5324-21-0Relevant academic research and scientific papers
A regioselective and stereoselective methoxy bromination of olefins using diacetoxyiodobenzene and phenyltrimethyl ammoniumtribromide
Hangirgekar,Shirodkar
experimental part, p. 179 - 184 (2012/01/13)
A facile regio and stereoselective methoxy-bromination of alkenes using phenyltrimethyl ammoniumtribromide (PTAB) and (diacetoxyiodo) benzene (DIB) as oxidant has been carried out in the present investigation. The IR, NMR and LCMS of all the synthesized compounds have been used to characterize them.
Clobenpropit analogs as dual activity ligands for the histamine H3 and H4 receptors: Synthesis, pharmacological evaluation, and cross-target QSAR studies
Lim, Herman D.,Istyastono, Enade P.,van de Stolpe, Andrea,Romeo, Giuseppe,Gobbi, Silvia,Schepers, Marjo,Lahaye, Roger,Menge, Wiro M.B.P.,Zuiderveld, Obbe P.,Jongejan, Aldo,Smits, Rogier A.,Bakker, Remko A.,Haaksma, Eric E.J.,Leurs, Rob,de Esch, Iwan J.P.
experimental part, p. 3987 - 3994 (2009/10/02)
Previous studies have demonstrated that clobenpropit (N-(4-chlorobenzyl)-S-[3-(4(5)-imidazolyl)propyl]isothiourea) binds to both the human histamine H3 receptor (H3R) and H4 receptor (H4R). In this paper, we describe the synthesis and pharmacological characterization of a series of clobenpropit analogs, which vary in the functional group adjacent to the isothiourea moiety in order to study structural requirements for H3R and H4R ligands. The compounds show moderate to high affinity for both the human H3R and H4R. Furthermore, the changes in the functional group attached to the isothiourea moiety modulate the intrinsic activity of the ligands at the H4R, ranging from neutral antagonism to full agonism. QSAR models have been generated in order to explain the H3R and H4R affinities.
A new catalytic route for the oxidative halogenation of cyclic enol ethers using tungstate exchanged on takovite
Sels,Levecque,Brosius,De Vos,Jacobs,Gammon,Kinfe
, p. 93 - 104 (2007/10/03)
An efficient and benign method for the regio- and stereoselective synthesis of halohydrins and β-halo ethers from dihydropyrans, dihydrofurans and anhydro sugars in the presence of a halide salt and hydrogen peroxide is presented with tungstate-exchanged takovite as oxidation catalyst.
Synthesis of 3-[1H-imidazol-4-yl] propyl 4-[18F] fluorobenzyl ether ([18F] fluoroproxyfan): A potential radioligand for imaging histamine H3 receptors
Iwata, Ren,Horvath, Geza,Pascali, Claudio,Bogni,Yanai, Kazuhiko,Kovacs, Zoltan,Ido, Tatsuo
, p. 873 - 882 (2007/10/03)
3-[1H-Imidazol-4-yl]propyl 4-fluorobenzyl ether (fluoroproxyfan), a potential histamine H3 receptor ligand, was labeled with 18F for clinical PET studies. The synthesis involved the O-alkylation of 3-(1 -triphenylmethyl-1H-imidazol-4
β-Halogeno Ether Synthesis of Olefinic Alcohols: Stereochemistry and Conformation of 2-Substituted 3-Halogenotetrahydro-pyran and furan Precursors
Crombie, Leslie,Wyvill, Robert D.
, p. 1971 - 1982 (2007/10/02)
Ring-scission of cis- or trans-2-alkyl- (or aryl-) 3-chlorotetrahydropyrans proceeds regioselectively and highly stereoselectively to give (E)-alk-4-en-1-ols, but in the parallel tetrahydrofuran series (Z)-/(E)-mixtures, dependent on percursor geometry, are formed.In this paper the stereochemistry and conformation of the tetrahydro-pyran and - furan precursors are considered.The cis/trans-composition of 2,3-dihalogenotetrahydro-pyrans and-furans made by various routes is reported.Reaction with Grignard reagents gives separable cis-/trans-mixtures the stereoisomeric composition of which, in the cases examined, does not depend on the stereoisomeric composition of the dihalide, but does vary with the halogen and the composition of the Grignard or dialkylmagnesium; possible reasons are discussed.The stereochemistry and conformation of the 2-alkyl- (or aryl-)3-chlorotetrahydropyrans is analysed by n.m.r. methods (J2a,3acis ca. 1.5 Hz; J2a,3atrans ca. 9.8 Hz) but assignments for the two tetrahydrofuran series with J2,3 2.6-3.6 and 4.3-5.9 are made uncertain by pseudorotation.The stereochemical identity of the two series is rigorously proved by isolation of cis- and trans-2-allyl-3-chlorotetrahydrofuran.On the one hand the former is hydrogenated to the cis-2-propyl compound, correlated with other members of the alkyl series, but on the other it is oxidised and the acid is converted into the cis-p-bromophenyl ester.The stereochemistry and conformation of the latter is rigorously demonstrated by an X-ray structure.The stereochemistries and conformations of the 2-deuterio- and 2-methoxy-3-chlorotetrahydropyrans are discussed, and consideration is then extended to the 2-alkyl-3-chloro-2-methyltetrahydro-pyran and -furan series.
