Synthesis, characterization, X-ray structural analysis, and iodination ability of benzyl(triphenyl)phosphonium dichloroiodate.

Benzyl(triphenyl)phosphonium dichloroiodate (BTPPICl2), BnPh3P+(ICl2)−, is easily synthesized in a nearly quantitative yield by the addition of BnPh3P+Cl− to a CH2Cl2 solution of iodine monochloride (ICl). BnPh3P+Cl− can be prepared by the reaction of Ph3P and BnCl. The compound was characterized by physicochemical and spectroscopic methods (elemental analysis, FT-IR, and 1H-NMR). The use of phosphonium counterion improves the quality of the BTPPICl2 crystals. BTPPICl2 crystallizes in the monoclinic system, and its crystal and molecular structure has been determined at 100(1) K by X-ray diffraction. The structure was solved by the direct method and had refined R value of 0.0637 for 699 reflections (I>2σ(I)), space group P21/n with a=12.4700(3), b=13.2196(3), c=14.4580(3) Å, β=102.6340(10)°, V=2325.67(9) Å3, and Z=4. The I-atom is coordinated by two Cl-atoms as ligands in a linear geometry. This compound is a versatile reagent for the efficient and selective iodination of organic substrates, in particular of aromatic phenols to the corresponding iodo compounds, under mild conditions. To assess the generality of method, a wide variety of phenols with electron-donating and electron-withdrawing substituents were studied. BTPPICl2 is a mild iodination reagent, which offers a new avenue for an expeditious iodination of phenols. The inexpensive, relatively non-toxic reagent, and mild conditions are the positive features of the procedure and reagent

Disesquiterpene and sesquiterpene coumarins from Ferula pseudalliacea, and determination of their absolute configurations

The first disesquiterpene coumarin, sanandajin, five sesquiterpene coumarins, kamolonol acetate, fekrynol acetate, ethyl galbanate, methyl galbanate, farnesiferol B, and a sesquiterpene, aristolone, were isolated from a n-hexane extract of Ferula pseudalliacea roots. The structures were elucidated by 1D and 2D NMR, HR-ESIMS data, and kamolonol acetate was confirmed by single-crystal X-ray analysis. The absolute configuration of compounds was established by comparison of experimental and simulated ECD spectra using time dependence density function theory (TDDFT). In vitro antiplasmodial activity against Plasmodium falciparum K1 strain was determined. sanandajin, kamolonol acetate and methyl galbanate showed moderate antiplasmodial activity, with IC50 values of 2.6, 16.1 and 7.1 μM, respectively

Hydrangenone, a new Isoprenoid with an unprecedented skeleton from Salvia hydrangea

Hydrangenone, a new heptacyclic isoprenoid with a 6/7/6/5/5 membered carbon ring skeleton, was isolated from the aerial parts of Salvia hydrangea. The structure was established by extensive NMR spectroscopic methods. The relative and absolute configuration of 1 was assigned by NOESY and X-ray crystallographic analysis and by comparison of experimental and calculated electronic circular dichroism (ECD) spectra. Compound 1 showed in vitro antiplasmodial activity, with an IC(50) value of 1.4 muM against P. falciparum. A plausible biosynthetic pathway of 1 was also proposed

New labdane diterpenoids from Salvia leriifolia: Absolute configuration, antimicrobial and cytotoxic activities

Fractionation of an n-hexane extract of the aerial parts of Salvia leriifolia led to the isolation of two new (1, 2) and two known (3, 4) labdane diterpenoids, together with three other known compounds. The structures were established by a combination of 1D and 2D NMR, and HRESIMS. The structures of 1 and 3 were confirmed by single-crystal X-ray analysis. The absolute configuration of 1–4 was established by electronic circular dichroism spectroscopy. Compounds 1–4 were evaluated for their cytotoxic activities against MCF-7 human breast cancer cells. Labdanes 3 and 4 were additionally tested against MDA-MB231 human breast cancer and DU-145 human prostate cancer cell lines. Compound 4 showed IC50 values of 25, 50, and 50 µM against MCF-7, MDA-MB231, and DU-145 cells, respectively. Compounds 1–4 were tested for activity against gram-positive (Staphylococcus aureus) and gram-negative (Escherichia coli) bacteria. Compound 3 showed an MIC of 213 µM against methicillin-resistant S. aureus