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.
-
Grosheintz,Fischer
, p. 2022 (1941)
-
-
Gilman,Soddy
, p. 565 (1957)
-
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).
-
Zymalkowski
, p. 682,690 (1959)
-
-
Klosa
, p. 426 (1955)
-
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.
Nickel-Catalyzed Conversion of Amides to Carboxylic Acids
Bulger, Ana S.,Garg, Neil K.,Knapp, Rachel R.
supporting information, (2020/04/02)
We report the conversion of amides to carboxylic acids using nonprecious metal catalysis. The methodology strategically employs a nickel-catalyzed esterification using 2-(trimethylsilyl)ethanol, followed by a fluoride-mediated deprotection in a single-pot operation. This approach circumvents catalyst poisoning observed in attempts to directly hydrolyze amides using nickel catalysis. The selectivity and mildness of this transformation are shown through competition experiments and the net-hydrolysis of a complex valine-derived substrate. This strategy addresses a limitation in the field with regard to functional groups accessible from amides using transition metal-catalyzed C-N bond activation and should prove useful in synthetic applications.
