65921-41-7Relevant academic research and scientific papers
NOVEL BETULINIC SUBSTITUTED AMIDE DERIVATIVES AS HIV INHIBITORS
-
Page/Page column 46, (2017/02/24)
The present invention relates to novel betulinic substituted amide compounds of formula (I); and pharmaceutically acceptable salts thereof, wherein R1, R2, R3, R4, R5, R6, R7, R8, X, Y, Z1, Z2, Z3 and are Formula (II) as defined herein. The invention novel betulinic substituted amide derivatives, related compounds, and pharmaceutical compositions useful for the therapeutic treatment of viral diseases and particularly HIV mediated diseases.
Resin-immobilized pyrrolidine-based chiral organocatalysts for asymmetric Michael additions of ketones and aldehydes to nitroolefins
Zhang, Richeng,Yin, Guohui,Li, Yang,Yan, Xilong,Chen, Ligong
, p. 3461 - 3464 (2015/02/18)
Based on the electrostatic adsorption between acidic resins and organocatalysts, a series of resin-supported chiral organocatalysts were designed and synthesized. They were evaluated for the asymmetric Michael addition of cyclohexanone with nitrostyrene, in which, catalyst 3 (Fig. 1) exhibited the best catalytic performance. This reaction proceeded under catalyst 3 smoothly at room temperature without any solvent or additive and could give product with high yield (95%) and good stereoselectivity (90% ee, 98:2 dr). Encouragingly, catalyst 3 was easily isolated and reused for 16 consecutive runs without obvious loss of reaction enantioselectivity. Furthermore, it was successfully applied to catalyze the reactions of a series of ketones and aldehydes with nitroolefins.
Chiral amine catalyzed enantio- and diastereoselective Michael reaction in brine
Singh, Sarbjit,Chimni, Swapandeep Singh
, p. 1068 - 1079 (2012/11/06)
Simple pyrrolidine-based chiral amines were synthesized and used for the Michael addition of different ketones to a variety of nitro-olefins in brine. The effect of different surfactants and acids on the yields and stereochemical outcome of the Michael ad
Highly regio- and enantioselective organocatalytic conjugate addition of alkyl methyl ketones TO A β-silylmethylene malonate
Chowdhury, Raghunath,Ghosh, Sunil K.
supporting information; experimental part, p. 3270 - 3273 (2009/12/01)
(S)-N-(2-Pyrrolidinylmethyl)pyrrolidine/trifluoroacetic acid (3:1) combination catalyzed the direct addition of alkyl methyl ketones to β-dimethyl(phenyl)silylmethylene malonate at the methyl terminal with high yield and excellent regio- and enantioselectivity. The silyl group played crucial roles in regioselection and substrate reactivity.
Amides of aminoalkyl-substituted azetidines, pyrrolidines, piperidines and azepanes
-
, (2008/06/13)
Novel amides of aminoalkyl-substituted azetidines, pyrrolidines, piperidines and azepanes, use of these compounds as pharmaceutical compositions, pharmaceutical compositions comprising the compounds, and a method of treatment employing these compounds and compositions. The compounds show a high and selective binding affinity to the histamine H3 receptor indicating histamine H3 receptor antagonistic, inverse agonistic or agonistic activity. As a result, the compounds are useful for the treatment of diseases and disorders related to the histamine H3 receptor.
Synthesis of chiral diamines using novel 2-trichloromethyloxazolidin-4-one precursors derived from 5-oxo-proline and proline
Amedjkouh, Mohamed,Ahlberg, Per
, p. 2229 - 2234 (2007/10/03)
Efficient syntheses of chiral vicinal diamines derived from (S)-oxo-proline and (S)-proline are described. The novel diastereomerically pure precursor (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo-[3.3.0]-octan-4,8-dione 3 and its enantiomer are readily available by reaction of the inexpensive enantiomers of 5-oxo-proline with chloral. Compound 3 reacts with primary and secondary amines to afford the 5-oxo-prolylamides 4 in quantitative yield. In contrast, the (S)-proline-derived precursor (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one 6 gave (S)-N-formylprolylamides 9 and/or (S)-prolylamides 8 depending on the reaction conditions. Upon reduction with LiAlH4, amides 4 and 9 afforded the proline-derived (S)-2-(alkylaminomethyl)pyrrolidines 1 and (S)-N-methyl-2-(alkylaminomethyl)-pyrrolidines 5 in 70-90% yields.
ASYMMETRIC ALDOL-TYPE REACTION BETWEEN BOTH A CHIRAL KETENE SILYL ACETALS OF ACETIC ACID ESTERS AND ALDEHYDES BY USE OF A CHIRAL PROMOTER
Mukaiyama, Teruaki,Kobayashi, Shu,Sano, Tetsuya
, p. 4653 - 4662 (2007/10/02)
Highly enantioselective aldol-type reaction between achiral ketene silyl acetals of acetic acid esters and achiral aldehydes is successfully carried out by the use of a chiral diamine coordinated tin (II) trifluoromethanesulfonate (tin (II) triflate) and tributyltin fluoride.The structure of this new promoter and the mechanism of the present asymmetric aldol-type reaction are discussed.
The direct synthesis of the cyclic sulphamidate of (S)-prolinol: Simultaneous N-protection and activation towards nucleophilic displacement of oxygen
Alker,Doyle,Harwood,McGregor
, p. 877 - 880 (2007/10/02)
The preparation of the cyclic sulphamidate of (S)-prolinol has been achieved by reaction with sulphuryl chloride at low temperature. This material has been shown to be susceptible to acid catalysed nucleophilic attack to furnish 2-(N,N-dialkylamino)methyl- and 2-(methoxymethyl)pyrrolidines after hydrolysis of the intermediate sulphamic acid derivatives.
PREPARATION OF PROLINE DERIVED LITHIUM AMIDE BASES AND THEIR USE IN ENANTIOSELECTIVE DEPROTONATION OF MESO EPOXIDES
Hendrie, Shirley K.,Leonard, John
, p. 3289 - 3294 (2007/10/02)
An alternative method of preparation for a range of proline derived chiral lithium amide bases is described. (S)-2-(Pyrrolidinomethyl) pyrrolidine, prepared by the new route, has been used to deprotonate cis and trans tbutyldimethylisiloxy-3,4-epoxycyclopentane enantioselectively, thus generating chiral cis and trans tbutyldimethylsiloxy-2-cyclopenten-4-ols.The products had higher enantiomeric purity than those produced when the base was prepared by a previously reported method.
