191796-95-9Relevant academic research and scientific papers
A convenient synthesis of 1-(ω-aminoalkyl)-5-nitro-1H-pyrimidine-2,4- diones
Wegrzynek,Walczak
experimental part, p. 57 - 64 (2009/07/25)
Several monoacylated alkylene diamines have been obtained in the reaction of appropriate amine with methyl phenylacetate or ethyl formate. The mono protected diamines were used as alkylating agents in reactions with 1-(2,4-dinitrophenyl)-5-nitrouracil. The series of hitherto unknown 1-(ω-aminoalkyl)-5-nitrouracil derivatives have been obtained as a result of the uracil ring transformation. The best yield of 1-(ω-aminoalkyl)-5- nitrouracils was obtained when N-Boc protected alkylene diamines were applied in this reaction. The N-Boc protecting group was cleaved using diluted trifluoroacetic acid, and the liberated amines were subjected to reaction with phthalic anhydride and naphthalene 1,8-dicarboxylic anhydride.
Selective Monoacylation of Symmetrical Diamines via Prior Complexation with Boron
Zhang, Zhongxing,Yin, Zhiwei,Meanwell, Nicholas A.,Kadow, John F.,Wang, Tao
, p. 3399 - 3402 (2007/10/03)
(Equation presented) Pretreatment of a symmetrical primary or secondary diamine with 9-BBN prior to the addition of an acyl chloride significantly suppressed undesired diacylation, and the product of monoacylation predominated. The reactive preference is interpreted as the result of a selective deactivation of one nitrogen atom of the diamine by 9-BBN.
Design, synthesis, and biological evaluation of novel non-piperazine analogues of 1-[2-(diphenylmethoxy)ethyl]- and 1-[2-[bis(4- fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazines as dopamine transporter inhibitors
Choi, Sung-Woon,Elmaleh, David R.,Hanson, Robert N.,Fischman, Alan J.
, p. 3647 - 3656 (2007/10/03)
A series of novel diamine, amine-amide, and piperazinone analogues of N- [2-(bisarylmethoxy)-ethyl]-N'-(phenylpropyl)piperazines, GBR 12909 and 12935, were synthesized and evaluated as inhibitors of presynaptic monoamine neurotransmitter transporters. The primary objective of the study was to determine the structural requirements for selectivity of ligand binding and potency for neurotransmitter reuptake inhibition. In general, the target compounds retained transporter affinity; however, structural variations produced significant effects on reuptake inhibition and transporter selectivity. For example, analogues prepared by replacing the piperazine ring in the GBR structure with an N,N'-dimethylpropyldiamine moiety displayed enhanced selectivity for binding and reuptake inhibition at the norepinephrine (NE) transporter site (e.g. 4 and 5). Congeners in which the amide nitrogen atom was attached to the aralkyl moiety of the GBR molecule showed moderate affinity (K(i) = 51-61 nM) and selectivity for the dopamine transporter (DAT) site. In contrast, introduction of a carbonyl group adjacent to either nitrogen atom of the piperazine ring (e.g. 25 and 27) was not well tolerated. From the compounds prepared, analogue 16 was selected for further evaluation. With this congener, locomotor activity induced by cocaine at a dose of 20 mg/kg was attenuated with an-AD50 (dose attenuating cocaine-induced stimulation by 50%) of 60.0 ± 3.6 mg/kg.
SYNTHESIS OF 2-ALKYLPYRIMIDINES VIA 2-ALKYL-1,4,5,6-TETRAHYDROPYRIMIDINES
Pews, Richard Garth
, p. 1867 - 1872 (2007/10/02)
The condensation of 1,3-diaminopropane with alkanoic acids gives 2-alkyl-1,4,5,6-tetrahydropyrimidines.Dehydrogenation of the tetrahydropyrimidine derivatives over a palladium catalyst produces the 2-alkylpyrimidines in high yields.
