35167-81-8Relevant academic research and scientific papers
Asymmetric synthesis of O-methylneferine
Nishimura, Katsumi,Horii, Shinji,Tanahashi, Takao
, p. 865 - 876 (2019/04/26)
Diastereoselective Pictet-Spengler reaction of 2-arylethylamine bearing an N-(R)-1-(1-naphthyl)ethylcarbamoyl group with arylacetaldehyde gave 1-benzyltetrahydroisoquinoline in good yield with moderate diastereoselectivity. The reaction was applied to asymmetric synthesis of O-methyl derivative of neferine, an alkaloid of the lotus embryo, Nelumbo nucifera Gaertner.
Design and Synthesis of 4-Alkylidene-β-lactams: Benzyl- and Phenethyl-carbamates as Key Fragments to Switch on Antibacterial Activity
Giacomini, Daria,Martelli, Giulia,Piccichè, Miriam,Calaresu, Enrico,Cocuzza, Clementina Elvezia,Musumeci, Rosario
, p. 1525 - 1533 (2017/09/25)
The emergence of multidrug-resistant bacterial strains is particularly important in chronic pathologies such as cystic fibrosis (CF), in which persistent colonization and selection of resistant strains is favored by the frequent and repeated use of antibacterial agents. Staphylococcus aureus is a common pathogen in CF patients that has an associated increased multidrug resistance. In previous studies we demonstrated that the presence of a 4-alkylidene side chain directly linked to a β-lactam appeared to strengthen the potency against S. aureus, especially against methicillin-resistant S. aureus (MRSA) strains. In the present study, 21 new 4-alkylidene-β-lactams were synthesized and evaluated for antibacterial activity. We designed the new compounds to have aryl, benzyl, or phenethyl-carbamate groups on the C3 hydroxyethyl side chain. We found a correlation between biological activity and the nitrogen substituent of the carbamate group, and two phenethyl-carbamate β-lactams were shown to be valuable antibacterial agents against selected linezolid-resistant strains, with a minimum inhibitory concentrations of 2–4 mg L?1.
Synthesis of 3,4-dihydroisoquinolin-1-ones from N-Boc-(β-Arylethyl) carbamates via isocyanate intermediates
In, Jinkyung,Hwang, Soonho,Kim, Changhun,Seo, Jae Hong,Kim, Sanghee
, p. 965 - 971 (2013/03/14)
Mild reaction conditions for the regioselective synthesis of isoquinolin-1-ones and related fused-ring heterocycles from N-Boc-protected (β-arylethyl)carbamates are described. The reactions involved the use of Tf2O and 2-chloropyridine and isocyanates are likely to be key intermediates. The method was extended to substrates bearing less nucleophilic aryl moieties by using Lewis acid additives, such as BF3· Et2O, to enhance the Friedel-Crafts-type cyclization of the isocyanate intermediates. This method allowed the synthesis of various substituted isoquinolin-1-ones, β-carbolines, thiophene-fused ring systems and tetrahydrobenzoazepin-1-ones in good yields and with high regioselectivities. Copyright
Synthesis and evaluation of novel compounds as potent dipeptidyl peptidase IV inhibitors
Wang, Liutang,Zhang, Bin,Ji, Jianxin,Li, Bogang,Yan, Jufang,Zhang, Weiyu,Wu, Yong,Wang, Xuechao,Hou, Hui
experimental part, p. 52 - 57 (2010/03/24)
A series of new 2-cyanopyrrolidine derivatives with constrained imidazolidin ring were synthesized, Their structures were confirmed by 1H NMR spectroscopy and/or mass spectrometry, and their activities were evaluated in vitro. They were proven to possess submicromolar inhibitory activities against dipeptidyl peptidase IV.
Efficient synthesis of tetrahydro-b-carbolin-1-one and dihydroisoquinolin- 1-one derivatives as versatile Intermediates
Judd, Katie E.,Mahon, Mary F.,Caggiano, Lorenzo
experimental part, p. 2809 - 2817 (2010/01/21)
An efficient one-pot procedure is described in which an isocyanate intermediate, generated from the corresponding carboxylic acid by a modified Curtius rearrangement, is captured by a tethered aromatic ring in the presence of BF3?OEt2 to generate various
Organosilicon synthesis of isocyanates: II. Synthesis of aliphatic, carbocyclic, and fatty-aromatic isocyanates
Lebedev,Lebedeva,Sheludyakov,Ovcharuk,Kovaleva,Ustinova
, p. 469 - 477 (2008/02/07)
Silylation of a series of aliphatic, carbocyclic, and fatty-aromatic amines gave the corresponding silyl derivatives whose yield depended on the electronic and steric structure of the substrate and the nature of the silylating agent. The yield of isocyanates obtained by phosgenation of the silyl derivatives under mild conditions decreased in going from aliphatic amines to benzylamines and rose as the length of the alkyl chain in fatty-aromatic amines extended. The most convenient procedure for the synthesis of low-boiling alkyl isocyanates was found to be based on the transformation of amines or ammonium salts into silyl or silyl silyl-carabamates, followed by pyrolysis of the latter in the presence of trichloro(phenyl)silane. Pleiades Publishing, Inc., 2006.
