620159-08-2Relevant articles and documents
De Novo Construction of Substituted Terephthalates via Phosphine Catalyzed Domino Benzannulation Reactions
Wang, Dan,Lin, Junhui,Zhu, Yannan,Huang, You
supporting information, p. 1873 - 1877 (2021/02/16)
The robustness of phosphine catalysis enabling the domino benzannulation reactions of allenoates with enamines is described. A broad array of substituted terephthalates were delivered under simple and practical reaction conditions. Furthermore, the reaction could be carried out on a gram scale with higher yield, and various conversions of the terephthalate products demonstrate the versatility of this transformation. (Figure presented.).
Asymmetric Transfer Hydrogenation of gem-Difluorocyclopropenyl Esters: Access to Enantioenriched gem-Difluorocyclopropanes
Archambeau, Alexis,Cossy, Janine,Meyer, Christophe,Pierre, Hugo,Yamani, Khalil
supporting information, p. 18505 - 18509 (2020/08/27)
Catalytic enantioselective access to disubstituted functionalized gem-difluorocyclopropanes, which are emerging fluorinated motifs of interest in medicinal chemistry, was achieved through asymmetric transfer hydrogenation of gem-difluorocyclopropenyl este
Organocatalytic trans Phosphinoboration of Internal Alkynes
Fritzemeier, Russell G.,Nekvinda, Jan,Rosenblum, Carol Ann,Santos, Webster L.,Slebodnick, Carla,Vogels, Christopher M.,Westcott, Stephen A.
supporting information, p. 14358 - 14362 (2020/07/04)
We report the first trans phosphinoboration of internal alkynes. With an organophosphine catalyst, alkynoate esters and the phosphinoboronate Ph2P-Bpin are efficiently converted into the corresponding trans-α-phosphino-β-boryl acrylate products in moderate to good yield with high regio- and Z-selectivity. This reaction operates under mild conditions and demonstrates good atom economy, requiring only a modest excess of the phosphinoboronate. X-ray crystallography experiments allowed structural assignment of the unprecedented and densely functionalized (Z)-α-phosphino-β-boryl acrylate products.
Efficient Access to Chiral β-Borylated Carboxylic Esters via Rh-Catalyzed Hydrogenation
Liu, Gang,Li, Anqi,Qin, Xueyuan,Han, Zhengyu,Dong, Xiu-Qin,Zhang, Xumu
, p. 2844 - 2848 (2019/04/26)
Rh/bisphosphine?thiourea ligand (ZhaoPhos)-catalyzed asymmetric hydrogenation of (Z)-β-substituted-β-boryl-α,β-unsaturated esters was successfully developed, furnishing a variety of chiral β-borylated carboxylic esters with high yields and excellent enantioselectivities (up to 99% yield and >99% ee). The gram-scale asymmetric hydrogenation was performed efficiently in the presence of only 0.05 mol% (S/C=2 000) catalyst loading with full conversion, 99% yield and 99% ee. Moreover, the hydrogenation product was easily converted to other versatile synthetic intermediates, such as methyl (S)-3-hydroxy-3-phenylpropanoate and methyl (S)-3-(furan-2-yl)-3-phenylpropanoate. (Figure presented.).
Synthesis of Chiral β-Borylated Carboxylic Esters via Nickel-Catalyzed Asymmetric Hydrogenation
Han, Zhengyu,Liu, Gang,Zhang, Xianghe,Li, Anqi,Dong, Xiu-Qin,Zhang, Xumu
, p. 3923 - 3926 (2019/06/14)
The highly efficient Ni-catalyzed asymmetric hydrogenation of β-boronic ester substituted-α,β-unsaturated carboxylic esters was successfully developed using (S,S)-Ph-BPE as the ligand. A series of chiral β-borylated carboxylic esters were obtained with high yields (94%-99% yields) and excellent enantioselectivities (89%-99% ee). The gram-scale asymmetric hydrogenation with a low catalyst loading (0.25 mol %) and synthetic transformation of hydrogenation product demonstrated the great synthetic utility of this methodology.
Trans-Hydroboration of Propiolamides: Access to Primary and Secondary (E)-β-Borylacrylamides
Grams, R. Justin,Fritzemeier, Russell G.,Slebodnick, Carla,Santos, Webster L.
supporting information, p. 6795 - 6799 (2019/08/26)
A base-mediated trans-hydroboration of propiolamides that provides access to previously elusive primary and secondary (E)-β-borylacrylamide products has been developed. In the presence of n-butyllithium and pinacolborane, complete regioselectivity and ste
Transition Metal-Free Trans Hydroboration of Alkynoic Acid Derivatives: Experimental and Theoretical Studies
Fritzemeier, Russell,Gates, Ashley,Guo, Xueying,Lin, Zhenyang,Santos, Webster L.
, p. 10436 - 10444 (2018/07/21)
We report a phosphine-catalyzed trans hydroboration of alkynoate esters and amides. The reaction proceeds under mild conditions with exclusive (E)-selectivity to afford (E)-β-boryl acrylates and (E)-β-boryl acrylamides in good to excellent yields. The reaction is tolerant of a variety of functional groups and allows efficient access to novel oxaboroles as well as a pargyline derivative (MAO inhibitor). Theoretical calculations suggest an internal hydride generates a phosphonium allenoxyborane followed by the formation of a key phosphonocyclobutene intermediate that collapses in a stereoselective, rate-limiting step.
Rhodium(III)-Catalyzed Redox-Neutral Cascade [3 + 2] Annulation of N-Phenoxyacetamides with Propiolates via C-H Functionalization/Isomerization/Lactonization
Pan, Jin-Long,Chen, Chao,Hao, Yu,Liu, Chang,Bai, He-Yuan,Ding, Jun,Zhang, Shu-Yu,Wang, Li-Ren,Xie, Peipei,Xia, Yuanzhi
supporting information, p. 7131 - 7136 (2018/12/14)
A Rh(III)-catalyzed cascade [3 + 2] annulation of N-phenoxyacetamides with propiolates under mild conditions using the internal oxidative O-N bond as the directing group has been achieved. This catalytic system provides a regio- and stereoselective access to benzofuran-2(3H)-ones bearing exocyclic enamino motifs with exclusive Z configuration selectivity, acceptable to good yields and good functional group compatibility. Mechanistic investigations by experimental and density functional theory studies suggest that a consecutive process of C-H functionalization/isomerization/lactonization is likely to be involved in the reaction.
Pyranone, thiopyranone, and pyridone inhibitors of phosphatidylinositol 3-kinase related kinases. Structure-activity relationships for DNA-dependent protein kinase inhibition, and identification of the first potent and selective inhibitor of the ataxia telangiectasia mutated kinase
Hollick, Jonathan J.,Rigoreau, Laurent J. M.,Cano-Soumillac, Celine,Cockcroft, Xiaoling,Curtin, Nicola J.,Frigerio, Mark,Golding, Bernard T.,Guiard, Sophie,Hardcastle, Ian R.,Hickson, Ian,Hummersone, Marc G.,Menear, Keith A.,Martin, Niall M. B.,Matthews, Ian,Newell, David R.,Ord, Rachel,Richardson, Caroline J.,Smith, Graeme C. M.,Griffin, Roger J.
, p. 1958 - 1972 (2008/02/02)
Structure-activity relationships have been investigated for inhibition of DNA-dependent protein kinase (DNA-PK) and ATM kinase by a series of pyran-2-ones, pyran-4-ones, thiopyran-4-ones, and pyridin-4-ones. A wide range of IC50 values were observed for pyranones and thiopyranones substituted at the 6-position, with the 3- and 5-positions proving intolerant to substitution. Related pyran-2-ones, pyran-4-ones, and thiopyran-4-ones showed similar IC50 values against DNA-PK, whereas the pyridin-4-one system proved, in general, ineffective at inhibiting DNA-PK. Extended libraries exploring the 6-position of 2-morpholinopyran-4-ones and 2-morpholino- thiopyrano-4-ones identified the first highly potent and selective ATM inhibitor 2-morpholin-4-yl-6-thianthren-1-yl-pyran-4-one (151C; ATM; IC50 = 13 nM) and revealed constrained SARs for ATM inhibition compared with DNA-PK. One of the most potent DNA-PK inhibitors identified, 2-(4-methoxyphenyl)-6- (morpholin-4-yl)pyran-4-one (16; DNA-PK; IC50 = 220 nM) effectively sensitized HeLa cells to the topoisomerase II inhibitor etoposide in vitro.
NOVEL COMPOUNDS, ISOMER THEREOF, OR PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF AS VANILLOID RECEPTOR ANTAGONIST; AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME
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Page/Page column 102-103, (2008/06/13)
This present invention relates to novel compounds, isomer thereof or pharmaceutically acceptable salts thereof as vanilloid receptor (Vanilloid Receotor 1; VR1; TRPV1 )antagonist; and a pharmaceutical composition containing the same. The present invention provides a pharmaceutical composition for preventing or treating a disease such as pain, migraine, arthralgia, neuralgia, neuropathies, nerve injury, skin disorder, urinary bladder hypersensitiveness, irritable bowel syndrome, fecal urgency, a respiratory disorder, irritation of skin, eye or mucous membrane, stomach-duodenal ulcer, inflammatory diseases, ear disease, and heart disease.