65012-11-5Relevant academic research and scientific papers
Catalytic asymmetric synthesis of dihydrofurans and cyclopentenols with tertiary stereocenters
Wu, Zhongtao,Madduri, Ashoka V. R.,Harutyunyan, Syuzanna R.,Minnaard, Adriaan J.
, p. 575 - 582 (2014/02/14)
A new asymmetric synthesis of dihydrofurans and cyclopentenols has been developed and is based on the copper-catalyzed 1,2-addition of Grignard reagents to enones in combination with Sonogashira coupling/cyclization or ring-closing metathesis. By this approach, dihydrofurans with an oxygen-containing tertiary stereocenter and chiral tertiary cyclopentenols are efficiently prepared. The absolute stereochemistry of the products has been established. The copper-catalyzed 1,2-addition of Grignard reagents to enones, combined with Sonogashira coupling/cyclization or ring-closing metathesis, provides a new asymmetric synthesis of dihydrofurans and cyclopentenols. Two different kinds of dihydrofurans are obtained with medium-to-high enantioselectivities. Copyright
Analogues of oxybutynin. Synthesis and antimuscarinic and bladder activity of some substituted 7-amino-1-hydroxy-5-heptyn-2-ones and related compounds
Carter,Noronha-Blob,Audia,Dupont,McPherson,Natalie Jr.,Rzeszotarski,Spagnuolo,Waid,Kaiser
, p. 3065 - 3074 (2007/10/02)
Oxybutynin chloride [4-(diethylamino)-2-butynyl α-cyclohexyl-α-hydroxybenzeneacetate hydrochloride, Ditropan] is widely used for the relief of symptoms in neurogenic bladder. This is a result of its combined anticholinergic, antispasmodic, and local anesthetic activities. In a study directed toward development of agents possessing the beneficial properties of oxybutynin, but having a longer duration of action, a series of metabolically more stable keto analogues of the parent ester, i.e. substituted 7-amino-1-hydroxy-5-heptyn-2-ones along with some analogues and derivatives, was prepared and evaluated for in vitro and in vivo antimuscarinic action in guinea pig preparations. Several members of the series were potent antimuscarinics having a longer duration of activity than that of oxybutynin in a guinea pig cystometrogram model. On the basis of its in vitro and in vivo antimuscarinic activity, coupled with a 5-fold greater duration of action than that of oxybutynin, 1-cyclobutyl-7-(dimethylamino)-1-hydroxy-1-phenyl-5-heptyn-2-one (14b) was selected for clinical evaluation.
