289889-03-8Relevant articles and documents
METHOD FOR PRODUCING L-CARNOSINE DERIVATIVE AND ITS SALT
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, (2018/09/08)
PROBLEM TO BE SOLVED: To provide a method for producing an L-carnosine derivative or its salt by a safe and simple method. SOLUTION: There is provided a method for producing an L-carnosine derivative or its salt from N-substituted benzyl-carboxylic anhydride by performing a desubstitution benzyl reaction and as necessary, a de-esterification reaction, which comprises a step of reacting N-substituted benzyl-carboxylic anhydride and a histidine compound or its salt in the presence of a base, followed performing at least a decarboxylation reaction by converting the inside of the reaction system into an acidic atmosphere to produce an N-substituted benzyl-L-carnosine derivative represented by the formula (3). SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT
Synthesis of 1,5,6,7-tetrahydro-4H-pyrazolo[4,3-c]pyridin-4-ones as conformationally constrained pyrazole analogues of histamine
Zerovnik, Darja,Groselj, Uros,Kralj, David,Malavasic, Crt,Bezensek, Jure,Dahmann, Georg,Stare, Katarina,Meden, Anton,Stanovnik, Branko,Svete, Jurij
experimental part, p. 3363 - 3373 (2010/11/19)
Three synthetic methods for the preparation of 1,5-disubstituted 1,5,6,7-tetrahydro-4H-pyrazolo[4,3-c]pyridin-4-ones as heterocyclic histamine analogues were developed. The first method starts from easily available methyl 5-(2-aminoethyl)-1H-pyrazole-4-carboxylates, which were N-alkylated and the resulting secondary amines were cyclised in the presence of a base to give the title compounds in 17-92% yields (method A). Alternatively, the amines were first cyclised to the 5-unsubstituted pyrazolo[4,3-c]pyridin-4-ones. Subsequent N-benzylation afforded three of the title compounds in 36-49% yields (method B). The third method comprises a six-step transformation of methyl acrylate into 1-benzylpiperidine-2,4-dione. Treatment of the latter with N,N-dimethylformamide dimethylacetal (DMFDMA) followed by acid-catalysed cyclisation of the formed enaminone with methyl-, phenyl- and tert-butylhydrazine afforded the same three title compounds in 79-87% yields (method C). Georg Thieme Verlag Stuttgart New York.
New anti-HIV derivatives: Synthesis and antiviral evaluation
De Michelis,Rocheblave,Priem,Chermann,Kraus
, p. 1253 - 1262 (2007/10/03)
A small focused library of 18 compounds incorporating the motif 1,3-(N,N'-dibenzyl)diamino-2-propanol has been synthesized, using adapted synthetic methodologies. These series of compounds were evaluated for their in vitro anti-HIV activity on infected MT4 cells (syncytium formation observation). Some of the new synthesized compounds show potent anti-HIV activities. EC50 values for compounds (31, 40, 34, 37 and 46Scheme 3(i) Na2SO4, CH2Cl2, rt; (ii) NaBH4, EtOH, 0°C; (iii) Boc2O, CH2Cl2, 0°C; (iv) DMSO, TFAA, Et3N, CH2Cl2, -60°C; (v) TFA, CH2Cl2, rt; (vi) BOP, RCOOH, Et3N, CH2Cl2, rt.) range from 0.1 to 1μM. In order to determine at which level these new derivatives interfere with the HIV replicative cycle, inhibition assays on recombinant HIV protease and HIV integrase have been performed. None of the compounds were found active on these two enzymatic targets. Experiments are in progress in order to identify their biological target within the HIV replicative cycle. Copyright (C) 2000 Elsevier Science Ltd.
