56066-20-7Relevant academic research and scientific papers
SPIRO-BENZIMIDAZOLES AS INHIBITORS OF GASTRIC ACID SECRETION
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Page/Page column 31, (2008/06/13)
The invention provides compounds of the formula (1), in which the substituents and symbols are as defined in the description. The compounds inhibit the secretion of gastric acid.
Inhibition of gibberellin 3β-hydroxylase by novel acylcyclohexanedione derivatives
Brown, Robert G. S.,Yan, Li,Beale, Michael H.,Hedden, Peter
, p. 679 - 687 (2007/10/03)
The 2-acyl-5-carboxycyclohexane-1,3-diones are plant growth retardants which are believed to act by competing with the natural co-substrate, 2- oxoglutarate, at the active site of dioxygenases involved in the later stages of the biosynthesis of the gibberellin (GA) plant-hormones. A number of 2- acyl-5-carboxycyclohexanediones and related compounds were synthesized and compared with pyridine dicarboxylic acids and hydroxybenzoic acids as inhibitors of a GA 3β-hydroxylase from Cucurbita maxima endosperm. The most effective inhibitors of this enzyme possessed a 1,3-dioxo-2-acylcyclohexane- 5-carboxylic acid structure. The nature of the 2-acyl group had a relatively minor effect on the potency of enzyme inhibition in vitro. A related chloro- substituted compound was shown to be a potential affinity label for this GA hydroxylase.
Preparation of Some 9-Hydroxy-2-oxaspirodec-8-ene-1,7-dione Derivatives by Reductive Alkylation of 3,5-dimethoxybenzoic Acid with 1,2-Dihaloalkane and Oxiran Electrophiles
Wilkie, John S.,Winzenberg, Kevin N.
, p. 1207 - 1216 (2007/10/02)
Lithium in liquid ammonia mediated reductive alkylation of 3,5-dimethoxybenzoic acid (3) with 1,2-dibromoethane, or 1-bromo-2-chloroethane, followed by acid hydrolysis, afforded 9-hydroxy-2-oxaspirodec-8-ene-1,7-dione (1a).Reductive alkylation of (3) with unbranched 1,2-dibromoalkanes (5b-g), 1,2-dibromo-3-methylbutane and 1,2-dibromo-3,3-dimethylbutane gave 3-alkyl-9-hydroxy-2-oxaspirodec-8-ene-1,7-dione derivatives (1b-i) in moderate yields with the exception of (1i).The major product of the last reaction was 1-(2-bromo-3,3-dimethylbutyl)-3-hydroxy-5-oxocyclohex-3-ene-1-carboxylic acid (9).No reductive alkylation of (3) was observed with 2,3-dibromobutane or 1,2-dibromo-2-methylpropane.Reductive alkylation of (3) with the oxiran derivatives (8a-d) afforded the 2-oxaspirodec-8-ene-1,7-dione derivatives (1a-c,j).Reductive alkylation of (3) with 1,3-dibromopropane and 1-bromo-3-chloropropane gave, after hydrolysis, 1-(3-bromopropyl)-3-hydroxy-5-oxocyclohex-3-ene-1-carboxylic acid (12a) and 1-(3-chloropropyl)-3-hydroxy-5-oxocyclohex-3-ene-1-carboxylic acid (12b).The conversion of (1a) into 8--9-hydroxy-2-oxaspirodec-8-ene-1,7-dione (2a) is described.
TOTAL SYNTHESIS OF THE PANICULIDES.
Smith III,Richmond
, p. 575 - 585 (2007/10/02)
The first total synthesis is disclosed of paniculides A-C, three highly oxygenated sesquiterpenes isolated from hypocotyl and stem tissue cultures of Andrographis paniculata. The present approach serves to confirm for the first time the structural assignm
Reactions of Umpolung Reagents with Enol Ethers of β-Diketones: Sterically Induced Selectivity of the Dithiane Anion
Tobin, Paul S.,Basu, Swapan K.,Grosserode, Robert S.,Wheeler, Desmond M.S.
, p. 1250 - 1253 (2007/10/02)
In work on the synthesis of a tricyclic analogue of daunomycinone, the reactions of several umpolung equivalents of acetaldehyde with enol ether esters of 3,5-dioxocyclohexanecarboxylic acid have been examined.The dithiane reagent 1 and the sulfoxide 2 give 1,2 attack on the carbonyl group of the vinylogous ester system and also react at a similar rate with ester groups.The latter reaction can be retarded by using esters formed with isobutyl rather than methyl alcohol.In order to get selective attack on the carbonyl of the vinylogous esters in preference to thatof the ester, it is best to use reverse addition at low temperature.
