10210-17-0Relevant articles and documents
Nitric oxide donating anilinopyrimidines: Synthesis and biological evaluation as EGFR inhibitors
Han, Chun,Huang, Zhangjian,Zheng, Chao,Wan, Ledong,Lai, Yisheng,Peng, Sixun,Ding, Ke,Ji, Hongbin,Zhang, Yihua
, p. 82 - 90 (2013)
To search for potent nitric oxide (NO) donating epidermal growth factor receptor (EGFR) inhibitors, a series of phenylsulfonylfuroxan-based anilinopyrimidines 10a-h were synthesized and biologically evaluated. Compounds 10f-h exhibited potent inhibitory activity against EGFR L858R/T790M and were as potent as WZ4002 in inhibition of H1975 cells harboring EGFR L858R/T790M. Additionally, 10h produced high levels of NO in H1975 cells but not in normal human cells, and its antiproliferative activity was diminished by hemoglobin, an NO scavenger. Furthermore, 10h inhibited EGFR activation and downstream signaling in H1975 cells. These results suggest that the strong antiproliferative activity of 10h could be attributed to the synergic effects of high levels of NO production and inhibition of EGFR and downstream signaling in the cancer cells.
A convenient method to reduce hydroxyl-substituted aromatic carboxylic acid with NaBH4/Me2SO4/B(OMe)3
Zhou, Yuhan,Gao, Guchao,Li, Hui,Qu, Jingping
, p. 3260 - 3263 (2008)
The reduction of hydroxyl-substituted aromatic carboxylic acid with NaBH4/Me2SO4/B(OMe)3 is described. Borane is generated by the reaction of NaBH4 with Me2SO4 in THF, which is as efficient as the commercial one. B(OMe)3 has been successfully applied to increase the reactivity and selectivity of this reaction. The optimum ratio of borane/B(OMe)3/acid is studied, and a variety of hydroxyl-substituted aromatic acids are reduced in good yields.
Copper-catalyzed asymmetric silylative cyclization of cyclohexadienone-containing 1,6-enynes
He, Cheng-Yu,Xie, Li-Bo,Ding, Rui,Tian, Ping,Lin, Guo-Qiang
, p. 1682 - 1688 (2019)
The first copper-catalyzed asymmetric silylative cyclization of cyclohexadienone-containing 1,6-enynes has been accomplished through a tandem process: regioselective silylcupration of terminal unactivated alkynes and subsequently enantioselective conjugate addition to cyclohexadienones. This reaction proceeded smoothly to afford the cis-hydrobenzofuran and cis-hydroindole frameworks bearing two consecutive chiral carbon centers in high to excellent yields and moderate enantioselectivities. Additionally, the cyclization products could be readily subjected to several transformations for elaborating synthetic utilities.
Synthesis and antiproliferative activity of a new compound containing an α-methylene-γ-lactone group
González, Antonio G.,Silva, Margarita Hernández,Padrón, Juan I.,León, Francisco,Reyes, Eduardo,álvarez-Mon, Melchor,Pivel, Juan P.,Quintana, José,Estévez, Francisco,Bermejo, Jaime
, p. 2358 - 2361 (2002)
The biological activity of compound 9 obtained by introducing an α-methylene-γ-butyrolactone group into 3-(4-hydroxyphenyl)propionic acid, 1, was studied for possible effects on HL-60 cells, murine splenocytes, and human peripheral mononuclear cells (PBMC). 9 induced apoptosis in the HL-60 cell line and has a clear capacity to inhibit proliferation induced in murine splenocytes and PBMC by different mitogenic agents with no apparent toxic side effects. 9 was synthesized from 1, and its structure and stereochemistry were elucidated by spectroscopic methods.
New approaches to the synthesis of aromatic polyesters
Mikitaev,Bedanokov, A. Yu.,Mikitaev
, p. 1998 - 2005 (2009)
A new method of the synthesis of high molecular polybutylene terephthalate (PBT) is developed with the use of Irganox 1010, tris(nonylphenyl) phosphite and hypophosphite as stabilizers and boron nitride or boron oxide as a catalyst is proposed.
DITERPENES FROM BACCHARIS SPECIES
Bohlmann, Ferdinand,Kramp, Wolfgang,Grenz, Michael,Robinson, Harold,King, Robert M.
, p. 1907 - 1914 (1981)
The investigation of ten Baccharis species afforded in addition to known compounds eight new diterpenes, four ent-labdanes, three kaurenes and a clerodane derivative.Furthermore, two new p-hydroxyacetophenones, a flavone, 3'-methoxyxanthomicrol and two matricaria ester derivatives were isolated.The structures were elucidated by spectroscopic methods and a few chemical transformations.The chemotaxonomic situation of the large genus is discussed briefly. - Keywords: Baccharis species; Compositae; diterpenes; ent-labdanes; clerodane; ent-kauranes; p-hydroxyacetophenone derivatives; acetylenes; flavone; 3'-methoxyxanthomicrol.
CINNAMIC ACID BRIDGES BETWEEN CELL WALL POLYMERS IN WHEAT AND PHALARIS INTERNODES
Lam, Thi Bach Tuyet,Iiyama, Kenji,Stone, Bruce A.
, p. 1179 - 1184 (1992)
A method has been devised for the quantitative determination of cinnamic acids participating in ester-ether bridges between cell wall polymers based on the different reactivities of free carboxylic acids and their esters towards borohydride reductants and the different susceptibilities of cinnamic acid ester and benzyl ether linkages to alkaline treatments.Lignin-poylsaccharide containing fractions extracted with dioxane-H2O from cell walls of wheat (Triticum aestivum) and phalaris (phalaris aquatica) internodes are hydrogenated using a Pd/C catalyst at room temperature to convert cinnamic acids to their corresponding dihydrocinnamic acids.The sample is subsequently reduced with LiBH4 in ether-toluene to convert ester-linked dihydrocinnamates to their corresponding alcohols, hydrolysed with 4 M NaOH at 170 deg, and the dihydrocinnamic acid derivatives released from their etherified forms determined by GC.Using model compounds it was shown that these reactions proceeded quantitatively.The results indicate that all of the etherified ferulic acid in the dioxane-H2O-soluble fractions of walls of wheat and phalaris internodes is also ester-linked.It has been calculated that there are nine to 10 ferulic acid ester-ether bridges for every 100 C6-C3 lignin monomers. p-Coumaric acid is not involved in ester-ether bridges. Key Word Index - Triticum aestivum; Phalaris aquatica; Gramineae; lignin; polysaccharide; p-coumaric acid; ferulic acid; esterified cinnamic acid; etherified cinnamic acid.
Scope and limitations of biocatalytic carbonyl reduction with white-rot fungi
Zhuk, Tatyana S.,Skorobohatko, Oleksandra S.,Albuquerque, Wendell,Zorn, Holger
supporting information, (2021/02/02)
The reductive activity of various basidiomycetous fungi towards carbonyl compounds was screened on an analytical level. Some strains displayed high reductive activities toward aromatic carbonyls and aliphatic ketones. Utilizing growing whole-cell cultures of Dichomitus albidofuscus, the reactions were up-scaled to a preparative level in an aqueous system. The reactions showed excellent selectivities and gave the respective alcohols in high yields. Carboxylic acids were also reduced to aldehydes and alcohols under the same conditions. In particular, benzoic, vanillic, ferulic, and p-coumaric acid were reduced to benzyl alcohol, vanillin, dihydroconiferyl alcohol and 1-hydroxy-3-(4-hydroxyphenyl)propan, respectively.
Biocatalytic reduction of α,β-unsaturated carboxylic acids to allylic alcohols
Aleku, Godwin A.,Leys, David,Roberts, George W.
, p. 3927 - 3939 (2020/07/09)
We have developed robust in vivo and in vitro biocatalytic systems that enable reduction of α,β-unsaturated carboxylic acids to allylic alcohols and their saturated analogues. These compounds are prevalent scaffolds in many industrial chemicals and pharmaceuticals. A substrate profiling study of a carboxylic acid reductase (CAR) investigating unexplored substrate space, such as benzo-fused (hetero)aromatic carboxylic acids and α,β-unsaturated carboxylic acids, revealed broad substrate tolerance and provided information on the reactivity patterns of these substrates. E. coli cells expressing a heterologous CAR were employed as a multi-step hydrogenation catalyst to convert a variety of α,β-unsaturated carboxylic acids to the corresponding saturated primary alcohols, affording up to >99percent conversion. This was supported by the broad substrate scope of E. coli endogenous alcohol dehydrogenase (ADH), as well as the unexpected CC bond reducing activity of E. coli cells. In addition, a broad range of benzofused (hetero)aromatic carboxylic acids were converted to the corresponding primary alcohols by the recombinant E. coli cells. An alternative one-pot in vitro two-enzyme system, consisting of CAR and glucose dehydrogenase (GDH), demonstrates promiscuous carbonyl reductase activity of GDH towards a wide range of unsaturated aldehydes. Hence, coupling CAR with a GDH-driven NADP(H) recycling system provides access to a variety of (hetero)aromatic primary alcohols and allylic alcohols from the parent carboxylates, in up to >99percent conversion. To demonstrate the applicability of these systems in preparative synthesis, we performed 100 mg scale biotransformations for the preparation of indole-3-aldehyde and 3-(naphthalen-1-yl)propan-1-ol using the whole-cell system, and cinnamyl alcohol using the in vitro system, affording up to 85percent isolated yield.
CLASS OF BIFUNCTIONAL COMPOUNDS WITH QUATERNARY AMMONIUM SALT STRUCTURE
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Paragraph 0241, (2019/11/11)
The invention provides a class of compounds represented by formula (I), having bifunctional active quaternary ammonium salt structure of a β2-adrenoreceptor agonist and an M receptor antagonist, a pharmaceutically acceptable salt, solvate, and optical isomer thereof. A pharmaceutical composition comprising such a compound with quaternary ammonium salt structure, a method for preparing such a compound with quaternary ammonium salt structure and an intermediate thereof, and uses thereof in treating pulmonary disorders are also provided. The compounds of the invention have high selectivity to the M receptor subtype, and have less adverse reaction and lower toxic and side effects in the treatment of pulmonary diseases such as COPD and asthma.
