84583-08-4Relevant articles and documents
Synthesis of analogs of (1,4)-3- and 5-imino oxazepane, thiazepane, and diazepane as inhibitors of nitric oxide synthases
Shankaran,Donnelly, Karla L.,Shah, Shrenik K.,Caldwell, Charles G.,Chen, Ping,Hagmann, William K.,MacCoss, Malcolm,Humes, John L.,Pacholok, Stephen G.,Kelly, Theresa M.,Grant, Stephan K.,Wong, Kenny K.
, p. 5907 - 5911 (2007/10/03)
The preparation and SAR of a series of iNOS inhibitors leading to the most potent compound, incorporating a (1,4)-5-imino thiazepane (R = n-Pr) is disclosed. A series of 3- and 5-imino analogs from oxazepane, thiazepane, and diazepane was prepared and eva
The stereochemistry of the thermal cheletropic decarbonylation of 3-cyclopentenone as determined by multiphoton infrared photolysis/thermolysis
Unruh, Gregory R.,Birney, David M.
, p. 8529 - 8533 (2007/10/03)
There are two allowed pathways for the thermal cheletropic decarbonylation of 3-cyclopentenone. The stereochemistry of decarbonylation of an unconstrained derivative (trans, trans-2,5-dimethyl-3-cyclopentenone, 4) has been determined for the first time. Under conventional pyrolysis conditions, thermal rearrangements of the initial product (trans, trans-2,4-hexadiene, 5) occur at the high temperatures required for the decarbonylation. However, by using multiphoton infrared photolysis/thermolysis to initiate decarbonylation, it was shown that the initial products from thermal decarbonylation of 4 are solely carbon monoxide and stereospecifically 5. The stereochemistry of decarbonylation is thus disrotatory, in accord with prior theoretical studies. A survey of crystal structures reveals ground-state distortions along this reaction coordinate as well.
Phencyclidine derivatives, preparation method and pharmaceutical compositions containing same
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, (2008/06/13)
The invention concerns novel phenylcyclidine derivatives with selective affinity for low affinity receptors, methods for preparing them, pharmaceutical compositions containing them and their use as protective agents for central or peripheral nervous system cells against acute or chronic degeneration, or as an anticonvulsant.
The search for TCP analogues binding to the low affinity PCP receptor sites in the rat cerebellum
Hamon, Jacques,Espaze, Florence,Vignon, Jacques,Kamenka, Jean-Marc
, p. 125 - 135 (2007/10/03)
With the aim of obtaining selective ligands of the low affinity binding sites of [3H]-1-[1-(2-thienyl)cyclohexyl]piperidine ([3H]TCP) in the rat cerebellum, oxygen and sulfur atoms were introduced in the TCP structure and derivatives to obtain analogues with a lowered lipophilicity. These compounds, and others already obtained, were assayed comparatively to determine their affinities for three sites labeled with [3H]TCP: one in the forebrain, the originally described PCP receptor, and two in the rat cerebellum. Lowering the lipophilicity and modifying the hetero-aromatic moiety yielded some ligands with increased affinity for the low affinity sites in the rat cerebellum and decreased affinity for the high affinity sites in the forebrain. Particularly, two compounds displaying both a high affinity and a good selectivity might be valuable tools to elucidate the pharmacology of the low affinity PCP sites labeled with [3H]TCP in the rat cerebellum.
Thiomethylation of ketones by sodium sulphide and formaldehyde
Ulendeyeva,Bayeva,Lyapina,Shmakov,Galkin
, p. 177 - 186 (2007/10/03)
The thiomethylation of propanol, butanol, cyclohexanone and acetophenone with a mixture of formaldehyde and sodium sulphide proceeds at 20°C and normal pressure for 1-7 hr. It has been established that the reactivity of ketones increases in the order butanone-cyclohexanone-propanone-acetophenone. The conversion of sodium sulphide depends on its initial concentration, the nature of the ketone, and the presence in the reaction medium of sodium hydroxide and ethyl alcohol. It has been shown that the reaction proceeds with the preferential formation of keto- and diketosulphides.
Preparation of 3-Substituted 4-Thianones and Their 1,1-Dioxides via Palladium Mediated Deallyloxycarbonylation
Casy, Guy,Sutherland, Alan G.,Taylor, Richard J. K.,Urben, Peter G.
, p. 767 - 769 (2007/10/02)
3-Alkyl-4-thianones 4 (3-alkyl-thiacyclohexan-4-ones) can be conveniently prepared by the alkylation of 3-allyloxycarbonyl-4-thianone (1b) followed by deallyloxycarbonylation mediated by tetrakis(triphenylphospine)palladium in the presence of morpholine.The corresponding sulphones 9, as well as 2,3-dialkyl-4-thianone derivatives 12 and 13 can be prepared by analogous procedures.
Enolate Equilibria and Force Field Parameters
Spears, Glen W.,Caufield, Craig E.,Still, W. Clark
, p. 1226 - 1231 (2007/10/02)
Lithium enolates with differing degrees of alkyl substitution were prepared and geometrically equilibrated by using catalytic phenylmercuric chloride in tetrahydrofuran.With the resulting thermodynamic data, MM2 force field parameters were evaluated by using an automatic force field refinement program.
Enzymes in Organic Synthesis. 27. Horse Liver Alcohol Dehydrogenase Catalyzed Oxidoreductions of 3-Alkylthiopyran Ketones and Alcohols
Takemura, Tetsuo,Jones, Brian J.
, p. 791 - 796 (2007/10/02)
The stereospecificity of horse liver alcohol dehydrogenase (HLADH) toward S-heterocyclic substrates has been studied further.While 3-methyl- and 3-ethyltetrahydrothiopyran-4-ones (1) and -4-ols (2,3) are not good substrates, the ketones 1 and trans alcohols 3 do undergo highly stereoselective enzyme-mediated oxidoreductions in preparative-scale (up to 2 g of substrate) reactions.In contrast, HLADH-catalyzed oxidations of the cis alcohols 2 are too slow to be preparatively viable.Reductions of the racemic ketones 1 occur with high enantiomeric- and stereoselectivity,with the 3S enantiomers being converted in excellent yields to the corresponding 3S,4S trans alcohols 3 of 78-90 percent ee.The unreactive 3R ketone enantiomers of 58-66 percent ee are recovered from the same reactions.Oxidations of the racemic trans alcohols 3 are also markedly stereoselective, permitting the unreactive (3R,4R)-3 enantiomers of 65-85 percent ee to be isolated in good yields.
