- DNA interaction of bromomethyl-substituted acridines
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A series of acridines with bifunctional substituents was synthesized with the dual properties of DNA alkylation and intercalation. 4,5-Bis(bromomethyl)acridine (1) was previously reported to crosslink and intercalate with DNA. In this study, 1,8-bis(bromomethyl)acridine (2) and 2,7-bis(bromomethyl)acridine (3), monofunctional 2-(bromomethyl)-7-methylacridine (4) and 2,7-dimethylacridine (5) were synthesized, and their crosslinking and intercalative activities were investigated to assess the reactivity of bromomethyl acridines with DNA. Interstrand crosslinking activity was similar among the three bis(bromomethyl)acridines. The acridines exhibited intercalation activity for calf thymus DNA as follows: 3 > 4 > 2 = 1 5. Intracellular DNA-crosslinking and DNA-intercalating activities were evaluated using the Ames assay. 4 was mutagenic in Salmonella typhimurium TA100 and TA98, indicating that the bromomethyl group alkylated DNA bases. All three bis(bromomethyl)acridines were mutagenic in S. typhimurium TA92 and TA94, which can detect intracellular crosslinking DNA damage, whereas 5 was not mutagenic in these strains. The results showed that the bis(bromomethyl)acridines crosslinked DNA and intercalated between DNA bases, and 3 exhibited the highest crosslinking and intercalating activity.
- Harada, Kazuya,Imai, Takahiro,Kizu, Junko,Mochizuki, Masataka,Inami, Keiko
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p. 3375 - 3383
(2017/10/07)
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- PROCESS FOR THE PREPARATION OF NITRATED AROMATICS AND MIXTURES THEREOF
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A process for the preparation of mononitroaromatics and dinitroaromatics, in which a hydrate melt of at least one metal nitrate M(NO3)3 is used as a nitrating medium, it being possible for M to be the metals Fe, Cr, Y, La, Ce, Al, Bi and In, and the metal nitrate having a water content of from 4 to 9 mol of water per M(NO3)3, leads to simplifications of the process and improved yields.
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Page/Page column 5
(2012/01/03)
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- Ethyl acetate as a pro-reducing agent in an one-pot reductive deamination of nitroanilines
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The reductive deamination of various nitro-substituted anilines by the new method (20% H2SO4/NaNO2/ethyl acetate, Method 1) was studied and compared that with a similar procedure previously developed by Pare et al. (i.e., concentrated H2SO4/NaNO2/ethanol, Method 2) for the dediazonization of 4-methyl-2,6-dinitroaniline. The deaminated products derived from the mononitro-substituted anilines were obtained in good-to-high yield by Method 1 depending upon the position of the nitro group to the amino function. The higher yield of the de-aminated products was observed from the substituted meta-nitroanilines. Method 1 was more suitable for the deamination of 3-nitroanilines. Method 2 was more favorable for the de-amination of denitro-substituted anilines than that for the mononitroanilines. Ethyl acetate was more suitable for the reductive deamination of mononitroanilines, while ethanol was more appropriate for dinitroanilines.
- Bacherikov, Valeriy A.,Wang, May-Jane,Cheng, Shu-Yun,Chen, Ching-Huang,Chen, Kuo-Tung,Su, Tsann-Long
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p. 1027 - 1032
(2007/10/03)
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- The Kinetics of the Reactions of Picryl Chloride with Some Substituted Anilines. Part 5.
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Arrhenius parameters have been measured for the reactions of picryl chloride with the following substituted anilines in acetonitrile: 3-amino- and 3-methyl-aniline, 3-amino-5-nitroaniline, 3-fluoro-5-methylsulphonylaniline, 3-X-5-methylanilines (X=NO2, OMe, CH3, F, Cl, Br, or I) and 3,5-X2-anilines (X = F, Cl, Br, or I).A total of 33 3,5-disubstituted anilines have now been examined for the additivity of substituent effects on the free energy of activation, and it has been shown that with the exception of 3-amino-5-nitroaniline this hypothesis reproduces experimental rate constants within a factor of 2.A rationalization is proposed for the deviations that occur in some cases when more stringent criteria of additivity are used.
- Emokpae, Thomas A.,Eguavoen, Osa,Hirst, Jack
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p. 829 - 831
(2007/10/02)
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- Process for the production of nitro derivatives of aromatic compounds
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Nitroderivates of aromatic compounds which are difficult to nitrate, can readily be obtained by nitration providing that the aromatic compound is treated with nitric acid or another nitrating agent in the presence of aliphatic or cycloaliphatic hydrocarbons monosubstituted or polysubstituted by halogen, the nitro group or an alkyl sulphonyl group, and the nitro derivative formed subsequently isolated.
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