Synthesis and biological studies of some new acrylic acid ethyl esters of quinolinone

Abstract  

A series of new acrylic acid ethyl esters of quinolinones were synthesized from 4-(bromomethyl)quinolinones and screened for in vitro antimicrobial and in vivo analgesic and anti-inflammatory activities. Most of the compounds with chloro substitution at the C-6 or C-7 position in the quinolinone moiety and a methoxy group in the aryloxy moiety showed potent antibacterial and antifungal activities when compared with non-halogenated quinolinones and the quinolinones bearing a CH₃ at the C-8 position. In a pharmacological evaluation, the halogen substitution at the C-6 or C-7 position in quinolinones was found to enhance both analgesic and anti-inflammatory activities of the molecule when compared with a simple unsubstituted (non-halogenated) quinolinone. The structures of all newly synthesized compounds were characterized by elemental analysis, IR, ¹H NMR, ¹³C NMR, and FAB-MS.     

Studies of some new bioactive acrylic esters

Four typical bioactive esters of acrylic monomers, N-p-acryloxybenzoyloxysuccinimides, 3-ac-ryloxy-4-oxo-3,4-dihydro-1,2,3-benzotriazines, N-acryloxy-5-norbornene-2,3-dicarboximides, and I-p-acryloxybenzoyloxybenzotriazoles, were Synthesized and polymerized as reactive polymers. Twelve new monomers were prepared by coupling acrylic acid, methacrylic acid, p-acryloxybenzoic acid, or p-methacryloxybenzoic acid with four N-hydroxy compounds such as N-hydroxysuccinimide (HOSu), 3-hydroxy-4-oxo-3,4-dihydro-1,2,3-benzotriazine (HOObt), N-hydroxy-5-norbornene-2,3-dicarboximide (HONB), and I -hydroxybenzotriazole (HOBT) in the presence of dicyclohexylcarbodimide. All monomers polymerized readily in solution with azobisisobutyronitrile (AIBN) as free radical initiator. The resulting reactive polymers with reactive ? OSu, ? OObt, ? ONB, or ? OBT group on the side chain are equally reactive toward n-butylamine at room temperature in the formation of corresponding polyacrylamides. Reactive polymers were used to immobilizetrypsin. It has been found that poly(N-p-methacryloxybenzoyloxy-5-norbornene-2,3-dicarboximide)-trypsin matrix had high activity around three times that of the poly(N-methacryloxy-5-norbornene-dicarboximide)-trypsin matrix. It is proposed that this activity may be due to the presence of a long spacer arm with a hydrophobic and rigid benzene ring between the ligand and matrix. The reactive poly(N-p-methacryloxybenzoyloxysuccinimide-p-methacryloxybenzoic acid) copolymer was used to immobilize the serum protein. This immobilized protein was a hopeful bioactive solid immunoadsorbent.     

Synthesis of some mixed esters of thiophosphoric acid

Summary Six esters of O,O-dialkyl S-carbalkoxymethylphosphinic acids that have not been described in the literature were prepared and their structures demonstrated.     

Synthesis and properties of ethyl esters of some 1,2-dihydropyridine-3,5-dicarboxylic acids

The oxidation of diethyl 1-methyl- or 1-aryl-2,6-dimethyl-4-aryl-1,4-dihydropyridine-3,5-dicarboxylates with hydrogen peroxide in the presence of perchloric acid gave the perchlorates of the corresponding pyridinium ions, the reduction of which with NaBH₄ is a preparative method for the synthesis of diethyl esters of 1-substituted 2,6-dimethyl-1,2-dihydropyridine-3,5-dicarboxylic acids. Derivatives of the 5-carboxylic acid of the corresponding 1,2-dihydropyridine are formed by alkaline hydrolysis of these esters.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1225–1228, September, 1982.     

吲哚-1-甲酸酯类化合物的合成及生物活性研究

以吲哚和脂肪醇为原料设计合成了6种吲哚-1-甲酸酯类化合物,采用IR,1HNMR,EA及HRMS分析确定了产物结构。测试了该化合物对球等鞭金藻、亚心形扁藻、舟型藻三种海洋藻类的生长抑制作用,目标化合物对舟型藻的生长抑制作用较强,球等鞭金藻较弱;研究了其对藤壶幼虫的抑制性能,化合物侧链上连接的碳链越长,抑制活性越强;浅海挂板研究表明,该类化合物能有效地抑制海洋生物的附着生长。     

The interaction between some ethyl esters of aminoacids and acetic acid in carbon tetrachloride

The dimerization constant, K₁ of acetic acid in CCl₄ is determined by an IR spectrometric method and is found to have a value of 2252M⁻¹ at 20°. The association constants, K₂, for the interaction between the acetic acid monomer and some aminoacid ethyl esters are determined by the same method and found to have the values given (in M⁻¹ at 20°) for the esters of the following aminoacids: glycine (282 ± 24), dl-alanine (236 ± 33), dl-α-aminobutyric acid (139 ± 11), α-aminoisobutyric acid (172 ± 18). dl-norvaline (104 ± 13), dl-valine (150 ± 8), dl-leucine (108 ± 18) and 3-phenyl-dl-alanine (140 ± 21). A correlation of these experimental values with some structural parameters related to the steric effect of the substituents on the esters is proposed.     

Synthesis and some physicochemical properties of the carbazine acid silyl esters

Structure of the dimethylcarbazine acid trimethylsilyl ether and pyrolysis of its derivative, the trimethylsilyl ester of N,N-dimethyl-N′-trimethylsilylcarbazine acid, were studied by the metods of X-ray diffraction and gas chromatography/mass spectrometry. The presence of the bifurcated hydrogen bonds between the trimethylsilyl dimethylcarbazinate molecules was detected. It was revealed why impossible to obtain dimethylaminoisocyanate even by the low-temperature pyrolysis.     

Synthesis,physico-chemical studies and biological evaluation of new metal complexes with some pyrazolone derivatives

A series of N-substituted-4-thiocarbamoyl-5-pyrazolone derivatives (HL¹-HL⁴) is presented as chelating agents for complexation with Fe(III), Ni(II) and Cu(II) metal ions. The synthesized pyrazolone ligands and their newly metal complexes are characterized by different spectral and analytical methods such as UV–Vis, IR, ¹H NMR, ¹³C NMR, ESR, MS, magnetic measurement, and TGA. The spectral data reveal that ligands coordinated to metal ions in a bidentate pattern via O & N atoms of the OH group at C(5) and thiocarbamoyl (–CSNHR) at C(4) of the pyrazolone ring. Also, the analytical data suggest the stoichiometries 2:3 (M:L) for both Cu(II) & Ni(II) complexes and 1:3 for Fe(III) complexes. Besides, the normal magnetic moments values for Fe(III) complexes confirm high spin octahedral structure while the diamagnetic nature of all Ni(II) complexes is consistent with square planar geometry. However, the subnormal magnetic values for Cu(II) complexes suggest the proposal of their binuclear structures. The ESR spectra of the Cu(II) complexes support the distorted square planar geometry with a considerably strong intradimeric spin-exchange interaction. Moreover, the anticancer, antibacterial and antifungal activities are screened. Among the synthesized compounds, HL⁴ ligand exhibits a significant broad spectrum of action against Gram-positive (S. aureus), Gram-negative bacteria (P. vulgaris), and antifungal potency against A. fumigatus & C. albicans in comparison with gentamicin and ketoconazole drug. Such potency of HL⁴ could be related to the insertion of the p-chloro in the phenyl group attached to the pharmacophoric thiocarbamoyl group at C(4). Furthermore, IC₅₀ values of two Cu(II) complexes derived from HL² and HL³ display nearly twofold or threefold more cytotoxicity impact against three cell lines (MCF-7, HCT116 and HepG-2) compared with cis-platin as positive control.     

Synthesis and biological activity of some new pyridazine derivatives

Summary Condensation of -aroyl--[1,3-diphenyl-5(4H)-oxo-pyrazol-4-yl] propionic acid with hydrazine hydrate affords 4,5-dihydro-3(2H)-pyridazinone (2). Reaction of2 with POCl₃ and P₂S₅ gives a dichloro derivative (7) and a dithione (4). The behavior of the dichloro and dithione derivatives toward various reagents was studied. Thein vitro antibacterial screening reveals moderate activities against certain bacteria.

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Synthese und biologische Aktivität einiger neuer Pyridazinderivate

Zusammenfassung Kondensation von -Aroyl--[1,3-diphenyl-5(4H)-oxo-pyrazol-4-yl]-propionsäure mit Hydrazinhydrat ergibt 4,5-Dihydro-3(2H)-pyridazinon (2). Reaktion von2 mit POCl₃ und P₂S₅ liefert ein Dichlorderivat (7) und ein Dithion (4). Das Verhalten dieser beiden Verbindungen gegenüber verschiedenen Reagentien wurde untersucht. Antibakterielles screening (in vitro) ergab mäßige Aktivität gegenüber verschiedenen Bakterienstämmen.

     

Synthesis and biological activities of novel ethers of quinolinone linked with coumarins

Abstract  

A series of new ethers of quinolinone linked with different substituted coumarins and benzofurans were synthesized from 4-(bromomethyl)quinolinones. All newly synthesized compounds were screened for their in vitro antibacterial and antifungal activities. Most of the compounds with chloro substitution at the C-6 or C-7 position in quinolinone showed potent antibacterial and antifungal activities. In pharmacological evaluations, some of these chloroquinolinones also showed 70–77% inhibition of inflammation after 8 h, whereas the other compounds showed 51–55% inhibition. Most of the compounds showed potent analgesic activity compared to the standard and control. The structures of all newly synthesized compounds were characterized by elemental analysis, IR, ¹H NMR, ¹³C NMR, and EI-MS.     

Determination of ethyl glucuronide and fatty acid ethyl esters in hair samples

Hair testing for alcohol biomarkers is an important tool for monitoring alcohol consumption. We propose two methods for assessing alcohol exposure through combined analysis of ethyl glucuronide (EtG) and fatty acid ethyl esters (FAEEs) species (ethyl myristate, palmitate, stearate and oleate) in hair (30 mg). EtG was analysed by liquid chromatography–tandem mass spectrometry, while FAEEs were analysed by gas chromatography–tandem mass spectrometry using electron impact ionization. Both methods were validated according to internationally accepted guidelines. Linearity was proven between 3 and 500 pg/mg for EtG and 30–5000 pg/mg for FAEEs, and the limits of quantification were 3 pg/mg for EtG and 30 pg/mg for each of the four FAEEs. Precision and accuracy were considered adequate, processed EtG samples were found to be stable for up to 96 h left in the injector and processed FAEEs samples for up to 24 h. Matrix effects were not significant. Both methods were applied to the analysis of 15 authentic samples, using the cut‐off values proposed by the Society of Hair Testing for interpretation. The results agreed well with the self‐reported alcohol consumption in most cases, and demonstrated the suitability of the methods to be applied in routine analysis of alcohol biomarkers, allowing monitoring consumption using low sample amounts.     

Synthesis and biological evaluations of some Schiff-base esters of ferrocenyl aniline and simple aniline

The synthesis and biological studies of some long chain esters containing Schiff bases and their ferrocenyl analogues were carried out. The 4-amino ferrocene was prepared by the reported method. Long chain esters were synthesized by the condensation of different aliphatic acids with the corresponding aldehyde. The esters were then reacted with aniline as well as with 4-aminophenyl ferrocene to give corresponding Schiff bases. All the synthesized compounds were analyzed by elemental, FTIR and proton NMR studies, were also investigated for a range of biological activities. Determined by crown gall tumor inhibition assay. Antioxidant and DNA protective activities were determined by DPPH free radical scavenging assay and OH radical induced oxidative DNA damage assay, respectively. Among all test compounds, o-hydroxy-p-n-octadecanoyloxy-benzylidine-p-ferrocenyl aniline (FA2.1: a ferrocene containing Schiff base) showed highest antitumor, DPPH free radical scavenging and DNA protective activities.     

Synthesis and urease inhibition studies of some new quinazolinones

In this study, novel quinazolinones were designed, synthesized, characterized by FT-IR, ¹H-NMR, ¹³C-NMR spectral data, and LC–MS. New compounds inhibitory activities on urease were assessed. All of the compounds exhibited potent urease inhibitory activities. Especially in the synthesized compounds, 2-benzyl-3-({5-[(4-nitrophenyl)amino]-1,3,4-thiadiazol2-yl}methyl)quinazolin-4(3H)-one has the best inhibitory effect against Jack bean urease with IC₅₀ = 3.30 ± 0.09 μg/mL. And also, N-(4-nitrophenyl)-2-[(4-oxoquinazolin-3(4H)-yl)acetyl] hydrazinecarbothioamide, N-(4-fluorophenyl)-2-[(4-oxoquinazolin-3(4H)-yl)acetyl] hydrazinecarbothioamide, and 2-benzyl-3-({5-[(4-fluorophenyl)amino]-1,3,4-thiadiazol-2yl} methyl)quinazolin-4(3H)-one have best activities among the synthesized compounds.     

Molecular interaction studies of acrylic esters with 1-alcohols

Hydrogen bonding between 1-alcohols and acrylic esters in n-heptane has been studied by FTIR spectroscopic method. The formation constant of the 1:1 complexes has been calculated using Nash method. The values of formation constant and free energy change vary with alcohol and ester chain length, which suggests that the strengths of the intermolecular O-H...O=C bonds are shown to be dependent on the alkyl group of acrylic esters and the 1-alcohols and the results shows that the proton donating ability of 1-alcohols is in the order: 1-propanol<1-butanol<1-pentanol and the accepting ability of acrylic esters is in the order: methyl methacrylate相似文献   

Synthesis and properties of some butylphenylarsinothious esters

Conclusions Butylphenylarsinothious esters were prepared for the first time by the reactions of butylphenylarsinous halides with thiols, and some of their properties were studied.This article is published in accordance with a resolution of the Conference of Editors-in-Chlef of Journals of the Academy of Sciences of the USSR of July 12, 1962, as a dissertation paper by M. P. Osipova.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1326–1331, June, 1969.     

Synthesis of some novel isatin-thiazole conjugates and their computational and biological studies

Structural Chemistry - The present work describes the synthesis of novel 3-[2-(5-phenyl-1,3-thiazol-2-yl)hydrazinyl]-1,3-dihydro-2H-indol-2-one derivatives 4(a-h) and the characterization of...     

Synthesis of some α-fluoroacryl esters

Russian Journal of Applied Chemistry - A possibility of producing α-fluoroacrylic esters by dehydrochlorination of the products of reaction of α-fluoro-β-chloropropanoic acid or...