61227-48-3Relevant academic research and scientific papers
Programmed Sequential Additions to Halogenated Mucononitriles
Zahara, Adam J.,Hinds, Elsa M.,Nguyen, Andrew L.,Wilkerson-Hill, Sidney M.
, p. 8065 - 8069 (2020/11/02)
Dihalomucononitriles were synthesized and their reactivity evaluated to assess their ability to function as linchpin reagents. Bis(2-chloroacrylonitrile) and bis(2-bromoacrylonitrile) were synthesized from 2,1,3-benzothiadiazole and undergo conjugate addition/elimination reactions with both nitrogen (40-95% yield) and carbon nucleophiles (72-93% yield). Secondary amines undergo monosubstitutions, while carbon nucleophiles are added twice. The sequence of addition of the nucleophiles could be controlled to give mixed addition products. The multicomponent coupling products could then be converted to natural product like motifs using intramolecular cyclization reactions.
Aryltrifluoromethylative cyclization of unactivated alkenes by the use of PhICF3Cl under catalyst-free conditions
Guo, Jia,Xu, Cong,Liu, Xiaowei,Wang, Mang
supporting information, p. 2162 - 2168 (2019/02/27)
A concise and catalyst-free aryltrifluoromethylative cyclization of unactivated alkenes has been developed herein. The use of PhICF3Cl as a powerful trifluoromethylating agent allows easy transformations. A set of trifluoroethylated carbocycles and aza-hereocycles were efficiently synthesized in good yield and selectivity. A broad substrate scope, mild reaction conditions, and easy operation would make this method well-suited for applications.
Modified pyrimidine glucocorticoid receptor modulators
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Page/Page column 16, (2008/06/13)
The present invention provides a novel class of modified pyrimidine compounds and compositions and methods of using the compounds as glucocorticoid receptor modulators.
SYNTHESIS OF 13C-LABELLED ESTROGEN ANALOGUES
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Page 20, (2010/02/08)
There is provided a method of producing novel 13C-labelled estrogen analogues. The method preferably proceeds via an intermediate A or B or which is a mixture of (A) or (B): wherein a13C atom is located at one or more of positions 1, 2, 3 or 4 and wherein R is an optionally substituted alkane, alkene, alkyne or aryl group. Preferably R is -CH2Ph. An alternative preferred intermediate compound is 13C-resorcinol.
Structure-activity relationships of dimethindene derivatives as new M2-selective muscarinic receptor antagonists
B?hme, Thomas M.,Keim, Christine,Kreutzmann, Kai,Linder, Matthias,Dingermann, Theo,Dannhardt, Gerd,Mutschler, Ernst,Lambrecht, Günter
, p. 856 - 867 (2007/10/03)
A series of 2,3-disubstituted indenes, which are analogues of the widely used histamine H1 receptor antagonist dimethindene, have been synthesized and studied as muscarinic and histamine receptor antagonists. The affinities of these compounds for the five human muscarinic receptor subtypes (M1-M5) and for human histamine H1 receptors were determined in radioligand binding studies using membranes from transfected Chinese hamster ovary (CHO) cells and [3H]N-methylscopolamine ([3H]NMS). The results demonstrate that the diisopropyl analogue 19 has a similar high affinity as (S)-dimethindene at M2 receptors ((S)-dimethindene: pKi = 7.52; (-)-19: pKi = 7.37) with an improved selectivity pattern ((S)-dimethindene: M2/M1 = 6-fold, M2/M3 = 5-fold, M2/M4 = 10-fold, M2/M5 = 25-fold; (-)-19: M2/M1 = 36-fold, M2/M3 = 96-fold, M2/M4 = 42-fold, M2/M5 = 275-fold). In addition, compound (-)-19 showed 35-fold lower affinity at histamine H1 receptors (pKi = 5.61) than (S)-dimethindene (pKi = 7.16). Another interesting compound is the fluoroethyl derivative 20 (pKi/M2 = 7.49), which also exhibits a higher M2 selectivity (M2/M1 = 19-fold; M2/M3 = 22-fold; M2/M4 13-fold; M2/M5 = 62-fold) than (S)-dimethindene. Unfortunately, compound 20 also shows a high affinity for histamine H1 receptors (pKi = 8.14). The compound with the highest affinity for M2 receptors (pKi = 7.91), the dimethylaminomethylene analogue 31, displayed only a small preference for M2 receptors. In conclusion, compound (-)-19 might be useful to test the hypothesis that blockade of muscarinic M2 receptors in the brain is a viable mechanism by which to produce improved cognition. This second-generation dimethindene analogue might also be the starting point for the development of M2-selective muscarinic antagonists useful for quantifying M2 receptors in the central nervous system with positron emission tomography imaging.
Ru(II)- and Pt(II)-catalyzed cycloisomerization of ω-Aryl-1-alkynes. Generation of carbocationic species from alkynes and transition metal halides and its interception by an aromatic ring
Chatani, Naoto,Inoue, Hiroki,Ikeda, Tsutomu,Murai, Shinji
, p. 4913 - 4918 (2007/10/03)
The treatment of aryl-1-alkynes, such as 4-aryl-1-butyne, 5-aryl-1-pentyne, and 6-aryl-1-hexyne, with catalytic amounts of transition metal chlorides, such as PtCl2 and [RuCl2(CO)3]2, at 80 °C in toluene results in cycloisomerization to give dihydronaphthalenes or dihydrobenzocycloheptenes, in which the cyclization mode is dependent on the length of the tethers. The reaction is limited to substrates containing terminal alkynes. A key step of the reaction is the intramolecular interception by an aromatic ring of the vinylmetal complex 2, which contains a cation center at the β-position, generated from the electrophilic addition of transition metal halides toward an alkyne. The more electron-rich aryl systems are more reactive.
Metabolism of dimetindene in rats
Radler,Wermeille,Blaschke
, p. 1086 - 1092 (2007/10/02)
The preparative separation of dimetindene (CAS 5636-83-9) enantiomers was achieved by fractionated crystallization of the diastereomeric tartrate salts. HPLC on α-AGP (α1-acid glycoprotein) was used for confirmation of the enantiomeric purity.
Solid-liquid phase transfer catalytic synthesis. XII: Microwave irradiated alkylation of diethyl malonate
Wang,Deng,Mi,Jiang
, p. 1761 - 1764 (2007/10/02)
The anion derived from diethyl malonate reacts with a series of halides readily under microwave irradiation, and the isolated yield of alkylated products varying from 64% to 86%.
Synthesis of Substituted 14-Crown-4 Compounds
Czech, Bronislaw P.,Zazulak, Wolodymyr,Kumar, Anand,Olsher, Uriel,Feinberg, Hadar,et al.
, p. 1389 - 1400 (2007/10/02)
Seventeen new substituted 14-crown-4 derivatives 3-10, 35-40, 42, 45 and 46 are described.A series of nine compounds 2-10 with two, three or four substituents in the 6- and/or 13-positions was synthesized in good yields from the appropriate diols and ditosylates using improved cyclization conditions.The solid state structures of 6,6,13,13-tetra(benzyloxymethyl)-14-crown-4 (8) and lithium thiocyanate complexes of trans- and cis-6,13-bis(spiro-2,2-dichlorocyclopropyl)-14-crown-4 (45) and (46), respectively, have been determined.
Synthesis of Substituted Tetrahydronaphthalenes by Mn(III), Ce(IV), and Fe(III) Oxidation of Substituted Diethyl α-Benzylmalonates in the Presence of Olefins
Citterio, Attilio,Sebastiano, Roberto,Marion, Antonio,Santi, Roberto
, p. 5328 - 5335 (2007/10/02)
The oxidation of substituted diethyl α-benzylmalonates (1a-m) by manganese(III) acetate in acetic acid, cerium(IV) ammonium nitrate in methanol, or iron(III) perchlorate in acetonitrile in the presence of substituted olefins 2a-u was investigated.The results are consistent with a common mechanism.It involves selective generation of malonyl radicals from high-valent metal malonyl complexes, their addition to the olefin, and competition of the adduct radical between intramolecular cyclization to produce highly functionalized tetrahydronaphthalenes (3) and oxidation bymetal salt to give mainly γ-lactones (5).Several electron-withdrawing and releasing substituents on the aromatic ring and on the olefin can be successfully used in the synthesis of 3 without olefin telomerization.The influence of metal and olefin or aromatic substituents on the homolytic addition and intramolecular aromatic substitution is discussed.
