20256-77-3Relevant academic research and scientific papers
Structure-based screening and optimization of cytisine derivatives as inhibitors of the menin-MLL interaction
Zhong, Hai-Jing,Lee, Bo Ra,Boyle, Joshua William,Wang, Wanhe,Ma, Dik-Lung,Hong Chan, Philip Wai,Leung, Chung-Hang
supporting information, p. 5788 - 5791 (2016/05/19)
The natural product-like compound 1 was identified as a direct inhibitor of the menin-MLL interaction by in silico screening. Structure-based optimization furnished analogue 1a, which showed significantly higher potency than both the lead structure 1 and the reference compound MI-2.
Al(OTf)3-mediated epoxide ring-opening reactions: Toward piperazine-derived physiologically active products
Williams, D. Bradley G.,Cullen, Adam
supporting information; experimental part, p. 9509 - 9512 (2010/03/04)
(Chemical Equation Presented) Al(OTf)3 is a good catalyst for the ring opening of epoxides, forming β-amino alcohols bearing the piperazine motif. Two different strategies were examined, where the glycidyl ether resided on one-half of the molec
Substituent effects on the regiochemical and stereochemical course of the nussbaumer-frater variation of the prins cyclization
Bennett, Chad E.,Figueroa, Ruth,Hart, David J.,Yang, Dexi
, p. 119 - 128 (2007/10/03)
Eleven vinylogous carbonates were examined in the Nussbaumer-Frater variation of the Prins cyclization to provide 2,3,4,6-tetrasubstituted tetrahydropyrans. Results indicate that substrate olefin geometry is a more reliable control element than preset sub
Regiochemical and Stereochemical Studies on Halocyclization Reactions of Unsaturated Sulfides
Ren, Xiao-Feng,Turos, Edward,Lake, Charles H.,Churchill, Melvyn Rowen
, p. 6468 - 6483 (2007/10/03)
The regiochemistry and stereochemistry for the halocyclization reactions of unsaturated benzyl sulfides have been examined as a function of tether length, type of unsaturation (carbon-carbon double bond versus carbon-carbon triple bond), substituents, and halogenating agent.Alkenyl sulfides were found to react with iodine or bromine at room temperature to give five-membered ring cycloadducts exclusively over those having four-membered rings, while for larger systems, six-membered ring products are formed preferentially over their five-membered ring isomers and exclusively over the seven-membered ring adducts.The endo- versus exo-regioselectivity of these alkenyl sulfide ring closure most likely reflects the difference in thermodynamic stabilities of the β-halo sulfide cycloadducts, which are able to equilibrate via a common episulfonium intermediate.The efficiency of cyclization process markedly drops off for these alkenyl sulfides as the tether length increases beyond four intervening carbon centers.Thus, while the halogenations of 3-butenyl sulfides and 4-pentenyl sulfides give high yields of cycloadducts, those of 5-hexenyl sulfides afford only small amounts of cyclized products and large quantities of acyclic dibromides.Conversely, the reactions of acetylenic sulfides with iodine give uniformly high yields and regiochemical control regardless of the tether length.Thus, 3-butynyl and 4-pentynyl sulfides cyclize cleanly to the five-membered ring while 5-hexynyl sulfides give exclusively the six-membered ring.The products arising from these alkynyl sulfide ring closures are believed to be formed under kinetic control.The methodology has been applied to the synthesis of unusual bicyclic β-lactams related to the penicillin family of antibiotics.
The First Practical Method of Selective Heteroatom-Directed Chlorohydroxylation
Lai, Jin-Yu,Wang, Fu-Song,Guo, Guang-Zhong,Dai, Li-Xin
, p. 6944 - 6946 (2007/10/02)
A new Pd(II)-catalyzed nucleophilic chlorohydroxylation reaction of allylic amines and sulfides was achieved, and the regioselective reaction gives high yields of the chlorohydrin products, which can be transformed into epoxy compounds or aziridine compou
