105250-16-6Relevant academic research and scientific papers
Regioselective hydroxylation of 2,4-lutidine: A practical synthesis of 4-hydroxymethyl-2-methylpyridine
Ragan, John A.,Jones, Brian P.,Meltz, Clifford N.,Teixeira Jr., John J.
, p. 483 - 486 (2002)
A practical synthesis of 4-hydroxymethyl-2-methylpyridine has been developed which makes use of Evans' regioselective lithiation of readily available 2,4-lutidine and trapping with dimethylformamide.
Photochemical C-H Silylation and Hydroxymethylation of Pyridines and Related Structures: Synthetic Scope and Mechanisms
Rammal, Fatima,Gao, Di,Boujnah, Sondes,Hussein, Aqeel A.,Lalevée, Jacques,Gaumont, Annie-Claude,Morlet-Savary, Fabrice,Lakhdar, Sami
, p. 13710 - 13717 (2020/11/30)
Considering the synthetic relevance of heteroarenes in various areas ranging from organic synthesis to medicinal chemistry, developing practically simple methodologies to access functionalized heteroarenes is of a significant value. Described herein is an efficient approach for C-H silylation and hydroxymethylation of pyridines and related heterocycles by the combination of silanes or methanol with readily available N-methoxypyridinium ions with a low catalyst loading (2 mol %) under blue light irradiation. The synthetic importance of the developed reactions is demonstrated by the synthesis of biologically relevant compounds. Electron paramagnetic resonance spectroscopy, quantum yield measurements, and density-functional theory calculations allowed us to understand reaction mechanisms of both photocatalytic reactions.
QUINAZOLINE DERIVATIVES AS TYROSINE KINASE INHIBITOR, COMPOSITIONS, METHODS OF MAKING THEM AND THEIR USE
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Page/Page column 547, (2020/05/13)
The present disclosure relates to new compounds or pharmaceutically acceptable salts or stereoisomers thereof of formula I as inhibitors of receptor tyrosine kinases (RTK), in particular extracellular mutants of ErbB-receptors. The present disclosure also relates to methods of preparation these compounds, compositions comprising these compounds, and methods of using them in the treatment of cancer in mammals (e.g. humans).
An anthrone-based Kv7.2/7.3 channel blocker with improved properties for the investigation of psychiatric and neurodegenerative disorders
Porter, Jacob D.,Vivas, Oscar,Weaver, C. David,Alsafran, Abdulmohsen,DiMilo, Elliot,Arnold, Leggy A.,Dickson, Eamonn J.,Dockendorff, Chris
supporting information, (2019/11/11)
A set of novel Kv7.2/7.3 (KCNQ2/3) channel blockers was synthesized to address several liabilities of the known compounds XE991 (metabolic instability and CYP inhibition) and the clinical compound DMP 543 (acid instability, insolubility, and lipophilicity). Using the anthrone scaffold of the prior channel blockers, alternative heteroarylmethyl substituents were installed via enolate alkylation reactions. Incorporation of a pyridazine and a fluorinated pyridine gave an analog (compound 18, JDP-107) with a promising combination of potency (IC50 = 0.16 μM in a Kv7.2 thallium flux assay), efficacy in a Kv7.2/7.3 patch clamp assay, and drug-like properties.
Spin-Center Shift-Enabled Direct Enantioselective α-Benzylation of Aldehydes with Alcohols
Nacsa, Eric D.,MacMillan, David W. C.
supporting information, p. 3322 - 3330 (2018/03/13)
Nature routinely engages alcohols as leaving groups, as DNA biosynthesis relies on the removal of water from ribonucleoside diphosphates by a radical-mediated "spin-center shift" (SCS) mechanism. Alcohols, however, remain underused as alkylating agents in synthetic chemistry due to their low reactivity in two-electron pathways. We report herein an enantioselective α-benzylation of aldehydes using alcohols as alkylating agents based on the mechanistic principle of spin-center shift. This strategy harnesses the dual activation modes of photoredox and organocatalysis, engaging the alcohol by SCS and capturing the resulting benzylic radical with a catalytically generated enamine. Mechanistic studies provide evidence for SCS as a key elementary step, identify the origins of competing reactions, and enable improvements in chemoselectivity by rational photocatalyst design.
INDOLIZINE INHIBITORS OF 5-LIPOXYGENASE
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, (2011/04/24)
Described herein are compounds and pharmaceutical compositions containing such compounds, which inhibit the activity of 5-lipoxygenase (5-LO). Also described herein are methods of using such 5-LO inhibitors, alone and in combination with other compounds, for treating respiratory, cardiovascular, and other leukotriene-dependent or leukotriene mediated conditions, diseases, or disorders.
COMPOUNDS AND METHODS FOR INHIBITION OF RENIN, AND INDICATIONS THEREFOR
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Page/Page column 64, (2010/11/18)
Compounds active as inhibitors of renin are described, as well as methods of using such compounds to treat diseases and conditions associated with the renin-angiotensin system. Formula (I)
PYRIDINE DERIVATIVES SUBSTITUTED BY HETEROCYCLIC RING AND PHOSPHONOAMINO GROUP, AND ANTI-FUNGAL AGENT CONTAINING SAME
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Page/Page column 96, (2009/04/24)
Anti-fungal agent having excellent anti-fungal action physicochemical properties including safety and water solubility. Compound represented by formula (I), or salt thereof: wherein R1 represents hydrogen, halogen, amino, R11-NH- wherein R11 represents C1-6 alkyl, hydroxy C1-6 alkyl, C1-6 alkoxy C1-6 alkyl, or C1-6alkoxycarbonyl C1-6 alkyl, R12-(CO)-NH- wherein R12 represents C1-6 alkyl group or C1-6 alkoxy C1-6 alkyl, C1-6 alkyl, hydroxy C1-6 alkyl, cyano C1-6 alkyl, C1-6 alkoxy, or C1-6 alkoxy C1-6 alkyl or a phosphonoamino group; R2 represents hydrogen, C1-6 alkyl, amino, or a di C1-6 alkylamino group or a phosphonoamino group; one of X and Y is nitrogen while the other is nitrogen or oxygen; ring A represents a 5- or 6-member heteroaryl ring or a benzene ring which may have a halogen atom or 1 or 2 C1-6 alkyl groups; Z represents a single bond, a methylene group, an ethylene group, oxygen, sulfur, -CH2O-, -OCH2-, -NH-, -CH2NH-, -NHCH2-, -CH2S-, or -SCH2-; R3 represents hydrogen or halogen or C1-6 alkyl, C3-8 cycloalkyl, C6-10 aryl, a 5- or 6-member heteroaryl group or a 5- or 6-member nonaromatic heterocyclic group which may have 1 or 2 substituents; and R4 represents hydrogen or halogen; provided that either R1 or R2 represents a phosphonoamino group.
BICYCLOSULFONYL ACID (BCSA) COMPOUNDS AND THEIR USE AS THERAPEUTIC AGENTS
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Page/Page column 69-70; 131, (2009/01/20)
This invention pertains generally to the field of therapeutic compounds, and more particularly, to certain bicyclosulfonyl acid (BCSA) compounds which act as inhibitors of Tumour Necrosis Factor-α Converting Enzyme (TACE). The compounds are useful in the
Novel HIV reverse transcriptase inhibitors
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Page/Page column 97, (2008/06/13)
The invention is related to compounds of Formula (I), (II), or (III): or a pharmaceutically acceptable salt, solvate, ester, and/or phosphonate thereof, compositions containing such compounds, and therapeutic methods that include the administration of such compounds.
