2903-75-5Relevant articles and documents
New and facile synthesis of aminobicyclo[22.1]heptane-2-carboxylic acids
Kim, Taek-Soo,Seo, Seung-Yong,Shin, Dongyun
supporting information, p. 1243 - 1247 (2015/03/31)
Abstract A facile approach for the stereoselective synthesis of a- and b-2-aminobicyclo[2.2.1]heptane-2-carboxylic acid is described. Substrate-controlled α-carboxylation of norbonene monoester delivered the asymmetric diester intermediate with high diastereoselectivity (up to 35:1). Sequential chemoselective ester cleavage, Curtius rearrangement, and hydrolysis gave the a- and b-isomers of 2-aminobicyclo[2.2.1]heptane-2-carboxylic acid, respectively.
Novel Potassium-Channel Openers: Preparation and Pharmacological Evaluation of Racemic and Optically Active N-(6-Amino-3-pyridyl)-N'-bicycloalkyl-N"-cyanoguanidine Derivatives
Eda, Masahiro,Takemoto, Tadahiro,Ono, Shin-ichiro,Okada, Takehiro,Kosaka, Keigo,et al.
, p. 1983 - 1990 (2007/10/02)
The previous paper reported on the synthesis and pharmacological evaluation of N-(6-amino-3-pyridyl)-N'-bicycloalkyl-N"-cyanoguanidine derivatives, from among which three compounds were selected as potent potassium-channel openers. In the present study, selected compounds were tested for antagonism of potassium-induced contraction of rat aorta, hypotensive activity in normotensive rats, and diuretic activity in spontaneously hypertensive rats. This led to further evaluation of compound (+/-)-10 and selection of (+)-N-(6-amino-3-pyridyl)-N'-hept-2-yl>-N"-cyanoguanidine ((+)-10) (AL0670) for development as an antihypertensive agent. Although AL0670 is regarded as a pinacidil-type K+-channel opener, it showed different pharmacological and conformational profiles from pinacidil.
Transformations of unsaturated acyclic sugars into enantiomerically pure norbornene derivatives
Horton, Derek,Usui, Takayuki
, p. 33 - 49 (2007/10/02)
The C7 acyclic unsaturated-sugar ester 1, derived from L-arabinose, and its enantiomer serve as convenient dieneophiles for chirality transfer for synthesis of optically pure carbocyclic derivatives through cycloaddition reactions.Reaction of 1 with cyclopentadiene may be controlled to give preparative access to the 5,6-disubstituted norbornene adducts 4a, 5a and 7a, according to the conditions used.The distribution of the four possible isomeric products from this cycloaddition was quantitated, and the effect of substitutional variation on the precursor dienophile 1 was also examined.Adducts 4a and 5a were transformed into such substituted carbocycles of known absolute configuration as the methyl esters (11 and 12) of norbornene (bicyclohept-2-ene)-6-carboxylic acid and nortricyclane (tricyclo2,6>heptane)-3-carboxylic acid in optically pure form, specifically through decarbonylation reactions using RhCl(PPh3)3 (Wilkinson's complex) and Cl.The optical purity of 12 was established by the use of a chiral lanthanide shift-reagent.
