157124-43-1Relevant academic research and scientific papers
A stereocontrolled 1,2-addition reaction of tetrazoles with alkyl propiolates for the synthesis of highly functionalized enamines
Luo, Kai,Meng, Lingguo,Zhang, Yicheng,Zhang, Xiuli,Wang, Lei
, p. 765 - 780 (2013/04/10)
A stereocontrolled 1,2-addition reaction of 1-aryl-1H-tetrazoles with alkyl propiolates for the synthesis of highly functionalized enamines was developed. In the presence of silver oxide (Ag2O), the 1,2-addition reaction generated (Z)-N-cyano enamines in good yields with exclusive formation of the Z-isomers. Meanwhile, the 1,2-addition reaction generated (E)-N-cyano enamines in the presence of Ag2O and potassium carbonate (K2CO 3) with high stereoselectivity and yields. Copyright
Synthesis and evaluation of 1,5-disubstituted tetrazoles as rigid analogues of combretastatin A-4 with potent antiproliferative and antitumor activity
Romagnoli, Romeo,Baraldi, Pier Giovanni,Salvador, Maria Kimatrai,Preti, Delia,Aghazadeh Tabrizi, Mojgan,Brancale, Andrea,Fu, Xian-Hua,Li, Jun,Zhang, Su-Zhan,Hamel, Ernest,Bortolozzi, Roberta,Basso, Giuseppe,Viola, Giampietro
experimental part, p. 475 - 488 (2012/02/16)
Tubulin, the major structural component of microtubules, is a target for the development of anticancer agents. Two series of 1,5-diaryl substituted 1,2,3,4-tetrazoles were concisely synthesized, using a palladium-catalyzed cross-coupling reaction, and identified as potent antiproliferative agents and novel tubulin polymerization inhibitors that act at the colchicine site. SAR analysis indicated that compounds with a 4-ethoxyphenyl group at the N-1 or C-5 position of the 1,2,3,4-tetrazole ring exhibited maximal activity. Several of these compounds also had potent activity in inhibiting the growth of multidrug resistant cells overexpressing P-glycoprotein. Active compounds induced apoptosis through the mitochondrial pathway with activation of caspase-9 and caspase-3. Furthermore, compound 4l significantly reduced in vivo the growth of the HT-29 xenograft in a nude mouse model, suggesting that 4l is a promising new antimitotic agent with clinical potential.
One-pot syntheses of 5-amino-1-aryltetrazole derivatives
Vorobiov, Andrey N.,Gaponik, Pavel N.,Petrov, Petr T.,Ivashkevich, Oleg A.
, p. 1307 - 1312 (2007/10/03)
A novel facile route for the introduction of 5-amino and 5-alkylamino substituents into 1-aryltetrazoles has been developed. A range of 5-amino-1-aryltetrazoles was obtained directly from the corresponding 1-aryltetrazoles in one pot by consecutive ring-opening, azidation and intramolecular cyclization. 5-Alkylamino-1-aryltetrazoles were formed by a similar mechanism from 1,4-disubstituted tetrazolium salts. An influence of the nature of aryl substituents and reaction conditions on the regioselectivity of the intramolecular cyclization of intermediate guanyl azides is revealed. Georg Thieme Verlag Stuttgart.
