95926-80-0Relevant academic research and scientific papers
Synthesis and antiproliferative evaluation of 5-oxo and 5-thio derivatives of 1,4-diaryl tetrazoles
Gundugola, Aditya S.,Chandra, Kusum Lata,Perchellet, Elisabeth M.,Waters, Andrew M.,Perchellet, Jean-Pierre H.,Rayat, Sundeep
supporting information; experimental part, p. 3920 - 3924 (2010/09/03)
A series of 1,4-diaryl tetrazol-5-ones were synthesized by copper mediated N-arylation of 1-phenyl-1H-tetrazol-5(4H)-one with aryl boronic acids, o-R 1C6H4B(OH)2 where R1 = H, OMe, Cl, CF3, Br, CCH. The 1,4-diaryl tetrazol-5-ones substituted with OMe, Cl, CF3, Br underwent thionation with Lawesson's reagent to yield the corresponding 5-thio derivatives. The 1-(2-bromophenyl)-4-phenyl-1H- tetrazole-5(4H)-thione so obtained was subjected to lithiation/protonation and Sonogashira coupling to produce 1,4-diphenyl-1H-tetrazole-5(4H)-thione and 1-(2-ethynylphenyl)-4-phenyl tetrazole-5-thione, respectively. The title compounds were found to be stable to strong Lewis acid conditions. Three of these novel compounds were found to inhibit L1210 leukemia cell proliferation and SK-BR-3 breast cancer cell growth over several days in culture in vitro. Shorter tetrazole derivative treatments also reduced the expression of the Ki-67 marker of cell proliferation in SK-BR-3 cells and the rate of DNA synthesis in L1210 cells.
Photochemical Elimination of Molecular Nitrogen from Phenyl-Substituted 1,4-Dihydro-5-imino-5H-tetrazoles. Products of Phenyl-Substituted Tris(imino)methane Diradicals
Quast, Helmut,Fuss, Andreas,Nahr, Uwe
, p. 2164 - 2185 (2007/10/02)
The reaction of 5-(methylthio)tetrazolium salts 11 with primary amines produces the phenyl-substituted 5-iminotetrazoles 7b - h.In contrast to the results of the electron impact-induced fragmentation in the mass spectrometer, irradiation of the 5-iminotet
Photoextrusion of Nitrogen from 1,4-Dihydro-1-phenyl-5H-tetrazol-5-ones and -thiones. Benzimidazolones and Carbodiimides
Quast, Helmut,Nahr, Uwe
, p. 526 - 540 (2007/10/02)
Alkylation of 1-phenyltetrazolone 10a with 2-cyclohexen-1-yl bromide followed by dehydrogenation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone permits introduction of a phenyl group at N-4 of the tetrazole ring via the sequence 10a -> 10f -> 10g.The photoextrusion of molecular nitrogen from the (N-4)-substituted 1-phenyltetrazolones, 10a (hydrogen), 10b (methyl), 10d,e (propenyl), and 10g (phenyl) produces essentially quantitative yields of the corresponding benzimidazolones 14a,b,d,e,g.On irradiation of the 1-phenyltetrazolethiones 8b,f,g the carbodiimides 22b,f,g are obtained together with molecular nitrogen and sulfur, while 8a affords phenylcyanamide (25).In contrast to the thermolysis, which is known to give 2-(methylamino)benzothiazole (21b), photolysis of the (phenylimino)-1,2,3,4-thiatriazole 24, an isomer of methylphenyltetrazolethione 8b, also yields molecular nitrogen, sulfur, and methylphenylcarbodiimide (22b).
