Selective one-pot multicomponent synthesis and anti-tubercular evaluation of 5-(aryl/cyclohexylsulfanyl)-2-alkoxy-4,6-diarylnicotinonitriles.

A new set of highly substituted pyridine derivatives has been synthesized by a product selective four component reaction of aryl aldehyde, malononitrile and 2-aryl/cyclohexylsulfanyl-1-aryl-1-ethanones in presence of sodium hydroxide in methyl/ethyl alcohol. Among the compounds, 4,6-bis(4-chlorophenyl)-5-[(4-chlorophenyl)sulfanyl]-2-methoxynicotinonitrile (4n) inhibited Mycobacterium tuberculosis (MTB) with minimum inhibitory concentration (MIC) of 3.1 microM and was more potent than ethambutol and pyrazinamide.

(E)-3-(4-Bromo-phen-yl)-3-[3-(4-bromo-phen-yl)-1H-pyrazol-1-yl]prop-2-enal.

There are two crystallographically independent mol-ecules in the asymmetric unit of the title compound, C(18)H(12)Br(2)N(2)O. In each mol-ecule, one of the bromo-phenyl rings lies almost in the plane of pyrazole unit [dihedral angles of 5.8 (3)° in the first mol-ecule and and 5.

3-(4-Chloro-phen-yl)-1-[(E)-1-(4-chloro-phen-yl)-2-(4-methyl-phenyl-sulfan-yl)ethen-yl]-4-(4-methyl-phenyl-sulfan-yl)-1H-pyrazole.

In the title compound, C(31)H(24)Cl(2)N(2)S(2), the pyrazole ring adopts planar conformation with a maximum deviation of 0.002 (2) Å. The chloro-phenyl rings are twisted out of the plane of the pyrazole ring by 75.

(E)-3-(4-Methyl-phen-yl)-3-[3-(4-methyl-phen-yl)-1H-pyrazol-1-yl]-2-propenal.

In the title compound, C(20)H(18)N(2)O, the pyrazole ring adopts a planar conformation. The C-N bond lengths in the pyrazole ring are shorter than a standard C-N single bond (1.443 Å), but longer than a standard double bond (1.

4-(Cyclo-hexyl-sulfan-yl)-1-[(E)-2-(cyclo-hexyl-sulfan-yl)-1-phenyl-ethen-yl]-3-phenyl-1H-pyrazole.

In the title compound, C(29)H(34)N(2)S(2), the pyrazole ring is planar and both cyclo-hexane rings adopt chair conformations. The dihedral angles between the pyrazole ring and the two benzene rings are 59.9 (2) and 19.

1-(2,4-Dinitro-phenyl)-3-(4-methyl-phenyl)-4-phenyl-sulfanyl-1H-pyrazole.

In the title compound, C(22)H(16)N(4)O(4)S, the dihedral angles between the pyrazole ring and the pendant aromatic rings are 26.2 (1), 41.1 (1) and 89.

4-(4-Chloro-phenyl-sulfan-yl)-1-[(E)-2-(4-chloro-phenyl-sulfan-yl)-1-phenyl-ethen-yl]-3-phenyl-1H-pyrazole.

In the title compound, C(29)H(20)Cl(2)N(2)S(2), the pyrazole ring adopts a planar conformation. The chlorophenyl rings are twisted from the pyrazole ring at angles of 52.74 (14) and 29.

3-Cyclo-hexyl-sulfan-yl-2-(4-methyl-phen-yl)-5,7-dinitro-1H-indole.

In the title compound, C(21)H(21)N(3)O(4)S, the cyclo-hexane ring adopts a chair conformation. The nitro and methyl-phenyl groups are all coplanar with the indole ring system. Intra-molecular N-H⋯O and C-H⋯S hydrogen bonds generate S(6) ring motifs.

1-[(E)-2-Formyl-1-(4-methyl-phen-yl)ethen-yl]-3-(4-methyl-phen-yl)pyrazole-4-carbaldehyde.

In the crystal structure of the title compound, C(21)H(18)N(2)O(2), mol-ecules are linked through C-H⋯O inter-actions. Two symmetry-related mol-ecules form a cyclic centrosymmetric R(2) (2)(20) dimer. These dimers are further connected into chains running along the b axis.