Synthesis and potential cytotoxic activity of some new benzoxazoles, imidazoles, benzimidazoles and tetrazoles

The present work deals with the synthesis of some novel heterocyclic compounds such as benzoxazoles 2, 7, 13 and 19, imidazoles 3, 8, 14 and 20, benzimidazole 4, 9, 15 and 21, tetrazoles 10, 16, and 22. The synthesized compounds were characterized by IR, 1H NMR, mass spectrometry and elemental analysis. The compounds were evaluated for cytotoxicity against human cancer cell line such as, MCF-7 (breast cancer) and HT-29 (colon cancer) by MTT assay method. Among the tested compounds, compounds 4,4’-sulfonylbis(N-(2-(1H-benzo[d]imidazol-2-yl)ethyl)aniline (9), N-bis(2-(benzo[d]oxazol-2-yl)ethyl)-6-phenyl-1,3,5-triazine-2,4-diamine (13), N-bis(2-(1H-benzo[d]imidazol-2-yl)ethyl)-6-phenyl-1,3,5-triazine-2,4-diamine (15) and N-tris(2-1H-benzo[d]imidazol-2-yl)ethyl)-1,3,5-triazine-2,4,6-triamine (21) show potent cytotoxicity

2-Chloro-4,6-bis­(piperidin-1-yl)-1,3,5-triazine

The title compound, C13H20ClN5, crystallizes with two mol­ecules in the asymmetric unit. The piperidine rings in both mol­ecules adopt chair conformations. Weak π–π inter­actions [centroid–centroid distance = 3.9815 (8) Å] are observed in the crystal structure

N-[2-(3,4-Dimeth­oxy­phen­yl)eth­yl]-N,4-dimethyl­benzene­sulfonamide

In the title compound, C18H23NO4S, the dihedral angle between the two aromatic rings is 29.14 (7)°. The S atom has a distorted tetra­hedral geometry [106.15 (9)–119.54 (10)°]. The crystal structure exhibits weak C—H⋯O and π–π inter­actions

6-Methyl-2,7-diphenyl-1,4-diazepan-5-one

The title compound, C18H20N2O, crystallizes with two mol­ecules in the asymmetric unit. The seven-membered ring in both mol­ecules adopts a distorted chair conformation. The dihedral angles between the phenyl rings are 43.2 (1) and 54.7 (1)° in the two mol­ecules. The crystal packing features N—H⋯O and weak N—H⋯π and C—H⋯π inter­actions

2-(4-Bromo­phen­yl)-3-(4-hy­droxy­phen­yl)-1,3-thia­zolidin-4-one

In the title compound, C15H12BrNO2S, the dihedral angle between the two aromatic rings is 87.81 (8)°. The five-membered thia­zolidine ring has an envelope conformation, with the S atom displaced by 0.4545 (7) Å from the mean plane of the other four ring atoms. The crystal structure exhibits O—H⋯O, C—H⋯O, C—H⋯Br and C—H⋯ π inter­actions

4-Amino­phenyl naphthalene-1-sulfonate

In the title compound, C16H13NO3S, the plane of the amino­benzene ring makes a dihedral angle of 61.04 (6)° with the naphthalene ring system. Both ring systems form weak intra­molecular C—H⋯O hydrogen bonds with the sulfonate group. In the crystal structure, weak inter­molecular N—H⋯O hydrogen bonds and a C—H⋯π inter­action are observed

N-[2-(3,4-Dimeth­oxy­phen­yl)eth­yl]-N-methyl­benzene­sulfonamide

In the title compound, C17H21NO4S, the phenyl and dimeth­oxy­phenyl rings are almost perpendicular to each other, making a dihedral angle of 82.57 (5)°. The structure is stabilized by inter­molecular C—H⋯O inter­actions and the packing is further enhanced by C—H ⋯π inter­actions

2-Phenyl-4H-3,1-benzoxazin-4-one

The title mol­ecule, C14H9NO2, is nearly planar with a dihedral angle of 3.72 (4)° beteewn the plane of the phenyl ring and the 3,1-benzoxazin-4-one fragment. The mol­ecules are arranged into stacks parallel to the b axis via π–π stacking inter­actions [centroid-centroid distance = 4.2789 (11) Å] and the crystal packing is additionally stabilized by weak inter­molecular C—H⋯O inter­actions

1-Naphthyl 9H-carbazole-4-sulfonate

In the title compound, C22H15NO3S, the plane of the carbazole ring system forms a dihedral angle of 65.06 (4)° with the naphthalene ring system. In the crystal structure, a weak intra­molecular C—H⋯O inter­action is observed between the naphthalene ring system and the sulfonate group. Two weak inter­molecular C—H⋯O inter­actions are also observed