13,179 research outputs found
3-(3-Chlorophenylsulfinyl)-2,4,6-trimethyl-1-benzofuran
In the title compound, C17H15ClO2S, the 3-chlorophenyl ring makes a dihedral angle of 71.46 (4)° with the mean plane of the benzofuran fragment. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds and a slipped π–π interaction between the 3-chlorophenyl rings of adjacent molecules [centroid–centroid distance = 3.630 (2) Å, interplanar distance = 3.375 (2) Å and slippage = 1.337 (2) Å]
2-(3-Fluorophenyl)-5-iodo-7-methyl-3-methylsulfinyl-1-benzofuran
In the title compound, C16H12FIO2S, the 3-fluorophenyl ring makes a dihedral angle of 34.93 (7)° with the mean plane [r.m.s. deviation = 0.019 (1) Å] of the benzofuran fragment. In the crystal, molecules are linked via pairs of I⋯O contacts [3.088 (2) Å] into inversion dimers. These dimers are connected by weak C—H⋯O hydrogen bonds
Sp1 up-regulates cAMP-response-element-binding protein expression during retinoic acid-induced mucous differentiation of normal human bronchial epithelial cells.
CREB [CRE (cAMP-response element)-binding protein] is an important transcription factor that is differentially regulated in cells of various types. We recently reported that RA (retinoic acid) rapidly activates CREB without using RARs (RA receptors) or RXRs (retinoid X receptors) in NHTBE cells (normal human tracheobronchial epithelial cells). However, little is known about the role of RA in the physiological regulation of CREB expression in the early mucous differentiation of NHTBE cells. In the present study, we report that RA up-regulates CREB gene expression and that, using 5\u27-serial deletion promoter analysis and mutagenesis analyses, two Sp1 (specificity protein 1)-binding sites located at nt -217 and -150, which flank the transcription initiation site, are essential for RA induction of CREB gene transcription. Furthermore, we found that CREs located at nt -119 and -98 contributed to basal promoter activity. Interestingly, RA also up-regulated Sp1 in a time- and dose-dependent manner. Knockdown of endogenous Sp1 using siRNA (small interfering RNA) decreased RA-induced CREB gene expression. However, the converse was not true: knockdown of CREB using CREB siRNA did not affect RA-induced Sp1 gene expression. We conclude that RA up-regulates CREB gene expression during the early stage of NHTBE cell differentiation and that RA-inducible Sp1 plays a major role in up-regulating human CREB gene expression. This result implies that co-operation of these two transcription factors plays a crucial role in mediating early events of normal mucous cell differentiation of bronchial epithelial cells
Methyl 2-(5-methyl-3-methylsulfinyl-1-benzofuran-2-yl)acetate
The title compound, C13H14O4S, was prepared by oxidation of methyl 2-(5-methyl-3-methylsulfanyl-1-benzofuran-2-yl)acetate with 3-chloroperoxybenzoic acid. The O atom and methyl group of the methylsulfinyl substituent lie on opposite sides of the plane of the benzofuran system. The crystal structure is stabilized by intermolecular aromatic π–π interactions between the benzene rings of neighbouring molecules, with a centroid–centroid separation of 3.841 (3) Å
5-Bromo-2-phenyl-3-phenylsulfinyl-1-benzofuran
In the title compound, C20H13BrO2S, the O atom and the phenyl group of the phenylsulfinyl substituent are located on opposite sides of the plane of the benzofuran system. The S-bound phenyl ring is almost perpendicular to this plane [80.35 (8)°]. The phenyl ring in the 2-position is twisted with respect to the benzofuran plane, making a dihedral angle of 16.0 (1)°
Isopropyl 2-(5-fluoro-3-methylsulfinyl-1-benzofuran-2-yl)acetate
In the title compound, C14H15FO4S, the O atom and the methyl group of the methylsulfinyl substituent are located on opposite sides of the plane of the benzofuran fragment which is essentially planar with a mean deviation of 0.008 (1) Å from its least-squares plane. The crystal structure stabilized by three different intermolecular non-classical C—H⋯O hydrogen bonds. The crystal structure also exhibits aromatic π–π interactions between the benzene rings of adjacent benzofuran ring systems [centroid–centroid distance = 3.688 (2) Å
2,5,7-Trimethyl-3-phenylsulfinyl-1-benzofuran
The title compound, C17H16O2S, was prepared by the oxidation of 2,5,7-trimethyl-3-phenylsulfanyl-1-benzofuran with 3-chloroperoxybenzoic acid. The O atom and the phenyl group of the phenylsulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment. The phenyl ring is nearly perpendicular to the plane of the benzofuran unit [88.30 (9)°] and is tilted slightly towards it. No π–π or C—H⋯π interactions are observed between neighbouring molecules in the crystal structure because of steric hindrance induced by the three methyl groups
2-(3-Ethylsulfanyl-5-phenyl-1-benzofuran-2-yl)acetic acid
The title compound, C18H16O3S, crystallizes with two symmetry-independent molecules in the asymmetric unit. The phenyl rings are rotated out of the benzofuran planes, making dihedral angles of 43.38 (7) and 56.13 (6)° in the two molecules. The carboxyl groups are involved in inversion-related intermolecular O—H⋯O hydrogen bonds, which link the molecules into centrosymmetric dimers. These dimers are further packed into stacks along the b axis by weak non-classical intermolecular C—H⋯O hydrogen bonds. The crystal structure also exhibits intermolecular C—H⋯π interactions, and two aromatic π–π interactions between the furan rings of neighbouring benzofuran systems; the centroid–centroid distances are 3.500 (3) and 3.605 (3) Å
Ethyl 2-(5-bromo-3-ethylsulfinyl-1-benzofuran-2-yl)acetate
The title compound, C14H15BrO4S, was prepared by the oxidation of ethyl 2-(5-bromo-3-ethylsulfanyl-1-benzofuran-2-yl)acetate with 3-chloroperoxybenzoic acid. The crystal structure is stabilized by aromatic π–π interactions between the benzene rings of neighbouring molecules [centroid–centroid distance = 3.814 (9) Å], and possibly by weak C—H⋯π interactions. In addition, the crystal structure exhibits three intermolecular C—H⋯O non-classical hydrogen bonds. The ethyl group bonded to carboxylate O atom is disordered over two positions, with refined site-occupancy factors of 0.686 (18) and 0.314 (18)
2-(3-Fluorophenyl)-3-methylsulfanyl-5-phenyl-1-benzofuran
In the title compound, C21H15FOS, the dihedral angles between the mean plane of the benzofuran fragment and the pendant 3-fluorophenyl and phenyl rings are 1.76 (5) and 32.29 (5)°, respectively. In the crystal, molecules are linked by a slipped π–π interaction between the furan and benzene rings of neighbouring molecules [centroid–centroid distance = 3.665 (2) Å, interplanar distance = 3.391 (2) Å and slippage = 1.390 (2) Å]
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