116228-41-2Relevant articles and documents
Synthesis of sulfonamides from azoles and sodium sulfinates at ambient temperature
Fu, Lili,Bao, Xiaodong,Li, Shanshan,Wang, Lingtian,Liu, Zhiguo,Chen, Wanzhi,Xia, Qinqin,Liang, Guang
, p. 2504 - 2511 (2017/04/03)
NBS or NIS mediated direct S[sbnd]N bond formation between azoles and sodium sulfinates is described. The reaction shows good substrate scope and tolerates a wide range of functionalities in both azoles and sodium sulfinate substrates. Pyrazoles are also suitable for this method, various 4-halopyrazoles derivatives were obtained by using N-halosuccinimide (NXS) as the halogen source.
Design, synthesis and X-ray crystallographic study of NAmPRTase inhibitors as anti-cancer agents
You, Hyun,Youn, Hyung-Seop,Im, Isak,Bae, Man-Ho,Lee, Sang-Kook,Ko, Hyojin,Eom, Soo Hyun,Kim, Yong-Chul
experimental part, p. 1153 - 1164 (2011/04/17)
NAmPRTase (PBEF/Visfatin) plays a pivotal role in the salvage pathway of NAD+ biosynthesis. NAmPRTase has been an attractive target for anti-cancer agents that induce apoptosis of tumor cells via a declining plasma NAD+ level. In this report, a series of structural analogs of FK866 (1), a known NAmPRTase inhibitor, was synthesized and tested for inhibitory activities against the proliferation of cancer cells and human NAmPRTase. Among them, compound 7 showed similar anti-cancer and enzyme inhibitory activities to compound 1. Further investigation of compound 7 with X-ray analysis revealed a co-crystal structure in complex with human NAmPRTase, suggesting that Asp219 in the active site of the enzyme could contribute to an additional interaction with the pyrrole nitrogen of compound 7.
Direct synthesis of pyrazolo[5,1-a]isoindoles via intramolecular palladium-catalyzed C-H bond activation
Choi, Young Lok,Lee, Hyuk,Kim, Bum Tae,Choi, Kihang,Heo, Jung-Nyoung
supporting information; experimental part, p. 2041 - 2049 (2010/11/19)
An efficient, direct synthesis of pyrazolo-[5,1-a]isoindoles employing a palladium-catalyzed intramolecular C-H bond activation of 1-(2-halobenzyl) pyrazoles has been developed. The use of lithium chloride (LiCl) was found to be essential in these reactions, to suppress further C-H bond activation at the C-3 position of pyrazolo[5,1-a]isoindole, when C-3 is unsubstituted. This protocol can be applied to the synthesis of a pyrazolo[5,1-a]isoquinoline possessing a six-membered central ring system and a fully substituted pyrazolo[5,1-a]isoindole using sequential intra- and intermolecular C-H bond activation.
Bu3SnH-mediated radical cyclisation onto azoles
Allin, Steven M.,Barton, William R.S.,Russell Bowman,Bridge (née Mann), Emma,Elsegood, Mark R.J.,McInally, Tom,McKee, Vickie
, p. 7745 - 7758 (2008/12/21)
Alkyl radicals have been cyclised onto pyrroles, imidazoles and pyrazoles, and acyl radicals cyclised onto pyrroles, using Bu3SnH-, (TMS)3SiH- and Bu3GeH-mediated aromatic homolytic substitution for the synthesis of bicyclic N-heterocycles. The reactions yield intermediate π-radicals that lose hydrogen in the?rearomatisation step of the aromatic homolytic substitution. Mechanistic studies of these rearomatisation steps indicate aromatic homolytic substitution in which the initiator or breakdown products from the inhibitor are responsible for the H-abstraction step.
Radical cyclisation onto pyrazoles: Synthesis of withasomnine
Allin, Steven M.,Barton, William R.S.,Bowman, W.Russell,McInally, Tom
, p. 4191 - 4193 (2007/10/03)
A novel synthetic protocol for the synthesis of [1,2-b]-fused bicyclic pyrazoles has been developed using radical cyclisation. The protocol uses cyclisation of pyrazole-1-(ω-alkyl) radicals generated from 1-[ω-(phenylselenyl)alkyl]-pyrazole precursors. The pyrazole natural product, withasomnine (3-phenyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole), and larger ring analogues have been synthesised in good yield using the protocol. A Bu3SnH-mediated oxidative cyclisation mechanism is facilitated by azo or Et3B radical initiators acting as oxidants of the intermediate π-radicals.
Nucleophilic substitution at a four-coordinate sulfur atom. IV. Reactivity of anionic nitrogen-containing nucleopiles
Savelova,Karpichev,Simanenko,Prokop'eva,Lobachev,Belousova
, p. 530 - 539 (2007/10/03)
The second-order rate constants for reactions of anions derived from azoles, arenesulfonamides, and arenesulfonohydrazides with aryl toluenesulfonates and methyl iodide in 5% aqueous ethanol (μ 1.0) at 25°C were compared with corresponding rate constants for aliphatic and heterocyclic amines. The kinetic behavior of neutral and anionic nitrogen-containing bases in reactions involving acyl (4-nitrophenyl acetate and 4-nitrophenyl heptanoate) and toluenesulfonyl group transfer suggests that deviation from the Bronsted dependence is due to unfavorable solvation effects for nucleophiles with pKa ≥ 11.0 rather than to change in the transition state structure. In reactions with a soft substrate, methyl iodide, solvation effects scarcely play the determining role, and the reduced reactivity of the anionic nucleophiles relative to neutral species is most likely to result from structural differences in the transition states corresponding to methyl group transfer to neutral and anionic nitrogen-containing compounds. The α-effect with arenesulfonohydrazides was revealed for the first time. 1996 MAEe Cyrillic signΚ Hayκa/Interperiodica Publishing.
On the Chemistry of Pyrazolylalkines; Pyrazoles II.
Heinisch, Gottfried,Holzer, Wolfgang,Obala, Claudia
, p. 253 - 262 (2007/10/02)
Palladium-catalyzed reactions of 1-benzoyl-4-iodopyrazole (2a) with monosubstituted acetylenes 3a,3b and 3c in triethylamine solution provide convenient access to the cross-coupled products 4a,4b and 4c.The 4-ethinylpyrazoles 5a and 7 obtained after metha
