- Selective Aromatic Hydroxylation with Dioxygen and Simple Copper Imine Complexes
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The formation of a bis(μ-oxido)dicopper complex with the ligand 2-(diethylaminoethyl)-6-phenylpyridine (PPN) and its subsequent hydroxylation of the pendant phenyl group (studied earlier by Holland et al., Angew. Chem. Int. Ed. 1999, 38, 1139-1142) has been reinvestigated to gain a better understanding of such systems in view of the development of new synthetic applications. To this end, we prepared a simple copper imine complex system that also affords selective o-hydroxylation of aromatic aldehydes by using dioxygen as the oxidant: Applying the ligand N′-benzylidene-N,N-diethylethylenediamine (BDED), salicylaldehyde was prepared in good yields and we show that this reaction also occurs through an intermediate bis-μ-oxido copper complex. The underlying reaction mechanism for the PPN-supported complex was studied at the BLYP-D/TZVP level of density functional theory and the results for representative stationary points along reaction paths of the BDED-supported complex reveal a closely related mechanistic scenario. The results demonstrate a new facile synthetic way to introduce OH groups into aromatic aldehydes.
- Becker, Jonathan,Gupta, Puneet,Angersbach, Friedrich,Tuczek, Felix,N?ther, Christian,Holthausen, Max C.,Schindler, Siegfried
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p. 11735 - 11744
(2015/08/11)
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- Molecular structure and linkage isomerization in copper(II) complexes containing N,N-dialkyl-N'-benzylethylenediamine and thiocyanate ligands: A combined crystallographic, spectroscopic and DFT study
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A combined experimental and computational study of three thiocyanate-Cu(II) complexes with general formula [Cu(L n )2(NCS)]ClO 4, (L1 = N,N-dimethyl,N'-benzyl-ethylenediamine, L 2 = N,N-diethylyl,N'-b
- Golchoubian, Hamid,Koohzad, Sara
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p. 327 - 335
(2014/04/17)
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- QUINAZOLINE DERIVATIVES AS A MULTIPLEX INHIBITOR AND METHOD FOR THE PREPARATION THEREOF
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The present invention relates to a novel quinazoline derivative and a pharmaceutically acceptable salt thereof as a multiplex inhibitor, a method for the preparation thereof, and a pharmaceutical composition and a therapeutic composition comprising same as an active ingredient. The inventive quinazoline derivative as a multiplex inhibitor can selectively and effectively inhibit diseases caused by the overactivity of a tyrosine kinase.
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Page/Page column 81-82
(2008/06/13)
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- THERAPEUTIC AGENT FOR URINARY INCONTINENCE
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PROBLEM TO BE SOLVED: To provide a new higher safe compound having higher effectiveness against urinary incontinence with smaller adverse effects. SOLUTION: A prophylactic and/or therapeutic agent for the urinary incontinence comprises a compound represented by formula (I) {wherein, A is a single bond or methylene; E and G are each a lower straight-chain alkylene which may be substituted with a lower alkyl; m is 0-5; R1s are each a halogen, a CF3, an OCF3, a CN, an NO2, a carboxy, an OH, an SH, a lower alkoxycarbonyl, a (substituted) carbamoyl, a lower alkanoyloxy, a (substituted) sulfamoyl group or a lower alkyl group or the like which may be substituted with an ORa (wherein, Ra is an H or a lower alkyl), a COORa, an SRa or an N(Ra)2; R2, R3 and R4 are each an H or a lower alkyl; n is 0-5; R5s are each a CN, an NO2, a COOH, an SO3H, a lower alkoxycarbonyl, a lower alkanoyl or the like; R6 and R7 are each an H or a lower alkyl which may be substituted with an ORa or a COOH; or an NR6R7 is a 5- to a 6-membered saturated heterocyclic ring}, an optically active substance or a pharmacologically acceptable salt thereof as an active ingredient. The drug exhibits excellent effects on treatment and/or prophylaxis of the urinary incontinence without causing adverse effects on the cardiovacular system such as blood pressure elevation.
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Page/Page column 62
(2008/06/13)
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- Synthesis of novel succinamide derivatives having the 5,11-dihydro-6h- pyrido[2,3-b][1,4]benzodiazepin-6-one skeleton as potent and selective M2 muscarinic receptor antagonists. I
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A series of 5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one derivatives containing the succinamide skeleton has been synthesized and evaluated for M1, M2 and M3 muscarinic receptor binding affinities (in vitro) and M2 and M3 muscarinic receptor antagonistic activities (in vivo). Some of them showed higher and more selective binding affinities for M2 muscarinic receptors than that of AF-DX 116. Among them, 11-[3-[N-[2-(N- benzyl-N-methylamino)ethyl]-N-ethylearbamoyl]propionyl]-5,11-dihydro-6H- pyrido[2,3-b][1,4]benzodiazepin-6-one (68) was found to be the most potent and selective M2 muscarinic receptor antagonist in vitro. This compound also strongly inhibited the oxotremorine-induced bradycardia after intravenous administration and showed 130-fold selectivity for M2 muscarinic receptors over M3 muscarinic receptors in vivo.
- Watanabe, Toshihiro,Kinoyama, Isao,Kakefuda, Akio,Okazaki, Toshio,Takizawa, Kenji,Hirano, Seiko,Shibata, Hiroshi,Yanagisawa, Isao
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p. 996 - 1007
(2007/10/03)
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- An efficient one-pot synthesis of 3-(aryl and alkyl)methylene-1H-isoindolin-1-ones via aryne cyclization and horner reaction of o-(and m-) halogeno-N-phosphorylmethylbenzamide derivatives
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A series of 3-(alkyl and aryl)methylene-2,3-dihydro-1H-isoindol-1-one derivatives was synthesized by a one-pot reaction sequence involving lithiation of 2- (or 3-)halogeno-N-phosphoryl-methylbenzamides, cyclization of the aryne intermidiate, metal migration and Horner reaction of the resulting phosphorylated aminocarbanion with selected aromatic and aliphatic aldehydes.
- Couture, Axel,Deniau, Eric,Grandclaudon, Pierre
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p. 10313 - 10330
(2007/10/03)
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- Method of treating cardiac disorders with N-(aryloxyalkyl)-N'-(aminoalkyl)ureas
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N-(Aryloxyalkyl)-N'-(aminoalkyl)ureas and thioureas having the formula: STR1 wherein R1 and R2 are hydrogen, loweralkyl, cycloalkyl, phenyl or phenyllower alkyl, and R3 and R4 are hydrogen, loweralkyl, phenyl and phenylalkyl or R3 and R4 taken together with the adjacent nitrogen form a heterocyclic residue are disclosed in a method of suppressing cardiac arrhythmias.
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