- Reaction of β-alkoxyvinyl α-ketoesters with acyclic NCN binucleophiles – Scalable approach to novel functionalized pyrimidines
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Two protocols for synthesis of series of low-molecular-weight di- and tri-substituted pyrimidines bearing a functional group at the 4th position, which rely on a base-mediated condensation of amidines or guanidines with β-alkoxyvinyl α-keto esters, have been developed. This approach allowed for multigram preparation of novel pyrimidine-4-carboxylates in 21–90% yield. The synthetic utility of these compounds was demonstrated by some standard functional group transformations providing promising building blocks for organic synthesis and drug discovery.
- Stepaniuk, Oleksandr O.,Rudenko, Tymofii V.,Vashchenko, Bohdan V.,Matvienko, Vitalii O.,Kondratov, Ivan S.,Tolmachev, Andrey A.,Grygorenko, Oleksandr O.
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supporting information
p. 3472 - 3478
(2019/05/17)
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- 4-PHENYL-5-OXO-1,4,5,6,7,8-HEXAHYDROQUINOLINE DERIVATIVES THE TREATMENT OF INFERTILITY
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The present invention relates to 4-phenyl-5-oxo-l,4)5,6,7,8-hexahydroquinoline derivatives according to Formula I, Formula I or a pharmaceutically acceptable salt thereof, wherein R1 is (l-6C)alkyl, (2-6C)alkenyl or (2-6C)aDcynyl; R2, R3 are independently halogen, (l-4C)allcyl, (2-4C)alkenyl, (2-4C)- alkynyl, (1 -4C)aBcoxy, (3-4C)alkenyloxy or (3-4C)alkynyloxy; R4 is phenyl or (2-5C)- heteroaryl, both substituted with R7 and optionally substituted on the (hetero)aromatic ring with one or more substituents selected from hydroxy, amino, halogen, nitro, trifluoromethyl, cyano, (l-4C)alkyl, (l-4C)alkoxy , (l-4C)alkylthio and (di)(l-4C)- alkylamino. The invention also relates to pharmaceutical compositions comprising said derivatives, as well as to the use of these 4-phenyl-5-oxo-l, 4,5,6, 7,8-hexahydro- quinoline derivatives in therapy, more specifically for the treatment of infertility
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Page/Page column 46
(2010/11/24)
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- Development of orally bioavailable bicyclic pyrazolones as inhibitors of tumor necrosis factor-α production
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2-Aryl-3-pyrimidinyl based tumor necrosis factor-α (TNF-α) inhibitors, which contain a novel bicyclic pyrazolone core, are described. Many showed low-nanomolar activity against lipopolysaccharide-induced TNF-α production in monocytic cells. Secondary scre
- Clark, Michael P.,Laughlin, Steven K.,Laufersweiler, Matthew J.,Bookland, Roger G.,Brugel, Todd A.,Golebiowski, Adam,Sabat, Mark P.,Townes, Jennifer A.,VanRens, John C.,Djung, Jane F.,Natchus, Michael G.,De, Biswanath,Hsieh, Lily C.,Xu, Susan C.,Walter, Rick L.,Mekel, Marlene J.,Heitmeyer, Sandra A.,Brown, Kimberly K.,Juergens, Karen,Taiwo, Yetunde O.,Janusz, Michael J.
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p. 2724 - 2727
(2007/10/03)
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- N-substituted nonaryl-heterocyclo amidyl NMDA/NR2B Antagonists
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Compounds represented by Formula (I): or pharmaceutically acceptable salts thereof, are effective as NMDA NR2B antagonists useful for relieving pain.
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- Synthesis of Pyrimidin-2-one Nucleosides as Acid-Stable Inhibitors of Cytidine Deaminase
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One of the problems encountered in the use of the tetrahydrouridine (THU, 2) and saturated 2-oxo-1,3-diazepine nucleosides as orally administered cytidine deaminase (CDA) inhibitors is their acid instability.Under acid conditions these compounds are rapid
- Kim, Chong-Ho,Marquez, Victor E.,Mao, David T.,Haines, David R.,McCormack, John J.
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p. 1374 - 1380
(2007/10/02)
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- Lithiation in the Synthesis of 5-Pyrimidinyl Ketones
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A method for the preparation of 2-substituted 5-pyrimidinyl aryl or heteroaryl ketones from 5-bromo-2-methylthiopyrimidine-4-carboxylic acid is described.The latter was lithiated and reacted with an aroyl or heteroaroyl chloride to give the corresponding
- Arukwe, Joseph,Undheim, Kjell
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p. 588 - 592
(2007/10/02)
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