- Synthesis and antitumor activity evaluation of compounds based on toluquinol
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Encouraged by the promising antitumoral, antiangiogenic, and antilymphangiogenic properties of toluquinol, a set of analogues of this natural product of marine origin was synthesized to explore and evaluate the effects of structural modifications on their cytotoxic activity. We decided to investigate the effects of the substitution of the methyl group by other groups, the introduction of a second substituent, the relative position of the substituents, and the oxidation state. A set of analogues of 2-substituted, 2,3-disubstituted, and 2,6-disubstituted derived from hydroquinone were synthesized. The results revealed that the cytotoxic activity of this family of compounds could rely on the hydroquinone/benzoquinone part of the molecule, whereas the substituents might modulate the interaction of the molecule with their targets, changing either its activity or its selectivity. The methyl group is relevant for the cytotoxicity of toluquinol, since its replacement by other groups resulted in a significant loss of activity, and in general the introduction of a second substituent, preferentially in the para position with respect to the methyl group, was well tolerated. These findings provide guidance for the design of new toluquinol analogues with potentially better pharmacological properties.
- Cheng-Sánchez, Iván,Torres-Vargas, José A.,Martínez-Poveda, Beatriz,Guerrero-Vásquez, Guillermo A.,Medina, Miguel ángel,Sarabia, Francisco,Quesada, Ana R.
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- Continuous Flow Homolytic Aromatic Substitution with Electrophilic Radicals: A Fast and Scalable Protocol for Trifluoromethylation
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We report an operationally simple and rapid continuous flow radical C?C bond formation under Minisci-type reaction conditions. The transformations are performed at or below room temperature employing hydrogen peroxide (H2O2) and dimethylsulfoxide (DMSO) as reagents in the presence of an FeIIcatalyst. For electron-rich aromatic and heteroaromatic substrates, C?C bond formation proceeds satisfactorily with electrophilic radicals including.CF3,.C4F9,.CH2CN, and.CH2CO2Et. In contrast, electron-poor substrates exhibit minimal reactivity. Importantly, trifluoromethylations and nonafluororobutylations using CF3I and C4F9I as reagents proceed exceedingly fast with high conversion for selected substrates in residence times of a few seconds. The attractive features of the present process are the low cost of the reagents and the extraordinarily high reaction rates. The direct application of the protocol to dihydroergotamine, a complex ergot alkaloid, yielded the corresponding trifluoromethyl ergoline derivative within 12 seconds in a continuous flow microreactor on a 0.6 kg scale. The trifluoromethyl derivative of dihydroergotamine is a promising therapeutic agent for the treatment of migraines.
- Monteiro, Júlia L.,Carneiro, Paula F.,Elsner, Petteri,Roberge, Dominique M.,Wuts, Peter G. M.,Kurjan, Katherine C.,Gutmann, Bernhard,Kappe, C. Oliver
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supporting information
p. 176 - 186
(2017/01/09)
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- Direct aromatic C-H trifluoromethylation via an electron-donor-acceptor complex
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A novel electron-donor-acceptor (EDA) complex-mediated direct C-H trifluoromethylation of arenes with Umemoto's reagent has been developed. This transformation has been enabled by an unprecedented EDA complex formed by Umemoto's reagent and an amine, whic
- Cheng, Yuanzheng,Yuan, Xiangai,Ma, Jing,Yu, Shouyun
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supporting information
p. 8355 - 8359
(2015/06/02)
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- Liquid crystalline compound, liquid crystal composition and their polymers
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The present invention provides a compound represented by formula (1) defined in the specification and a liquid crystal composition comprising the compound. The invention further provides a polymer obtained by polymerization of compound or composition abov
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- The aqueous photolysis of TFM and related trifluoromethylphenols. An alternate source of trifluoroacetic acid in the environment
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The lampricide 3-trifluoromethyl-4-nitrophenol (TFM) is added annually to the Great Lakes (approximately 50 000 kg/y), with treatment concentrations varying from 1 to 14 mg/L at source. TFM was shown to undergo photohydrolytic degradation, at 365 nm and u
- Ellis, David A.,Mabury, Scott A.
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p. 632 - 637
(2007/10/03)
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- New Electrophilic Trifluoromethylating Agents
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Synthetic routes to S-(trifluoromethyl)phenyl-4-fluorophenylsulfonium triflate (8), S-(trifluoromethyl)phenyl-2,4-difluorophenylsulfonium triflate (9), S-(trifluoromethyl)phenyl-3-nitrophenylsulfonium triflate (10), and S-(trifluoromethyl)-4-fluorophenyl-3-nitrophenylsulfonium triflate (11) are described. They are stable molecules and conveniently prepared by treating phenyl trifluoromethyl sulfoxide with benzene and its derivatives. These novel electrophilic trifluoromethylating agents react under mild conditions with a variety of aromatic rings (p-hydroquinone, pyrrole, and aniline) to give trifluoromethylated compounds (2-trifluoromethyl-p-hydroquinone, 2-trifluoromethylpyrrole, 2-trifluoromethylaniline, and 4-trifluoromethylaniline) in moderate to high yields. The electrophilic trifluoromethylating potential can be altered by placing electron-withdrawing substituents on the benzene rings.
- Yang, Jing-Jing,Kirchmeier, Robert L.,Shreeve, Jean'ne M.
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p. 2656 - 2660
(2007/10/03)
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- TRIFLUORMETHYLIERUNGSREAKTIONEN VON CF3I, Te(CF3)2, Sb(CF3)3, Hg(CF3)2, UND Cd(CF3)2*D MIT FURAN, THIOPHEN, PYRROL UND p-BENZOCHINON
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The trifluoromethylation reactions of Cd(CF3)2*glyme, Hg(CF3)2, Sb(CF3)3, CF3I, and Te(CF3)2 with furan, thiophene, pyrrol, and p-benzoquinone are compared under similar conditions.During the photochemical reactions the reactivity increases in the series
- Naumann, Dieter,Kischkewitz, Juergen
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p. 265 - 281
(2007/10/02)
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