32511-34-5Relevant articles and documents
CYANO-PYRIMIDINE INHIBITORS OF EGFR/HER2
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Page/Page column 58-59, (2021/07/17)
Provided herein are compounds, pharmaceutical compositions comprising such compounds, and methods of using such compounds to treat diseases or disorders associated with EGFR and/or HER2 activity.
Enantioselective deprotometalation of alkyl ferrocenecarboxylates using bimetallic bases
Bentabed-Ababsa, Ghenia,Blot, Marielle,Chevallier, Floris,Dayaker, Gandrath,Dorcet, Vincent,Erb, William,Gros, Philippe C.,Hedidi, Madani,Hilmersson, G?ran,Mongin, Florence,Roisnel, Thierry
supporting information, p. 22579 - 22590 (2021/12/24)
The enantioselective deprotometalation of alkyl ferrocenecarboxylates (FcCO2R) using mixed lithium-zinc or lithium-cadmium bases is described. By using FcCO2Me as the substrate, chiral lithium alkyl-amidozincates prepared from exo-(αR)- or endo-(αS)-N-(α-phenylethyl)bornylamine (H-exo-born-R or H-endo-born-S) were tested; the best results (27% yield and 62% ee in favor of the RP enantiomer) were obtained by using Bu2(endo-born-S)ZnLi in tetrahydrofuran (THF) at -30 °C before iodolysis. Due to the low compatibility of FcCO2Me with alkyl-containing lithium zincates, 1?:?1 mixtures of lithium and zinc amides were tested. Chiral (H-exo-born-R or H-endo-born-S) or/and achiral (lithium 2,2,6,6-tetramethylpiperidide or lithium diisopropylamide) secondary amines gave good results, the best (81% yield and 44% ee in favor of the RP enantiomer) being obtained by using (endo-born-S)3ZnLi in THF at room temperature. Among other secondary amines also prepared and/or tested, commercial (S,S)-bis(α-phenylethyl)amine (H-PEA-S) proved promising. After optimization of the reaction conditions, the best enantioselectivity (26% yield and 80% ee in favor of the RP enantiomer) was observed by treating a THF solution of FcCO2Me and Zn(PEA-S)2 with Li-PEA-S at -80 °C before iodolysis. That no reaction took place with cadmium instead of zinc suggests the formation of 'ate complexes upon treatment of Cd(PEA-S)2 by Li-PEA-S while Zn(PEA-S)2 and Li-PEA-S would rather work in tandem (Li-PEA-S as the base and Zn(PEA-S)2 as the in situ trap for the formed ferrocenyllithium). While FcCO2Me, FcCO2tBu and FcCO2iPr could be converted into their racemic 2-iodinated derivatives with a yield of 84 to 87% by employing LiTMP (2 equiv.) in the presence of ZnCl2·TMEDA (1 equiv.) as an in situ trap, their enantioselective deprotometalation rather required Li-PEA-S together with Zn(PEA-S)2 to produce the enantio-enriched derivatives with yields of 45-82% and 71% ee. This journal is
New chemical agents based on adamantane-monoterpene conjugates against orthopoxvirus infections
Agafonov, Alexander P.,Bormotov, Nikolay I.,Korchagina, Dina V.,Maksyutov, Rinat A.,Mozhaytsev, Evgenii S.,Salakhutdinov, Nariman F.,Serova, Olga A.,Shishkina, Larisa N.,Suslov, Evgenii V.,Volcho, Konstantin P.,Yarovaya, Olga I.
, p. 1185 - 1195 (2020/11/03)
Currently, the spectrum of agents against orthopoxviruses, in particular smallpox, is very narrow. Despite the fact that smallpox is well controlled, there is, for many reasons, a real threat of epidemics associated with this or a similar virus. In order to search for new low molecular weight orthopoxvirus inhibitors, a series of amides combining adamantane and monoterpene moieties were synthesized using 1- and 2-adamantanecarboxylic acids as well as myrtenic, citronellic and camphorsulfonic acids as acid components. The produced compounds exhibited high activity against the vaccinia virus (an enveloped virus belonging to the poxvirus family), which was combined with low cytotoxicity. Some compounds had a selectivity index higher than that of the reference drug cidofovir; the highest SI = 1123 was exhibited by 1-adamantanecarboxylic acid amide containing the (-)-10-amino-2-pinene moiety. The produced compounds demonstrated inhibitory activity against other orthopoxviruses: cowpox virus (SI = 30-406) and ectromelia virus (mousepox virus, SI = 39-707). This journal is
New chiral ebselen analogues with antioxidant and cytotoxic potential
Pacu?a, Agata J.,Kaczor, Katarzyna B.,Antosiewicz, J?drzej,D?ugosz, Angelika,Janecka, Anna,Janecki, Tomasz,Wojtczak, Andrzej,?cianowski, Jacek,Santi, Claudio,Bagnoli, Luana,Dembinski, Roman
, (2017/04/03)
New chiral camphane-derived benzisoselenazol-3(2H)-ones and corresponding diselenides have been synthetized using a convenient one-pot procedure. Se-N bond was efficiently converted to an Se-Se bond, which could also be easily re-oxidized to the initial benzisoselenazolone moiety. The antioxidant activity of camphor derivatives was evaluated and compared to the reactivity of a series of N-amino acid benzisoselenazol-3(2H)-ones obtained by a modified procedure involving the improved synthesis and isolation of the diseleno bis(dibenzoic) acid. The most efficient peroxide scavengers, N-bornyl and N-leucine methyl ester benzisoselenazol-3(2H)-ones, were further evaluated as cytotoxic agents on four cancer cell lines (MCF-7, HEP G2, HL 6, and DU 145) and normal cell line PNT1A. The highest antiproliferative potential was evaluated for two compounds bearing a 3-methylbutyl carbon chain, N-leucine methyl ester and N-3-methylbutyl benzisoselenazol-3(2H)-ones.
Diastereoselective desymmetrization of diarylphosphinous acid-borane amides under Birch reduction
Stankevi?, Marek
, p. 6082 - 6102 (2015/06/08)
Treatment of diarylphosphinous acid-borane amides possessing chiral amido functionality with an alkali metal solution in liquid ammonia induced a preferential dearomatization of one aryl substituent at phosphorus leading to the formation of non-equimolar amounts of diastereomers. Diastereoselectivity of dearomatization depends strongly on the structure of a chiral auxiliary.
Direct amination of bio-alcohols using ammonia
Pingen, Dennis,Diebolt, Olivier,Vogt, Dieter
, p. 2905 - 2912 (2013/10/21)
A slightly adapted catalyst system has been successfully applied in the direct amination of primary and secondary alcohols. Moreover, the applicability to diols has been shown, giving high selectivity towards the primary diamines. It was found that the Ru/P ratio as well as the amount of ammonia used are highly important in this system, especially for higher substrate loadings. The catalyst was employed on a larger batch scale for the conversion of isomannide to the corresponding diamine. Additionally, it was shown that the catalyst is stable for at least six consecutive runs. No significant loss of activity and selectivity was observed.
The effects of added ammonium chloride in the reductive amination of some carbonyl compounds over Ru and Pd catalysts
Ikenaga, Tomoaki,Matsushita, Kumiko,Shinozawa, Junichi,Yada, Satoru,Takagi, Yuzuru
, p. 2105 - 2109 (2007/10/03)
The reductive amination of acetophenone, (+)-camphor, and 5α-cholestan-3-one over Ru and Pd metals as well as their carbon-supported catalysts gave corresponding amines together with alcohols as by-products. However, we found that the corresponding amines are selectively synthesized by the addition of ammonium chloride to the reaction system with depression of the formation of alcohol, as exemplified with acetophenone. Although alcohols are usually not formed over Pd with alicyclic ketones, the alcohols formation was effectively depressed over Ru in the presence of ammonium chloride. The effects of the additive on the stereoselectivity of the formation of amines are also discussed in the cases of (+)-camphor and 5α-cholestan-3-one.
The endo- and exo-1,7,7-Trimethylbicyclo-heptan-2-amines (Bornan-2-amines) and Their Acetamides
Carman, Raymond M.,Greenfield, Kay L.
, p. 1785 - 1790 (2007/10/02)
Melting points provide a poor method for differentiation between the exo and endo N-(bornan-2-yl)-acetamides, and have led to errors by previous workers.Spectral differences leading to unambiguous assignment are discussed in this paper.Trapping of the bornan-2-yl carbenium ion with acetonitrile leads to exo products.
