37673-11-3Relevant academic research and scientific papers
Design, synthesis, acetylcholinesterase inhibition and larvicidal activity of girgensohnine analogs on Aedes aegypti, vector of dengue fever
Carre?o Otero, Aurora L.,Vargas Méndez, Leonor Y.,Duque L., Jonny E.,Kouznetsov, Vladimir V.
, p. 392 - 400 (2014/04/17)
Girgensohnine alkaloid was used as a natural model in the design and generation of new alkaloid-like α-aminonitrile series that was completed by the use of SSA-catalyzed Strecker reaction between commercial and inexpensive substituted benzaldehydes, piperidine (pyrrolidine, morpholine and N-methylpiperazine) and acetone cyanohydrin. Calculated ADMETox parameters of the designed analogs revealed their good pharmacokinetic profiles indicating lipophilic characteristics. In vitro AChE enzyme test showed that obtained α-aminonitriles could be considered as AChEIs with micromolar IC 50 values ranging from 42.0 to 478.0 μM (10.3-124.0 μg/mL). Among this series, the best AChE inhibitor was the pyrrolidine α-aminonitrile 3 (IC50 = 42 μM), followed by the piperidine α-aminonitriles 2 and 6 (IC50 = 45 μM and IC50 = 51 μM, respectively), and the compound 7 (IC50 = 51 μM). In vivo insecticidal activity of more active AChEIs against Aedes aegypti larvae was also performed showing a good larvicidal activity at concentrations less than 140 ppm, highlighting products 2 and 7 that could serve as lead compounds to develop new potent and selective insecticides.
Silica-bonded N-propyl diethylenetriamine sulfamic acid as a recyclable solid acid catalyst for the synthesis of α-aminonitriles
Rahi, Tahere,Baghernejad, Mojtaba,Niknam, Khodabakhsh
, p. 1095 - 1100 (2013/01/14)
Silica-bonded N-propyl diethylenetriamine sulfamic acid (SBPDSA) is employed as a recyclable catalyst to synthesize a-aminonitriles. These syntheses involved one-pot condensation of an aldehyde, an amine, and trimethylsilyl cyanide under mild reaction conditions at room temperature. SBPDSA was recycled seven times in the condensation of benzaldehyde, aniline, and trimethylsilyl cyanide without reduction of its catalytic activity.
Silica-Bonded N-Propyl Diethylenetriamine Sulfamic Acid as a Recyclable Solid Acid Catalyst for the Synthesis of α-Aminonitriles
Rahi, Tahere,Baghernejad, Mojtaba,Niknam, Khodabakhsh
, p. 1095 - 1100 (2015/06/30)
Silica-bonded N-propyl diethylenetriamine sulfamic acid (SBPDSA) is employed as a recyclable catalyst to synthesize a-aminonitriles. These syntheses involved one-pot condensation of an aldehyde, an amine, and trimethylsilyl cyanide under mild reaction conditions at room temperature. SBPDSA was recycled seven times in the condensation of benzaldehyde, aniline, and trimethylsilyl cyanide without reduction of its catalytic activity.
The asymmetric synthesis of aryltetralin lignans: (-)-isolariciresinol dimethyl ether and (-)-deoxysikkimotoxin
Coltart, Don M.,Charlton, James L.
, p. 88 - 94 (2007/10/03)
The total asymmetric syntheses of (-)-isolariciresinol dimethyl ether (6) and (-)-deoxysikkimotoxin (7) have been carried out, in an attempt to exploit a synthetic strategy recently developed for the synthesis of (-)-deoxypodophyllotoxin (1, R1 = -CH2-, Ar = 3,4,5-trimethoxyphenyl). In so doing, a generalized method for the synthesis of aryltetralin lignans has been developed that should be applicable to a variety of substitution patterns and stereochemistries. A one-pot, 100% regio-selective reduction-lactonization procedure has been developed for the conversion of the ester 18b to (-)-deoxysikkimotoxin, which gave 93% isolated yield in that step.
