Oligosaccharides aberrantly expressed on tumor cells influence processes such as cell adhesion and modulation of the cell's microenvironment resulting in an increased malignancy. Schmidt's imidate strategy offers an effective method to synthesize libraries of various oligosaccharide mimetics. With the aim to perturb interactions of tumor cells with extracellular matrix proteins and host cells, ...

The crystal structures of three cyclo-penta-[c]furans with various substituents at the 4-, 5- and 6-positions of the ring system are reported, namely, (±)-(3aR,4S,5S,6aS)-4-methyl-5-phenyl-hexa-hydro-1H-cyclo-penta-[c]furan-4,5-diol, C14H18O3, (I), (±)-(3aR,4S,5S,6aS)-4-benz-yloxy-4-methyl-5-phenyl-hexa-hydro-1H-cyclo-penta-[c]furan-5-ol, C21H24O3, (II), and (±)-(1aR,1bS,4aR,5S,5aR)-5-benz-ylox...

We have developed novel methods for the preparation of multimicromole quantities of extremely pure, uniquely photoadducted psoralen-DNA cross-links, furan-side monoadducted DNA and pyrone-side monoadducts. Psoralen cross-linked and furan-side monoadducted DNA were produced by employing high intensity argon ion and krypton ion lasers as light sources. Pyrone-side monoadducts were prepared by bas...

In an effort to find novel agents which selectively target the kappa opioid receptor (KOPR), we modified the furan ring of the highly potent and selective KOPR agonist salvinorin A. Introduction of small substituents at C-16 was well tolerated. 12-epi-Salvinorin A, synthesized in four steps from salvinorin A, was a selective partial agonist at the KOPR. No clear SAR patterns were observed for C...

In the title compound, C13H14O5, the furan ring is essentially planar [maximum deviation = 0.031 (3) Å] with a stereogenic center (R) at the sp (3) hybridized C atom. The C atom bearing the dihy-droxy ethyl group is S. The absolute configuration is based on the precursor in the synthesis. The two O-H groups are in an anti conformation with respect to each other. The mean plane of the furan-one ...

In the title 1:1 adduct, C(6)H(12)N(2)O(2)·C(9)H(10)N(2)O(2), the maximum deviations from the 1H-pyrazole-5-ol and furan rings are 0.014 (1) and 0.003 (1) Å, respectively. The dihedral angle formed between the 1H-pyrazol-5-ol and 2,5-dimethyl-furan rings is 21.07 (5)°. In the crystal, pairs of inter-molecular O-H⋯N hydrogen bonds form inversion dimers of the 3-(2,5-dimethyl-furan-3-yl)-1H-pyraz...

Infrared photodissociation spectra of aniline+–M (M = thiophene, furan and phenol) are measured in the 2700–3700 cm–1 region and analyzed by density functional theory calculations. Only a structure with a π-type hydrogen bond is found for aniline+–thiophene. Two structural isomers are identified for aniline+–furan and aniline+–phenol, which have either a π-type or a σ-type hydrogen bond, where ...

In the title compound, C(15)H(14)N(2)O(3), the furan ring is disordered over two positions with a refined site-occupancy ratio of 0.587 (11):0.413 (11). The mean plane of the approximately planar pyrazole ring [maximum deviation = 0.0469 (11) Å] makes dihedral angles of 86.13 (11) and 4.5 (5)° with the phenyl and furan rings, respectively. The dihedral angle between the phenyl ring and the majo...

Singlet Oxygen, Radicals, Fluorescein, Diphenylisobenzofuran, Reversed Micelles The 1,3-diphenylisobenzofuran oxidation was investigated in methanolic and dodecylammonium propionate reversed micellar solutions using fluorescein sodium as photosensitizer. The furan oxidation was caused by the singlet oxygen mechanism (Type II). Aniline enhanced remarkably the furan oxidation in methanolic soluti...

An efficient and convergent route for the synthesis of the natural product (+)-lithospermic acid, which possesses anti-HIV activity, was accomplished. The (±)-trans-dihydrobenzo[b]furan core therein was prepared by two different strategies. The first strategy involved the use of a palladium-catalyzed annulation to generate an appropriately substituted benzo[b]furan ester followed by a stereosel...