80354-49-0Relevant academic research and scientific papers
Tin(IV) chloride-sodium nitrite as a new nitrosating agent for N-nitrosation of amines, amides and ureas under mild and heterogeneous conditions
Celaries, Benoit,Parkanyi, Cyril
, p. 2371 - 2375 (2008/02/03)
We have developed a new method of N-nitrosation of various secondary and tertiary amines, amides and ureas using a mixture of tin(IV) chloride and sodium nitrate. This method leads to a selective, high-yielding and mild heterogeneous N-nitrosation by in situ generation of nitrosyl chloride (NOCl). The reaction can be carried out in several different solvents such as chloroform, dichloromethane, ethers, ethyl acetate and alcohols, at room temperature. Georg Thieme Verlag Stuttgart.
In the search for new anticancer drugs. 28. Synthesis and evaluation of highly active aminoxyl labeled amino acid derivatives containing the [N'-(2- chloroethyl)-N'-nitrosoamino]carbonyl group
Sosnovsky,Baysal,Erciyas
, p. 999 - 1005 (2007/10/02)
The aminoxyl (nitroxyl) labeled (2-chloroethyl)nitrosocarbamoyl (CNC) derivatives of amino acids, i.e., N-[[N'-(2-chloroethyl)-N'- nitrosoamino]carbonyl]-A-(1-oxy-2,2,6,6-tetramethylpiperidin-4-yl)amides, A = glycyl (10a), A = L-alanyl (10b), A = L-valyl (10c), A = L-phenylalanyl (10d), were synthesized and evaluated in vitro for their anticancer activities against the murine lymphocytic leukemia P388. Compounds 10a-d possessed activities ranging from 242 to 456% increase in life span (%ILS). All CDF1 male mice treated with the highly active compounds 10b and 10c at 12 mg/kg/day for 9 days were alive after 30 days. Compounds 10a-d were then tested in vivo against the murine lymphoid leukemia L1210. Compounds 10a-d exhibited, on day 60, a %ILS of 496, 663, 663, and 581, respectively. All CDF1 male mice treated with the highly active compounds 10b and 10c at 12 mg/kg/day for 9 days were alive after 60 days. The lipophilicities of compounds 10a-d were determined using the UV method. The %ILS parameters obtained against the P388 and L1210 tumor lines were correlated with the corresponding lipophilicities, and a trend was generally observed toward an increase in cytotoxicity with a concomitant decrease in hydrophobicity.
In the search for new anticancer drugs. XXIV: Synthesis and anticancer activity of amino acids and dipeptides containing the 2-chloroethyl- and [N'- (2-chloroethyl)-N'-nitroso]-aminocarbonyl groups
Sosnovsky,Prakash,Rao
, p. 1 - 10 (2007/10/02)
A series of L,L-(42, 44, 46, and 60) and D,D-(43, 45, 47, and 61) dipeptide derivatives composed of phenylglycine, phenylalanine, homophenylalanine, and valine and containing a 2-chloroethylamino group at the C-terminus and an N'-(2-chloroethyl)-N'-nitrosoaminocarbonyl group at the N-terminus of the dipeptides were prepared. The dipeptide derivatives (42- 47, 60, and 61) were first evaluated in vivo for their anticancer activities against the murine lymphocytic leukemia P388. Compounds 42, 44, 46, and 60 possessed activities ranging from 46 to 111 percent increase in life span (%ILS), whereas 43 was marginal (%ILS = 31) and 45, 47, and 61 were inactive. In general, the L,L-series exhibited low to good activity (%ILS = 46-111), whereas the corresponding D,D-series, except for 43 (%ILS = 31), was devoid of activity. The analogously structured monoamino acid derivatives of L- alanine (74), L-phenylalanine (75), and L-aspartic acid (76) exhibited higher activity against P388 than the dipeptide derivatives (i.e., 481, 297, and 481 %ILS, respectively). The more active representatives of dipeptides (i.e., 42, 44, and 60) and the amino acids derivatives 74-76 were then tested in vivo against the murine lymphoid leukemia L1210. Compounds 42, 44, and 60 exhibited either low or marginal activity (i.e., the %ILS values were 46, 31, and 26, respectively). Compounds 74, 75, and 76 possessed low to moderate activity, as evidenced by the %ILS values of 56, 48, and 64, respectively. The %ILS parameters obtained against the P388 and L1210 tumor lines were correlated with the corresponding lipophilicities, and there is a trend towards higher activity with concomitant decrease in hydrophobicity.
Convenient Methods for Syntheses of Active Carbamates, Ureas and Nitrosoureas Using N,N'-disuccinimido Carbonate (DSC)
Takeda, Kazuyoshi,Akagi, Yoshie,Saiki, Atsuko,Tsukahara, Toshiko,Ogura, Haruo
, p. 4569 - 4572 (2007/10/02)
The reaction of DSC and amino compounds afforded the corresponding carbamates which were able to be converted into ureas and nitrosoureas.
Activated N-Nitrosocarbamates for Regioselective Synthesis of N-Nitrosoureas
Martinez, Jean,Oiry, Joel,Imbach, Jean Louis,Winternitz, Francois
, p. 178 - 182 (2007/10/02)
A practical and convenient method for synthesizing antitumor compounds, N-alkyl-N-nitrosoureas, regioselectively nitrosated on the nitrogen atom bearing the alkyl group is proposed.N-Alkyl-N-nitrosocarbamates are interesting intermediates in these syntheses and yield, by reaction with amino compounds, the regioselectively nitrosated N-alkyl-N-nitrosoureas.As an interesting example, N,N'-biscystamine, a new attractive oncostatic derivative, has been prepared.The cytotoxic activity of these various compounds were tested on L1210 leukemia.
