- Palladium-catalyzed remote C-H functionalization of 2-aminopyrimidines
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A straightforward strategy was developed for the arylation and olefination at the C5-position of the N-(alkyl)pyrimidin-2-amine core with readily available aryl halides and alkenes, respectively. This approach was highly regioselective, and the transformation was achieved based on two different (Pd(ii)/Pd(iv)) and (Pd(0)/Pd(ii)) catalytic cycles.
- Das, Animesh,Jana, Akash,Maji, Biplab
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supporting information
p. 4284 - 4287
(2020/04/27)
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- COMPOSITIONS PROVIDING ENHANCED ANTIBACTERIAL ACTIVITY AGAINST GRAM-POSITIVE BACTERIA AND USE THEREOF
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A method of inhibiting, reducing growth of or destroying gram positive bacteria comprising contacting the gram positive bacteria with an effective amount of a 2-(substituted-amino)-imidazole compound and with an additional antibacterial compound separatel
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Page/Page column 20
(2020/09/08)
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- N-Methylamino Pyrimidyl Amides (MAPA): Highly Reactive, Electronically-Activated Amides in Catalytic N-C(O) Cleavage
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Despite recent progress in catalytic cross-coupling technologies, the direct activation of N-alkyl-N-aryl amides has been a challenging transformation. Here, we report the first Suzuki cross-coupling of N-methylamino pyrimidyl amides (MAPA) enabled by the controlled nN → πAr conjugation and the resulting remodeling of the partial double bond character of the amide bond. The new mode of amide activation is suitable for generating acyl-metal intermediates from unactivated primary and secondary amides.
- Meng, Guangrong,Lalancette, Roger,Szostak, Roman,Szostak, Michal
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supporting information
p. 4656 - 4659
(2017/09/12)
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- Substituted 4-phenyl-2-aminoimidazoles and 4-phenyl-4,5-dihydro-2- aminoimidazoles as voltage-gated sodium channel modulators
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Voltage-gated sodium channels play an integral part in neurotransmission and their dysfunction is frequently a cause of various neurological disorders. On the basis of the structure of marine alkaloid clathrodin, twenty eight new analogs were designed, sy
- Zidar, Nace,Jakopin, ?iga,Madge, David J.,Chan, Fiona,Tytgat, Jan,Peigneur, Steve,Dolenc, Marija Sollner,Toma?i?, Tihomir,Ila?, Janez,Ma?i?, Lucija Peterlin,Kikelj, Danijel
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supporting information
p. 23 - 30
(2014/02/14)
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- New 5-aryl-1H-imidazoles display in vitro antitumor activity against apoptosis-resistant cancer models, including melanomas, through mitochondrial targeting
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We designed and synthesized 48 aryl-1H-imidazole derivatives and investigated their in vitro growth inhibitory activity in cancer cell lines known to present various levels of resistance to proapoptotic stimuli. The IC50 in vitro growth inhibitory concentration of these compounds ranged from >100 μM to single digit μM. Among the most active compounds, 2i displayed similar in vitro growth inhibition in cancer cells independent of the cells' levels of resistance to proapoptotic stimuli and was found to be cytostatic in melanoma cell lines. Compound 2i was then tested by the National Cancer Institute Human Tumor Cell Line Anti-Cancer Drug Screen, and the NCI COMPARE algorithm did not reveal any correlation between its growth inhibition profiles with the NCI database compound profiles. The use of transcriptomically characterized melanoma models then enabled us to highlight mitochondrial targeting by 2i. This hypothesis was further confirmed by reactive oxygen production measurement and oxygen consumption analysis.
- Mathieu, Véronique,Van Den Berge, Emilie,Ceusters, Justine,Konopka, Tomasz,Cops, Antonin,Bruyère, Céline,Pirker, Christine,Berger, Walter,Trieu-Van, Tran,Serteyn, Didier,Kiss, Robert,Robiette, Rapha?l
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p. 6626 - 6637
(2013/10/01)
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- NOVEL TUBULIN INHIBITORS AND METHODS OF USING THE SAME
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Compounds represented by the formula (I) or pharmaceutically acceptable salts thereof: [in-line-formulae]R2—Y—Z-Q-A-R1??Formula (I)[/in-line-formulae] wherein R1, R2, Y, Z, Q, and A are as defined. These compoun
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Page/Page column 37-38
(2012/07/14)
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- HETEROCYCLIC COMPOUNDS CONTAINING AN INDOLE CORE
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Disclosed are novel compounds which inhibit RSK, methods of making such compounds and pharmaceutical compositions comprising such compounds. Also disclosed are methods of treating RSK2 regulated disorders using compounds of the invention.
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Page/Page column 99
(2011/06/26)
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- Structure-activity relationship of 4(5)-aryl-2-amino-1 H -imidazoles, N 1-substituted 2-aminoimidazoles and imidazo[1,2- a ]pyrimidinium salts as inhibitors of biofilm formation by salmonella typhimurium and pseudomonas aeruginosa
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A library of 112 4(5)-aryl-2-amino-1H-imidazoles, 4,5-diphenyl-2-amino-1H- imidazoles, and N1-substituted 4(5)-phenyl-2-aminoimidazoles was synthesized and tested for the antagonistic effect against biofilm formation by Salmonella Typhimurium and Pseudomo
- Steenackers, Hans P. L.,Ermolatev, Denis S.,Savaliya, Bharat,De Weerdt, Ami,De Coster, David,Shah, Anamik,Van Der Eycken, Erik V.,De Vos, Dirk E.,Vanderleyden, Jozef,De Keersmaecker, Sigrid C. J.
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experimental part
p. 472 - 484
(2011/04/15)
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- A divergent synthesis of substituted 2-aminoimidazoles from 2-aminopyrimidines
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(Chemical Equation Presented) A new divergent and efficient synthesis of substituted 2-aminoimidazoles 5 and 6 has been developed starting from the readily available 2-aminopyrimidines 1 and α-bromocarbonyl compounds 2, using conventional heating or microwave irradiation. Thus, the cleavage of 1,2,3-substituted imidazo[1,2-a]pyrimidin-1-ium salts 4 with hydrazine or secondary amines led to 1,4,5-trisubstituted 2-aminoimidazoles 5, when the hydrazinolysis of 2-hydroxy-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-4-ium salts 3, followed by a novel Dimroth-type rearrangement, resulted in formation of 2-amino-1H-imidazoles 6. The relevant pathway of transformations was identified by characterization of the intermediates.
- Ermolat'ev, Denis S.,Van Der Eycken, Erik V.
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p. 6691 - 6697
(2008/12/22)
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- Fluorescence studies of selected 2-alkylaminopyrimidines
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The reactions of 2-chloropyrimidine with methylamine, ethylamine and piperidine gave the corresponding 2-N-methylamino-, 2-N-ethylamino- and 2N-piperidinopyrimidines, respectively. The fluorescence properties of these alkylamino derivatives in chloroform, ethyl acetate, carbon tetrachloride, acetone, ether, ethanol and methanol were studied. All the alkylamino derivatives showed the highest fluorescence intensity in polar protic solvents; thus 2-N-methylaminopyrimidine (highest fluorescence intensity at 377 nm when excited at 282 nm) and 2-N-ethylaminopyrimidine (highest fluorescence intensity at 375 nm, when excited at 286 nm) showed the highest fluorescence in methanol. In ethanol, 2-N-piperidinopyrimidine showed a fluorescence peak at 403 nm when excited at 360 nm and in chloroform it fluoresced at 392 nm when excited at 356 nm.
- Abdullah,Tahir, N. Mohd.,Abas,Aiyub,Low
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p. 520 - 526
(2007/10/03)
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- A Facile Synthesis of Trifluoromethylamines by Oxidative Desulfurization-Fluorination of Dithiocarbamates
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Trifluoromethylamines are easily synthesized from dithiocarbamates by a reagent system consisting of tetrabutylammonium dihydrogentrifluoride and an N-halo imide under mild conditions. When this reaction was applied to dithiocarbamates ArN(R)CS2Me at higher temperatures, the trifluoromethylation was accompanied by halogen substitution at the p-position of the Ar group. The synthesis of trifluoromethyl-substituted adenosine is also described.
- Kanie, Kiyoshi,Mizuno, Katsuya,Kuroboshi, Manabu,Hiyama, Tamejiro
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p. 1973 - 1991
(2007/10/03)
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- Meso-ionic Compounds. Part 12. Synthesis of 1-Alkyl-4-oxopyrimido-s-triaziniumolates and their 4-Thio-derivatives
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Treatment of 2-alkylaminopyrimidines (1) and (2) with ethoxycarbonyl isocyanate gave the acyclic urea derivatives, namely, 3-alkyl-1-ethyloxycarbonyl-3-(2-pyrimidyl)ureas (3) and (4), which cyclized to 1-alkyl-4-oxopyrimido-s-triazin-1-ium-2-olates
- Greco, Claude V.,Gala, Kanti J.
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p. 331 - 335
(2007/10/02)
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