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The nitro group remains intact [6].

However, nitrones are formed by reaction of a hydroxylamine and a carbonyl compound, not directly from a nitrocompound.

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Synthesis and Application of Glycopeptide and Glycoprotein Mimetics.

An -nitroso group was used to activate chloropyrimidines toward nucleophilic substitution by amines. This permitted a simple, one-pot, high-yielding synthesis of pyrimidine-4,6- and -2,4-diamines.

Organonitroso compounds are used as ligands for synthesizing transition metal complexes.

N2 - We compared the effects of CAP and its nitroso derivative on DNA synthesis, CFU-C growth, and cell viability in human bone marrow and on mouse CFU-S viability in vitro. As previously reported from this laboratory, CAP inhibited DNA synthesis only when used in high concentrations (>3 x 10 -4M), and the inhibition was largely reversible. It also caused a reversible concentration-dependent inhibition of CFU-C growth but did not affect marrow cell viability. In sharp contrast, nitroso-CAP inhibited DNA synthesis in much lower concentrations and caused irreversible inhibition of CFU-C growth and cell death at 5 x 10 -5M as well as irreversible mouse CFU-S damage. In a rapidly growing human lymphoid cell line, nitroso-CAP caused accumulation of cells in the G 2M phase and increasing cell death within the arrested population. We have postulated from these and other observations that CAP-induced aplastic anemia occurs in the predisposed host who provides the milieu for the transformation of the p-NO 2 group of the drug to toxic intermediates.

H., His6 tag-assisted chemical protein synthesis.

Topchiev, Nitration of Hydrocarbons and Other Organic Compounds, London, UK: Pergamon, 1959, p.

According to Gattermann, this compound loses acetic acid to give o-nitrostyrene and by further loss of a molecule of water is changed into “indolone”, which corresponds to half of the indigo molecule and polymerises to the dye.

Ahmed M. Tafesh was born in 1957 in Acre, Israel, and following his arrival in the United States in the fall of 1977, he received his B.S. degree in chemistry at Portland State University in 1981. In 1984 he received his M.S. at Oregon State University in the area of physical organic chemistry working on mechanistic investigation of conjugated carbenes with Professor Peter Freeman. He then moved east to Salt Lake City, where he received his Ph.D. in the area of free radical methodology development as well as the total synthesis of pseudomonic acid under the supervision of Professor Gary Keck. After graduation in 1989 he joined Hoechst Celanese Corp. in Corpus Christi, TX, as a Research Chemist working in exploratory research. In 1991 he was promoted to Research Chemist II and worked on the development of pharmaceutical intermediates. In 1993 he was promoted to Senior Research Chemist and in 1994 he was awarded a two year assignment in Hoechst AG Corporate Research in Frankfurt, Germany. In Germany, Ahmed was active in the area of development of oxidation reagents as well as the development of water soluble catalysts for the reductive carbonylation of aromatic nitro compounds. Ahmed holds more than 20 patents in different areas. Upon completion of his assignment, Ahmed will return to Texas for his new role as a group leader in the area of asymmetric catalysis.

S.; Etzkorn, M., Direct oxidation of azides to nitro compounds.

Living Radical Polymerization as a Tool for the Synthesis of Polymer-Protein/Peptide Bioconjugates.

Novel N-nitroso-N-(acetoxymethyl)-ω-chloroalkylamines were synthesized and their chemical and biological properties were evaluated. The nitrosamines were expected to decompose through ω-chloroalkyldiazohydroxides in aqueous solution, and then to alkylate various cellular macromolecules. N-Nitroso-N-(acetoxymethyl)-2-chloroethylamine rapidly decomposed in aqueous solution, and the reaction rate was apparently independent of the pH of the solution. On the other hand, the rate of decomposition of chloropropyl and chlorobutyl homologs was pH-dependent, and increased in alkaline solution. When mutagenicity was assayed in Salmonella typhimurium TA1535 and TA92 for preliminary evaluation, all three compounds were directly mutagenic. The mutagenicity in Salmonella typhimurium TA1535, which can detect base-pair change mutation, clearly showed that these compounds induced DNA alkylation in vivo. The increase of alkyl chain length in chloroalkyl compounds increased the mutagenic activity, and the activities were stronger than those of the corresponding simple α-acetoxy nitrosamines lacking a chloro group, N-nitroso-N-(acetoxymethyl)alkylamines. Furthermore, the positive result in TA92 suggested that chlorinated nitrosamines cross-linked DNA like antitumor chloroethylnitrosoureas and that they are expected to be new lead compounds for antitumor agents.

()IN search of a better and convenient method for the reduction of the5-nitroso group of substituted pyrimidines, an intermediate for thesynthesis of substituted pteridines, required for the synthesis ofantagonist of folic acid, as a possible tumour-inhibiting agent (cf.

M., Synthesis of bio-inspired hybrid polymers using peptide synthesis and protein engineering.
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  • Efficient Nitroso Group Transfer fromN-Nitrosoindoles …

    Besides, there are no experimental examples of nitro group participations in dehydrations of this type.

  • Efficient Nitroso Group Transfer fromN-Nitrosoindoles to ..

    Ono, The Nitro Group in Organic Synthesis, Wiley Series in Organic Nitro Chemistry, Germany: Wiley-VCH, 2001, pp.30-69.

  • Reduction of Nitroso Group in Heterocyclics - …

    Total synthesis of marine natural products without using protecting groups, Nature, 2007, 446, 404-408.

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Reduction of Nitroso Group in Heterocyclics - Nature

A distinct C–H activation-based traceless synthetic protocol via electrophilic removal of a directing group is reported, complementing the currently exclusively used nucleophilic strategy. Rh(III)-catalyzed, -nitroso-directed C–H activation allows the development of a traceless, atom- and step-economic, cascade approach for the synthesis of indole skeletons, starting from readily available -nitroso and α-diazo-β-keto compounds. Importantly, the cyclization/denitrosation reaction represents a hitherto unobserved reactivity pattern for the -nitroso group.

Reduction of Nitroso Group in Heterocyclics

An -nitroso group was used to activate chloropyrimidines toward nucleophilic substitution by amines. This permitted a simple, one-pot, high-yielding synthesis of pyrimidine-4,6- and -2,4-diamines.

Amino, Nitroso, Nitro and Related Groups

N2 - Novel N-nitroso-N-(acetoxymethyl)-ω-chloroalkylamines were synthesized and their chemical and biological properties were evaluated. The nitrosamines were expected to decompose through ω-chloroalkyldiazohydroxides in aqueous solution, and then to alkylate various cellular macromolecules. N-Nitroso-N-(acetoxymethyl)-2-chloroethylamine rapidly decomposed in aqueous solution, and the reaction rate was apparently independent of the pH of the solution. On the other hand, the rate of decomposition of chloropropyl and chlorobutyl homologs was pH-dependent, and increased in alkaline solution. When mutagenicity was assayed in Salmonella typhimurium TA1535 and TA92 for preliminary evaluation, all three compounds were directly mutagenic. The mutagenicity in Salmonella typhimurium TA1535, which can detect base-pair change mutation, clearly showed that these compounds induced DNA alkylation in vivo. The increase of alkyl chain length in chloroalkyl compounds increased the mutagenic activity, and the activities were stronger than those of the corresponding simple α-acetoxy nitrosamines lacking a chloro group, N-nitroso-N-(acetoxymethyl)alkylamines. Furthermore, the positive result in TA92 suggested that chlorinated nitrosamines cross-linked DNA like antitumor chloroethylnitrosoureas and that they are expected to be new lead compounds for antitumor agents.

N-nitroso compounds and cancer incidence: the …

AB - Novel N-nitroso-N-(acetoxymethyl)-ω-chloroalkylamines were synthesized and their chemical and biological properties were evaluated. The nitrosamines were expected to decompose through ω-chloroalkyldiazohydroxides in aqueous solution, and then to alkylate various cellular macromolecules. N-Nitroso-N-(acetoxymethyl)-2-chloroethylamine rapidly decomposed in aqueous solution, and the reaction rate was apparently independent of the pH of the solution. On the other hand, the rate of decomposition of chloropropyl and chlorobutyl homologs was pH-dependent, and increased in alkaline solution. When mutagenicity was assayed in Salmonella typhimurium TA1535 and TA92 for preliminary evaluation, all three compounds were directly mutagenic. The mutagenicity in Salmonella typhimurium TA1535, which can detect base-pair change mutation, clearly showed that these compounds induced DNA alkylation in vivo. The increase of alkyl chain length in chloroalkyl compounds increased the mutagenic activity, and the activities were stronger than those of the corresponding simple α-acetoxy nitrosamines lacking a chloro group, N-nitroso-N-(acetoxymethyl)alkylamines. Furthermore, the positive result in TA92 suggested that chlorinated nitrosamines cross-linked DNA like antitumor chloroethylnitrosoureas and that they are expected to be new lead compounds for antitumor agents.

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