3488-44-6Relevant articles and documents
Practical Application of the Aqueous 'Sulfonyl-Azide-Free' (SAFE) Diazo Transfer Protocol to Less α-C-H Acidic Ketones and Esters
Dar'In, Dmitry,Kantin, Grigory,Krasavin, Mikhail
, p. 4284 - 4290 (2019/11/14)
The earlier described 'sulfonyl-Azide-free' ('SAFE') protocol for diazo transfer to CH-Acidic 1,3-dicarbonyl compounds (and their similarly activated congeners) has been extended to the less reactive monocarbonyl substrates, which previously required a se
Phosphoric Acid Catalyzed [4 + 1]-Cycloannulation Reaction of ortho-Quinone Methides and Diazoketones: Catalytic, Enantioselective Access toward cis-2,3-Dihydrobenzofurans
Suneja, Arun,Schneider, Christoph
supporting information, p. 7576 - 7580 (2019/01/03)
A highly straightforward route to enantiomerically highly enriched cis-2,3-dihydrobenzofurans has been achieved via addition of α-diazocarbonyl compounds to in situ generated o-QMs catalyzed by a chiral Br?nsted acid. This catalytic strategy provides a direct access to 2,3-dihydrobenzofurans in high yields and with up to 91:9 dr and 99:1 er at ambient temperature. Moreover, a unique phenonium-type rearrangement accounts for product formation with an inverted 2,3-substitution pattern.
SAR exploration at the C-3 position of tetrahydro-β-carboline sstr3 antagonists
He, Shuwen,Dobbelaar, Peter H.,Guo, Liangqin,Ye, Zhixiong,Liu, Jian,Jian, Tianying,Truong, Quang,Shah, Shrenik K.,Du, Wu,Qi, Hongbo,Bakshi, Raman K.,Hong, Qingmei,Dellureficio, James D.,Sherer, Edward,Pasternak, Alexander,Feng, Zhe,Reibarkh, Mikhail,Lin, Melissa,Samuel, Koppara,Reddy, Vijay B.,Mitelman, Stan,Tong, Sharon X.,Chicchi, Gary G.,Tsao, Kwei-Lan,Trusca, Dorina,Wu, Margaret,Shao, Qing,Trujillo, Maria E.,Fernandez, Guillermo,Nelson, Donald,Bunting, Patricia,Kerr, Janet,Fitzgerald, Patrick,Morissette, Pierre,Volksdorf, Sylvia,Eiermann, George J.,Li, Cai,Zhang, Bei B.,Howard, Andrew D.,Zhou, Yun-Ping,Nargund, Ravi P.,Hagmann, William K.
, p. 1529 - 1535 (2016/07/27)
MK-4256, a tetrahydro-β-carboline sstr3 antagonist, was discontinued due to a cardiovascular (CV) adverse effect observed in dogs. Additional investigations revealed that the CV liability (QTc prolongation) was caused by the hERG off-target activity of MK-4256 and was not due to sstr3 antagonism. In this Letter, we describe our extensive SAR effort at the C3 position of the tetrahydro-β-carboline structure. This effort resulted in identification of 5-fluoro-pyridin-2-yl as the optimal substituent on the imidazole ring to balance sstr3 activity and the hERG off-target liability.
