PMCC PMCC

Search tips
Search criteria

Advanced
Results 1-16 (16)
 

Clipboard (0)
None

Select a Filter Below

Journals
Authors
Year of Publication
Document Types
1.  Novel Antimicrobial Agents: Fluorinated 2-(3-(Benzofuran-2-yl) pyrazol-1-yl)thiazoles 
A new series of 2-pyrazolin-1-ylthiazoles 8a–d and 13–16 was synthesized by cyclization of N-thiocarboxamide-2-pyrazoline with different haloketones and 2,3-dichloroquinoxaline. The structures of the new compounds were confirmed by elemental analyses as well as NMR, IR, and mass spectral data. The newly synthesized compounds were evaluated for their antimicrobial activities, and also their minimum inhibitory concentration (MIC) against most of test organisms was performed. Amongst the tested ones, compound 8c displayed excellent antimicrobial activity.
doi:10.1155/2013/986536
PMCID: PMC4207413  PMID: 25379293
2.  2-[3-(4-Bromo­phenyl)-5-(4-fluoro­phenyl)-4,5-di­hydro-1H-pyrazol-1-yl]-4-phenyl-1,3-thia­zole 
In the title compound, C24H17BrFN3S, the pyrazole ring is almost planar (r.m.s. deviation = 0.043 Å), with all but the perpendicular fluoro­benzene ring substituents [dihedral angle = 77.9 (3)°] being very approximately coplanar [dihedral angle with the 2-thienyl ring = 19.4 (3)° and with the bromo­benzene ring = 20.3 (3)°; dihedral angle between the 2-thienyl and attached phenyl ring = 11.0 (4)°], so that the mol­ecule has a T-shape. In the crystal, supra­molecular chains along the b-axis direction are sustained by C—H⋯S and C—Br⋯π inter­actions.
doi:10.1107/S1600536813010039
PMCID: PMC3648267  PMID: 23723887
3.  (2E)-3-(4-Fluoro­phen­yl)-1-[5-methyl-1-(4-methyl­phen­yl)-1H-1,2,3-triazol-4-yl]prop-2-en-1-one1  
With respect to the triazole ring in the title compound, C19H16FN3O, the p-tolyl ring is inclined [dihedral angle = 51.79 (11)°], whereas the chalcone residue is almost coplanar [O—C—C—N and C—C—C—C torsion angles = −178.71 (19) and 178.42 (18)°, respectively]. The conformation about the C=C bond [1.328 (3) Å] is E, and the triazole methyl group and the carbonyl O atom are syn. In the crystal, centrosymmetrically related mol­ecules are connected by π–π inter­actions between the triazole and p-tolyl rings [centroid–centroid distance = 3.6599 (12) Å] and these are linked into a three-dimensional architecture by C—H⋯N and C—H⋯π inter­actions.
doi:10.1107/S1600536813008246
PMCID: PMC3647839  PMID: 23723805
4.  (2E)-1-[5-Methyl-1-(4-methyl­phen­yl)-1H-1,2,3-triazol-4-yl]-3-[4-(piperidin-1-yl)phen­yl]prop-2-en-1-one1  
Two independent mol­ecules comprise the asymmetric unit of the title compound, C24H26N4O. The major difference between them is found in the relative orientation of the triazole-bound p-tolyl group which have the opposite sense of twist [N—N—C—C torsion angles = 55.8 (3) and −49.8 (3)°]. The chalcone residue is almost coplanar with the triazole ring [N—C—C—O and C—C—C—C torsion angles = −178.9 (2) and −178.5 (2)°, respectively; cf. 177.9 (3) and 168.5 (3)°, respectively, in the second mol­ecule]. The conformation about each C=C double bond is E and in each case the triazole methyl group is syn to the carbonyl O atom. In the crystal, mol­ecules aggregate into layers parallel to (-113). The first independent mol­ecule self-associates into a layer via C—H⋯O and C—H⋯π inter­actions. By contrast, layers comprising the second independent mol­ecule do not feature specific inter­actions between mol­ecules. The global crystal packing comprises alternating layers.
doi:10.1107/S1600536813008258
PMCID: PMC3647840  PMID: 23723806
5.  4-[5-(4-Fluoro­phen­yl)-1-(4-phenyl-1,3-thia­zol-2-yl)-4,5-dihydro-1H-pyrazol-3-yl]-5-methyl-1-(4-methyl­phenyl)-1H-1,2,3-triazole 
In the title compound, C28H23FN6S, the pyrazole ring adopts an envelope conformation, with the methine C atom being the flap atom. With respect to this ring, the 2-thienyl, triazole and fluoro­benzene rings are approximately coplanar, coplanar and perpendicular, respectively [dihedral angles = 8.56 (17), 6.03 (19) and 73.1 (2)°, respectively] so that to a first approximation the mol­ecule has a T-shape. In the crystal, mol­ecules are consolidated into a three-dimensional architecture by C—H⋯F (involving a bifurcated F atom), C—H⋯S and C—H⋯π inter­actions.
doi:10.1107/S1600536813008179
PMCID: PMC3629653  PMID: 23634140
6.  5-(4-Fluoro­phen­yl)-3-[5-methyl-1-(4-methyl­phen­yl)-1H-1,2,3-triazol-4-yl]-N-phenyl-4,5-dihydro-1H-pyrazole-1-carbothio­amide 
In the title compound, C26H23FN6S, the pyrazole ring has an envelope conformation, with the methine C atom being the flap atom. The thio­urea group is close to being coplanar with the pyrazole N atoms [N—N—C—S torsion angle = 176.78 (15)°], which allows for an intra­molecular N—H⋯N hydrogen bond; the connected triazole ring is nearly coplanar with this ring [N—C—C—N = −172.65 (19)°]. There is a significant twist between the pyrazole ring and attached fluoro­benzene ring [N—C—C—C = −18.8 (3)°] and a greater twist between triazole and attached tolyl ring [dihedral angle = 58.25 (14)°]. In the crystal, supra­molecular chains aligned along [40,10] are consolidated by π–π inter­actions between the triazole and phenyl rings [centroid–centroid distance = 3.7053 (13) Å].
doi:10.1107/S1600536813008155
PMCID: PMC3629654  PMID: 23634141
7.  2-[3-(4-Chloro­phen­yl)-5-(4-fluoro­phenyl)-4,5-dihydro-1H-pyrazol-1-yl]-4-phenyl-1,3-thia­zole 
In the title compound, C24H17ClFN3S, the pyrazole ring is almost planar (r.m.s. deviation = 0.030 Å). With the exception of the methine-bound benzene ring, which forms a dihedral angle of 85.77 (13)° with the pyrazole ring, the remaining non-C atoms lie in an approximate plane (r.m.s. deviation = 0.084 Å) so that overall the mol­ecule has a T-shape. In the crystal, centrosymmetrically related mol­ecules are connected via π–π inter­actions between pyrazole rings [centroid–centroid distance = 3.5370 (15) Å] and these stack along the a axis with no specific inter­actions between them.
doi:10.1107/S1600536813007496
PMCID: PMC3629623  PMID: 23634110
8.  5-Methyl-N′-[(3Z)-2-oxo-2,3-dihydro-1H-indol-3-yl­idene]-1-phenyl-1H-1,2,3-triazole-4-carbohydrazide 
In the title compound, C18H14N6O2, the benzene ring is slightly twisted out of the plane of the 1,2,3-triazole ring (r.m.s. deviation = 0.010 Å), forming a dihedral angle of 6.20 (13)°. The nine non-H ring atoms of the fused five- and six-membered ring system are almost coplanar (r.m.s. deviation = 0.032 Å). The near coplanarity in the central residue is consolidated by an intra­molecular bifurcated N—H⋯(O,N) hydrogen bond. The conformation about the N=C bond is Z. In the crystal, supra­molecular chains along [101] are sustained by N—H⋯O hydrogen bonds and C—H⋯O inter­actions. These are consolidated into a three-dimensional architecture by C—H⋯π and π–π inter­actions; the latter occur between centrosymmetrically related 1,2,3-triazole rings [centroid–centroid distance = 3.6056 (14) Å].
doi:10.1107/S1600536813007502
PMCID: PMC3629624  PMID: 23634111
9.  4-Dimethyl­amino-1-(4-meth­oxy­phen­yl)-2,5-dioxo-2,5-dihydro-1H-pyrrole-3-carbonitrile 
In the title compound, C14H13N3O3, a twist occurs, as seen in the dihedral angle of 53.60 (12)° between the pyrrole and benzene rings. A three-dimensional architecture is formed in the crystal whereby layers of mol­ecules in the ac plane are connected by C—H⋯O and C—H⋯π inter­actions.
doi:10.1107/S1600536813004893
PMCID: PMC3588536  PMID: 23476607
10.  3-(4-Chloro­phen­yl)-5-(4-fluoro­phen­yl)-4,5-dihydro-1H-pyrazole-1-carbothio­amide 
In the title compound, C16H13ClFN3S, the pyrazole ring adopts an envelope conformation with the methine C atom being the flap atom. The chloro- and fluoro­benzene rings are twisted out of the plane of the pyrazole ring [dihedral angles = 15.12 (11) and 80.55 (10)°, respectively]. The amine group is orientated towards a ring N atom, forming an intra­molecular N—H⋯N hydrogen bond. This H atom also forms a hydrogen bond to the F atom, which along with N—H⋯S hydrogen bonding leads to a supra­molecular chain along the c axis. Connections between chains of the type Cl⋯π lead to a layer in the bc plane.
doi:10.1107/S1600536813004492
PMCID: PMC3588515  PMID: 23476591
11.  2-[5-(4-Fluoro­phen­yl)-3-(4-methyl­phen­yl)-4,5-dihydro-1H-pyrazol-1-yl]-4-phenyl-1,3-thia­zole 
In the title compound, C25H20FN3S, two independent mol­ecules comprise the asymmetric unit, which differ in the relative orientation of the fluoro­benzene ring with respect to the pyrazole ring to which it is attached [dihedral angles = 89.39 (17) and 75.23 (16)° in the two mol­ecules]. Each pyrazole ring adopts an envelope conformation with the methine C atom being the flap atom. There are additional twists in the mol­ecules, e.g. between the five-membered rings [dihedral angles = 18.23 (16) and 17.84 (16)°] and between the thia­zole and attached phenyl ring [10.26 (16) and 20.87 (15)°]. Overall, each mol­ecule has a T-shape. In the crystal, mol­ecules are connected into a three-dimensional architecture by weak C—H⋯π inter­actions.
doi:10.1107/S1600536813004339
PMCID: PMC3588500  PMID: 23476577
12.  5-(4-Fluoro­phen­yl)-3-(4-methyl­phen­yl)-4,5-dihydro-1H-pyrazole-1-carbothio­amide 
The central pyrazole ring in the title compound, C17H16FN3S, adopts an envelope conformation with the methine C atom bearing the 4-fluoro­phenyl substituent as the flap atom. Whereas the tolyl ring is slightly twisted out of the least-squares plane through the pyrazole ring [dihedral angle = 13.51 (11)°], the fluoro­benzene ring is almost perpendicular [dihedral angle = 80.21 (11)°]. The thio­amide group is almost coplanar with the N—N bond of the ring [N—N—C—N torsion angle = 1.2 (3)°] and the amine group forms an intra­molecular hydrogen bond with a ring N atom. In the crystal, supra­molecular double layers in the bc plane are formed via N—H⋯S, N—H⋯F and C—H⋯F inter­actions.
doi:10.1107/S1600536813004194
PMCID: PMC3588501  PMID: 23476571
13.  2-(2,4-Dichloro­phen­oxy­meth­yl)-5-(4-methyl­phen­yl)imidazo[2,1-b][1,3,4]thia­diazole1  
In the title compound, C18H13Cl2N3OS, the eight atoms comprising the central imidazo/thia­diazo­lethia­diazole residue are coplanar (r.m.s. deviation = 0.009 Å). The dihedral angle of 8.72 (13)° between the dichloro­benzene and tolyl rings reflects a twist about the O—C(benzene) bond; the Cm—O—Cb—Cb torsion angle = −168.5 (2)° (m = methyl­ene C and b is benzene C). Supra­molecular tapes along the b axis are found in the crystal structure which are mediated by π–π inter­actions occurring between centrosymmetrically related thia­diazole rings [inter-ring centroid distance = 3.6907 (16) Å] and between the benzene and tolyl rings [inter-ring centroid distance = 3.7597 (16) Å].
doi:10.1107/S160053681300384X
PMCID: PMC3588533  PMID: 23476564
14.  3-[5-Methyl-1-(4-methyl­phen­yl)-1H-1,2,3-triazol-4-yl]-N-phenyl-5-[4-(piperidin-1-yl)phen­yl]-4,5-dihydro-1H-pyrazole-1-carbothio­amide dimethyl­formamide hemisolvate 
The essentially planar pyrazole ring (r.m.s. deviation = 0.013 Å) in the title hemisolvate, C31H33N7S·0.5C3H7NO, is almost coplanar with the pendant thio­urea residue [N—N—C—S torsion angle = −173.2 (4)°] and slightly twisted with respect to the triazole ring [dihedral angle = 7.7 (3)°]. An intra­molecular thio­urea–pyrazole N—H⋯N hydrogen bond, via an S(5) loop, is formed. Supra­molecular chains along the c axis are formed in the crystal via piperidine–triazole C—H⋯N inter­actions. These are bridged into loosely associated double chains via C—H⋯O inter­actions involving the disordered (over two positions) dimethyl­formamide solvent mol­ecules. The thio­urea-bound phenyl ring is also disordered over two positions of equal occupancy.
doi:10.1107/S1600536812024488
PMCID: PMC3393261  PMID: 22807818
15.  5-(4-Fluoro­phen­yl)-3-[5-methyl-1-(4-methyl­phen­yl)-1H-1,2,3-triazol-4-yl]-4,5-dihydro-1H-pyrazole-1-carbothio­amide 
In the title compound, C20H19FN6S, the pyrazole ring has an envelope conformation, with the methine C atom being the flap atom. The dihedral angle between the least-squares plane through the pyrazole and triazole rings is 7.59 (9)°, and the triazole and attached benzene ring form a dihedral angle of 74.79 (9)°. The thio­urea group is coplanar with the pyrazole ring [N—N—C—S torsion angle = −179.93 (11)°], which enables the formation of an intra­molecular N—H⋯N hydrogen bond. In the crystal, inversion-related mol­ecules associate via N—H⋯S hydrogen bonds and eight-membered {⋯HNCS}2 synthons feature in the crystal packing. These synthons are connected into supra­molecular chains along the a axis via N—H⋯F hydrogen bonds, and the chains are consolidated into layers in the ab plane via C—H⋯S and C—H⋯F contacts.
doi:10.1107/S1600536812024245
PMCID: PMC3379505  PMID: 22719703
16.  4-{1-[4-(4-Bromo­phen­yl)-1,3-thia­zol-2-yl]-5-(4-fluoro­phen­yl)-4,5-dihydro-1H-pyrazol-3-yl}-5-methyl-1-(4-methyl­phen­yl)-1H-1,2,3-triazole 
In the title compound, C28H22BrFN6S, the central pyrazole ring has an envelope conformation, with the methine C atom being the flap atom. The dihedral angles between the least-squares plane through this ring and the adjacent thia­zole [18.81 (15)°] and triazole [1.83 (16)°] rings indicate a twist in the mol­ecule. A further twist is evident by the dihedral angle of 64.48 (16)° between the triazole ring and the attached benzene ring. In the crystal, C—H⋯N, C—H⋯F, C—H⋯π and π–π inter­actions [occurring between the thia­zole and triazole rings, centroid–centroid distance = 3.571 (2) Å] link mol­ecules into a three-dimensional architecture. The sample studied was a non-merohedral twin; the minor twin component refined to 47.16 (7)%.
doi:10.1107/S1600536812024257
PMCID: PMC3379506  PMID: 22719704

Results 1-16 (16)