4487-59-6Relevant academic research and scientific papers
Benzoheterocyclic amodiaquine analogues with potent antiplasmodial activity: Synthesis and pharmacological evaluation
Ongarora, Dennis S.B.,Gut, Jiri,Rosenthal, Philip J.,Masimirembwa, Collen M.,Chibale, Kelly
scheme or table, p. 5046 - 5050 (2012/09/07)
The synthesis and evaluation of antiplasmodial activity of benzothiazole, benzimidazole, benzoxazole and pyridine analogues of amodiaquine is hereby reported. Benzothiazole and benzoxazole analogues with a protonatable tertiary nitrogen atom possessed excellent activity against the W2 and K1 chloroquine resistant strains of Plasmodium falciparum, with IC50s ranging from 7 to 22 nM.
Nitrosation of aryl and heteroaryltrifluoroborates with nitrosonium tetrafluoroborate
Molander, Gary A.,Cavalcanti, Livia N.
experimental part, p. 4402 - 4413 (2012/06/18)
Organotrifluoroborates have emerged as an alternative to toxic and air- and moisture-sensitive organometallic species for the synthesis of functionalized aryl and heteroaryl compounds. It has been shown that the trifluoroborate moiety can be easily converted into a variety of different substituents in a late synthetic stage. In this paper, we disclose a mild, selective, and convenient method for the ipso-nitrosation of organotrifluoroborates using nitrosonium tetrafluoroborate (NOBF4). Aryl- and heteroaryltrifluoroborates were converted into the corresponding nitroso products in good to excellent yields. This method proved to be tolerant of a broad range of functional groups.
Nitropyridines: X.* Palladium-catalyzed cross-coupling of 2-bromo-5-nitropyridine with terminal acetylenes
Sagitullina,Vorontsova,Garkushenko,Poendaev,Sagitullin
experimental part, p. 1830 - 1834 (2011/04/15)
Substituted 5-nitro-2-ethynylpyridines were synthesized by the Sonogashira reaction of 2-bromo-5-5-nitropyridine with terminal acetylenes. Desilylation, oxidative decarbonylation, and the retro-Favorskii reaction of the cross-coupling products of 2-bromo-5-nitropyridine with trimethylsilylacetylene, prop-2-ynyl alcohol, and 2-methylbut-3-yn-2-ol, respectively, gave 2-ethynyl-5-nitropyridine. The hydration of 2-ethynyl-5-nitropyridine and 5-nitro-2-(phenylethynyl)pyridine according to Kucherov afforded 2-acetyl-5-nitropyridine and 5-nitro-2-phenacylpyridine, respectively. Pleiades Publishing, Ltd., 2010.
Therapeutic quinazoline derivatives
-
, (2008/06/13)
A compound of formula (I) or a salt, ester, amide or prodrug thereof; where X is O, or S, S(O), S(O)2 or NR6 where R6 is hydrogen of C1-6alkyl; R5 is an optionally substituted 6-membered aromatic ring containing at least one nitrogen atom, and R1, R2, R3, R4 are independently selected from halogeno, cyano, nitro, C1-3alkylsulphanyl, —N(OH)R7— (wherein R7 is hydrogen, or C1-3alkyl), or R9X1— (wherein X1 represents a direct bond, —O—, —CH2—, —OC(O), —C(O)—, —S—, —SO—, —SO2—, —NR10C(O)—, —C(O)NR11—, —SO2NR12—, —NR13SO2— or NR14— (wherein R10, R11, R12, R13 and R14 each independently represents hydrogen, C1-3alkyl or C1-3alkoxyC2-3alkyl), and R9 is hydrogen, optionally substituted hydrocarbyl, optionally substituted heterocyclyl or optionally substituted alkoxy; provided that at least one of R2 or R3 is other than hydrogen. These compounds inhibit aurora 2 kinase and are useful in the preparation of medicaments for the treatment of proliferative disease such as cancer.
The Synthesis of the High-Potency Sweetener, NC-00637. Part 2: Preparation of the Pyridine Moiety
Ager, David J.,Erickson, Robert A.,Froen, Diane E.,Prakash, Indra,Zhi, Ben
, p. 62 - 71 (2013/09/04)
The pyridine moiety within the high-potency sweetener, NC-00637 (1), 5-amino-2-cyanopyridine (4), was prepared from 2-hydroxy-5-nitropyridine (10). The sequence involved the conversion of the hydroxy group to bromide followed by substitution with cyanide to give 2-cyano-5-nitropyridine (8). Reduction of the nitro group proved to be troublesome when catalytic hydrogenation was used. Iron with an acid gave a reproducible reaction that could be used at scale.
Triazolylated teritiary amine compound or salt thereof
-
, (2008/06/13)
A triazolylated tertiary amine compound represented by general formula (I) or a salt thereof, having an aromatase inhibitory activity and being useful for preventing and treating breast cancer, mastopathy, endometriosis, prostatomergaly, etc., wherein A represents a single bond, lower alkylene or carbonyl; B represents lower alkyl, aryl, a 5- or 6-membered heterocyclic group, or a bicyclic fused heterocyclic group; D represents aryl, a 5- or 6-membered heterocyclic group, or a bicyclic fused heterocyclic group; and E represents 4H-1,2,4-triazolyl, 1H-1,2,4-triazolyl or 1H-1,2,3-triazolyl.
The preparation of Some 4- and 5-Substituted Pyridine-2-carboxylic Acids as Fusaric Acid Analogues.
Oehlke, J.,Schroetter, E.,Dove, S.,Schick, H.,Niedrich, H.
, p. 591 - 596 (2007/10/02)
In view of future studies on the structure-activity relationships involved in the inhibition of dopamine β-hydroxylase, the authors synthetized 5-substituted picolinic acids and 4-substituted fusaric acids selected by means of a random sampling procedure suited for small series.On this occasion, they succeeded in improving markedly the well-known synthesis of 5-nitropicolinic acid via a Rosenmund-v.Braun reaction with 2-bromo-5-nitropyridine. 5-Hydroxypicolinic acid which is easily accessible in the same way could be converted into 5-alkyloxypicolinic acids by reaction with alkyl halides in DMSO in the presence of silver oxide. 4-Substituted fusaric acids became accessible via 5-n-butyl-2-methyl-4-nitropyridine-N-oxide.
