4361-44-8Relevant articles and documents
Remote Regioselective Radical C-H Functionalization of Unactivated C-H Bonds in Amides: The Synthesis of gem-Difluoroalkenes
Hu, Qu-Ping,Cheng, Jing,Wang, Ying,Shi, Jie,Wang, Bi-Qin,Hu, Ping,Zhao, Ke-Qing,Pan, Fei
supporting information, p. 4457 - 4462 (2021/05/26)
The site-selective functionalization of unactivated aliphatic amines is an attractive and challenging synthetic approach. We herein report a general strategy for the remote site-selective functionalization of unactivated C(sp3)-H bonds in amides by photogenerated amidyl radicals to form gem-difluoroalkenes with trifluoromethyl-substituted alkenes. The site selectivity is controlled by a 1,5-hydrogen atom transfer (HAT) process of the amide. This photocatalyzed transformation shows both chemo- and site-selectivity, facilitating the formation of a secondary, tertiary, or quaternary carbon center.
Remote Directed Isocyanation of Unactivated C(sp3)-H Bonds: Forging Seven-Membered Cyclic Ureas Enabled by Copper Catalysis
Zhang, Hongwei,Tian, Peiyuan,Ma, Lishuang,Zhou, Yulu,Jiang, Cuiyu,Lin, Xufeng,Xiao, Xiao
supporting information, p. 997 - 1002 (2020/02/15)
Reported herein is an unprecedented copper-catalyzed site-selective ?-C(sp3)-H bonds activation of aliphatic sulfonamides for constructing the synthetically useful seven-membered N-heterocycles. A key to success is the use of in-situ-formed amide radicals, to activate the inert C(sp3)-H bond, and inexpensive TMSNCO, as a coupling reagent under mild conditions. To the best of our knowledge, this represents the first use of alkylamine derivatives as a five-membered synthon to prepare a seven-membered N-heterocycles.
Exploration of flexible phenylpropylurea scaffold as novel cardiac myosin activators for the treatment of systolic heart failure
Manickam, Manoj,Jalani, Hitesh B.,Pillaiyar, Thanigaimalai,Sharma, Niti,Boggu, Pulla Reddy,Venkateswararao, Eeda,Lee, You-Jung,Jeon, Eun-Seok,Jung, Sang-Hun
, p. 379 - 391 (2017/04/24)
A series of flexible urea derivatives have been synthesized and demonstrated as selective cardiac myosin ATPase activator. Among them 1-phenethyl-3-(3-phenylpropyl)urea (1, cardiac myosin ATPase activation at 10?μM?=?51.1%; FS?=?18.90; EF?=?12.15) and 1-benzyl-3-(3-phenylpropyl)urea (9, cardiac myosin ATPase activation?=?53.3%; FS?=?30.04; EF?=?18.27) showed significant activity in?vitro and in?vivo. The change of phenyl ring with tetrahydropyran-4-yl moiety viz., 1-(3-phenylpropyl)-3-((tetrahydro-2H-pyran-4-yl)methyl)urea (14, cardiac myosin ATPase activation?=?81.4%; FS?=?20.50; EF?=?13.10), and morpholine moiety viz., 1-(2-morpholinoethyl)-3-(3-phenylpropyl)urea (21, cardiac myosin ATPase activation?=?44.0%; FS?=?24.79; EF?=?15.65), proved to be efficient to activate the cardiac myosin. The potent compounds 1, 9, 14 and 21 were found to be selective for cardiac myosin over skeletal and smooth myosins. Thus, these urea derivatives are potent scaffold to develop as a newer cardiac myosin activator for the treatment of systolic heart failure.