ABSTRACT
We have isolated the stable as well as the metastable tautomers of 1-deazapurine in the solid state by exploiting principles of supramolecular selectivity in the context of cocrystal design.
ABSTRACT
An efficient three-step synthesis of 2-halo-3-aryl-4(3H)-quinazoliniminium halides from commercially available materials is described. Upon reaction with hydrogen halides, generated in situ from a Lewis acid (MX) and trace water, a variety of easily accessible heteroenyne-allenes underwent facile intramolecular cyclization to afford the title compounds in good yields. The method is highly versatile and provides a general way to construct quinazoliniminium ring systems with a variety of different substitutions.
Subject(s)
Alkadienes/chemistry , Hydrocarbons, Halogenated/chemical synthesis , Quinazolines/chemical synthesis , Catalysis , Cyclization , Hydrocarbons, Halogenated/chemistry , Molecular Structure , Quinazolines/chemistryABSTRACT
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(1)C(6)H(4)B(OH)(2) where R(1)=H, OMe, Cl, CF(3), Br, CCH. The 1,4-diaryl tetrazol-5-ones substituted with OMe, Cl, CF(3), 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.
