59460-38-7Relevant articles and documents
Synthesis, electrochemistry and liquid crystal properties of 1,2,3-(NH)-triazolylferrocene derivatives
Zhao, Hai-Ying,Guo, Le,Chen, Shu-Feng,Bian, Zhan-Xi
, p. 164 - 169 (2013)
A series of aryl(5-ferrocenyl-2H-1,2,3-triazol-4-yl)methanone 3a-3d have been firstly synthesized and characterized. The X-ray crystal structure of phenyl(5-ferrocenyl-2H-1,2,3-triazol-4-yl)methanone 3a confirms that 1,2,3-triazole ring exists in the crystal as the 2H isomer form. The UV-vis absorption spectra of these compounds correspond to the assembled spectra of ferrocene and aryl substitute groups, and the fluorescence spectra show a maximum at 374 nm in CH2Cl2. The cyclic voltammograms of 3b-3d show the reversible oxidation waves of the ferrocenyl groups, and these waves anodically shift in comparison with ferrocene standard due to the electron withdrawing effect of the 1,2,3-triazoles ring. According to thermal polarizing microscopy and differential scanning calorimetry studies, compounds 3b-3d display liquid crystal behaviors over wider mesophase range during first heating.
Alkynyl?B(dan)s in Various Palladium-Catalyzed Carbon?Carbon Bond-Forming Reactions Leading to Internal Alkynes, 1,4-Enynes, Ynones, and Multiply Substituted Alkenes
Tani, Tomohiro,Sawatsugawa, Yuuki,Sano, Yusuke,Hirataka, Yo,Takahashi, Naomi,Hashimoto, Sadahiro,Sugiura, Tetsuya,Tsuchimoto, Teruhisa
supporting information, p. 1815 - 1834 (2019/03/07)
It was found that the C(sp)?B(dan) bond of alkynyl?B(dan)s can be directly used for palladium-catalyzed carbon?carbon bond-forming reactions with aryl(alkenyl) halides and allylic carbonates as electrophiles, thus delivering unsymmetrical internal alkynes and unconjugated 1,4-enynes, respectively. With acyl chlorides as electrophiles, ynone synthesis is also promoted by a palladium catalyst with the assistance of a copper co-catalyst. These reactions can be achieved as more convenient one-pot reactions, without isolating the alkynyl?B(dan) formed in situ by the zinc-catalyzed dehydrogenative borylation of alkynes with HB(dan). In addition to direct C(sp)?B(dan) bond transformations, the C≡C bond in an alkynyl?B(dan) proved to be a promising scaffold for the construction of a multisubstituted alkene, which is synthesized by diboration of the C≡C?B(dan) moiety, leading to a triborylalkene followed by iterative regio- and stereoselective Suzuki?Miyaura cross-coupling reactions. As one example, the synthesis of the ethene with four different aryl groups, p-MeC6H4, p-MeOC6H4, p-NCC6H4, and p-F3CC6H4, was attained in high overall yield of 64% in six steps starting from the terminal alkyne, p-MeC6H4C≡CH. Besides these synthetic applications of the alkynyl?B(dan), the scope of the alkynyl substrate in the zinc-catalyzed dehydrogenative borylation was expanded to enhance the reliability as a provider of the alkynyl?B(dan). Consequently, 42 alkynes were found to participate in the dehydrogenative borylation as substrates; these are alkyl-, alkenyl-, aryl-, heteroaryl-, ferrocenyl-, silyl-, and borylalkynes, with or without a variety of functional groups. Lastly, a new method for preparing HB(dan), as a sulfide-free, cost-saving, and reaction-time-saving route, is disclosed. (Figure presented.).
Ferrocenyl, Alkyl, and Aryl-Pyrido[2,3-d]Pyrimidines as Vasorelaxant of Smooth Muscle of Rat Aorta via cAMP Conservation Through Phosphodiesterase Inhibition
Arellano, Ivonne,Rodríguez-Ramos, Fernando,González-Andrade, Martín,Navarrete, Andrés,Sharma, Manju,Rosas, Noé,Sharma, Pankaj
, p. 1147 - 1154 (2016/07/29)
New pyrido[2,3-d]pyrimidines 11, 12, 13, and 21 have been synthesized. The vasorelaxant effect on smooth muscle isolated from rat aorta, via PDEs inhibition, of these compounds along with other pyrido[2,3-d]pyrimidines 14, 15, 16, 17, 18, 19, 20 reported earlier by our group, has also been determined. These pyrido[2,3-d]pyrimidines 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 were synthesized by the reaction of ferrocenyl-ethynyl ketones (1, 2, 3, 4) or α-alkynyl ketones (5, 6, 7, 8, 9, 10) with 6-amino-1,3-dimethyluracil using [Ni(CN)4]?4as an active catalytic species, formed in situ in a Ni(CN)2/NaOH/H2O/CO/KCN aqueous system. Evaluation of the vasorelaxant effect of compounds 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 demonstrated that all compounds relax the tissue in a concentration-dependent manner. The structural changes do not alter the effectiveness; however, there are differences related to potency expressed as EC50. Compounds 12 (7-ferrocenyl-1,3-dimethyl-5-(m-tolyl)-pyrido[2,3-d]pyrimidine) and 13 (7-ferrocenyl-1,3-dipropyl-5-(4-metoxyphenyl)-pyrido[2,3-d]pyrimidine) were the most potent compounds, even more than rolipram, reference drug; the EC50was 0.41 ± 0.02 μM and 0.81 ± 0.11 μM for 12 and 13, correspondingly. The EC50of compounds 15 (7-ferrocenyl-1,3-dimethyl-5-phenyl-pyrido[2,3-d]pyrimidine), 14 (7-ferrocenyl-5-(3,5-dimethoxyphenyl)-1,3-dimethylpyrido[2,3-d]pyrimidine), and 19 (5-n-butyl-7-ethyl-1,3-dimethylpyrido[2,3-d]pyrimidine) was similar to EC50of rolipram. Compounds 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 significantly induce concentration-dependent vasorelaxation in endothelium-intact aortic rings. In addition, the relaxation responses to each compound in either endothelium-intact or endothelium denuded aortic rings were comparable, suggesting that removal of the functional endothelium has no significant influence on its intrinsic vasorelaxant activity. In vitro capability of conserving cyclic-AMP or cyclic-GMP (adenosine and guanosine 3′, 5′-cyclic monophosphate) via PDE inhibition for compounds 12, 13, 14, 15 and 19 was evaluated. Compounds 15 and 19 show the highest percent inhibition effect (94.83% and 83.98%, respectively) for the decomposition of c-AMP. Docking studies showed that the compound 15 was selective for the inhibition of PDE-4.
