Two new stilbene glucosides and a new benzoic acid derivative from Tournefortia sibirica.

Two new stilbene glucosides, trans-3,5-dihydroxy-4-methoxystilbene 3-O-ß-D-glucopyranoside (1), cis-3,5-dihydroxy-4-methoxystilbene 3-O-ß-D-glucopyranoside (2), one new benzoic acid derivative, cis-4-hydroxy-3-hydroxymethyl-2-butenyl benzoate 4-O-ß-D-glucopyranoside (3), and four known compounds (4 - 7) were isolated from Tournefortia sibirica L. The structures of these compounds were elucidated on the basis of spectral data. Anti-inflammatory effects of compounds (1 - 7) were evaluated in terms of inhibition on production of NO, TNF-α and IL-6 in LPS-induced RAW 264.7 cells. Compounds 1, 2 and 5 - 7 could inhibit the levels of NO, TNF-α and IL-6 in LPS-induced RAW264.7 cells with IC50 values ranging from 40.96 to 88.76 µM.

Benzoic acid derivatives from the root barks of Ailanthus altissima.

Two new benzoic acid derivatives (1-2), together with four known compounds (3-6) have been isolated from the n-BuOH soluble fraction of ethanolic extract from Ailanthus altissima. The gross structures of the new compounds were deduced by detailed spectroscopic analysis including HRESIMS and 1D/2D NMR spectroscopy. The stereochemistry of 1 was determined by modified Mosher's method. All compounds were evaluated for their neuroprotective effects against H2O2-induced oxidative stress in human neuroblastoma SH-SY5Y cells and none of them displayed obvious neuroprotective activities. [Formula: see text].

Synthesis and antimicrobial activity of the hybrid molecules between amoxicillin and derivatives of benzoic acid.

Due to the increasing problem of bacterial resistance worldwide, the demand for new antibiotics is becoming increasingly urgent. We wished to: (a) prepare hybrid molecules by linking different pharmacophores by chemical bonds; (b) investigate the antib acterial activity of these hybrids using drug-sensitive and drug-resistant pathogens in vitro and vivo. A series of hybrid molecules with a diester structure were designed and synthesized that linked amoxicillin and derivatives of benzoic acid via a methylene bridge. Synthesized compounds were evaluated for activities against Gram-positive bacteria (Staphylococcus aureus American Type Culture Collection [ATCC] 29213, ATCC 11632; methicillin-resistant S. aureus [MRSA] 11; Escherichia coli ATCC 25922) and Gram-negative bacteria (Salmonella LS677, GD836, GD828, GD3625) by microdilution of broth. Synthesized compounds showed good activity against Gram-positive and Gram-negative bacteria in vitro. In particular, amoxicillin-p-nitrobenzoic acid (6d) showed good activity against Salmonella species and had better activity against methicillin-resistant S. aureus (minimum inhibitory concentration [MIC] = 64 µg/ml) than the reference drug, amoxicillin (MIC = 128 µg/ml). Amoxicillin-p-methoxybenzoic acid (6b) had the best antibacterial activity in vivo (ED50 = 13.2496 µg/ml). The hybrid molecules of amoxicillin and derivatives of benzoic acid synthesized based on a diester structure can improve the activity of amoxicillin against Salmonella species and even improve the activity against MRSA.

Removal of BTEX from water system by synergistic flocculation of biosurfactant and iron salt.

The adsorption micelle flocculation (AMF) effect of biosurfactants (rhamnolipids, RL) and polymerized ferric sulfate (PFS) on the removal of low molecular weight benzoic acid (benzoic acid and p-methyl benzoic acid) and phenol (2,4-dichlorophenol and bisphenol A) organics was investigated. The coexistence system of RL and organic matter was constructed, and the effects of pH, Fe concentration, RL concentration and initial concentration of organic matter on the removal effect were discussed. For benzoic acid and p-methyl benzoic acid, the increase of Fe and RL concentrations was beneficial to their removal rates under weak acidic conditions, and the removal rate of the coexistence system was higher for methyl benzoic acid (87.7 %) than for benzoic acid (78.6 %), which might be attributed to the stronger hydrophobicity of the coexistence system for methyl benzoic acid; while for 2,4-dichlorophenol and bisphenol A, pH and Fe concentration changes had less effect on the removal rate, but the increase in RL concentration was favorable to the removal rate, which was 93.1 % and 86.7 % for BPA and 2,4-dichlorophenol, respectively. These findings provide feasible ideas and directions for the removal of organics by AMF using biosurfactants.

Benzoic acid derivative-modified chitosan-g-poly(N-isopropylacrylamide): Methoxylation effects and pharmacological treatments of Glaucoma-related neurodegeneration.

Long-acting drug delivery systems with advanced functionalities are critically important to pharmacologically treat glaucomatous optic neuropathy, a chronic and multifactorial neurodegenerative disease. Here, a novel strategy based on the methoxylation effects of benzoic acid derivatives was exploited to rationally design a biodegradable and injectable thermogel, which possesses potent antioxidant activities and sustained drug delivery abilities for treating glaucomatous nerve damage. In particular, 4-hydroxy-3,5-dimethoxybenzoic acid, consisting of two methoxyl groups and one hydroxyl group at the position para to the carboxylic group, was demonstrated to contribute to the strong antioxidant activities of a chitosan-g-poly(N-isopropylacrylamide) biomaterial while maintaining the drug encapsulation/release efficiencies of the thermogel. The pharmacological treatment relies on the intracameral injection of the thermogel coloaded with pilocarpine and RGFP966 and exhibits significant improvement in the attenuation of neurodegeneration via suppressing oxidative stress, lowering ocular hypertension, reducing retinal ganglion cell loss and enhancing myelin growth and neuron regeneration. These findings on the development of long-acting drug delivery systems with extended functions show great promise for the management of glaucoma-related neurodegeneration.

Crystal structure, Hirshfeld surface analysis and computational study of the 1:2 co-crystal formed between N,N'-bis-[(pyridin-4-yl)meth-yl]ethanedi-amide and 3-chloro-benzoic acid.

The asymmetric unit of the title 1:2 co-crystal, C14H14N4O2·2C7H5ClO2, comprises a half-mol-ecule of oxalamide (4 LH2), being located about a centre of inversion, and a mol-ecule of3-chloro-benzoic acid (3-ClBA) in a general position. From symmetry, the 4 LH2 mol-ecule has a (+)anti-periplanar conformation with the 4-pyridyl residues lying to either side of the central, planar C2N2O2 chromophore with the dihedral angle between the core and pyridyl ring being 74.69 (11)°; intra-molecular amide-N-H⋯O(amide) hydrogen bonds are noted. The 3-ClBA mol-ecule exhibits a small twist as seen in the C6/CO2 dihedral angle of 8.731 (12)°. In the mol-ecular packing, three-mol-ecule aggregates are formed via carb-oxy-lic acid-O-H⋯N(pyrid-yl) hydrogen bonding. These are connected into a supra-molecular tape along [111] through amide-N-H⋯O(carbon-yl) hydrogen bonding. Additional points of contact between mol-ecules include pyridyl and benzoic acid-C-H⋯O(amide), methyl-ene-C-H⋯O(carbon-yl) and C-Cl⋯π(pyrid-yl) inter-actions so a three-dimensional architecture results. The contributions to the calculated Hirshfeld surface are dominated by H⋯H (28.5%), H⋯O/O⋯H (23.2%), H⋯C/C⋯H (23.3%), H⋯Cl/Cl⋯H (10.0%) and C⋯Cl/C⋯Cl (6.2%) contacts. Computational chemistry confirms the C-Cl⋯π inter-action is weak, and the importance of both electrostatic and dispersion terms in sustaining the mol-ecular packing despite the strong electrostatic term provided by the carb-oxy-lic acid-O-H⋯N(pyrid-yl) hydrogen bonds.

Crystal structure of catena-poly[[[di-aqua-bis-(2,4,6-tri-methyl-benzoato-κO)cobalt(II)]-µ-aqua-κ2O:O] dihydrate].

The asymmetric unit of the title one-dimensional polymeric compound, {[Co(C10H11O2)2(H2O)3]·2H2O} n , contains one CoII cation situated on a centre of inversion, one-half of a coordinating water mol-ecule, one 2,4,6-tri-methyl-benzoate (TMB) anion together with one coordinating and one non-coordinating water mol-ecule; the TMB anion acts as a monodentate ligand. In the anion, the carboxyl-ate group is twisted away from the attached benzene ring by 84.9 (2)°. The CoII atom is coordinated by two TMB anions and two water mol-ecules in the basal plane, while another water mol-ecule bridges the CoII atoms in the axial directions, forming polymeric chains running along [001]. The coordination environment for the CoII cation is a slightly distorted octa-hedron. The coordinating and bridging water mol-ecules link to the carboxyl-ate groups via intra- and inter-molecular O-H⋯O hydrogen bonds, enclosing S(6) ring motifs, while the coordinating, bridging and non-coordinating water mol-ecules link to the carboxyl-ate groups and the coordinating water mol-ecules link to the non-coordinating water mol-ecules via O-H⋯O hydrogen bonds, enclosing R22(8) and R33(8) ring motifs. Weak C-H⋯O and C-H⋯π inter-actions may further stabilize the crystal structure.

Crystal structure of 2-methyl-3-nitro-benzoic anhydride.

The title mol-ecule, C16H12N2O7, lies on a twofold rotation axis which bis-ects the central O atom. The dihedral angle between two symmetry-related benzene rings is 48.54 (9)°. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds which generate C(13) chains running parallel to [31-1].