174195-95-0Relevant articles and documents
Building the Housane: Diastereoselective Synthesis and Characterization of Bicyclo[2.1.0]pentane Carboxylic Acids
Grygorenko, Oleksandr O.,Iminov, Rustam T.,Lutsenko, Dmytro O.,Semeno, Volodymyr V.,Vashchenko, Bohdan V.,Vasylchenko, Vadym O.,Volovenko, Olesia B.
, (2020)
An approach to 1,3-disubstitued bicyclo[2.1.0]pentane (housane) derivatives was developed. The method relied on lithium bis(trimethylsilyl)amide-mediated intramolecular cyclization of trisubstitued cyclopentane carboxylates bearing a leaving group (at the C-4 position) and an additional substituent (at the C-3 atom), in turn synthesized from cyclopent-3-ene carboxylate. The synthetic sequence allowed for the preparation of both cis- and trans-1,3-disubstituted housane-1-carboxylic acids in diastereoselective manner on up to 80 g scale. In particular, bicyclic γ-amino acids - γ-aminobutyric acid analogues - were synthesized. It was shown that the bicyclo[2.1.0]pentane did not significantly affect pKa of the corresponding derivatives and slightly increased their hydrophilicity (by 0.07-0.25 Log P units) as compared to cyclopentane. X-ray diffraction studies showed that cis- and trans-1,3-disubstituted housanes can be considered as flattened analogues of the corresponding cyclopentane derivatives with fixed envelope conformation of the five-membered ring.
COMPOSITIONS AND METHODS FOR TREATING AND PREVENTING NEURODEGENERATIVE DISORDERS
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Page/Page column 115; 116; 117, (2017/03/08)
Compounds, pharmaceutical compositions, methods and kits are described for treating or preventing neurodegenerative diseases such as Alzheimer's disease.
Discovery of a potent and orally bioavailable CCR2 and CCR5 dual antagonist
Pasternak, Alexander,Goble, Stephen D.,Struthers, Mary,Vicario, Pasquale P.,Ayala, Julia M.,Di Salvo, Jerry,Kilburn, Ruth,Wisniewski, Thomas,Demartino, Julie A.,Mills, Sander G.,Yang, Lihu
scheme or table, p. 14 - 18 (2010/11/04)
This report describes the discovery of a potent, orally bioavailable CC chemokine receptor 2 (CCR2) antagonist which, while optimized for CCR2 potency, also had potent CC chemokine receptor 5 (CCR5) activity.