257861-50-0Relevant articles and documents
Catalyst-free Mannich-type reaction of 1-(N-acylamino)alkyltriphenylphosphonium salts with silyl enolates
Pa?dzierniok-Holewa, Agnieszka,Wal?cka-Kurczyk, Alicja,Musio?, Szymon,Stecko, Sebastian
, p. 732 - 742 (2019/01/10)
A catalyst-free reaction of 1-(N-acylamino)alkyltriphenylphosphonium tetrafluoroborates with silyl enolates was developed to prepare β-amino carbonyl compounds. The reported method is a useful approach for the preparation of N-protected β-amino esters as
Discovery of a novel CCR5 antagonist lead compound through fragment assembly
Liu, Yanqing,Zhou, Enkun,Yu, Kunqian,Zhu, Jin,Zhang, Yu,Xie, Xin,Li, Jian,Jiang, Hualiang
experimental part, p. 2426 - 2441 (2009/04/11)
CCR5, as the major co-receptor for HIV-1 entry, is an attractive novel target for the pharmaceutical industry in the HIV-1 therapeutic area. In this study, based on the structures of maraviroc and 1,4-bis(4-(7-chloroquinolin-4- yl)piperazin-1-yl)butane-1,4-dione (1), which was identified using structure-based virtual screening in conjunction with a calcium mobilization assay, a series of novel small molecule CCR5 antagonists have been designed and synthesized through fragment assembly. Preliminary SARs were obtained, which are in good agreement with the molecular binding model and should prove helpful for future antagonist design. The novel scaffold presented here might also be useful in the development of maraviroc-derived second generation CCR5 antagonists.
An allyltitanium derived from acrolein 1,2-dicyclohexylethylene acetal and (η2-propene)Ti(o-i-Pr)2 as a chiral propionaldehyde homoenolate equivalent that reacts with imines with excellent stereoselectivity. An efficient and practical access to optically active γ-amino carbonyl compounds
Okamoto,Teng,Fujii,Takayama,Sato
, p. 3462 - 3471 (2007/10/03)
A chiral allyltitanium compound 2, prepared in situ by the reaction of optically active acrolein 1,2-dicyclohexylethylene acetal (3) with (η2-propene)Ti(O-i-Pr)2 (1), reacts with a variety of acyclic and cyclic imines 4 in a regiospecific way to afford α-addition products 5 as a mixture of the E- and Z-isomers in good combined yield, where the former is predominant in a ratio of 92: 8 to >95:5. The mixture of (E)- and (Z)-5 and pure (E)-5 which could be isolated in several cases were respectively converted to the corresponding β-amino ester 6 to confirm the absolute configuration and enantiomeric purity. The ee of the newly formed asymmetric center of 5 is more than 78% for the mixture of (E)- and (Z)-5 and more than 96% for pure (E)-5. By taking advantage of the versatility of the vinyl ether moiety in 5, optically active γ-amino aldehydes 8, γ-amino aldehyde acetals 7 and 10, γ-amino acids 9, β-amino esters 6, and pyrrolidinoisoquinolines 12 were readily prepared. In the reaction of 2 with optically active α-silyloxyimine 4n, remarkable double stereodifferentiation was observed; thus, the reaction of 2 derived from (S,S)- or (R,R)-3 provided syn- and anti-5n in a ratio of 55:45 or 0:100, respectively. Meanwhile, the stereochemistry of the product in the reaction of 2 with β-silyloxyimine 4o was controlled mainly by 2. Thus, the reaction of β-silyloxyimine 14 with 2 derived from 1 and (R,R)-3 afforded γ-silyloxyimine 15 with 92% diastereoselectivity, from which 4-amino6-hydroxypentadecanal dimethyl acetal (13), a key intermediate for the synthesis of batzelladine D, was synthesized.
