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.
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Grosheintz,Fischer
, p. 2022 (1941)
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Gilman,Soddy
, p. 565 (1957)
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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).
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Zymalkowski
, p. 682,690 (1959)
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Klosa
, p. 426 (1955)
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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.
Design, synthesis and biological evaluation of novel thiohydantoin derivatives as potent androgen receptor antagonists for the treatment of prostate cancer
Wang, Ao,Wang, Yawan,Meng, Xin,Yang, Yushe
, (2021/01/07)
Prostate cancer (PC) is the most common malignancy in men worldwide. Here, two series of novel thiohydantoin derivatives of enzalutamide as potent androgen receptor (AR) antagonists were designed and synthesized. Among them, compound 31c was identified as an AR antagonist which is 2.3–fold more potent than enzalutamide. Molecular docking studies were performed to explain the improved potency of 31c at AR. In cell proliferation assays, 31c exhibited similar anti-proliferative activities with enzalutamide against hormone sensitive LNCaP cells and AR-overexpressing LNCaP/AR cells. These data indicate that 31c can be a good lead compound for further structure optimization for the treatment of prostate cancer.
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.
