30932-84-4

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 94, p. 3877, 1972 DOI: 10.1021/ja00766a036

Upstream product

• 114724-98-0 (+/-)-1-methyl-2-oxo-pyrrolidine-3-carboxylic acid methyl ester 
• 872-50-4 1-methyl-pyrrolidin-2-one 
• 1370017-97-2 benzyl-1-methyl-2-oxopyrrolidine-3-carboxylate 
• 30932-85-5 1-methyl-2-oxo-pyrrolidine-3-carboxylic acid ethyl ester 

Downstream Products

• 949557-96-4 N-(3-fluoro-4-(3-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl)-1-methyl-2-oxopyrrolidine-3-carboxamide 
• 1370018-09-9 N-benzyl-1-methyl-2-oxo-N-phenylpyrrolidine-3-carboxamide 
• 1370018-10-2 N-(4-chlorophenyl)-N,1-dimethyl-2-oxopyrrolidine-3-carboxamide 
• 1370018-46-4 N-(2,4-dimethoxybenzyl)-N-(4-methoxyphenyl)-1-methyl-2-oxopyrrolidine-3-carboxamide 
• 891186-81-5 (S)-1-(2,4-dimethoxybenzyl)-5-methoxy-1'-methylspiro[indoline-3,3'-pyrrolidine]-2,2'-dione 
• 81197-57-1 (±)-1-methyl-2-oxo-N-phenylpyrrolidine-3-carboxamide 
• 1370018-06-6 N,1-dimethyl-2-oxo-N-phenylpyrrolidine-3-carboxamide 
• 1370018-47-5 1-(2,4-dimethoxybenzyl)-5-methoxy-1'-methylspiro[indoline-3,3'-pyrrolidine]-2,2'-dione 
• 1370018-31-7 1-benzyl-1'-methylspiro[indoline-3,3'-pyrrolidine]-2,2'-dione 
• 946505-34-6 N-(3-fluoro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)phenyl)-1-methyl-2-oxopyrrolidine-3-carboxamide 

Relevant academic research and scientific papers

Discovery and Structure-Based Optimization of Next-Generation Reversible Methionine Aminopeptidase-2 (MetAP-2) Inhibitors

Co- and post-translational processing are crucial maturation steps to generate functional proteins. MetAP-2 plays an important role in this process, and inhibition of its proteolytic activity has been shown to be important for angiogenesis and tumor growth, suggesting that small-molecule inhibitors of MetAP-2 may be promising options for the treatment of cancer. This work describes the discovery and structure-based hit optimization of a novel MetAP-2 inhibitory scaffold. Of critical importance, a cyclic tartronic diamide coordinates the MetAP-2 metal ion in the active site while additional side chains of the molecule were designed to occupy the lipophilic methionine side chain recognition pocket as well as the shallow cavity at the opening of the active site. The racemic screening hit from HTS campaign 11a was discovered with an enzymatic IC50 of 150 nM. The resynthesized eutomer confirmed this activity and inhibited HUVEC proliferation with an IC50 of 1.9 μM. Its structural analysis revealed a sophisticated interaction pattern of polar and lipophilic contacts that were used to improve cellular potency to an IC50 of 15 nM. In parallel, the molecular properties were optimized on plasma exposure and antitumor efficacy which led to the identification of advanced lead 21.

Copper-catalyzed intermolecular chloro- and bromotrifluoromethylation of alkenes

A highly practical copper-catalyzed intermolecular halotrifluoromethylation of alkenes has been developed under mild reaction conditions. A variety of Cl/Br-containing trifluoromethyl derivatives were directly synthesized from a wide range of alkenes, including electron-deficient and unactivated alkenes.

DDQ-mediated direct Intramolecular-Dehydrogenative-Coupling (IDC): Expeditious approach to the tetracyclic core of ergot alkaloids

An efficient route to 2-oxindoles bearing an all-carbon quaternary center at the pseudobenzylic position has been developed via a DDQ-mediated Intramolecular-Dehydrogenative-Coupling (IDC). The methodology involves a one-pot C-alkylation of β-N-arylamido esters (7) concomitant with dehydrogenative-coupling in the presence of stoichiometric amount of DDQ. A tentative mechanistic route has been proposed for the oxidative coupling. The methodology provides a two-step entry to the ergoline structure of ergot alkaloids.

Copper-catalysed approach to spirocyclic oxindoles via a direct C-H, Ar-H functionalisation

A practical and efficient entry to spirocyclic oxindoles from readily accessible anilide precursors, using only catalytic amounts of an inexpensive copper salt together with air as the sole re-oxidant, is described. In addition to providing access to a br

Heterobicyclic pyrazole compounds and methods of use

Compounds of Formulas Ia and Ib, and stereoisomers, geometric isomers, tautomers, solvates, metabolites and pharmaceutically acceptable salts thereof, are useful for inhibiting receptor tyrosine kinases and for treating disorders mediated thereby. Methods of using compounds of Formula Ia and Ib, and stereoisomers, geometric isomers, tautomers, solvates and pharmaceutically acceptable salts thereof, for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions are disclosed.

QUINOLINE COMPOUNDS AND METHODS OF USE

Compounds of Formula I, and stereoisomers, geometric isomers, tautomers, solvates, metabolites, salts and pharmaceutically acceptable prodrugs thereof, are useful for inhibiting receptor tyrosine kinases and for treating hyperproliferative disorders mediated thereby. Methods of using compounds of Formula I, and stereoisomers, geometric isomers, tautomers, solvates and pharmaceutically acceptable salts thereof, for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions are disclosed. [ Formula I]