydroxymethylene-2-oxabicyclo-6-octen-3-one were obtained.The possibility of functional substitution of the bicyclic γ-lactones at the α position to the carbonyl group was thereby demonstrated.
Enzyme-catalysed Baeyer-Villiger Oxidations of Some Substituted Bicycloheptanones
Carnell, Andrew J.,Roberts, Stanley M.,Sik, Vladimir,Willetts, Andrew J.
, p. 1438 - 1439 (2007/10/02)
The ketones 1 and 4 are oxidized to γ-lactones 2 and 5 with low enantioselectivity by both Acinetobacter sp.NCIB 9871 and Pseudomonas sp.NCIB 9872; in contrast the ketones 7 and 10 are biotransformed to products 8/9 and 11 respectively of very high optical purity.
