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Anti-Cancer Activity of Phenyl and Pyrid-2-yl 1,3-Substituted Benzo[1,2,4]triazin-7-ones and Stable Free Radical Precursors.

ABSTRACT: Cell viability studies for benzo[1,2,4]triazin-7-ones and 1,2,4-benzotriazinyl (Blatter-type) radical precursors are described with comparisons made with 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO). All of the stable free radicals were several orders of magnitude less cytotoxic than the benzo[1,2,4]triazin-7-ones. The synthesis and evaluation of two new pyrid-2-yl benzo[1,2,4]triazin-7-ones are described, where altering the 1,3-substitution from phenyl to pyrid-2-yl increased cytotoxicity against most cancer cell lines, as indicated using National Cancer Institute (NCI) one-dose testing. COMPARE analysis of five-dose testing data from the NCI showed very strong correlations to the naturally occurring anti-cancer compound pleurotin. COMPARE is program, which analyzes similarities in cytotoxicity data of compounds, and enables quantitative expression as Pearson correlation coefficients. Compounds were also evaluated using the independent MTT assay, which was compared with SRB assay data generated at the NCI.

SUBMITTER: Keane LJ

PROVIDER: S-EPMC6017941 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Crystal structures of three substituted 3-aryl-2-phenyl-2,3-di-hydro-4H-1,3-benzo-thia-zin-4-ones.

Project description:Three ring-substituted 3-aryl analogs of 2-phenyl-2,3-di-hydro-4H-1,3-benzo-thia-zin-4-one, namely 3-(4-meth-oxy-phen-yl)-2-phenyl-4H-1,3-benzo-thia-zin-4-one, C21H17NO2S, (I), 2-phenyl-3-[4-(tri-fluoro-meth-yl)phen-yl]-2,3-di-hydro-4H-1,3-benzo-thia-zin-4-one toluene hemisolvate, C21H14F3NOS·0.5C7H8, (II), and 3-(3-bromo-phen-yl)-2-phenyl-2,3-di-hydro-4H-1,3-benzo-thia-zin-4-one toluene hemisolvate, C20H14BrNOS·0.5C7H8, (III), were synthesized and their crystal structures determined. The hemisolvates differ in that in (II), the asymmetric unit comprises two molecules of the benzo-thia-zinone compound and a toluene solvent mol-ecule, whereas in (III), the unit comprises one benzo-thia-zinone mol-ecule and a half-occupancy toluene solvent mol-ecule. All crystals are of racemic mixtures of the chiral 2-C atom of the thia-zine moiety, which in all structures has a screw-boat puckering, with the puckering amplitude values within the range 0.575-0.603 Å. In all three structures, the benzene plane of the benzo-thia-zine system makes a dihedral angle in the range 78.60 (5) to 98.40 (5)° with the unsubstituted benzene plane and in the range 70.50 (1) to 121.00 (5)° with the substituted benzene plane. The CF3 substituent group in one of the mol-ecules of (II) shows positional disorder, with an occupancy ratio of 0.57 (3):0.43 (3). In the crystals of (I) and (II), weak inter-molecular C-H⋯O inter-actions are present, giving in (I), mol-ecules arranged in a plane parallel to (010), and in (II), chains along a. In addition, all three structures show weak C-H⋯π inter-actions involving various aromatic rings.

| S-EPMC4971851 | biostudies-literature

Parallel synthesis of 1,6-disubstituted-1,2,4-triazin-3-ones on solid-phase.

Project description:A parallel solid-phase synthesis of 1,6-disubstituted-1,2,4-triazin-3-ones from MBHA resin is described. The reduction of resin-bound nitrosamino acids provides hydrazines efficiently without affecting the amide bond. The trityl protected hydrazine is then reduced with borane, and cyclized with 1,1-carbonyldiimidazole. The desired products are cleaved from their solid support and obtained in good yield and purity. This methodology is of value for the rapid parallel preparation of these potentially bioactive molecules.

| S-EPMC3875618 | biostudies-literature

4H-Benzo[d][1,3]oxazin-4-ones and Dihydro Analogs from Substituted Anthranilic Acids and Orthoesters.

Project description:A one-pot route to 2-alkyl and 2-aryl-4H-benzo[d][1,3]oxazin-4-ones (also known as 4H-3,1-benzoxazin-4-ones) has been developed and studied. The method involves the reaction of aryl-substituted anthranilic acids with orthoesters in ethanol catalyzed by acetic acid. Additionally, we have also investigated the reaction under microwave conditions. Not all of the substrates were successful in yielding the target heterocycles as some of the reactions failed to undergo the final elimination. This process led to the isolation of (±)-2-alkyl/aryl-2-ethoxy-1,2-dihydro-4H-benzo[d][1,3]oxazin-4-ones. The formation of the dihydro analogs correlated with the electron density on the aromatic ring: Electron-donating groups favored the 4H- benzo[d][1,3]oxazin-4-ones, while electron-withdrawing groups tended to favor the dihydro product. Substituting a pyridine ring for the benzene ring in the substrate acid suppressed the reaction.

| S-EPMC6804250 | biostudies-literature

7-Dimethyl-amino-2-phenyl-1,2,4-triazolo[1,5-a][1,3,5]triazin-5-amine methanol solvate.

Project description:7-Dimethyl-amino-2-phenyl-1,2,4-triazolo[1,5-a][1,3,5]triazin-5-amine crystallized with one mol-ecule of methanol to give the title compound, C(12)H(13)N(7)·CH(3)OH. The triazolo[1,5-a][1,3,5]triazine heterocyclic core is essentially planar as are both amino groups that are involved in ?-electron delocalization with the triazolo[1,5-a][1,3,5]triazine nucleus. The methyl groups of the dimethyl-amino fragment are involved in the formation of weak intra-molecular C-H?N hydrogen bonds with the N atoms of the heterocyclic system. The crystal packing is stabilized by inter-molecular N-H?N hydrogen bonds between the triazolo[1,5-a][1,3,5]triazine mol-ecules. The methanol solvent mol-ecule also participates in the formation of the crystal structure via inter-molecular O-H?N, N-H?O and weak C-H?O hydrogen bonds, linking the layers of triazolo[1,5-a][1,3,5]triazine mol-ecules.

| S-EPMC2959306 | biostudies-literature

2-Phenyl-7-(4-pyridyl-methyl-amino)-1,2,4-triazolo[1,5-a][1,3,5]triazin-5(4H)-one.

Project description:In the title compound, C(16)H(13)N(7)O, the 1,2,4-triazolo[1,5-a][1,3,5]triazine heterocyclic system is essentially planar (r.m.s. deviation = 0.0375?Å). The attached benzene ring lies almost in the mean plane of 1,2,4-triazolo[1,5-a][1,3,5]triazine [dihedral angle = 1.36?(23)°], while the pyridine ring is turned out of this plane by the amino-methyl bridge [dihedral angle = 69.22?(9)°]. The amino group H atom is involved in intra-molecular hydrogen bonding with a triazole N atom. In the crystal, mol-ecules are connected via C(=O)NH?N hydrogen bonds into C(11) chains parallel to [100]. The amino group H atom acts as a hydrogen-bond donor, forming an NH?O=C hydrogen bond with the carbonyl O atom, which links the mol-ecules into C(6) chains running along [011] and [01].

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5,6-Dimethyl-1,2,4-triazin-3-amine.

Project description:In the crystal structure of the title compound, C(5)H(8)N(4), adjacent mol-ecules are connected through N-H?N hydrogen bonds, resulting in a zigzag chain along [100]. The amino groups and heterocyclic N atoms are involved in further N-H?N hydrogen bonds, forming R(2) (2)(8) motifs.

| S-EPMC3254400 | biostudies-literature

4-(3-Methyl-phen-yl)-3-phenyl-5-(2-pyrid-yl)-4H-1,2,4-triazole.

Project description:In the title compound, C(20)H(16)N(4), the m-tolyl and phenyl substituents form dihedral angles of 74.20?(6) and 36.94?(8)°, respectively, with the 1,2,4-triazole ring and the dihedral angle between the triazole and pyridine rings is 36.06?(9)°. In the crystal, mol-ecules are linked by C-H?N and C-H?? inter-actions.

| S-EPMC2971754 | biostudies-literature

7-Chloro-3-phenyl-benzo[4,5]thia-zolo[2,3-c][1,2,4]triazole.

Project description:In the title compound, C(14)H(8)ClN(3)S, the dihedral angle between the approximately planar triple-fused ring system (r.m.s. deviation = 0.065?Å) and the pendant phenyl ring is 62.25?(5)°. In the crystal, mol-ecules are linked into infinite chains along the c-axis direction by C-H?N hydrogen bonds. Aromatic ?-? stacking inter-actions [centroid-centroid distances = 3.7499?(8) and 3.5644?(8)?Å] and weak C-H?? inter-actions are also observed.

| S-EPMC3201329 | biostudies-literature

Phenyl substituted 4-hydroxypyridazin-3(2H)-ones and 5-hydroxypyrimidin-4(3H)-ones: inhibitors of influenza A endonuclease.

Project description:Seasonal and pandemic influenza outbreaks remain a major human health problem. Inhibition of the endonuclease activity of influenza RNA-dependent RNA polymerase is attractive for the development of new agents for the treatment of influenza infection. Our earlier studies identified a series of 5- and 6-phenyl substituted 3-hydroxypyridin-2(1H)-ones that were effective inhibitors of influenza endonuclease. These agents identified as bimetal chelating ligands binding to the active site of the enzyme. In the present study, several aza analogues of these phenyl substituted 3-hydroxypyridin-2(1H)-one compounds were synthesized and evaluated for their ability to inhibit the endonuclease activity. In contrast to the 4-aza analogue of 6-(4-fluorophenyl)-3-hydroxypyridin-2(1H)-one, the 5-aza analogue (5-hydroxy-2-(4-fluorophenyl)pyrimidin-4(3H)-one) did exhibit significant activity as an endonuclease inhibitor. The 6-aza analogue of 5-(4-fluorophenyl)-3-hydroxypyridin-2(1H)-one (6-(4-fluorophenyl)-4-hydroxypyridazin-3(2H)-one) also retained modest activity as an inhibitor. Several varied 6-phenyl-4-hydroxypyridazin-3(2H)-ones and 2-phenyl-5-hydroxypyrimidin-4(3H)-ones were synthesized and evaluated as endonuclease inhibitors. The SAR observed for these aza analogues are consistent with those previously observed with various phenyl substituted 3-hydroxypyridin-2(1H)-ones.

| S-EPMC4191602 | biostudies-literature

7-Nitro-2-phenyl-imidazo[2,1-b][1,3]benzo-thia-zole.

Project description:In the title mol-ecule, C15H9N3O2S, the central imidazo[2,1-b][1,3]benzo-thia-zole heterotricyclic unit is essentially planar (r.m.s. deviation = 0.021 Å). The terminal phenyl ring and nitro group are twisted by 9.06 (1) and 11.02 (4)°, respectively, from the mean plane of the heterotricycle. In the crystal, mol-ecules are linked by π-π stacking inter-actions into columns along [100]; the inter-planar distance between neighboring imidazo[2,1-b][1,3]benzo-thia-zole planes within the columns is 3.370 (2) Å. Furthermore, the columns interact with each other by secondary S⋯O [2.9922 (10) and 3.1988 (11) Å] inter-actions, forming a three-dimensional framework.

| S-EPMC3998307 | biostudies-literature

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