- High Chemo-/Stereoselectivity for Synthesis of Polysubstituted Monofluorinated Pyrimidyl Enol Ether Derivatives
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A novel intramolecular Smiles rearrangement of α-fluoro-β-keto-pyrimidylsulfones (usually used as a carbon nucleophile) was developed, providing a versatile avenue for synthesis of tri/tetra-substituted monofluorinated pyrimidyl enol ethers. Among these, diverse (Z)-monofluorovinylsulfones and sulfinates were efficiently assembled by adding extra electrophile and fine-tuning reaction conditions. The process is triggered by a keto-enol tautomerism from enol oxyanion to pyrimidine 2-carbon, completely different from the classical carbon nucleophilic addition reaction approach.
- Kang, Lei,Wang, Fang,Zhang, Jinlong,Yang, Huameng,Xia, Chungu,Qian, Jinlong,Jiang, Gaoxi
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supporting information
p. 1669 - 1674
(2021/03/08)
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- FUSED-RING COMPOUNDS, PHARMACEUTICAL COMPOSITION AND USES THEREOF
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This disclosure is related to a fused-ring compound of formula (I) and/or a pharmaceutically acceptable salt thereof, a pharmaceutical composition comprising the fused ring compound of formula (I) and/or a pharmaceutically acceptable salt thereof, preparation methods thereof, and use thereof in modulating activity of indoleamine 2, 3-dioxygenase (IDO) and/or tryptophan 2, 3-dioxygenase (TDO). This disclosure further provides methods of treating IDO and/or TDO-associated diseases, including cancer, viral infection and autoimmune diseases.
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Paragraph 358; 359
(2016/09/15)
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- Synthesis and crystallographic insight into the structural aspects of some novel adamantane-based ester derivatives
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Adamantyl-based compounds are commercially important in the treatments for neurological conditions and type-2 diabetes, aside from their anti-viral abilities. Their values in drug design are chronicled as multi-dimensional. In the present study, a series of 2-(adamantan-1-yl)-2-oxoethyl benzoates, 2(a-q), and 2-(adamantan-1-yl)-2-oxoethyl 2-pyridinecarboxylate, 2r, were synthesized by reacting 1-adamantyl bromomethyl ketone with various carboxylic acids using potassium carbonate in dimethylformamide medium at room temperature. Three-dimensional structures studied using X-ray diffraction suggest that the adamantyl moiety can serve as an efficient building block to synthesize 2-oxopropyl benzoate derivatives with synclinal conformation with a looser-packed crystal packing system. Compounds 2a, 2b, 2f, 2g, 2i, 2j, 2m, 2n, 2o, 2q and 2r exhibit strong antioxidant activities in the hydrogen peroxide radical scavenging test. Furthermore, three compounds, 2p, 2q and 2r, show good anti-inflammatory activities in the evaluation of albumin denaturation.
- Kumar, C.S. Chidan,Kwong, Huey Chong,Mah, Siau Hui,Chia, Tze Shyang,Loh, Wan-Sin,Quah, Ching Kheng,Lim, Gin Keat,Chandraju, Siddegowda,Fun, Hoong-Kun
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p. 18827 - 18846
(2015/11/27)
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- Bromination of adamantane and its derivatives with tetrabromomethane catalyzed by iron compounds
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Catalytic bromination of adamantane and its derivatives with tetrabromomethane catalyzed by iron compounds has been performed. The favorable ratio of catalyst and reagents and the conditions of a selective synthesis of bromine-substituted adamantanes have been developed.
- Khusnutdinov,Shchadneva,Khisamova
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p. 184 - 187
(2015/04/14)
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- Halogenation of ketones with N-halosuccinimides under solvent-free reaction conditions
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Several aryl substituted ketones, cyclic ketones, 1,3-diketones and a β-ketoamide were halogenated with N-halosuccinimides under solvent-free reaction conditions (SFRC) at various temperatures (20-80 °C), whereas less enolized ketones required the presence of an acid catalyst (p-toluenesulfonic acid, PTSA). Bromination of substituted acetophenones obeys first order kinetics v=kBr[ketone] and the following correlation with the keto-enol equilibrium constant: log kBr=0.3pKE+C1, less enolized substrates being more reactive; the moderate positive charge developed in the rate determining step was confirmed by the Hammett correlation (ρ=-0.5). On the other hand, in cyclic ketones an opposite relation was observed: log kBr=-0.6pKE+C2, indicating higher reactivity of substrates with higher enolization constant (KE). The important role of the nature of the solvent (MeCN, MeOH) in preorganization of the ketone-NBS-PTSA mixture prior to SFRC bromination was found.
- Pravst, Igor,Zupan, Marko,Stavber, Stojan
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p. 5191 - 5199
(2008/09/21)
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- THERAPEUTIC AGENT FOR DIABETES
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A therapeutic agent for diabetes, which comprises a compound of the formula [I] wherein Xis a group of the formula wherein R4and R5are the same or different and each is a hydrogen atom, an optionally substituted alkyl having 1 to 5 carbon atoms and the like, and R6is a hydrogen atom or an amino-protecting group; R1is an optionally substituted alkyl having 1 to 5 carbon atoms, an optionally substituted alkenyl having 2 to 6 carbon atoms and the like, R2is a hydrogen atom, an optionally substituted alkyl having 1 to 5 carbon atoms and the like, R2' is a hydrogen atom, and R3is an optionally substituted alkyl having 1 to 5 carbon atoms and the like, a prodrug thereof, a pharmaceutically acceptable salt thereof, a hydrate thereof and a solvate thereof. The compound of the present invention shows superior blood sugar decreasing action on the state of hyperglycemia, but does not affect the blood sugar when it is in the normal range or in the hypoglycemic state, which means that it is free of serious side effects such as hypoglycemia. Therefore, the compound of the present invention is useful as a therapeutic drug for diabetes and also useful as a preventive of the chronic complications of diabetes.
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- SYNTHESIS OF DIOXIMES OF THE ADAMANTANE SERIES AND INVESTIGATION OF THEIR PROPERTIES
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anti-3-R-1-Adamantyl-amphi-glyoximes were obtained by the oximation of bromomethyl 3-R-1-adamantyl ketones.The configurational structure was confirmed by PMR spectroscopy.The dibenzoates of the anti-3-R-1-adamantyl-amphi-glyoximes were obtained by benzoylation.
- Moiseev, I. K.,Kalinina, M. I.,Zemtsova, M. N.,Trakhtenberg, P. L.
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p. 2058 - 2062
(2007/10/02)
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