280745-41-7Relevant academic research and scientific papers
Concise and practical route to tri- and tetra-hydroxy seven-membered iminocyclitols as glycosidase inhibitors from d-(+)-glucurono-γ-lactone
Kalamkar, Navnath B.,Kasture, Vijay M.,Chavan, Sanjay T.,Sabharwal, Sushma G.,Dhavale, Dilip D.
experimental part, p. 8522 - 8526 (2010/11/18)
An efficient and short total synthesis of tetrahydroxy-1c and trihydroxy-azepane 1d is reported in 72% and 57% overall yields, respectively, from d-(+)-glucurono-γ-lactone. Thus, d-glucuronolactone 2 on acetonide protection, DIBAL-H reduction and one-pot intermolecular reductive amination followed by -NCbz protection afforded 6-(N-benzyl-N-benzyloxycarbonyl) amino-6-deoxy-1,2-O-isopropylidene-α-d-gluco-1,4-furanose 5a. 1,2-Acetonide hydrolysis in 5a and Pd-mediated intramolecular reductive aminocyclization afforded tetrahydroxyazepane 1c. An analogous pathway with 5-deoxy-1,2-O-isopropylidene-α-d-glucurono-6,3-lactone 3b gave trihydroxy-azepane 1d. Glycosidase inhibitory activity of 1c/1d was studied and 1d was found to be potent inhibitor of α-mannosidase and β-galactosidase.
Short and efficient synthesis of (2S,3R,4R,5R) and (2S,3R,4R,5S)-tetrahydroxyazepanes via the Henry reaction
Chakraborty, Chaitali,Dhavale, Dilip D.
, p. 912 - 917 (2007/10/03)
The Henry reaction with the easily available α-d-xylo-pentodialdose afforded a diastereomeric mixture of nitroaldoses with the α-d-gluco- and β-l-ido-configuration, respectively, in good yield. When n-BuLi was used as the base, the reaction afforded the α
Syntheses of tetrahydroxyazepanes from chiro-inositols and their evaluation as glycosidase inhibitors
Painter, Gavin F.,Eldridge, Paul J.,Falshaw, Andrew
, p. 225 - 232 (2007/10/03)
Two pairs of C2-symmetric tetrahydroxyazepanes [(-), (+)-1 and (-), (+)-2] have been synthesized from the enantiomeric chiro-inositols and evaluated as glycosidase inhibitors. Alternative syntheses of ido-tetrahydroxyazepanes (-)- and (+)-2 fro
Concise and practical synthesis of (2S,3R,4R,5R) and (2S,3R,4R,5S)-1,6-dideoxy-1,6-iminosugars
Tilekar, Jayant N.,Patil, Nitin T.,Jadhav, Harishchandra S.,Dhavale, Dilip D.
, p. 1873 - 1876 (2007/10/03)
The syntheses of (2S,3R,4R,5R) and (2S,3R,4R,5S)-1,6-dideoxy-1,6 iminosugars 1a and 1b, respectively, from D-glucose are described. The key transformations in this reaction sequence include regio-selective epoxide ring opening with N-benzylamine followed
An easy route to seven-membered iminocyclitols from aldohexopyranosyl enamines
Fuentes, Jose,Gasch, Consolacion,Olano, David,Pradera,Repetto, Guillermo,Sayago, Francisco J.
, p. 1743 - 1753 (2007/10/03)
A new stereocontrolled and high yielding synthesis of biologically active polyhydroxyperhydroazepines is reported starting from easily available glycosylenamines (D-gluco, D-manno, and D-galacto configurations), which are transformed into 1,6-azaanhydropy
Hydroxyazepanes as inhibitors of glycosidase and HIV protease
-
, (2011/05/18)
Hydroxyazepanes display inhibitory activity with respect to glycosidase, with Kivalues from-moderate to low micromolar range. Benzyl and 3,6-dibenzyl derivatives of hydroxyazepanes display inhibitory activity with respect to HIV protease. These compounds are synthesized either by chemoenzymatic or chemical methodologies.
Chemo-enzymatic synthesis of polyhydroxyazepanes
Andreana, Peter R.,Sanders, Tom,Janczuk, Adam,Warrick, Joshua I.,Wang, Peng George
, p. 6525 - 6528 (2007/10/03)
Galactose oxidase (EC 1.1.3.9, GAO) is an extracellular copper-containing enzyme that utilizes molecular oxygen to convert the C6-primary hydroxyl moiety of D-galactopyranosides to hydrated aldehydes. Subsequent dehydratative coupling with hydroxylamines produces oximes (3a-f), which, when subjected to conditions of hydrogenolysis, give rise to polyhydroxyazepanes (11-17).
Short practical synthesis of (3R,4R,5R,6A)-tetrahydroxyazepane and (3S,4S,5S,6S)-trahydroxyazepane from D- And L-chiroinositol, respectively
Painter, Gavin F.,Falshaw, Andrew
, p. 1157 - 1159 (2007/10/03)
The polyhydroxylated azepanes (3R,4R,5R,6R)-tetrahydroxyazepane (-)-l and (35,45,5S,65)-tetrahydroxyazepane (+)-1 are synthesised from D-and L-c/j/ro-inositol, respectively. Key transformations in the reaction sequence include a glycol-fission reaction wi
Seven-membered ring azasugars as glycosidase inhibitors and anticancer agents
Lohray,Bhushan, Vidya,Prasuna,Jayamma,Raheem,Papireddy,Umadevi,Premkumar,Lakshmi,Narayanareddy
, p. 1311 - 1321 (2007/10/03)
Synthesis of various C2 symmetrical tetrahydroxyazepanes has been reported by the reaction of bisepoxides with various primary, amines. The tetrahydroxyazepanes inhibit β-glucosidases in micromolar range and also exhibit anticancer activity in
Synthesis of new N-containing maltooligosaccharides, α-amylase inhibitors, and their biological activities
Uchida, Riichiro,Nasu, Ayako,Tokutake, Shoichi,Kasai, Kouichi,Tobe, Koichiro,Yamaji, Nobuyuki
, p. 187 - 193 (2007/10/03)
Fifteen new N-containing maltooligosaccharides were obtained using the chemoenzymatic method. Among these compounds, maltooligosaccharides having 6- amino-6-deoxy-D-sorbitol residue, (3R,4R,5R,6S)-hexahydro-3,4,5,6- tetrahydroxy-1H-azepine residue, and (3R,5R)-3,4,5-trihydroxypiperidine residue at the reducing end showed strong inhibitory activities for human pancreatic α-amylase (HPA) (EC 3.2.1.1) and human salivary amylase (HSA). The administration of (3R,4R,5R,6S)-hexahydro-3,5,6-trihydroxy-1H-azepine-4- yl O-α-D-glucopyranosyl-(1→4)-α-D-glucopyranoside (13, IC50=4.3x10-5M for HPA, IC50=8.2x10-5M for HSA) and (3R,5R)-3,5-dihydroxypiperidine-4- yl O-α-D-glucopyranosyl-(1→4)-α-D-glucopyranoside (18, IC50=3.4x10-5M for HPA, IC50=4.6 x 10-5 M for HSA) to ICR mice suppressed postprandial hyperglycemia.
