2899-37-8Relevant articles and documents
Docking model of the nicotinic acetylcholine receptor and nitromethylene neonicotinoid derivatives with a longer chiral substituent and their biological activities
Nagaoka, Hikaru,Nishiwaki, Hisashi,Kubo, Takuya,Akamatsu, Miki,Yamauchi, Satoshi,Shuto, Yoshihiro
, p. 759 - 769 (2015/02/19)
In the present study, nitromethylene neonicotinoid derivatives possessing substituents that contain a sulfur atom, oxygen atom or aromatic ring at position 5 on the imidazolidine ring were synthesized to evaluate their affinity for the nicotinic acetylcholine receptor (nAChR) and their insecticidal activity against adult female houseflies. Comparing the receptor affinity of the alkylated derivative with the receptor affinity of compounds possessing either ether or thioether groups revealed that conversion of the carbon atom to a sulfur atom did not influence the receptor affinity, whereas conversion to an oxygen atom was disadvantageous for the receptor affinity. The receptor affinity of compounds possessing a benzyl or phenyl group was lower than that of the unsubstituted compound. Analysis of the three-dimensional quantitative structure-activity relationship using comparative molecular field analysis demonstrated that steric hindrance of the receptor should exist around the C3 of an n-butyl group attached at position 5 on the imidazolidine ring. A docking study of the nAChR-ligand model suggested that the ligand-binding region expands as the length of the substituent increases by brushing against the amino acids that form the binding region. The insecticidal activity of the compounds was positively correlated with the receptor affinity by considering log P and the number of heteroatoms, including sulfur and oxygen atoms, in the substituents, suggesting that the insecticidal activity is influenced by the receptor affinity, hydrophobicity, and metabolic stability of the compounds.
Green asymmetric synthesis: β-amino alcohol-catalyzed direct asymmetric aldol reactions in aqueous micelles
Pinaka, Afroditi,Vougioukalakis, Georgios C.,Dimotikali, Dimitra,Yannakopoulou, Elina,Chankvetadze, Bezhan,Papadopoulos, Kyriakos
, p. 119 - 125 (2013/08/24)
The ability of chiral β-amino alcohols to catalyze the direct asymmetric aldol reaction was evaluated for the first time in aqueous micellar media. A family of cheap and easily accessible β-amino alcohols, obtained in one step from naturally occurring amino acids, was shown to successfully catalyze the asymmetric aldol reaction between a series of ketones and aromatic aldehydes. These aldol reactions furnished the corresponding β-hydroxy ketones with up to 93% isolated yield and 89% ee. (S)-2-phenylglycinol and Triton X-100 proved to be the best organocatalyst and surfactant, respectively. Copyright
A convenient one-step synthesis of stable β-amino alcohol N-boranes from α-amino acids
Pinaka, Afroditi,Vougioukalakis, Georgios C.,Dimotikali, Dimitra,Psyharis, Vassilis,Papadopoulos, Kyriakos
experimental part, p. 1057 - 1062 (2012/05/21)
Novel, non-cyclic -amino alcohol N-boranes are isolated from the sodium borohydride-sulfuric acid assisted direct reduction of a series of -amino acids. The reduction takes place in one step under mild conditions and affords the products in good yields. Georg Thieme Verlag Stuttgart · New York.
Synthesis of selenium-linked neoglycoconjugates and pseudodisaccharides
Affeldt, Ricardo F.,Baldassari, Lucas L.,Luedtke, Diogo S.,Braga, Hugo C.
, p. 10470 - 10475,6 (2012/12/12)
The introduction of organoselenium moieties within the structure of carbohydrates has received attention recently. Herein, we report on the synthesis of selenium-containing neoglycoconjugates and pseudodisaccharides by the reaction of nucleophilic selenium species, generated from sugar diselenides, with chiral N-Boc aziridines and sugar tosylates. The reaction proceeds with moderate to good yields for various substrates. The introduction of organoselenium moieties within the framework of various sugars, with increased levels of complexity, thus allowing the synthesis of disaccharide and glycoconjugate mimetics.
A highly stereoselective synthesis of glycidic amides based on a new class of chiral sulfonium salts: Applications in asymmetric synthesis
Sarabia, Francisco,Vivar-García, Carlos,García-Castro, Miguel,García-Ruiz, Cristina,Martín-Gálvez, Francisca,Sánchez-Ruiz, Antonio,Chammaa, Samy
supporting information, p. 15190 - 15201 (2013/01/15)
A new type of chiral sulfonium salts that are characterized by a bicyclic system has been designed and synthesized from α-amino acids. Their corresponding ylides, which were prepared by basic treatment of the sulfonium salts, reacted smoothly with a broad array of simple and chiral aldehydes to provide trans-epoxy amides in reasonable to very good yields and excellent stereoselectivities (>98 %). The obtained epoxy amides were found to be useful as synthetic building blocks. Thus, they were reduced into their corresponding epoxy alcohols and subjected to oxirane-ring-opening reactions with different types of nucleophiles.
Simple methodology for the preparation of amino alcohols from amino acid esters using nabh4-methanol in THF
Goncalves,Pinheiro,Da Silva,Da Costa,Kaiser,De Souza
, p. 1276 - 1281 (2011/05/04)
Amino alcohols constitute a very useful and versatile class of organic compounds, with important applications in synthetic and medicinal chemistry. However, in most of the procedures described in the literature for the obtainment of these compounds, considerable limitations can be found, such as drastic conditions, long time reactions, poor yields, and purification problems. The present article describes a methodology that gives amino alcohols and N-protected amino alcohols based on the reduction of amino acid esters under mild conditions, employing NaBH4 in the presence of methanol. The reactions occurred in a short time (15-20min) and provide yields of 50-95%.
Synthesis of (-)-α-Kainic Acid via TMSCl-Promoted Pd-Catalyzed Zinc-ene Cyclization of an Allyl Acetate
Wei, Guoqing,Chalker, Justin M.,Cohen, Theodore
experimental part, p. 7912 - 7917 (2011/12/01)
A highly practical synthesis of enantiopure (-)-α-kainic acid is accomplished in 37% overall yield, using 13 linear steps and a minimum of chromatographic separations via an unprecedentedTMSClpromoted palladium-catalyzed zinc-ene cyclization of an allyl acetate. (Figure presented)
An efficient synthesis of (R)-3-aminothiolane
Pan, Xianhua,Tao, Xiaohu,Ruan, Libo,Li, Yiming,Ou, Wenhua,Liu, Feng
experimental part, p. 729 - 730 (2012/03/27)
An efficient synthesis of (R)-3-aminothiolane is described based on a one-pot tandem hydroxyl activation-intramolecular cyclisation of Ts-protected-D-methioninol in the presence of methanesulfonyl chloride/pyridine. Removal of the tosyl group then gave (R)-3-aminothiolane in good yield. (R)-3-Aminothiolane derivatives are important building blocks for the synthesis of biologically active compounds.
A highly efficient methodology of asymmetric epoxidation based on a novel chiral sulfur ylide
Sarabia, Francisco,Chammaa, Samy,Garcia-Castro, Miguel,Martin-Galvez, Francisca
supporting information; experimental part, p. 5763 - 5765 (2010/01/31)
A new type of chiral sulfur ylides has been synthesized and their reactivities against carbonyl compounds tested, showing a high degree of stereoselectivity in the formation of trans epoxy amides under very mild reaction conditions.
REVERSIBLE ROOM-TEMPERATURE IONIC LIQUIDS
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Page/Page column 96, (2008/12/07)
One aspect of the present invention relates to salts that are room-temperature ionic liquids (RTILs), methods of making them, and methods of using them in connection with temporary or permanent gas sequestration. Another aspect of the present invention relates to a class of solvents which can be transformed into RTILs by exposure to a gas, and methods of using them in connection with temporary or permanent gas sequestration.
