39891-55-9Relevant academic research and scientific papers
Development of an enolate alkynylation approach towards the synthesis of the taiwanschirin natural products
Christensen, Kirsten E.,Donohoe, Timothy J.,Haughey, Maxwell B.,Poole, Darren L.
, p. 13392 - 13397 (2021/11/01)
Through the use of model studies, an approach was conceived towards the synthesis of the taiwanschirin family of natural products. These are structurally complex compounds which represent highly challenging and biologically active targets for total synthesis. This work describes a successful synthesis of the complex taiwanschirin fused [8,6,5] core through a novel alkynylation reaction coupled with an intramolecular Heck reaction used to construct the 8-membered ring.
Photocarboxylation of Benzylic C-H Bonds
Meng, Qing-Yuan,Schirmer, Tobias E.,Berger, Anna Lucia,Donabauer, Karsten,K?nig, Burkhard
supporting information, p. 11393 - 11397 (2019/08/20)
The carboxylation of sp3-hybridized C-H bonds with CO2 is a challenging transformation. Herein, we report a visible-light-mediated carboxylation of benzylic C-H bonds with CO2 into 2-arylpropionic acids under metal-free conditions. Photo-oxidized triisopropylsilanethiol was used as the hydrogen atom transfer catalyst to afford a benzylic radical that accepts an electron from the reduced form of 2,3,4,6-tetra(9H-carbazol-9-yl)-5-(1-phenylethyl)benzonitrile generated in situ. The resulting benzylic carbanion reacts with CO2 to generate the corresponding carboxylic acid after protonation. The reaction proceeded without the addition of any sacrificial electron donor, electron acceptor or stoichiometric additives. Moderate to good yields of the desired products were obtained in a broad substrate scope. Several drugs were successfully synthesized using the novel strategy.
Modulators of the Cystic Fibrosis Transmembrane Conductance Regulator Protein and Methods of Use
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Paragraph 0967, (2018/09/16)
The present invention relates to compounds and their use in the treatment of cystic fibrosis, methods for their production, pharmaceutical compositions comprising the same, and methods of treating cystic fibrosis by administering a compound of the inventi
Dynamic kinetic resolution of 2,3-dihydrobenzo[be]furans: Chemoenzymatic synthesis of analgesic agent BRL 37959
Bongen, Patrick,Pietruszka, J?rg,Simon, Robert Christian
, p. 11063 - 11070 (2012/10/07)
An efficient asymmetric synthesis of (S)-2,3-dihydrobenzo[be]furan-3- carboxylic acid (8 ) and (S)-5-chloro-2,3-dihydrobenzo[be]furan-3-carboxylic acid (8a b) was established. Key to the success was the highly stereoselective enzymatic kinetic resolution
Further structure-activity relationships in the series of tropanyl esters endowed with potent antinociceptive activity
Scapecchi, Serena,Giorgi, Antonella,Bellucci, Cristina,Dei, Silvia,Ghelardini, Carla,Manetti, Dina,Romanelli, M. Novella,Teodori, Elisabetta
, p. 764 - 772 (2007/10/03)
Several analogs of the α-tropanyl esters of 2-(4-chlorophenoxy)butyric acid (SM21) and 2-phenylthiobutyric acid (SM32), endowed with potent antinociceptive and cognition enhancing activity, were synthesized, aimed at obtaining more potent and safe drug candidates. Variation of the acyl moiety, as well as the conformational restriction of atropine to give the α-tropanyl ester of 2,3-dihydrobenzofurane-3-carboxylic acid (18), practically abolished activity. In the case of 18, the antimuscarinic activity was also severely affected by the conformation restrain. On the contrary, conformational restriction of phenoxybutyric and phenylthiobutyric acid derivatives to give the α-tropanyl ester of 2,3-dihydro-benzofurane-2-carboxylic acid and 2,3-dihydro-benzothiophene-2-carboxylic acid, afforded potent analgesic drugs that unfortunately were too toxic to be reliable drug candidates. A series of related esters of benzofurane-3-carboxylic acid and benzothiophene-3-carboxylic acid were also studied and found to be potent but toxic analgesics.
