696-74-2Relevant articles and documents
Oxidative and hydrolytic cleavage of cyclopropane and spirocyclobutane derivatives of 6,8-dioxabicyclo[3.2.1]octane, the products of transformation of levoglucosenone
Novikov,Rafikov,Shulishov,Tomilov
, p. 1930 - 1936 (2010)
A new method for the synthesis of (1R,4S,5S)-4-hydroxymethyl-3- oxabicyclo[3.1.0]hexan-2-one, the cyclopropane analog of (S)-5-hydroxypent-2-en- 4-olide, has been suggested based on oxidation of (1S,2S,4R,6R)-7,9- dioxatricyclo[4.2.1.02,4]nonan-5-one. Oxidation of cyclobutanones, spirojoined with the fragments of 6,8-dioxabicyclo[3.2.1]oct-2-ene, 6,8-dioxabicyclo[3.2.1]octane (at position 4), or 7,9-dioxatricyclo[4.2.1.0 2,4]nonane (at position 5), upon the action of m-chloroperoxybenzoic acid or the KMnO4-H2SO4-H2O system leads to the corresponding spirojoined butanolides in 73-85% yields. The same cyclobutanones easily undergo the four-membered ring opening upon the action of dilute H2SO4 at 50-90 °C to form 6,8-dioxabicyclo[3.2. 1]octane-4-or 7,9-dioxatricyclo[4.2.1.02,4]nonane-5-propionic acid.
Cyclopropane derivatives as potential human serine racemase inhibitors: Unveiling novel insights into a difficult target
Beato, Claudia,Pecchini, Chiara,Cocconcelli, Chiara,Campanini, Barbara,Marchetti, Marialaura,Pieroni, Marco,Mozzarelli, Andrea,Costantino, Gabriele
, p. 645 - 652 (2016/05/09)
d-Serine is the co-agonist of NMDA receptors and binds to the so-called glycine site. d-Serine is synthesized by human serine racemase (SR). Over activation of NMDA receptors is involved in many neurodegenerative diseases and, therefore, the inhibition of SR might represent a novel strategy for the treatment of these pathologies. SR is a very difficult target, with only few compounds so far identified exhibiting weak inhibitory activity. This study was aimed at the identification of novel SR inhibitor by mimicking malonic acid, the best-known SR inhibitor, with a cyclopropane scaffold. We developed, synthesized, and tested a series of cyclopropane dicarboxylic acid derivatives, complementing the synthetic effort with molecular docking. We identified few compounds that bind SR in high micromolar range with a lack of significant correlation between experimental and predicted binding affinities. The thorough analysis of the results can be exploited for the development of more potent SR inhibitors.
Design, synthesis and activity of novel derivatives of Oxybutynin and Tolterodine
Kaur, Kirandeep,Aeron, Shelly,Bruhaspathy, Miriyala,Shetty, Shankar J.,Gupta, Suman,Hegde, Laxminarayan H.,Silamkoti, Arun D. V.,Mehta, Anita,Chugh, Anita,Gupta, Jang B.,Sarma,Kumar, Naresh
, p. 2093 - 2096 (2007/10/03)
Novel derivatives of Tolterodine (1) and Oxybutynin (2) have been designed using conformationally restricted azabicyclics as replacement for open-chain amines. The synthesis and structure-activity relationships are presented.
