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Acta Crystallographica. Section E,... Oct 2012In the title compound, C(16)H(13)BrFN(3)O(2)S, the dihedral angle between the aromatic rings is 2.55 (19)° and the C=N-N=C torsion angle is 178.9 (3)°. The...
In the title compound, C(16)H(13)BrFN(3)O(2)S, the dihedral angle between the aromatic rings is 2.55 (19)° and the C=N-N=C torsion angle is 178.9 (3)°. The conformation of the thia-zine ring is an envelope, with the S atom displaced by -0.811 (3) Å from the mean plane of the other five atoms (r.m.s. deviation = 0.042 Å). In the crystal, C-H⋯O inter-actions link the mol-ecules and weak aromatic π-π stacking between the fluoro-benzene and bromo-benzene rings [centroid-centroid separation = 3.720 (2) Å and inter-planar angle = 2.6 (2)°] is also observed.
PubMed: 23125654
DOI: 10.1107/S1600536812037403 -
Acta Crystallographica. Section E,... Jun 2012The asymmetric unit of the title compound, C(15)H(10)BrNO(4)S, contains two different conformers in which the benzisothia-zole rings are essentially planar, with r.m.s....
The asymmetric unit of the title compound, C(15)H(10)BrNO(4)S, contains two different conformers in which the benzisothia-zole rings are essentially planar, with r.m.s. deviations of 0.012 and 0.017 Å. The mean planes of the benzene rings form dihedral angles 70.49 (13) and 72.79 (11)° with the benzisothia-zole rings. The orientation of the Br atoms in the two conformers exhibit the most pronounced difference, with opposing orientations in the two mol-ecules. The crystal structure is stabilized by π-π inter-actions between the benzene rings of the benzisothia-zole moieties of one mol-ecule and bromo-benzene rings of the other mol-ecule, with distances between the ring centroids of 3.599 (3) and 3.620 (3) Å, respectively. The crystal packing is further consolidated by pairs of weak inter-molecular C-H⋯O hydrogen bonds, which form inversion dimers.
PubMed: 22719647
DOI: 10.1107/S1600536812022428 -
Acta Crystallographica. Section E,... Nov 2011In the title mol-ecule, C(24)H(15)BrCl(2)N(2)O, the dihedral angles betwen the pyrazole ring and its N-bonded phenyl (A) and C-bonded bromo-benzene (B) rings are...
In the title mol-ecule, C(24)H(15)BrCl(2)N(2)O, the dihedral angles betwen the pyrazole ring and its N-bonded phenyl (A) and C-bonded bromo-benzene (B) rings are 10.34 (16) and 40.95 (15)°, respectively. The dihedral angle between rings A and B is 56.89 (17)°. The title mol-ecule exists in a trans conformation with respect to the acyclic C=C bond. In the crystal, mol-ecules are linked into inversion dimers by pairs of C-H⋯O hydrogen bonds, generating R(2) (2)(14) loops. The crystal structure is further consolidated by C-H⋯π inter-actions.
PubMed: 22220107
DOI: 10.1107/S1600536811044424 -
Acta Crystallographica. Section E,... Oct 2008In the title compound, C(24)H(20)BrN(3)O(4)S, the central benzene ring makes dihedral angles of 17.13 (13), 39.83 (13) and 58.37 (13)°, respectively, with the...
In the title compound, C(24)H(20)BrN(3)O(4)S, the central benzene ring makes dihedral angles of 17.13 (13), 39.83 (13) and 58.37 (13)°, respectively, with the pyrazolone ring, the bromo-benzene ring and the terminal phenyl ring. In the crystal structure, the packing is stabilized by a weak non-classical inter-molecular C-H⋯O hydrogen bond which links the mol-ecules into a chain propagating in [100].
PubMed: 21581098
DOI: 10.1107/S1600536808035034 -
Acta Crystallographica. Section E,... Nov 2008In the title compound, C(24)H(20)BrN(3)O(4)S, the central benzene ring makes dihedral angles of 24.55 (8), 49.52 (12) and 59.65 (7)°, respectively, with the...
In the title compound, C(24)H(20)BrN(3)O(4)S, the central benzene ring makes dihedral angles of 24.55 (8), 49.52 (12) and 59.65 (7)°, respectively, with the pyrazolone ring, the bromo-benzene ring and the terminal phenyl ring. The packing is stabilized by weak non-classical inter-molecular C-H⋯O=C hydrogen bonds that form inversion-related dimers.
PubMed: 21581323
DOI: 10.1107/S160053680803688X -
IARC Monographs on the Evaluation of... 1990
Review
Topics: Animals; Bromobenzenes; Carcinogens; Chemical Phenomena; Chemistry; Female; Flame Retardants; Halogenated Diphenyl Ethers; Male; Mice; Phenyl Ethers; Polybrominated Biphenyls; Rats
PubMed: 2197464
DOI: No ID Found -
Acta Crystallographica. Section E,... Apr 2013In the title molecular salt, C19H18BrClN3O2 (+)·Cl(-), the dihedral angles between the pyrimidine ring and the chlorobenzene and bromobenzene rings are 72.4 (2) and...
In the title molecular salt, C19H18BrClN3O2 (+)·Cl(-), the dihedral angles between the pyrimidine ring and the chlorobenzene and bromobenzene rings are 72.4 (2) and 45.5 (2)°, respectively. The dihedral angle between the chlorobenzene and bromobenzene rings is 27.5 (2)°. The conformation of the mol-ecule is stabilized by an intra-molecular C-H⋯O inter-action. In the crystal, the anion and cation are linked by an N-H⋯Cl hydrogen bond. Pairs of weak C-H⋯O and C-H⋯Cl hydrogen bonds form inversion dimers. Further N-H⋯Cl hydrogen bonds form R 2 (1)(6) motifs and link the dimers into chains along [101]. Br⋯Cl short contacts [3.482 (2) Å] inter-link the hydrogen-bonded chains along the b-axis direction.
PubMed: 23634063
DOI: 10.1107/S1600536813006296 -
Drug Metabolism and Disposition: the... Oct 2023In the early '70s, Dr B. B. Brodie, Head of the LCP, NHI, NIH, initiated a program to elucidate the mechanism of hepatic necrosis induced in rats by bromobenzene. These...
In the early '70s, Dr B. B. Brodie, Head of the LCP, NHI, NIH, initiated a program to elucidate the mechanism of hepatic necrosis induced in rats by bromobenzene. These studies showed a crucial role for its 3,4-epoxide intermediate, known in part, to collapse to 4-bromophenol. To examine a possible contribution of this phenol to tissue toxicity, some rats were co-administered a high dose of acetaminophen to suppress phenolic clearance by glucuronidation and sulfation. Subsequent examination of liver slices showed that the acetaminophen-only control rats had extensive centrilobular liver necrosis. This article is a personal reminiscence of the events that led up to this accidental observation, how it happened, and the subsequent resolution of the underlying mechanism, including the covalent binding of NAPQI to liver protein as the initial "hit", the glutathione protective threshold, the antidotal activity of cysteine, and the existence of the "therapeutic window" for antidotal therapy. Collectively, these studies formed the basis for antidotal therapy of acetaminophen overdose patients, Not applicable.
PubMed: 37793785
DOI: 10.1124/dmd.123.001278 -
Acta Crystallographica. Section E,... May 2013In the title compound, C24H17BrFN3S, the pyrazole ring is almost planar (r.m.s. deviation = 0.043 Å), with all but the perpendicular fluoro-benzene ring substituents...
In the title compound, C24H17BrFN3S, the pyrazole ring is almost planar (r.m.s. deviation = 0.043 Å), with all but the perpendicular fluoro-benzene ring substituents [dihedral angle = 77.9 (3)°] being very approximately coplanar [dihedral angle with the 2-thienyl ring = 19.4 (3)° and with the bromo-benzene ring = 20.3 (3)°; dihedral angle between the 2-thienyl and attached phenyl ring = 11.0 (4)°], so that the mol-ecule has a T-shape. In the crystal, supra-molecular chains along the b-axis direction are sustained by C-H⋯S and C-Br⋯π inter-actions.
PubMed: 23723887
DOI: 10.1107/S1600536813010039 -
Tetrahedron Nov 2021A chemoenzymatic convergent synthesis of 10-benzyloxy narciclasine from bromobenzene was accomplished in 16 steps. The key transformations included toluene...
A chemoenzymatic convergent synthesis of 10-benzyloxy narciclasine from bromobenzene was accomplished in 16 steps. The key transformations included toluene dioxygenase-mediated hydroxylation, nitroso Diels-Alder reaction and intramolecular Heck cyclization. The unnatural derivative of narciclasine was subjected to biological evaluation and its activity was compared to other C-10 and C-7 compounds prepared previously.
PubMed: 35058668
DOI: 10.1016/j.tet.2021.132505