86953-46-0Relevant academic research and scientific papers
Natural α-methylenelactam analogues: Design, synthesis and evaluation of α-alkenyl-γ and δ-lactams as potential antifungal agents against Colletotrichum orbiculare
Delong, Wang,Lanying, Wang,Yongling, Wu,Shuang, Song,Juntao, Feng,Xing, Zhang
, p. 286 - 307 (2017/03/09)
In our continued efforts to improve the potential utility of the α-methylene-γ-lactone scaffold, 62 new and 59 known natural α-methylenelactam analogues including α-methylene-γ-lactams, α-arylidene-γ and δ-lactams, and 3-arylideneindolin-2-ones were synthesized as the bioisosteric analogues of the α-methylenelactone scaffold. The results of antifungal and cytotoxic activity indicated that among these derivatives compound (E)-1-(2, 6-dichlorobenzyl)-3-(2-fluorobenzylidene) pyrrolidin-2-one (Py51) possessed good selectivity with the highest antifungal activity against Colletotrichum orbiculare with IC50?=?10.4?μM but less cytotoxic activity with IC50?=?141.2?μM (against HepG2 cell line) and 161.2?μM (against human hepatic L02?cell line). Ultrastructural change studies performed by transmission electron microscope showed that Py51 could cause important cell morphological changes in C.?orbiculare, such as plasma membrane detached from cell wall, cell wall thickening, mitochondria disruption, a dramatic increase in vacuolation, and eventually a complete loss in the integrity of organelles. Significantly, mitochondria appeared one of the primary targets, as confirmed by their remarkably aberrant morphological changes. Analysis of structure–activity relationships revealed that incorporation of the aryl group into the α-exo-methylene and the N-benzyl substitution increased the activity. Meanwhile, the α-arylidene-γ-lactams have superiority in selectivity over the 3-arylideneindolin-2-ones. Based on the results, the N-benzyl substituted α-(2-fluorophenyl)-γ-lactam was identified as the most promising natural-based scaffold for further discovering and developing improved crop-protection agents.
Copper-catalyzed intermolecular chloro- and bromotrifluoromethylation of alkenes
Fu, Mingyang,Chen, Long,Jiang, Yongpeng,Jiang, Zhong-Xing,Yang, Zhigang
, p. 348 - 351 (2016/02/19)
A highly practical copper-catalyzed intermolecular halotrifluoromethylation of alkenes has been developed under mild reaction conditions. A variety of Cl/Br-containing trifluoromethyl derivatives were directly synthesized from a wide range of alkenes, including electron-deficient and unactivated alkenes.
Thermal elimination of diethyldithiocarbamates and application in the synthesis of (±)-ferrugine
Ahmed, Shamim,Baker, Luke A.,Grainger, Richard S.,Innocenti, Paolo,Quevedo, Camilo E.
, p. 8116 - 8119 (2008/12/22)
(Chemical Equation Presented) Dithiocarbamate-substituted lactams, prepared through group-transfer cyclization reactions of carbamoyl radicals, undergo a Chugaev-like thermal elimination of the dithiocarbamate group in refluxing diphenyl ether to form α,β
Synthesis of α,β-unsaturated lactams by palladium-catalysed intramolecular carbonylative coupling
Crisp, Geoffrey T.,Meyer, Adam G.
, p. 5585 - 5596 (2007/10/02)
Amino vinyl triflates have been shown to undergo an intramolecular, carbonylative coupling in the presence of a palladium catalyst to afford α,β-unsaturated lactams.
Palladium-Catalysed Synthesis of α-Methylene γ-Butyrolactams via Cyclisation of Homoallylic Chloroformamides
Henin, Francoise,Muzart, Jacques,Pete, Jean-Pierre
, p. 6339 - 6340 (2007/10/02)
3-Methylene 2-pyrrolidinones were prepared by intramolecular cyclisation of homoallylic chloroformamides catalysed by PdII or Pdo complexes.
Palladium-Catalyzed Carbonylation. A New Synthesis of α-Methylene γ-, δ-, and ε-Lactams and -Lactones Including Bicyclic Lactams of Pyrrolizidine and Indolizidine Skeletons
Mori, Miwako,Washioka, Yumiko,Urayama, Takao,Yoshiura, Kagari,Chiba, Katsumi,Ban, Yoshio
, p. 4058 - 4067 (2007/10/02)
The insertion of carbon monoxide into vinyl halides bearing the secondary amine or alcohol with a catalytic amount of Pd(OAc)2 and PPh3 was realized to give five-, six-, and seven-membered lactams and lactones carrying α-methylene groups in fairly good yields.Bicyclic heterocycles, pyrrolizidine and indolizidine derivatives, were also synthesized from pyrrolidine and piperidine derivatives possessing vinyl halide groups in the side chain at the 2-position of the ring by means of palladium-catalyzed carbonylation.
