Synthesis and characterization of a novel series of benzenesulfonylurea and thiourea derivatives of 2H-pyran and 2H-pyridine-2-ones as antibacterial, antimycobacterial and antifungal agents

Arylhydrazines reacted with dehydroacetic acid (1) to give the corresponding 2H-pyran-2-one hydrazones (2), which on treatment with hydrazine hydrate afforded the corresponding 1-amino-2H-pyridin-2-ones (3). Reaction of 3 with nitrous acid, aromatic aldehyde and substituted benzenesulfonyl chlorides yielded the corresponding 2H-pyridine-2-one derivatives. A series of urea and thiourea derivatives were also prepared. Some of these compounds have shown significant antibacterial and mild to moderate antimycobacterial and antifungal activities

(E)-2-Methyl-6-[(1-phenyl-1H-pyrazol-4-yl)methyl­idene]cyclo­hexa­none

The asymmetric unit of the title compound, C17H18N2O, contains two independent mol­ecules. In both, the cyclo­hexane ring adopts a flattened chair conformation, and the 3- and 4-methyl­ene C atoms as well as the methyl C atoms are disordered over two positions, the occupancy of the major component being 68 (1)% in one mol­ecule and 64 (1)% in the other. The phenyl and pyrazole rings in both mol­ecules are approximately coplanar, the r.m.s. deviations being 0.048 and 0.015 Å, respectively. Weak inter­molecular C—H⋯O hydrogen bonding is present in the crystal structure

4-{(4Z)-4-[(2Z)-3-(4-Fluoro­anilino)-1-hy­droxy­but-2-en-1-yl­idene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl}­benzene­sulfonamide

In the title compound, C20H19FN4O4S, the pyrazole and benzene­sulfonamide rings are coplanar [dihedral angle = 5.02 (15)°] but this planarity does not extend over the entire mol­ecule, the dihedral angle between the terminal six-membered rings being 33.24 (14)°. Intra­molecular hy­droxy–hy­droxy O—H⋯O and amine–hy­droxy N—H⋯O hydrogen bonds, as a well as a tight C—H⋯O(carbon­yl) inter­action, lead to a sequence of three fused S(6) rings. Supra­molecular chains along the a axis feature in the crystal packing; these chains are stabilized by amine–sulfonamide N—H⋯O and amine–pyrazole N—H⋯N hydrogen bonds

2-Amino-4-(3,4-dimeth­oxy­phen­yl)-5,6-dihydro­benzo[h]quinoline-3-carbo­nitrile–3-amino-1-(3,4-dimeth­oxy­phen­yl)-9,10-dihydro­phenanthrene-2,4-dicarbonitrile (1/19)

The asymmetric unit of the 1:19 title co-crystal of 2-amino-4-(3,4-dimeth­oxy­phen­yl)-5,6-dihydro­benzo[h]quinoline-3-carbo­nitrile and 3-amino-1-(3,4-dimeth­oxy­phen­yl)-9,10-dihydro­phenanthrene-2,4-dicarbonitrile, 0.05C22H19N3O2·0.95C24H19N3O2, has the atoms of the fused-ring system and those of the amino, cyano and dimeth­oxy­phenyl substitutents overlapped. The fused-ring system is buckled owing to the ethyl­ene linkage in the central ring with the two flanking aromatic rings being twisted by 31.9 (1)°. The ring of the dimeth­oxy­phenyl substituent is twisted by 72.4 (1)° relative to the amino- and cyano-bearing aromatic ring. In the crystal, mol­ecules are linked by duplex amine N—H⋯O(meth­oxy) hydrogen bonds in a cyclic association [graph-set R 2 2(7)], generating a helical chain structure extending along [201]

(2Z)-3-(4-Fluoro­anilino)-1-(5-hy­droxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)but-2-en-1-one

The central carbonyl group in the title compound, C20H18FN3O2, forms amine–hy­droxy N—H⋯O and hy­droxy–hy­droxy O—H⋯O hydrogen bonds, leading to two S(6) rings. The N-bound phenyl ring is coplanar with the five-membered ring to which it is attached [dihedral angle = 6.27 (10)°], but an overall twist in the mol­ecule is evident, the dihedral angle between the terminal phenyl and benzene rings being 27.30 (10)°. Mol­ecules aggregate into a three-dimensional architecture via C—H⋯F, C—H⋯O and C—H⋯π inter­actions

4-(3-Methyl-5-phenyl-1H-pyrazol-1-yl)benzene­sulfonamide

With respect to the planar five-membered ring of the title compound, C16H15N3O2S, the phenyl ring is aligned at 47.0 (1)° and the phenyl­ene ring at 37.6 (1)°. The amino group has the N atom in a pyramidal geometry; the group is a hydrogen-bond donor to the sulfonyl O atom of one mol­ecule and to the pyrazole N atom of another mol­ecule, resulting in the formation of a layer parallel to the bc plane

4-[5-(Furan-2-yl)-3-trifluoro­methyl-1H-pyrazol-1-yl]benzene­sulfonamide

In the title compound, C14H10F3N3O3S, there are significant twists in the mol­ecule, as seen in the values of the dihedral angles between the pyrazole ring and each of the furan [31.1 (2)°] and benzene rings [55.58 (10)°]. The amino N atom occupies a position almost normal to the benzene ring [N—S—Car—Car (ar = aromatic) torsion angle = 83.70 (19)°]. One amino H atom forms a hydrogen bond to the tricoordinate pyrazole N atom and the other inter­acts with a sulfonamide O atom, forming a supra­molecular chain along [010]. The chains are consolidated into a supra­molecular layers via C—H⋯O inter­actions involving the second sulfonamide O atom; layers stack along [10-1]. The furan ring was found to be disordered over two diagonally opposite orientations of equal occupancy

4-(2,7-Dimethyl-4-oxo-1,3-thia­zolo[4,5-d]pyridazin-5-yl)benzene­sulfonamide

The thia­zole–pyridazine fused-ring system of the title compound, C13H12N4O3S2, is approximately planar (r.m.s. deviation = 0.037 Å); the benzene ring connected to the fused-ring system through the N atom is twisted by 39.3 (1)°. The amine group uses an H atom to form a hydrogen bond to the ketonic O atom of an inversion-related mol­ecule to generate a dimer; adjacent dimers are linked by an N—H⋯O hydrogen bond to form a linear chain

Ethyl N-[4-(3-methyl-4,5-dihydro­benzo[g]indazol-1-yl)phenyl­sulfon­yl]thio­carbam­ate ethanol monosolvate

The title compound, C21H20N3O3S2·CH3CH2OH, comprises two independent organic mol­ecules and two ethanol solvent mol­ecules. The mol­ecules are related by pseudo-mirror symmetry. In both mol­ecules, the N-bound benzene ring is twisted out of the plane of the pyrazole ring [the dihedral angles are 51.4 (3) and 44.1 (3)°, respectively]. Similarly, the benzene ring of the 1,2-dihydro­naphthalene residue is inclined with respect to the five-membered ring [dihedral angles 18.3 (3) and 22.2 (3)°]. Overall, each mol­ecule has a flattened U shape. Dimeric aggregates mediated by O—H⋯N(pyrazole) and amide-N—H⋯O hydrogen bonds feature in the crystal packing, whereby the ethanol mol­ecules link the independent organic mol­ecules, leading to four-mol­ecule aggregates

N,N′-Bis[(E)-1-(thio­phen-3-yl)ethyl­idene]ethane-1,2-diamine

The complete mol­ecule of the title compound, C14H16N2S2, is generated by a crystallographic inversion centre. The thio­phene residue is close to being coplanar with the imine group [C—C—C—N torsion angle = 6.5 (2)°], and the conformation about the imine C=N bond [1.281 (2) Å] is E. In the crystal, the three-dimensional architecture is consolidated by C—H⋯N, C—H⋯π and S⋯S [3.3932 (7) Å] inter­actions