52321-07-0Relevant articles and documents
Exploiting morph-DAST mediated ring-expansion of substituted cyclic β-amino alcohols for the preparation of cyclic fluorinated amino acids. Synthesis of 5-fluoromethylproline and 5-fluoropipecolic acid
Mykhailiuk, Pavel K.,Shishkina, Svetlana V.,Shishkin, Oleg V.,Zaporozhets, Olga A.,Komarov, Igor V.
, p. 3091 - 3097 (2011)
The synthesis of proline analogues bearing a fluorine-containing substituent at the fifth position of the pyrrolidine ring, racemic trans- and cis-5-fluoromethyl prolines, was performed. The key step of the synthesis is a transformation of the CH2/s
Enantioselective biotransformations of racemic and meso pyrrolidine-2,5-dicarboxamides and their application in organic synthesis
Chen, Peng,Gao, Ming,Wang, De-Xian,Zhao, Liang,Wang, Mei-Xiang
experimental part, p. 4063 - 4072 (2012/06/18)
In this paper, we report the amidase-catalyzed hydrolysis of pyrrolidine-2,5-dicarboxamides and their application in organic synthesis. Catalyzed by Rhodococcus erythropolis AJ270, an amidase containing microbial whole cell catalyst, racemic trans-pyrrolidine-2,5-carboxamide was kinetically resolved into (2S,5S)-pyrrolidine-2,5-dicarboxamide and (2R,5R)-5- carbamoylpyrrolidine-2-carboxylic acid in high yields and excellent enantioselectivity. Biocatalytic desymmetrization of meso cis- pyrrolidinedicarboxamide afforded enantiomerically pure (2R,5S)-5- carbamoylpyrrolidine-2-carboxylic acid in an almost quantitative yield. In both kinetic resolution and desymmetrization, the amidase always exhibited excellent 2R-enantioselectivity, although its catalytic efficiency was influenced dramatically by the steric effect of the substituent on the nitrogen atom of pyrrolidine ring. The synthetic potential of biotransformation was demonstrated by the scalable preparation of (2R,5R)- and (2R,5S)-5-carbamoylpyrrolidine-2- carboxylic acids and their conversions to aza-nucleoside analogues and druglike pyrroline-fused diazepin-11(5H)-one compounds.
3,8-Diazabicyclo[3.2.1]octanes and their use in the treatment of cardiac arrhythmias
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, (2008/06/13)
There is provided compounds of formula (I), wherein R1, R2 and Ra to Rb have meanings given in the description, which are useful in the prophylaxis and in the treatment of arrhythmias, in particular atrial and v
Synthesis and Structure-Activity Relationship of Di-(3,8-diazabicyclo[3.2.1]octane) Diquaternary Ammonium Salts as Unique Analgesics
Liu, Hong,Cheng, Tie-Ming,Zhang, Hong-Mei,Li, Run-Tao
, p. 510 - 513 (2007/10/03)
Based on the structure characteristics of the lead compounds, 1,1′2-octanedioyl-4,4′-dimethyl-4,4′-dibenzyl dipiperazinium dibromide (2) and 3,8-disubstituted-3,8-diazabicyclo[3.2.1]octanes (DBO), di-(3,8-diazabicyclo[3.2.1]octane) diquaternary ammonium salts 3 a-c were designed and synthesized through a highly practical procedure. Target compounds 3 a-c and the hydrochloride salts of their precursors 10 a-c were evaluated for their in vivo analgesic and sedative activities. Interestingly, the introduction of an endoethylenic bridge in the piperazine of lead compound 2 causes loss of the analgesic activity and increases the toxicity dramatically. This result shows that the flexible conformation of piperazine in compound 2 is favorable for interaction with the receptor, and the quaternization of compounds 10 a-c is the main reason for the toxicity increase.
Studies of N-Terminal Templates for α-Helix Formation. Synthesis and Conformational Analysis of (2S,5S,8S,11S)-1-Acetyl-1,4-diaza-3-keto-5-carboxy-10-thiatricyclo4,8>tridecane (Ac-Hel1-OH)
Kemp, D. S.,Curran, Timothy P.,Davis, William M.,Boyd, James G.,Muendel, Christopher
, p. 6672 - 6682 (2007/10/02)
A convergent synthesis of the title compound, a conformationally restricted analogue of acetyl-L-prolyl-L-proline, from 1-acetyl-2(S)-carboxy-4(S)-mercaptopyrrolidine and trans-1-(tert-butoxycarbonyl)-2(S)-(methoxycarbonyl)-5(S)-pyrrolidine (Ac-Hel1-OH) is reported, along with a synthesis of (2S,8S,11S)-1-acetyl-1,4-diaza-3-keto-10-thiatricyclo4,8>tridecane.In the crystal and in CDCl3 solution the conformation of Ac-Hel1-OH is shown to approximate a staggered orientation at the 8,9-CC bond and an s-cis orientation at the acetyl amide bond.In DMF, DMSO, MeCN, and D2O significant amounts of the s-trans conformer are also present.
ASYMMETRIC ALKYLATION OF CARBOXYAMIDES BY USING trans-2,5-DISUBSTITUTED PYRROLIDINES AS CHIRAL AUXILIARIES
Kawanami, Yasuhiro,Ito, Yoshio,Kitagawa, Toshiyuki,Taniguchi, Yoshiyuki,Katsuki, Tsutomu,Yamaguchi, Masaru
, p. 857 - 860 (2007/10/02)
trans-2,5-Bis(methoxymethyl)- and trans-2,5-bis(methoxymethoxymethyl)pyrrolidines proved to be excellent chiral auxiliaries for the asymmetric alkylation of the corresponding carboxyamide enolates giving good chemical yield and high stereoselectivity (invariably over 95percent de), with remarkable flexibility to substrates and reaction conditions.
