One-pot Synthesis,Crystal Structures and Antimicrobial Activities of Two New 1,4-Disubstituted 1,2,3-Triazole-4-Carboxylates

Two new 1,4-disubstituted 1,2,3-triazoles-4-carboxylates were synthesized via click reaction. Compound 1a was synthesized by the interaction of 6-nitro-tetrazolo[1.5-a]-pyridine with ethyl propynoate at room temperature in the presence of Cu(OAc)2 as a catalyst and THF as solvent. Compound 1b was also synthesized by the same manner except that tert-butyl propionate, instead of ethyl propynoate, was used. The compounds were characterized by IR, 1H-NMR, 13C-NMR and single-crystal X-ray diffraction analysis. Compound 1a(C10H9N5O4) crystallizes in the triclinic system, space group P1 with a = 5.0894(9), b = 8.9834(13), c = 13.089(2) ?, α= 83.041(7), β= 80.256(7), γ=87.296(8)°, V = 585.24(16)?3, Z = 2, Mr = 263.22, crystal size(mm) = 0.37 × 0.20 ×0.18,(I 2σ(I)) = 8557, 2493, 1229, Rint = 0.057. Compound 1b(C12H13N5O4) crystallizes in the monoclinic system, space group P21/c with a = 6.8854(5), b = 21.783(2), c = 9.3986(8) ?,β = 93.239(4)°, V = 1407.4(2)?3, Z = 4, Mr = 291.27, crystal size(mm) = 0.38 × 0.22 × 0.20,(I 2σ(I)) = 11842, 3172, 1866, Rint = 0.047. Antimicrobial assay results showed that the title compounds display excellent activities to different bacterial and fungal strains.     

Local and global chirality at surfaces: succinic acid versus tartaric acid on Cu110

A detailed comparison of tartaric acid (HOOC-CHOH-CHOH-COOH) and succinic acid (HOOC-CH(2)-CH(2)-COOH) molecules on a Cu(110) surface is presented with a view to elucidate how the two-dimensional chirality exhibited by such robust, chemisorbed systems is affected when both OH groups of the former molecule are replaced with H groups, a stereochemical change that leaves the metal-bonding functionalities of the molecule untouched but destroys both chiral centers. It is found that this change does not significantly affect the thermodynamically preferred chemical forms that are adopted, namely the doubly deprotonated bicarboxylate at low coverages (theta 相似文献   

Three new cholinesterase-inhibiting cis-clerodane diterpenoids from Otostegia limbata

Three new tricyclic cis-clerodane type diterpenoids trivially named as limbatolide A (1), limbatolide B (2) and limbatolide C (3) have been isolated from the roots of Otostegia limbata along with two known compounds; oleanic acid and beta-sitosterol. The structure elucidation of the new compounds was based primarily on two-dimensional (2D) NMR techniques. Compounds 1-3 displayed inhibitory potential in a concentration-dependent manner against acetylcholinesterase (AChE; EC 3.1.1.7) and butyrylcholinesterase (BChE; EC 3.1.1.8) enzymes, respectively.     

Microbial transformation of prednisone

The microbial transformation of prednisone (17alpha,21-dihydroxy-pregna-1,4-diene-3,11,20-trione) (1) by Cunninghamella elegans afforded two metabolites, 17alpha,21-dihydroxy-5alpha-pregn-1-ene-3,11,20-trione (2) and 17alpha,20S,21-trihydroxy-5alpha-pregn-1-ene-3,11-dione (3), while the fermentation of 1 with Fusarium lini, Rhizopus stolonifer and Curvularia lunata afforded a metabolite 1,4-pregnadiene-17alpha,20S,21-triol-3,11-dione (4). Compound 3 was found to be a new metabolite. Their structures were elucidated on the basis of spectroscopic techniques. Compound 3 showed inhibitory activity against lipoxygenase enzyme.     

The structure and crystallization of thin water films on Pt(111)

When water is adsorbed on Pt(111) above 135 K several different ice structures crystallize, depending on the thickness of the ice layer. At low coverage water forms extended islands of ice with a (square root(37) x square root(37))R25(o) unit cell, which compresses as the monolayer saturates to form a (square root(39) x square root(39))R16(o) structure. The square root(39) low-energy electron diffraction (LEED) pattern becomes more intense as the second layer grows, remaining bright for films up of 10-15 layers and then fading and disappearing for films more than ca. 40 layers thick. The ice multilayer consists of an ordered square root(39) wetting layer, on which ice grows as a crystalline film which progressively loses its registry to the wetting layer. Ice films more than ca. 50 layers thick develop a hexagonal LEED pattern, the entire film and wetting layer reorienting to form an incommensurate bulk ice. These changes are reflected in the vibrational spectra which show changes in line shape and intensity associated with the different ice structures. Thin amorphous solid water films crystallize to form the same phases observed during growth, implying that these structures are thermodynamically stable and not kinetic phases formed during growth. The change from a square root(39) registry to incommensurate bulk ice at ca. 50 layers is associated with a change in crystallization kinetics from nucleation at the Pt(111) interface in thin films to nucleation of incommensurate bulk ice in amorphous solid water films more than 50 layers thick.     

Development and Optimization of Ciprofloxacin HCl-Loaded Chitosan Nanoparticles Using Box–Behnken Experimental Design

Various chitosan (CS)-based nanoparticles (CS-NPs) of ciprofloxacin hydrochloride (CHCl) have been investigated for therapeutic delivery and to enhance antimicrobial efficacy. However, the Box–Behnken design (BBD)-supported statistical optimization of NPs of CHCl has not been performed in the literature. As a result, the goal of this study was to look into the key interactions and quadratic impacts of formulation variables on the performance of CHCl-CS-NPs in a systematic way. To optimize CHCl-loaded CS-NPs generated by the ionic gelation process, the response surface methodology (RSM) was used. The BBD was used with three factors on three levels and three replicas at the central point. Tripolyphosphate, CS concentrations, and ultrasonication energy were chosen as independent variables after preliminary screening. Particle size (PS), polydispersity index (PDI), zeta potential (ZP), encapsulation efficiency (EE), and in vitro release were the dependent factors (responses). Prepared NPs were found in the PS range of 198–304 nm with a ZP of 27–42 mV. EE and drug release were in the range of 23–45% and 36–61%, respectively. All of the responses were optimized at the same time using a desirability function based on Design Expert^® modeling and a desirability factor of 95%. The minimum inhibitory concentration (MIC) of the improved formula against two bacterial strains, Pseudomonas aeruginosa and Staphylococcus aureus, was determined. The MIC of the optimized NPs was found to be decreased 4-fold compared with pure CHCl. The predicted and observed values for the optimized formulation were nearly identical. The BBD aided in a better understanding of the intrinsic relationship between formulation variables and responses, as well as the optimization of CHCl-loaded CS-NPs in a time- and labor-efficient manner.     

Validated TLC-densitometry method for the simultaneous analysis of pyrethroid insecticides in agricultural and domestic products

ABSTRACT: BACKGROUND: Pyrethroids are widely used for the control of pests and insects, as pyrethroids are believed to pose very little risk to human health and environment. However, exposure to the pyrethroids exceeding the label directions might adversely affect human health and environment. Hence a careful selection of environment friendly household product is required that must contain exactly the label claimed pyrethroids amount. RESULTS: A sensitive and robust TLC-densitometric method for simultaneous quantification of commonly used synthetic pyrethroids including esbiothrin, alpha-cypermethrin and cis/trans permethrin in agricultural and domestic products has been developed and validated. TLC aluminum plates, precoated with 0.2 mm thick layer of silica gel 60 F-254, were used for chromatographic process. Densitometric analysis of chromatoplates was carried out in absorbance mode at corresponding lamdamax of each pyrethroid. Equally valid common mobile phase for all pyrethroids consisted of hexane-dichloromethane-ethylacetate-formic acid (8:1.5:0.4:0.1 v/v/v/v) which provided sharp and symmetrical peaks of esbiothrin, alpha-cypermethrin, trans-permethrin and cis-permethrin, at Rf 0.31, 0.53, 0.6 and 0.65, respectively. Linear regression data for respective calibration curves showed a good linearity for all pyrethroids with r = 0.991-0.996. Limits of detection (LOD) and limits of quantification (LOQ) for all pyrethroids were found in the range of 1.6-2.8 and 4.9-8.5 ng/spot, respectively. CONCLUSIONS: The developed method is applicable for separating the mixture of pyrethroids and at the same time, it is also valid for separating their isomers. The method is reproducible, precise and accurate for the quantitative determination of pyrethroids in agricultural and domestic products.     

Flower-shaped ZnO nanoparticles as an efficient, heterogeneous and reusable catalyst in the synthesis of N-arylhomophthalimides and benzannelated isoquinolinones

A simple and green protocol, developed utilizing an efficient, heterogeneous and recyclable catalyst, i.e. zinc oxide nanoparticles (ZnO NPs)-mediated synthesis of N-arylhomophthalimides and benzannelated isoquinolinones, is reported. The structures of the desired products were characterized by FTIR, ¹H NMR, ¹³C NMR, and HRMS techniques. The ZnO NPs exhibited excellent catalytic activity and the proposed methodology is capable of providing the desired products in good yield and purity.