1199266-78-8Relevant articles and documents
Tandem one-pot CO2 reduction by PMHS and silyloxycarbonylation of aryl/vinyl halides to access carboxylic acids
Paridala, Kumaraswamy,Lu, Sheng-Mei,Wang, Meng-Meng,Li, Can
, p. 11574 - 11577 (2018)
The present study discloses the synthesis of aryl/vinyl carboxylic acids from Csp2-bound halides (Cl, Br, I) in a carbonylative path by using silyl formate (from CO2 and hydrosilane) as an instant CO-surrogate. Hydrosilane provides hydride for reduction and its oxidation product silanol serves as a coupling partner. Mono-, di-, and tri-carboxylic acids were obtained from the corresponding aryl/vinyl halides.
A new approach to the oxidation of methylquinolines with selenium dioxide
Achremowicz, Lucjan
, p. 1681 - 1684 (1996)
A study of some parameters which influence the oxidation of 2- and 4-methylquinolines with selenium dioxide (or selenious acid) in dioxane has allowed to correct some erroneous opinions of this method and to elaborate a general, simple, fast, and cheap procedure of oxidation of methylquinolines having a methyl group in the position 2 or 4.
Improved oxidation of active methyl group of N-heteroaromatic compounds by selenium dioxide in the presence of tert-butyl hydroperoxide
Tagawa, Yoshinobu,Yamashita, Katsuya,Higuchi, Yoshitaka,Goto, Yoshinobu
, p. 953 - 957 (2003)
The oxidation of active methyl group of N-heteroaromatic compounds including both of bicyclic and monocyclic compounds using SeO2 was considerably improved in the presence of tert-butyl hydroperoxde in dioxane to give the corresponding aldehyde or carboxylic acid in the moderate to good yields. The present oxidation proceeds more mildly and more selectively to form aldehyde rather than carboxylic acid, compared with conventional SeO2 oxidation without tert-butyl hydroperoxide.
Isolation and total synthesis of stolonines A-C, unique taurine amides from the Australian marine tunicate Cnemidocarpa stolonifera
Tran, Trong D.,Pham, Ngoc B.,Ekins, Merrick,Hooper, John N.A.,Quinn, Ronald J.
, p. 4556 - 4576 (2015)
Cnemidocarpa stolonifera is an underexplored marine tunicate that only occurs on the tropical to subtropical East Coast of Australia, with only two pyridoacridine compounds reported previously. Qualitative analysis of the lead-like enhanced fractions of C. stolonifera by LC-MS dual electrospray ionization coupled with PDA and ELSD detectors led to the identification of three new natural products, stolonines A-C (1-3), belonging to the taurine amide structure class. Structures of the new compounds were determined by NMR and MS analyses and later verified by total synthesis. This is the first time that the conjugates of taurine with 3-indoleglyoxylic acid, quinoline-2-carboxylic acid and β-carboline-3-carboxylic acid present in stolonines A-C (1-3), respectively, have been reported. An immunofluorescence assay on PC3 cells indicated that compounds 1 and 3 increased cell size, induced mitochondrial texture elongation, and caused apoptosis in PC3 cells.
Oxidation by Singlet Oxygen of 2-(2-Quinolyl)indan-1,3-dione
Kuramoto, Nobuhiro,Kitao, Teijiro
, p. 1569 - 1572 (1980)
Self-sensitised and Methylene Blue- or Rose Bengal-sensitised photo-oxidation of 2-(2-quinolyl)indan-1,3-dione (1) in solution gives phthalic acid, quinoline-2-carbaldehyde, and quinoline-2-carboxylic acid, via the reaction of singlet oxygen with (1).
Preparation of 4,7-diphenyl-1,10-phenanthroline-2,9-dicarboxylic acid catalyzed by iron(III)porphyrins with (diacetoxyiodo)benzene
Zhong, Qi-Di,Xue, Yun-Zhou,Yan, Hong,Song, Xiu-Qing,Zhong, Ru-Gang
, p. 5532 - 5535 (2010)
Using iron(III)porphyrins in combination with (diacetoxyiodo)benzene allows for the conversion of 2,9-bis(bromomethyl)-4,7-diphenyl-1,10-phenanthroline into 4,7-diphenyl-1,10-phenanthroline-2,9-dicarboxylic acid. This method provides a cost-effective and environmentally-friendly oxidation procedure using less toxic PhI(OAc)2 and biologically relevant iron(III)porphyrins. The catalytic activity of five kinds of iron-metallated functional porphyrins were investigated using different oxidants, including air, H2O 2, PhI(OAc)2, PhIO and NaClO. Our results showed that the use of T(p-NO2)PPFeCl with PhI(OAc)2 as the oxidant in the presence of water displays remarkable activity for the desired oxidation reaction. The generality of this method was examined by synthesizing the carboxylic acids of pyridines and quinolines.
1,2,3-Triazoles as versatile directing group for selective sp2 and sp3 C-H activation: Cyclization vs substitution
Ye, Xiaohan,He, Zhengrong,Ahmed, Tonia,Weise, Keith,Akhmedov, Novruz G.,Petersen, Jeffrey L.,Shi, Xiaodong
, p. 3712 - 3716 (2013)
Selective cyclization and substitution was achieved with designated 1,2,3-triazole acid auxiliary groups under Pd catalyzed C-H activation conditions. Both sp2 and sp3 C-H bonds were effectively activated, giving the desired products
Acid-induced degradation and ancillary ligand replacement of biscyclometalated iridium(III) complexes
Zhou, Yuyang,Li, Wanfei,Liu, Yang,Zhou, Ming
, p. 413 - 418 (2013)
Three biscyclometalated iridium(III) complexes with three different ancillary ligands have been investigated with respect to the final products of acid-induced transformation in coordinating or non-coordinating solvents. All of these complexes, represented as [Ir(LC^N)2L O^O] and [Ir(LC^N)2LN^O], are susceptible to acid attack, followed by the departure of the ancillary ligand, LO^O or LN^O. Depending on the coordinating ability of the solvent molecule and whether or not a coordinating anion exists, the final product will be either a solvento complex or a dichloro-bridged iridium(III) dimer. Although coexistence of the solvento complex and dichloro-bridged iridium(III) dimer was observed under certain conditions, the conversion of the solvento complex into the dichloro-bridged iridium(III) dimer has been proven. Remaining solvent: Three biscyclometalated iridium(III) complexes with three different ancillary ligands are investigated with respect to the final products of acid-induced transformation in coordinating or non-coordinating solvents (see picture). Although coexistence of the solvento complex and dichloro-bridged iridium(III) dimer is observed under certain conditions, the conversion of the solvento complex into the dichloro-bridged iridium(III) dimer is seen. Copyright
Design, synthesis and biological evaluation of amide-pyridine derivatives as novel dual-target (SE, CYP51)antifungal inhibitors
Sun, Bin,Dong, Yue,Lei, Kang,Wang, Jian,Zhao, Liyu,Liu, Min
, p. 2427 - 2437 (2019)
Based on the analysis of the squalene cyclooxygenase (SE)and 14α-demethylase (CYP51)inhibitors pharmacophore feature and the dual-target active sites, a series of compounds with amide-pyridine scaffolds have been designed and synthesized to treat the increasing incidence of drug-resistant fungal infections. In vitro evaluation showed that these compounds have a certain degree of antifungal activity. The most potent compounds 11a, 11b with MIC values in the range of 0.125–2 μg/ml had a broad-spectrum antifungal activity and exhibited excellent inhibitory activity against drug-resistant pathogenic fungi. Preliminary mechanism studies revealed that the compound 11b might play an antifungal role by inhibiting the activity of SE and CYP51. Notably compounds did not show the genotoxicity through plasmid binding assay. Finally, this study of molecular docking, ADME/T prediction and the construction of 3D QSAR model were performed. These results can point out the direction for further optimization of the lead compound.
Repurposing an Aldolase for the Chemoenzymatic Synthesis of Substituted Quinolines
Fansher, Douglas J.,Granger, Richard,Kaur, Satinderpal,Palmer, David R. J.
, p. 6939 - 6943 (2021/06/28)
Quinoline derivatives are important natural products and pharmaceuticals, but their synthesis can be challenging due to poor yields, harsh reaction conditions, and instability of starting materials. Here we report the chemoenzymatic synthesis of quinaldic acids under mild conditions using an aldolase, trans-o-hydroxybenzylidenepyruvate hydratase-aldolase (NahE, or HBPA). A series of 2-aminobenzaldehydes derived from reduction of the corresponding nitro analogue were reacted with pyruvate in the presence of NahE to give substituted quinolines in up to 93% isolated yield. This reaction differs from the aldol condensation catalyzed by NahE in vivo, instead resembling the heterocycle formation catalyzed by its homologue, dihydrodipicolinate synthase.
