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Acta Crystallographica. Section E,... Mar 2012In the title compound, C(20)H(18)BrN(3)O(2), the central carbonyl group forms amine-N-H⋯O and hy-droxy-O-H⋯O hydrogen bonds, which lead to two fused S(6) rings. The...
In the title compound, C(20)H(18)BrN(3)O(2), the central carbonyl group forms amine-N-H⋯O and hy-droxy-O-H⋯O hydrogen bonds, which lead to two fused S(6) rings. The N-bound phenyl ring is coplanar with the five-membered ring to which it is attached [dihedral angle = 5.22 (18)°], but the dihedral angle [33.87 (17)°] between the terminal phenyl and bromo-benzene rings indicates an overall twist in the mol-ecule. In the crystal packing, mol-ecules assemble into dimeric aggregates via C-H⋯π inter-actions.
PubMed: 22412678
DOI: 10.1107/S1600536812006939 -
Acta Crystallographica. Section E,... Mar 2012In the title compound, C(27)H(26)Br(2)N(2)O, the piperazine ring adopts a chair conformation with the N-C bonds in equatorial orientations. The C=C double bond has an E...
In the title compound, C(27)H(26)Br(2)N(2)O, the piperazine ring adopts a chair conformation with the N-C bonds in equatorial orientations. The C=C double bond has an E configuration. The dihedral angle between the bromo-benzene rings is 83.0 (4)°. In the crystal, inversion dimers linked through pairs of C-H⋯O hydrogen bonds generate R(2) (2)(10) loops.
PubMed: 22412518
DOI: 10.1107/S1600536812003820 -
Acta Crystallographica. Section E,... Sep 2011In the title compound, C(20)H(18)BrNO(4)S(2), the mean planes formed by the toluene substituents are inclined at a dihedral angle of 45.34 (8)°. The bromo-benzene...
In the title compound, C(20)H(18)BrNO(4)S(2), the mean planes formed by the toluene substituents are inclined at a dihedral angle of 45.34 (8)°. The bromo-benzene group is disordered over two positions with an occupancy ratio of 0.74:0.26, resulting in two conformations of the ring; the two rings are oriented at a dihedral angle of 6.6 (6)° with each other. In the crystal structure, weak C-H⋯O inter-actions connect the mol-ecules in a zigzag manner along the a axis.
PubMed: 22064782
DOI: 10.1107/S1600536811032533 -
Acta Crystallographica. Section E,... Apr 2013In the title compound, C21H15BrN2O2, the 14 non-H atoms of the 4H-benzo[h]chromene fused-ring system are approximately coplanar (r.m.s. deviation = 0.129 Å). Within...
In the title compound, C21H15BrN2O2, the 14 non-H atoms of the 4H-benzo[h]chromene fused-ring system are approximately coplanar (r.m.s. deviation = 0.129 Å). Within this system, the 4H-pyran ring adopts a flattened half-chair conformation with the methine C atom lying 0.281 (4) Å above the plane of the remaining atoms (r.m.s. deviation = 0.0446 Å). The bromo-benzene ring is almost perpendicular to the fused-ring system [dihedral angle = 85.34 (13)°]. In the crystal, supra-molecular layers parallel to (101) are sustained by amine-cyano N-H⋯N and amine-meth-oxy N-H⋯O hydrogen bonds. The layers stack with inter-actions of the type (bromo-benzene)C-H⋯π(outer-C6 ring of the fused-ring system) connecting them.
PubMed: 23634035
DOI: 10.1107/S1600536813005461 -
Acta Crystallographica. Section E,... Sep 2008In the mol-ecule of the title compound, C(17)H(16)BrN(3)O, the triazole ring is oriented at dihedral angles of 6.14 (9)° and 82.08 (9)°, respectively, with respect...
In the mol-ecule of the title compound, C(17)H(16)BrN(3)O, the triazole ring is oriented at dihedral angles of 6.14 (9)° and 82.08 (9)°, respectively, with respect to the phenyl and bromo-benzene rings. The dihedral angle between the bromo-benzene and phenyl rings is 87.28 (7)°. The intra-molecular C-H⋯O hydrogen bond results in the formation of a planar five-membered ring, which is oriented at a dihedral angle of 0.13 (6)° with respect to the bromo-benzene ring. There is an inter-molecular C-H⋯π contact between a methyl-ene group and the bromo-benzene ring.
PubMed: 21201123
DOI: 10.1107/S1600536808027748 -
Acta Crystallographica. Section E,... May 2010In the title compound, 2C(14)H(14)N(+)·C(6)H(4)BrO(3)S(-)·I(-), two crystallographically independent cations exist in an E configuration with respect to the C=C...
In the title compound, 2C(14)H(14)N(+)·C(6)H(4)BrO(3)S(-)·I(-), two crystallographically independent cations exist in an E configuration with respect to the C=C ethenyl bond. One cation is approximately planar, whereas the other is twisted slightly, the dihedral angles between the pyridinium and phenyl rings of each cation being 0.96 (15) and 7.05 (16)°. In the crystal structure, the cations are stacked in an anti-parallel manner along the a axis through weak C-H⋯π inter-actions and π-π inter-actions, with centroid-centroid distances of 3.5544 (19) and 3.699 (2) Å. The 4-bromobenzene-sulfonate anions and the cations are linked together by weak C-H⋯O inter-actions. A short Br⋯I contact [3.6373 (4) Å] and C-H⋯I interactions are also observed.
PubMed: 21579454
DOI: 10.1107/S1600536810017277 -
Journal of the American Chemical Society Mar 2016We report herein a simple, metal- and additive-free, photoinduced borylation of haloarenes, including electron-rich fluoroarenes, as well as arylammonium salts directly...
We report herein a simple, metal- and additive-free, photoinduced borylation of haloarenes, including electron-rich fluoroarenes, as well as arylammonium salts directly to boronic acids. This borylation method has a broad scope and functional group tolerance. We show that it can be further extended to boronic esters and carried out on gram scale as well as under flow conditions.
Topics: Boronic Acids; Bromobenzenes; Fluorobenzenes; Hydrocarbons, Aromatic; Photochemical Processes; Quaternary Ammonium Compounds
PubMed: 26914533
DOI: 10.1021/jacs.6b01376 -
Ecotoxicology and Environmental Safety Jun 2022Decabromodiphenyl ethane (DBDPE) is a major alternative to BDE-209 owing to its lower toxicity. However, the mass production and increased consumption of DBDPE in recent...
Decabromodiphenyl ethane (DBDPE) is a major alternative to BDE-209 owing to its lower toxicity. However, the mass production and increased consumption of DBDPE in recent years have raised concerns related to its adverse health effects. However, the effect and mechanism of DBDPE on cardiotoxicity have rarely been studied. In the present study, we investigated the impacts of DBDPE on the cardiovascular system in male SD rats and then explored the underlying mechanisms to explain the cardiotoxicity of DBDPE using AC16 cells. Under in vivo conditions, male rats were administered with an oral dosage of DBDPE at 0, 5, 50, and 500 mg/kg/day for 28 days, respectively. Histopathological analysis demonstrated that DBDPE induced cardiomyocyte injury and fibrosis, and ultrastructural observation revealed that DBDPE could induce mitochondria damage and dissolution. DBDPE could thus decrease the level of MYH6 and increase the level of SERCA2, which are the two key proteins involved in the maintenance of homeostasis during myocardial contractile and diastolic processes. Furthermore, DBDPE could increase the serum levels of glucose and low-density lipoprotein but decrease the content of high-density lipoprotein. In addition, DBDPE could activate the PI3K/AKT/GLUT2 and PPARγ/RXRα signaling pathways in AC16 cells. In addition, DBDPE decreased the UCP2 level and ATP synthesis in mitochondria both under in vitro and in vivo conditions, consequently leading to apoptosis via the Cytochrome C/Caspase-9/Caspase-3 pathway. Bisulfite sequencing PCR (BSP) identified the hypermethylation status of fat mass and obesity-associated gene (FTO). 5-aza exerted the opposite effects on the PI3K/AKT/GLUT2, PPARγ/RXRα, and Cytochrome C/Caspase-9/Caspase-3 signaling pathways induced by DBDPE in AC16 cells. In addition, the DBDPE-treated altered levels of UCP2, ATP, and apoptosis were also found to be significantly reversed by 5-aza in AC16 cells. These results suggested that FTO hypermethylation played a regulative role in the pathological process of DBDPE-induced glycolipid metabolism disorder, thereby contributing to the dysfunction of myocardial contraction and relaxation through cardiomyocytes fibrosis and apoptosis via the mitochondrial-mediated apoptotic pathway resulting from mitochondrial dysfunction.
Topics: Adenosine Triphosphate; Alpha-Ketoglutarate-Dependent Dioxygenase FTO; Animals; Apoptosis; Bromobenzenes; Cardiotoxicity; Caspase 3; Caspase 9; Cytochromes c; Fibrosis; Heart Diseases; Male; Obesity; PPAR gamma; Phosphatidylinositol 3-Kinases; Proto-Oncogene Proteins c-akt; Rats; Rats, Sprague-Dawley
PubMed: 35462195
DOI: 10.1016/j.ecoenv.2022.113534 -
BMJ Case Reports Jul 2022A man in his 30s, with a history of two operated penetrating keratoplasty (PK), primarily for viral keratitis, presented with pain, redness and diminution of vision in...
A man in his 30s, with a history of two operated penetrating keratoplasty (PK), primarily for viral keratitis, presented with pain, redness and diminution of vision in his left eye of 4 days duration. Postoperatively, he was prescribed oral antivirals, topical steroid eyedrops, lubricants and antiglaucoma medications. Eight months after transplantation, an epithelial defect with heaped up margins was noted on anterior segment evaluation on a routine follow-up visit. On checking his medications, it was found that the patient was unknowingly using bromfenac drops in place of brimonidine tartrate for the past month. A diagnosis of neurotrophic keratitis was made in the setting of PK performed for viral keratitis, incited by use of topical bromfenac. The patient was prescribed preservative-free lubricants with immediate discontinuation of bromfenac drops. Topical steroid drops were withheld till the epithelial defect healed. Complete healing of the defect was noted after 4 weeks of therapy.
Topics: Benzophenones; Bromobenzenes; Corneal Dystrophies, Hereditary; Corneal Transplantation; Humans; Keratitis; Lubricants; Male; Trigeminal Nerve Diseases
PubMed: 35817488
DOI: 10.1136/bcr-2022-249400 -
IUCrJ Mar 2023The transformation processes of non-solvated ibrutinib into a series of halogenated benzene solvates are explored in detail here. The transformation was studied in real...
The transformation processes of non-solvated ibrutinib into a series of halogenated benzene solvates are explored in detail here. The transformation was studied in real time by X-ray powder diffraction in a glass capillary. Crystal structures of chlorobenzene, bromobenzene and iodobenzene solvates are isostructural, whereas the structure of fluorobenzene solvate is different. Four different mechanisms for transformation were discovered despite the similarity in the chemical nature of the solvents and crystal structures of the solvates formed. These mechanisms include direct transformations and transformations with either a crystalline or an amorphous intermediate phase. The binding preference of each solvate in the crystal structure of the solvates was examined in competitive slurry experiments and further confirmed by interaction strength calculations. Overall, the presented system and online X-ray powder diffraction measurement provide unique insights into the formation of solvates.
PubMed: 36815712
DOI: 10.1107/S2052252523001197