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Acta Crystallographica. Section E,... Sep 2011In the title compound, C(16)H(12)BrNO(3), the butyrolactone core adopts the furan-2(5H)-one structure and forms dihedral angles of 44.80 (17) and 65.73 (18)° with...
In the title compound, C(16)H(12)BrNO(3), the butyrolactone core adopts the furan-2(5H)-one structure and forms dihedral angles of 44.80 (17) and 65.73 (18)° with the bromo-benzene and phenol rings, respectively. In the crystal, N-H⋯O and O-H⋯O hydrogen bonds link the mol-ecules, generating R(4) (3)(26) loops The edge-fused rings extend to form a chain running along the b-axis direction and C-H⋯π contacts help to consolidate the packing.
PubMed: 22058954
DOI: 10.1107/S1600536811031849 -
Chemistry (Weinheim An Der Bergstrasse,... Feb 2021The first intermolecular early main group metal-alkene complexes were isolated. This was enabled by using highly Lewis acidic Mg centers in the Lewis base-free cations (...
The first intermolecular early main group metal-alkene complexes were isolated. This was enabled by using highly Lewis acidic Mg centers in the Lewis base-free cations ( BDI)Mg and ( BDI)Mg with B(C F ) counterions ( BDI=CH[C(CH )N(DIPP)] , BDI=CH[C(tBu)N(DIPP)] , DIPP=2,6-diisopropylphenyl). Coordination complexes with various mono- and bis-alkene ligands, typically used in transition metal chemistry, were structurally characterized for 1,3-divinyltetramethyldisiloxane, 1,5-cyclooctadiene, cyclooctene, 1,3,5-cycloheptatriene, 2,3-dimethylbuta-1,3-diene, and 2-ethyl-1-butene. In all cases, asymmetric Mg-alkene bonding with a short and a long Mg-C bond is observed. This asymmetry is most extreme for Mg-(H C=CEt ) bonding. In bromobenzene solution, the Mg-alkene complexes are either dissociated or in a dissociation equilibrium. A DFT study and AIM analysis showed that the C=C bonds hardly change on coordination and there is very little alkene→Mg electron transfer. The Mg-alkene bonds are mainly electrostatic and should be described as Mg ion-induced dipole interactions.
PubMed: 33197075
DOI: 10.1002/chem.202004716 -
Molecules (Basel, Switzerland) Dec 2023A synthetic pathway to a novel 4-aryl-3,4-dihydro-2-1,4-benzoxazine scaffold was developed and a series of compounds based on the scaffold were synthesised as potential...
A synthetic pathway to a novel 4-aryl-3,4-dihydro-2-1,4-benzoxazine scaffold was developed and a series of compounds based on the scaffold were synthesised as potential anticancer agents. The 4-aryl-substituted compounds were prepared via Buchwald-Hartwig cross-coupling between substituted bromobenzenes and various 1,4-benzoxazines, which in turn were generated from a cascade hydrogenation and reductive amination one-pot reaction. These analogues exhibited moderate to good potency against various cancer cell lines. Structure-activity relationship analysis indicated that the inclusion of hydroxyl groups on ring A and ring B was beneficial to biological activity, while having a -amino group on ring C significantly enhanced potency. Molecule displayed the most potent anticancer activity (IC = 7.84-16.2 µM against PC-3, NHDF, MDA-MB-231, MIA PaCa-2, and U-87 MG cancer cell lines), indicating its potential as a lead compound for further structural optimisation. All the synthesised compounds were fully characterised with NMR, HMRS, and IR. The novel benzoxazine scaffold described in this study holds promise and deserves further in-depth studies.
Topics: Benzoxazines; Hydrogenation; Amination; Bromobenzenes; Cell Line
PubMed: 38202749
DOI: 10.3390/molecules29010166 -
Acta Crystallographica. Section E,... Feb 2012The title compound, C(14)H(11)BrClNO, consists of chloro-benzene and bromo-benzene units which are linked at either end of the N-methyl-propionamide group. The...
The title compound, C(14)H(11)BrClNO, consists of chloro-benzene and bromo-benzene units which are linked at either end of the N-methyl-propionamide group. The chloro-benzene unit [maximum deviation = 0.005 (4) Å] makes a dihedral angle of 68.21 (19)° with the bromo-benzene unit [maximum deviation = 0.012 (3) Å]. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules into chains along [010].
PubMed: 22347117
DOI: 10.1107/S1600536812002383 -
Acta Crystallographica. Section E,... Jun 2012In the title compound, C(11)H(9)BrN(4)S, the 1,2,4-triazole ring is essentially planar (r.m.s. deviation = 0.020 Å) and makes a dihedral angle of 29.1 (5)° with...
In the title compound, C(11)H(9)BrN(4)S, the 1,2,4-triazole ring is essentially planar (r.m.s. deviation = 0.020 Å) and makes a dihedral angle of 29.1 (5)° with the bromo-benzene ring. The 3,6-dihydro-1,3,4-thia-diazine ring adopts a twist-boat conformation. In the crystal, mol-ecules are linked by C-H⋯N inter-actions into sheets lying parallel to the (010) plane. The same N atom accepts two such hydrogen bonds.
PubMed: 22719475
DOI: 10.1107/S1600536812019885 -
Nature Communications Jan 2021Structured covalent two-dimensional patterning of graphene with different chemical functionalities constitutes a major challenge in nanotechnology. At the same time, it...
Structured covalent two-dimensional patterning of graphene with different chemical functionalities constitutes a major challenge in nanotechnology. At the same time, it opens enormous opportunities towards tailoring of physical and chemical properties with limitless combinations of spatially defined surface functionalities. However, such highly integrated carbon-based architectures (graphene embroidery) are so far elusive. Here, we report a practical realization of molecular graphene embroidery by generating regular multiply functionalized patterns consisting of concentric regions of covalent addend binding. These spatially resolved hetero-architectures are generated by repetitive electron-beam lithography/reduction/covalent-binding sequences starting with polymethyl methacrylate covered graphene deposited on a Si/SiO substrate. The corresponding functionalization zones carry bromobenzene-, deutero-, and chloro-addends. We employ statistical Raman spectroscopy together with scanning electron microscopy/energy dispersive X-ray spectroscopy for an unambiguous characterization. The exquisitely ordered nanoarchitectures of these covalently multi-patterned graphene sheets are clearly visualized.
PubMed: 33483478
DOI: 10.1038/s41467-020-20651-w -
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 -
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,... May 2012In the title compound, C(26)H(24)BrN(3)O(5)S, the central benzene ring makes dihedral angles of 6.27 (6), 33.63 (6) and 69.31 (5)°, respectively, with the...
In the title compound, C(26)H(24)BrN(3)O(5)S, the central benzene ring makes dihedral angles of 6.27 (6), 33.63 (6) and 69.31 (5)°, respectively, with the pyrazolone ring, the bromo-benzene ring and the terminal phenyl ring. An intra-molecular C-H⋯O hydrogen bond occurs. The crystal packing features weak non-classical C-Br⋯O inter-actions [Br⋯O = 3.222 (2) Å] that form inversion-related dimers.
PubMed: 22590234
DOI: 10.1107/S160053681201447X -
Acta Crystallographica. Section E,... May 2012In the title compound, C(22)H(15)BrO(4), the bromo-benzene ring is inclined at dihedral angles of 23.87 (11) and 52.37 (11)° with respect to the planes of the two...
In the title compound, C(22)H(15)BrO(4), the bromo-benzene ring is inclined at dihedral angles of 23.87 (11) and 52.37 (11)° with respect to the planes of the two benzene rings. The two benzene rings of the biphenyl unit form a dihedral angle of 49.08 (11)°. In the crystal, mol-ecules are linked into [100] chains by C-H⋯O hydrogen bonds.
PubMed: 22590413
DOI: 10.1107/S1600536812018053