- A convenient method for the synthesis of aminomethylmonoalkylphosphinate
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Starting from the readily available 4-methylbenzoic acid, an efficient protocol for the preparation of ethyl 4-(aminomethyl) benzyl (methyl) phosphinate (1), a novel aminomethylmonoalkylphosphinate was reported in this communication. The important step involves the selective monochlorination of phosphonic ester by POCl3 and forming the phosphonochloridate, and followed by nucleophilic addition of CH3MgBr to the acid chloride intermediate.
- Ding, Derong,Yan, Guang
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p. 1906 - 1908
(2012/10/29)
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- Synthesis of α-arylphosphonates using copper-catalyzed α-arylation and deacylative α-arylation of β-ketophosphonates
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Efficient methods for the direct arylation and deacylative arylation of β-ketophosphonates with iodoarenes in presence of a copper(I) or a copper(II) salt as the catalysts have been developed. The corresponding α-arylphosphonates were obtained in high yields. A tentative mechanism for the deacylative arylation reaction was proposed on the basis of the experimental data. Copyright
- Rout, Laxmidhar,Regati, Sridhar,Zhao, Cong-Gui
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experimental part
p. 3340 - 3346
(2012/01/17)
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- Direct conversion of benzylic and allylic alcohols to phosphonates
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Benzyl phosphonate esters often serve as reagents in Horner-Wadsworth- Emmons reactions. In most cases, they can be prepared from benzylic alcohols via formation of the corresponding halide followed by an Arbuzov reaction. To identify a more direct synthesis of phosphonate esters, we have developed a one-flask procedure for conversion of benzylic and allylic alcohols to the corresponding phosphonates through treatment with triethyl phosphite and ZnI2.
- Barney, Rocky J.,Richardson, Rebekah M.,Wiemer, David F.
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supporting information; experimental part
p. 2875 - 2879
(2011/05/19)
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- Rh-catalyzed Negishi alkyl-aryl cross-coupling leading to α- or β-phosphoryl-substituted alkylarenes
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The catalytic cross-coupling between ArZnX and ICH2(CH 2)nP(O)(OEt)2 (n = 0-3) has been investigated to determine the utility of the Rh catalyst during the alkyl-aryl cross-coupling and to develop a new syntheti
- Takahashi, Hideki,Inagaki, Shinya,Yoshii, Naoko,Gao, Fuxing,Nishihara, Yasushi,Takagi, Kentaro
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supporting information; experimental part
p. 2794 - 2797
(2009/09/08)
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- Synthesis and evaluation of stilbenylbenzoxazole and stilbenylbenzothiazole derivatives for detecting β-amyloid fibrils
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This paper describes a novel series of stilbenylbenzoxazole (SBO) and stilbenylbenzothiazole (SBT) derivatives for β-amyloid specific binding probes. These 24 compounds were synthesized and evaluated by competitive binding assay against β-amyloid 1-42 (Aβ42) aggregates using [125I]TZDM. All the derivatives displayed higher binding affinities with Ki value in the subnanomolar range (0.10-0.74 nM) than Pittsburgh Compound-B (PIB) (0.77 nM). Among these derivatives, SBT-2, 5-fluoroethoxy-2-{4-[2-(4-methylaminophenyl)vinyl]phenyl}benzothiazole, showed lowest Ki value (0.10 nM). In conclusion, the preliminary results suggest that these compounds are implying a possibility as a probe for detection of Aβ fibrils in Alzheimer's disease (AD) patients.
- Lee, Ji Hoon,Byeon, Seong Rim,Lim, Soo Jeong,Oh, Seung Jun,Moon, Dae Hyuk,Yoo, Kyung Ho,Chung, Bong Young,Kim, Dong Jin
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p. 1534 - 1537
(2008/12/20)
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- Heterocycles substituted pyridine derivatives and antifungal agent containing thereof
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An object of the present invention is to provide an antifungal agent which has excellent antifungal effects and is superior in terms of its physical properties, safety and metabolic stability. According to the present invention, there is disclosed a compound represented by the following formula (I), or a salt thereof: wherein R1 represents a hydrogen atom, a halogen atom, an amino group, a C1-6 alkyl group, a C1-6 alkoxy group or a C1-6 alkoxy C1-6 alkyl group; R2 represents a hydrogen atom, a C1-6 alkyl group, an amino group or a di C1-6 alkylamino group; one of X and Y is a nitrogen atom while the other is a nitrogen atom or an oxygen atom; ring A represents a 5- or 6-member heteroaryl ring or a benzene ring which may have a halogen atom, or 1 or 2 C1-6 alkyl groups; Z represents a single bond, a methylene group, an ethylene group, an oxygen atom, a sulfur atom, —CH2O—, —OCH2—, —NH—, —CH2NH—, —NHCH2—, —CH2S—, or —SCH2—; R3 represents a hydrogen atom, a halogen atom, a C1-6 alkyl group, a C3-8 cycloalkyl group, a C6-10 aryl group, a 5- or 6-member heteroaryl group, or 5- or 6-member non-aromatic heterocyclic group which may have 1 or 2 substituents; and R4 represents a hydrogen atom or a halogen atom.
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Page/Page column 138
(2010/11/27)
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- Carboxylic acids and the esters thereof, pharmaceutical compositions thereto and processes for the preparation thereof
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The present invention relates to carboxylic acids and esters of general formula wherein Ar, R, R1, X1, X3, X4, Y and Y1 are defined as in claim 1, the tautomers, the diastereomers, the enantiomers, the mixtures thereof and the salts thereof, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases, pharmaceutical compositions containing these compounds, the use thereof and processes for the preparation thereof, as well as the use thereof for the production and purification of antibodies and as labelled compounds in RIA and ELISA assays and as diagnostic or analytical aids in neurotransmitter research.
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- Luminescent supramolecular assemblies based on hydrogen-bonded complexes of stilbenecarboxylic acids and dithieno[3,2-b:2′,3′-d]thiophene-2-carboxylic acids with a tris(imidazoline) base
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The synthesis of a number of stilbenecarboxylic acids, tetrazolylstilbenes and dithieno[3,2-b:2′,3′-d]thiophene-2-carboxylic acids is reported. These organic acids form non-covalent complexes with an imidazoline base, 1,3,5-tris(4,5-dihydroimidazol-2-yl)benzene 13. Two X-ray crystal structures confirm hydrogen bonds between carboxylate ligands and meta-positioned protonated imidazoline groups. The complexes possess a surprisingly flat disk-like shape with various close contacts between adjacent molecules. Most stilbene and dithieno[3,2-b:2′,3′-d]thiophene derivatives show strong blue or blue-green photoluminescence in solution, whereas fluorescence in the solid state is almost completely quenched.
- Osterod,Peters,Kraft,Sano,Morrison,Feeder,Holmes
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p. 1625 - 1633
(2007/10/03)
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- Oxiranyls disubstituted with a phenyl group and a substituted chromanyl or tetrahydroquinolinyl group having retinoid like activity
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Compounds of the formula STR1 wherein all the symbols in the formula are as defined in the specification, have retinoid-like activity.
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- Reactivity of the acids of trivalent phosphorus and their derivatives. Part VI. The reaction of the >P-O- anions with benzyl bromides para-substituted in the phenyl ring
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The reaction of p-substituted benzyl bromides with the >P-O- ions in THF, alcohols and toluene as the solvents is described. According to the reduction potential of the p-substituted benzyl bromides and the solvent used the formation of the P-C bond, debromination and/or dimerization occur. The principal process is believed to be X-philic substitution, the dimers are formed through a secondary process via SET from the p-substituted benzyl anions into the p-substituted benzyl bromides.
- Witt, Dariusz,Rachon, Janusz
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p. 169 - 187
(2007/10/03)
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- Process for the preparation of esters of stilbenedicarboxylic acid
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Disclosed is a process for the preparation of 4,4'-stilbenedicarboxylate esters by a 3-step process utilizing p-toluic acid, an alkyl p-formylbenzoate and a trialkyl phosphite. The steps comprise (1) preparing p-(chloromethyl)benzoic acid by chlorinating p-toluic acid with sulfuryl chloride in the presence of a free radical initiator and chlorobenzene or dichlorobenzene; (2) contacting the p-(chloromethyl)benzoic acid of step (1) with a trialkyl phosphite to obtain a phosphonate compound; and (3) contacting the phosphonate ester compound of step (2) with an alkyl p-formylbenzoate in the presence of an alkali metal alkoxide and an inert solvent to obtain the dialkyl 4,4'-stilbenedicarboxylate.
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- Treatment of mammals afflicted with tumors with compounds having RXR retinoid receptor agonist activity
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Retinoid-like compounds which act as agonists of the RXR retinoid receptor sites induce apoptosis of tumor cells in cell cultures, and are used as drugs to treat tumors in mammals including humans. Compounds which are specific agonists of RXR receptors and also compounds which are agonists of both RAR and RXR agonist (pan-agonists) induce apoptosis, although the RXR agonist compounds are preferred as drugs to avoid undesirable side effects associated with RAR agonist activity. The RXR agonists compounds are administered to mammals afflicted with tumors in pharmaceutical compositions adapted for systemic topical or for intralesional administration. The range of concentration of the active ingredient RXR agonist compound in the pharmaceutical compositions is approximately between 0.001 and 5 percent by weight, and such that the composition delivers approximately 0.1 mg to 100 mg of the active ingredient per kg body weight of the patient, per day of treatment.
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- Substituted phenylethenyl compounds having retinoid-like biological activity
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Compounds of the formula STR1 wherein R 1, R 2, R 3 and R 4 independently are hydrogen, lower alkyl of 1 to 6 carbons, halogen or lower alkoxy of 1 to 6 carbons; R 5 and R 5 '' independently are hydrogen or lower alkyl of 1 to 6 carbons; Y is oxygen or su
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- Phenylethenyl compounds having retinoid-like activity
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Compounds of the following formula, useful for treating diseases affected by retinoids, are disclosed herein. STR1
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- Negative inotropic activity of para-substituted diethyl benzylphosphonates related to fostedil
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Several para-substituted diethyl benzylphosphonates related to the calcium antagonist diethyl 4-(2-benzothiazolyl)benzylphosphonate (fostedil) have been studied.They produce a dose-dependent negative inotropic effect on left atrial muscle isolated from guinea pig heart.Some of the compounds are equipotent or slightly more potent than fostedil and diltiazem taken as reference drugs.Structure-activity relationships are discussed.Keywords: calcium antagonists / p-substituted diethyl benzylphosphonates / cardiodepressant activity
- Bellucci, Christina,Gualtieri, Fulvio,Chiarini, Alberto
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p. 473 - 478
(2007/10/02)
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