58484-95-0Relevant academic research and scientific papers
Fused imidazoles as potential chemical scaffolds for inhibition of heat shock protein 70 and induction of apoptosis. Synthesis and biological evaluation of phenanthro[9,10-d] imidazoles and imidazo[4,5-f] [1,10]phenanthrolines
Patel, Alpa,Sharp, Swee Y.,Hall, Katelan,Lewis, William,Stevens, Malcolm F.G.,Workman, Paul,Moody, Christopher J.
, p. 3889 - 3905 (2016/05/19)
The imidazole ring is widespread in biologically active compounds, and hence imidazole-containing scaffolds are useful starting points for drug discovery programmes. We report the synthesis of a series of novel imidazole-containing compounds fused with either phenanthrene or phenanthroline, which show enhanced growth inhibitory potency against human colon, breast and melanoma cancer cell lines, as well as evidence of inhibition of the molecular chaperone heat shock protein 70 (Hsp70) pathway in cells, as shown by depletion of downstream oncogenic client proteins of the Hsp90 chaperone pathway, and induction of apoptosis.
Optimizing electron transfer mediators based on arylimidazoles by ring fusion: Synthesis, electrochemistry, and computational analysis of 2-aryl-1-methylphenanthro[9,10-d ]imidazoles
Francke, Robert,Little, R. Daniel
supporting information, p. 427 - 435 (2014/01/23)
A significant improvement of the properties of redox catalysts based on the triarylimidazole framework can be achieved with a simple structural modification. By linking the ortho-carbons of the aromatics positioned at C-4 and C-5, a fused framework is generated, removing the distortion from planarity and enhancing the influence of the substituents on the redox properties. This modification leads not only to a much broader range of available redox potentials for the resulting phenanthro[9,10-d]imidazoles but also to improved stability of the corresponding radical cation. These concepts were verified with eight new phenanthro[9,10-d]imidazole derivatives, using cyclic voltammetry and DFT calculations. For this purpose, an optimized and general synthetic route to the desired compounds was developed. An excellent linear correlation of the calculated effective ionization potentials with the experimental oxidation potentials was obtained, allowing for an accurate prediction of oxidation potentials of derivatives yet to be synthesized. Moreover, high catalytic activity was found for electro-oxidative C-H activation reactions.
Photochemistry of N-heterocycles. 7: Light induced reductive ring contractions of sixmembered cyclic iminium ions
Nagy, Jozsef,Madarasz, Zoltan,Rapp, Rudolf,Szoelloesy, Aron,Nyitrai, Jozsef,Doepp, Dietrich
, p. 281 - 290 (2007/10/03)
Photochemically induced reductive ring contractions, previously observed for 2,5-dihydro-1,2,4-triazines, have also been verified for 1,4-dihydropyrimidines 2a,b, the dihydro-1,2,4,5-tetrazine 9, and dihydro-1,3,5-triazines 11a,b giving rise to fivemembered fully unsaturated heterocycles (pyrroles 4a,b, imidazoles 13a,b, and triazole 10, respectively). The 1,4-dihydropyrazines 15a-j tend to decompose in acidified 2-propanol in the dark, but on irradiation they also undergo reductive ring contraction furnishing solely the 1,2,5-triarylpyrroles 16a-d rather than the (a priori also possible) isomeric 1,3,4-triarylpyrroles 17a-d. In contrast, the 3,6-diphenylpyrid-azine 18 gives the 4-isopropyl-analogue 19 in low yield upon irradiation in hydrogen chloride saturated 2-propanol. Wiley-VCH Verlag GmbH, 2000.
Photochemistry of N-Heterocycles. Part 3. Synthesis and Photochemistry of some New Dihydro-1,2,4-triazines and their Quaternary Salts
Nagy, Jozsef,Rapp, Rudolf,Alexovics, Maria,Doepp, Dietrich,Nyitrai, Jozsef,et al.
, p. 661 - 666 (2007/10/02)
Several new dihydro-1,2,4-triazines, 1b, 4, 5, 16 and 19, have been synthesized and their structures unambiguously determined.The existence of 1,2- and 1,4-dihydrotriazines, 20 and 22, described in the literature was ruled out.Irradiation of the aromatic triazines 6 and 15 and the novel quaternary dihydro-1,2,4-triazinium salts 4, 5, 19 furnished new evidence for both the reduction pathways and the mechanism of ring-contraction reactions.
PHOTOCHEMISTRY OF N-HETEROCYCLES. PART 1. SYNTHESIS AND PHOTOCHEMISTRY OF SOME 2(4),5-DIHYDRO-1,2,4-TRIAZINES. X-RAY MOLECULAR STRUCTURE OF 1-(4-METHYL-3,5,6-TRIPHENYL-1,4,5,6-TETRAHYDRO-1,2,4-TRIAZIN-6-YL)ETHANOL
Nagy, Jozsef,Nyitrai, Jozsef,Kolonits, Pal,Lempert, Karoly,Gergely, Anna,et al.
, p. 3267 - 3274 (2007/10/02)
Ethanolic solution of the hydrochlorides of the mostly new 2(4),5-dihydro-1,2,4-triazines (1)-(4) were irradiated with a high-pressure mercury immersion lamp (λ>=300 nm).The salts (1a)-(3a) underwent reductions, ring contractions, and dehydrogenations upo
EFFICIENT PHOTOCHEMICAL OXETANE FORMATION FROM 1-METHYL-2,4,5-TRIPHENYLIMIDAZOLE AND BENZOPHENONES
Ito, Yoshikatsu,Ji-Ben, Meng,Suzuki, Shin,Kusunaga, Yoshitaka,Matsuura, Teruo,Fukuyama, Keiichi
, p. 2093 - 2096 (2007/10/02)
In contrast to simple imidazoles, 1-methyl-2,4,5-triphenylimidazole (1) produced stable oxetane photoadducts 3b-e with good efficiency upon irradiation in the presence of benzophenone derivatives 2b-e in acetonitrile solution.Irradiation in the solid-phase was also studied.The oxetanes 3b-e readily underwent cycloreversion by acid catalysis or by heating.
