4237-73-4Relevant academic research and scientific papers
8-Hydroxyquinolin-2(1H)-one analogues as potential β2-agonists: Design, synthesis and activity study
Xing, Gang,Zhi, Zhengxing,Yi, Ce,Zou, Jitian,Jing, Xuefeng,Yiu-Ho Woo, Anthony,Lin, Bin,Pan, Li,Zhang, Yuyang,Cheng, Maosheng
, (2021/07/19)
β2-Agonists that bind to plasmalemmal β2-adrenoceptors causing cAMP accumulation are widely used as bronchodilators in chronic respiratory diseases. Here, we designed and synthesized a group of 8-hydroxyquinolin-2(1H)-one analogues and studied their β2-agonistic activities with a cellular cAMP assay. Compounds B05 and C08 were identified as potent (EC50 2-agonists among the compounds tested. They behaved as partial β2-agonists in non-overexpressed HEK293 cells, and possessed rapid smooth muscle relaxant actions and long duration of action in isolated guinea pig tracheal strip preparations. In summary, B05 and C08 are β2-agonists with potential applicability in chronic respiratory diseases.
Design, synthesis and biological evaluation of 8-(2-amino-1-hydroxyethyl)-6-hydroxy-1,4-benzoxazine-3(4H)-one derivatives as potent β2-adrenoceptor agonists
Yi, Ce,Xing, Gang,Wang, Siqi,Li, Xiaoran,Liu, Yichuang,Li, Jinyan,Lin, Bin,Woo, Anthony Yiu-Ho,Zhang, Yuyang,Pan, Li,Cheng, Maosheng
, (2019/11/26)
A series of β2-adrenoceptor agonists with an 8-(2-amino-1-hydroxyethyl)-6-hydroxy-1,4-benzoxazine-3(4H)-one moiety is presented. The stimulatory effects of the compounds on human β2-adrenoceptor and β1-adrenoceptor were characterized by a cell-based assay. Their smooth muscle relaxant activities were tested on isolated guinea pig trachea. Most of the compounds were found to be potent and selective agonists of the β2-adrenoceptor. One of the compounds, (R)-18c, possessed a strong β2-adrenoceptor agonistic effect with an EC50 value of 24 pM. It produced a full and potent airway smooth muscle relaxant effect same as olodaterol. Its onset of action was 3.5 min and its duration of action was more than 12 h in an in vitro guinea pig trachea model of bronchodilation. These results suggest that (R)-18c is a potential candidate for long-acting β2-AR agonists.
An improved preparation of a tertiary alcohol proline linker and its use in a synthesis of mosquito oostatic hormone
Kochansky,Wagner
, p. 8007 - 8010 (2007/10/02)
An improved synthesis of 4-(3'-hydroxy-3'-methylbutyl)phenoxyacetic acid was developed using THF to overcome solubility problems initially encountered in trying to reproduce the published preparation. This hydroxyacid linker was coupled to aminomethyl polystyrene resin and used for a synthesis of the mosquito oostatic hormone by the Fmoc protocol. Attempts to prepare this insect peptide by other techniques had failed because of loss of cyclo-Pro2 from the resin.
Fmoc-based Solid-phase Peptide Synthesis using a New t-Alcohol Type 4-(1',1'-Dimethyl-1'-hydroxypropyl)phenoxyacetyl Handle (DHPP)-Resin (Fmoc = fluoren-9-ylmethoxycarbonyl)
Akaji, Kenichi,Kiso, Yoshiaki,Carpino, Louis A.
, p. 584 - 586 (2007/10/02)
The loss of C-terminal dipeptide through diketopiperazine formation during Fmoc-based solid-phase peptide synthesis has been effectively suppressed by anchoring the first Fmoc amino acid chloride to a new 4-(1',1'-dimethyl-1'-hydroxypropyl)phenoxyacetyl handle (DHPP)-resin; this new t-alcohol type DHPP-resin has been successfully applied to the solid-phase synthesis of bradykinin potentiator B (an eleven-residue peptide) (Fmoc = fluoren-9-ylmethoxycarbonyl).
Synthesis of 3-Hydroxy-2,3,4,5-tetrahydro-3-methylbenzoxepins by Ring-closure of Isoprenyl Terminal Epoxides
Baird, Kenneth J.,Grundon, Michael F.
, p. 1820 - 1825 (2007/10/02)
Terminal olefins (13), obtained from reactions of tertiary chlorides (10) with triphenylmethyl-lithium, were converted into epoxides (14); base-induced ring-closure of the latter gave 2-hydroxymethyl-2-methylchromans (15) and 3-hydroxy-2,3,4,5-tetrahydro-3-methylbenzoxepins (17).Dehydration of the tetrahydrobenzoxepin (17a) furnished dihydrobenzoxepins.
