90645-84-4Relevant academic research and scientific papers
FUSED 6,5 BICYCLIC RING SYSTEM P2 LIGANDS, AND METHODS FOR TREATING HIV
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Page/Page column 32; 43, (2012/07/14)
Inhibitors of HIV-1 protease and compositions containing them are described. Use of the inhibitors and compositions containing them to treat HIV, AIDS, and AIDS-related diseases is described.
Design and synthesis of potent HIV-1 protease inhibitors incorporating hexahydrofuropyranol-derived high affinity P2 ligands: Structure-activity studies and biological evaluation
Ghosh, Arun K.,Chapsal, Bruno D.,Baldridge, Abigail,Steffey, Melinda P.,Walters, D. Eric,Koh, Yasuhiro,Amano, Masayuki,Mitsuya, Hiroaki
experimental part, p. 622 - 634 (2011/03/21)
The design, synthesis, and evaluation of a new series of hexahydrofuropyranol-derived HIV-1 protease inhibitors are described. We have designed a stereochemically defined hexahydrofuropyranol-derived urethane as the P2-ligand. The current ligand is designed based upon the X-ray structure of 1a-bound HIV-1 protease. The synthesis of (3aS,4S,7aR)-hexahydro-2H-furo[2,3-b] pyran-4-ol, (-)-7, was carried out in optically active form. Incorporation of this ligand provided inhibitor 35a, which has shown excellent enzyme inhibitory activity and antiviral potency. Our structure-activity studies have indicated that the stereochemistry and the position of oxygens in the ligand are important to the observed potency of the inhibitor. Inhibitor 35a has maintained excellent potency against multidrug-resistant HIV-1 variants. An active site model of 35a was created based upon the X-ray structure of 1b-bound HIV-1 protease. The model offers molecular insights regarding ligand-binding site interactions of the hexahydrofuropyranol-derived novel P2-ligand.
Photochemical and photophysical studies of bicyclo[4.3.0]non-1(6)-en-2-one
Schuster, David I.,Woning, Jan,Kaprinidis, Nikolas A.,Pan, Yanping,Cai, Bing,Barra,Rhodes, Christopher A.
, p. 7029 - 7034 (2007/10/02)
The properties of the lowest excited triplet state of bicyclo[4.3.0]non-1 (6)-en-2-one (BNEN) have been investigated by nanosecond transient absorption spectroscopy, photoacoustic calorimetry, measurements of 1O2 quantum yields, and photochemical studies in solution. Both the lifetime (1.4 μs) and the energy (74-76 kcal mol-1) of the BNEN triplet reflect its exceptional conformational rigidity, which prohibits relaxation along the 3(π,π*) potential energy surface by twisting around the C=C bond. Fumaro- and maleonitrile quench the BNEN triplet at a diffusion-controlled rate by triplet energy transfer. This process leads to cis-trans isomerization of the alkenes. The BNEN triplet displays extensive self-quenching with ksq = 2.6 × 107 M-1 s-1. This process involves intermolecular H-abstraction, but formation of dimeric triplet 1,4-biradicals cannot be excluded. The product of the former is a radical (3) with a lifetime of 4.1 μs. Its transient absorption spectrum (λmax 299 nm) is hypsochromically shifted with respect to that of the BNEN triplet (λmax 311 nm). The solvent effects on the photophysical properties suggest that the T1 state of BNEN is a (π,π*) state in acetonitrile and an (n,π*) state in benzene. The BNEN triplet undergoes neither [2 + 2] cycloaddition reactions with itself, cyclopentene, fumaronitrile, or maleonitrile nor the lumiketone rearrangement, but readily abstracts H-atoms from itself, cyclopentene, and 2-propanol.
STEREOSELECTIVITE DE L'ADDITION DE REACTIFS NUCLEOPHILES SUR DES CETONES POLYCYCLIQUES A JONCTION TRANS
Calmes, D.,Gorrichon-Guigon, L.,Maroni, P.,Accary, A.,Barret, R.,Huet, J.
, p. 879 - 885 (2007/10/02)
The nucleophilic additions of hindered organometallic compounds to polycyclic ketones with trans ring junctions involve predominant axial attack when flattening of the ring containing the carbonyl group occurs.The influence of nucleophile structure (O-Por C-metalled character) on equatorial or axial attack is discussed.
Organic Tellurium and Selenium Chemistry. Reduction of Tellurides, Selenides, and Selenoacetals with Triphenyltin Hydride
Clive, Derrick L. J.,Chittattu, Gim J.,Farina, Vittorio,Kiel, William A.,Menchen, Steven M.,et al.
, p. 4438 - 4447 (2007/10/02)
Preparative and mechanistic details are described for the conversion of selenides into hydrocarbons RH> by heating with triphenyltin hydride at about 120 deg C.The process has been extended to selenoacetals in a form that constitutes a reduction methods for carbonyl compounds RR'C(SePh)2 -> RR'CH2>.Selective reduction of selenoacetals in the presence of thioacetals is possible.Cold-labeled species can be prepared by using triphenyltin deuteride.Tellurides are available easily without problems arising from exposure to air provided that the work is done in a photographic darkroom equipped with a red safety light.These tellurides, as well as the corresponding dichlorides , are reduced under very mild conditions (25-80 deg C) by triphenyltin hydride.The selenium- and tellurium-based chemistry has been used for the unusual process of reducing an epoxide in the presence of a ketone carbonyl.
A REGIOSPECIFIC DOUBLE BOND SHIF INDUCED BY TITANOCENE CATALYSTS
Turecek, F.,Antropiusova', H.,Mach, K.,Hanus, V.,Sedmera, P.
, p. 637 - 640 (2007/10/02)
cis-Bicyclo(4.3.0)-3,7-nonadien is isomerized by titanocene-derived catalysts to bicyclo(4.3.0)-2,9-nonadiene.
