Effect of Alkyl Chain Length and Linker Atom on the Crystal Packing in 6,12-Dialkoxy- And 6,12-Dialkylsulfanyl-Benzo[1,2- b:4,5- b′]bis[ b]benzothiophenes

The effect of varying the chain length on the solid state conformation and packing of 6,12-dialkoxy- and 6,12-dialkylsulfanyl-benzo[1,2-b:4,5-b′]bis[b]benzothiophenes has been studied. The compounds were prepared by SNAr reaction of 6,12-difluorbenzo[1,2-b:4,5-b′]bis[b]benzothiophene with alkoxides or alkanethiolates derived from C7-C10 alcohols and alkanethiols. Single crystal X-ray diffraction analysis revealed that all but two compounds crystallize in the triclinic space group P1. Two compounds were obtained as monoclinic crystals with space group P21/c. The alkoxy substituted compounds adopted a molecular conformation with a step from the core and a gauche conformation about the C1′-C2′ bond placing the alkyl chains close to parallel with the pentacyclic arene ring system, whereas in the alkylsufanyl derivatives, the alkyl chains were arranged strongly deviated from the plane of the ring, with the sulfur atom antiperiplanar to C3′ of the alkyl chain. NMR measurement of T1 relaxation in CDCl3 showed both the alkoxy and alkylsulfanyl substituents to be freely rotating at ambient temperature in solution, indicating the orientation of the chains in the solid state was due to packing interactions during crystallization

μ-Pyrazine-2,5-dicarboxylato-bis[chlorido(η6-p-cymene)ruthenium(II)] tert-butanol disolvate

μ-Pyrazine-2,5-dicarboxylato-bis[chlorido(η6-p-cymene)ruthenium(II)] tert-butanol disolvat

2-Imino-3-(2-nitrophenyl)-1,3-thiazolidin-4-one

2-Imino-3-(2-nitrophenyl)-1,3-thiazolidin-4-on

Versatile routes to selenoether functionalised tertiary phosphines

New selenoether functionalised tertiary phosphines, based on aryl (2a, 2b) or alkyl (4) backbones, have been synthesised and characterised. P,Se-chelation has been achieved upon complexation to square-planar PtII (3a) or PdII (3b) metal centres. For 3a and 3b, weak non-covalent M◊ ◊ ◊ Se contacts were established using single crystal X-ray crystallography

4-Hydroxy-4,6a,6b,9,9,12a,14b-heptamethylperhydropicen-3-one hemihydrate isolated from Adiantum incisum

4-Hydroxy-4,6a,6b,9,9,12a,14b-heptamethylperhydropicen-3-one hemihydrate isolated from Adiantum incisu

4-Hydroxy-4,6a,6b,9,9,12a,14b-heptamethylperhydropicen-3-one hemihydrate isolated from Adiantum incisum

The title compound, C29H48O2·0.5H2O, is a triterpenoid isolated from the stems and rhizomes of Adiantum incisum. The basic skeleton of the mol­ecule contains five six-membered rings, all adopting chair conformations, bearing a total of seven methyl, one hydroxyl and a keto group. There are two mol­ecules of the triterpene and one water molecule of crystallization in the asymmetric unit. The two unique triterpenoid mol­ecules hydrogen-bond directly via an O—H⋯O=C inter­action, and are also bridged by the water mol­ecule. The water also bridges to another pair of hydrogen-bonded triterpenoid mol­ecules

2-Imino-3-(2-nitro­phen­yl)-1,3-thia­zolidin-4-one

In the title compound, C9H7N3O3S, the nitro and thia­zolidinone moieties are inclined with respect to the aromatic ring at dihedral angles of 9.57 (16) and 78.42 (4)°, respectively. In the crystal, N—H⋯O hydrogen bonding connects the mol­ecules along the c and a axes to form a two-dimensional polymeric network. A weak S⋯O inter­action [3.2443 (11) Å] and phenyl ring to phenyl ring off-set π⋯π stacking [with centroid–centroid separation of 3.6890 (7) Å and ring slippage of 1.479 Å] link the polymeric chains along the b and a axes, respectively

Pillared two-dimensional metal-organic frameworks based on a lower-rim acid appended calix[4]arene

Solvothermal reactions of the lower-rim functionalized diacid calix[4]arene 25,27-bis(methoxycarboxylic acid)-26,28-dihydroxy-4-tert-butylcalix[4]arene (LH₂) with Zn(NO₃)₂•6H₂O and the dipyridyl ligands 4,4/-bipyridyl (4,4/-bipy), 1,2-di(4-pyridyl)ethylene (DPE) or 4,4/-azopyridyl (4,4/-azopy) afforded a series of 2-D structures of the formulae {[Zn(4,4/-bipy)(L)]•2¼DEF}n (1), {[Zn₂(L)(DPE)]•DEF}n (2) and {[Zn(OH₂)₂(L)(4,4/-azopy)]•DEF}n (3) (DEF = diethylformamide)

Synthesis and activity of a novel Autotaxin inhibitor-Icodextrin conjugate

© Copyright 2018 American Chemical Society. Autotaxin is an extracellular phospholipase D that catalyses the hydrolysis of lysophosphatidyl choline (LPC) to generate the bioactive lipid lysophosphatidic acid (LPA). Autotaxin has been implicated in many pathological processes relevant to cancer. Intraperitoneal administration of an autotaxin inhibitor may benefit patients with ovarian cancer, however low molecular mass compounds are known to be rapidly cleared from the peritoneal cavity. Icodextrin is a polymer that is already in clinical use because it is slowly eliminated from the peritoneal cavity. Herein we report conjugation of the autotaxin inhibitor HA-155 to icodextrin. The conjugate inhibits autotaxin activity (IC50 = 0.86 ± 0.13 μg mL-1) and reduces cell migration. Conjugation of the inhibitor increased its solubility, decreased its membrane permeability and improved its intraperitoneal retention in mice. These observations demonstrate the first application of icodextrin as a covalently-bonded drug delivery platform with potential use in the treatment of ovarian cancer