Synthesis of substituted 2-ethyl-3-(4-hydrazinocarbonylphenyl)-4-quinazo-lones and 2-ethyl-3-(4-hydrazinocarbonylmethylphenyl)-4-quinazolones

Some substituted 2-ethyl-3-(4-hydrazinocarbonylphenyl)-4-quinazolones and 2-ethyl-3-(4-hydrazinocarbonylmethylphenyl)-4-quinazolones were synthesized and characterized by their sharp melting points, elemental analyses and spectral data.     

Dielectric Properties of 4-(2,3-Epoxypropoxy)- and 4-Propoxy-4'-alkoxyazoxybenzenes

The temperature dependences of the dielectric permittivity of 4-(2,3-epoxypropoxy)-4'-alkoxyazoxybenzenes (n = 1-10) and 4-propoxy-4'-alkoxyazoxybenzenes (n = 1-10) with mesomorphic properties were measured by dielectrometry. The introductrion of the terminal epoxy group increases the dielectric permittivity and its anisotropy. The dipole moments of molecules of 4-(2,3-epoxypropoxy)-4'-alkoxyazoxybenzenes (n = 1-10) and 4-propoxy-4'-alkoxyazoxybenzenes (n = 1-10) were determined by the second Debye method. The epoxy-substituted azoxybenzenes have higher dipole moments than their structural analogs.     

Synthesis and characterization of novel 2-(1-benzyl-3-[4-fluorophenyl]-1H-pyrazol-4-yl)-7-fluoro-4H-chromen-4-one derivatives

Novel 1-benzyl-3-(4-fluorophenyl)-1H-pyrazole-4-carbaldehydes 3a to 3e were synthesized via Vilsmeier-Haack reaction of the appropriate 1-benzyl-2-(1-(4-fluorophenyl)ethylidene)hydrazines, derived from 4-fluoroacetophenone 1 with substituted 2-benzylhydrazines 2a to 2e . The base catalyzed condensation of 1-benzyl-3-(4-fluorophenyl)-1H-pyrazole-4-carbaldehydes 3a to 3e with 1-(4-fluoro-2-hydroxyphenyl)ethanone 4 gave (E)-3-(1-benzyl-3-(4-fluorophenyl)-1H-pyrazol-4-yl)-1-(4-fluoro-2-hydroxyphenyl)prop-2-en-1-ones 5a to 5e . On cyclization with dimethyl sulfoxide (DMSO)/I₂, compounds 5a to 5e gave 2-(1-benzyl-3-(4-fluorophenyl)-1H-pyrazol-4-yl)-7-fluoro-4H-chromen-4-ones 6a to 6e . Structures of all novel compounds were confirmed by infrared (IR), proton nuclear magnetic resonance (¹H NMR), carbon nuclear magnetic resonance (¹³C NMR), and mass spectral data. All the synthesized compounds were screened for their antibacterial activities.     

Facile syntheses of 4-(trifluoromethyl)-L-spinacine and 4-(trifluoromethyl)spinaceamine

Reaction of L-histidine with trifluoroacetaldehyde ethyl hemiacetal (TFAE) in boiling water provides 4-(trifluoromethyl)-L-spinacine, 4-(trifluoromethyl)-L-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid, in near quantitative yield. The product contains two diastereoisomers in the ratio 68 : 32. The isomers were separated (silica gel) as their protected derivatives, 5-N-(trifluoroacetyl)-4-(trifluoromethyl)-L-spinacine methyl esters, and were regenerated by acid hydrolysis. The analogous reaction with histamine provides 4-(trifluoromethyl)spinaceamine in 91% yield.     

One-pot multi-component synthesis of novel ethyl-2-(3-((2-(4-(4-aryl)thiazol-2-yl)hydrazono)methyl)-4-hydroxy/isobutoxyphenyl)-4-methylthiazole-5-carboxylate derivatives and evaluation of their in vitro antimicrobial activity

A novel series of ethyl-2-(3-((2-(4-(4-aryl)thiazol-2-yl)hydrazono)methyl)-4-hydroxy/isobutoxyphenyl)-4-methylthiazole-5-carboxylate derivatives ( 4a-f and 5a-f ) were synthesized by employing one-pot multi-component approach involving ethyl 2-(3-formyl-4-oxy/isobutoxyphenyl)-4-methylthiazole-5-carboxylate, thiosemicarbazide and various phenacyl bromides/3-(2-bromoacetyl)-2H-chromen-2-one/2-(2-bromoacetyl)-3H-benzo[f]chromen-3-onein ethanol in the presence of catalytic amount of acetic acid. The structures of all the synthesized compounds were confirmed with spectral analysis, ie, IR, 1H NMR, 13C NMR and mass spectrometry, and all the compounds were screened for their in vitro antimicrobial activity.     

Synthesis and pharmacological activity of 4-(4'-(chlorophenyl)-4-hydroxypiperidine) derivatives

A new series of 4-(4'-chlorophenyl)-4-hydroxypiperidine derivatives (2-5), substituted at nitrogen, were synthesized and tested as potential analgesic compounds as well as evaluated for their effect on hypotensive activity. Results showed that all the derivatives exhibit significant analgesic activity in male Wistar rats at a dose of 50 mg/kg of body weight after intramuscular injection, when tested by thermal stimuli (tail flick test). Pethidine was used as reference drug. Compounds 2, 3 and 5 produced reduction in blood pressure in normotensive rat.     

Raman spectroscopy of liquid crystalline N-[4-(4-n-alkoxybenzoyloxy)-2-hydroxybenzylidene]-3-aminopyridines

New homologous series of N-[4-(4-n-alkoxybenzoyloxy)-2-hydroxybenzylidene]-3-aminopyridines were synthesized, they exhibited a nematic phase. The temperature dependence of their Raman spectra has been observed in the spectral range 900-1800 cm^-1. Some Raman bands show a marked change in their intensity and frequency through the phase transition from crystalline solid to nematic. These bands are ascribed to the vibrational modes related to the core part of the molecule. Such behaviour can be explained by the change of molecular conformation related to the core. Some members of these series exhibited photochromism in the solid state.     

含3-甲基苯基-2,3-二氮杂萘-1-酮结构聚醚酰胺的合成、表征与性能

合成了一种新型芳香二胺双-(4-氨基苯基)-4-(3-甲基-4-苯氧基)-2,3-二氮杂萘-1-酮(1)[2-(4-aminophenyl)-4-(3-methyl-4-phenoxy)-2,3-phthalazinone-1,DAMPP].采用Yamazaki体系,二胺(1)能与多种芳香二酸进行溶液亲核缩聚反应,制得一类新型聚芳醚酰胺,其特性粘度为0.40～0.60dL/g;以MS,FTIR和¹HNMR等分析手段研究了新型二胺单体及其聚合物的结构;利用DSC和TGA研究了聚合物的耐热性能,结果表明,新型聚芳酰胺具有高的玻璃化转变温度为598～620K,N2气气氛中10%热质量损失温度在673K以上.聚合物2a～2c的表面电阻系数为3.75×10¹⁴～9.87×10¹⁵Ω,体积电阻系数为1.39×10¹⁶～4.09×10¹⁶Ω·cm.聚合物在二甲基甲酰胺、1-甲基吡咯烷酮和间甲酚等极性有机溶剂中可溶解,并经浇注得到透明、韧性薄膜.     

study of liquid crystalline N -[4-(4- n -alkoxybenzoyloxy)-2-hydroxybenzylidene]methylanilines

New homologous series of N -[4-(4- n -alkoxybenzoyloxy)-2-hydroxybenzylidene]methylanilines [ n AH m M( n =1-8/10; m =2: ortho , m =3: meta , m =4: para )] were synthesized. They exhibited a nematic phase except for 1AH3M. The temperature dependence of their Raman spectra was observed in the spectral range of 900-1700 cm -1 . In one group of n AH m M compounds, the Raman band at about 1360 cm -1 abruptly decreased in intensity and wavenumber when the crystalline solid-liquid crystal phase transition was approached. In another group, the corresponding band increased through the phase transition. The bands have been assigned to the coupling mode between the in-plane CCH deformational vibration and the ring-N stretching vibration. Such a behaviour can be explained by the molecular conformation with different twist angles of the aniline ring in relation to the Schiff 's base plane of the molecule. Some n AH m Ms exhibited photochromism.     

Raman spectroscopy of liquid crystalline N-[4-(4-n-alkoxybenzoyloxy)-2-hydroxybenzylidene]-3-aminopyridines

New homologous series of N-[4-(4-n-alkoxybenzoyloxy)-2-hydroxybenzylidene]-3-aminopyridines were synthesized, they exhibited a nematic phase. The temperature dependence of their Raman spectra has been observed in the spectral range 900–1800?cm^?1. Some Raman bands show a marked change in their intensity and frequency through the phase transition from crystalline solid to nematic. These bands are ascribed to the vibrational modes related to the core part of the molecule. Such behaviour can be explained by the change of molecular conformation related to the core. Some members of these series exhibited photochromism in the solid state.     

4-(Arylaminothiocarbonyl)-1-(1-o-methoxyphenylcarbamido)-ethylpiperazines as anticonvulsants

Several 4-(arylaminothiocarbonyl)-1-(1-o-methoxyphenylcarbamido)-ethylpiperazines were synthesized and evaluated for their anticonvulsant activity against pentylenetetrazol-induced seizures in mice. The ability of substituted piperazines to inhibit in vitro respiratory activity of rat brain homogenates was also determined to study their structure-activity relationship.     

5-[5-(4-硝基苄基)-2H-四唑亚甲基]-2-芳酰氨基-1,3,4-噻二唑的合成

1-[5-(4-硝基苄基)-2H-四唑乙酰基]4-芳酰氨基硫脲(自制)在冰醋酸的存在下,经脱水、环化制备了5-[5-(4-硝基苄基)-2H-四唑亚甲基]-2-芳酰氨基-1,3,4-噻二唑。其结构经元素分析,IR,^1H NMR和MS确认。     

Preparation of 3-(4-chlorophenyl)-2-(2-aminothiazol-4-yl)-5-methoxybenzo[b]furan derivatives and their leukotriene B(4) inhibitory activity

A series of 3-(4-chlorophenyl)-2-(2-aminothiazol-4-yl)benzo[b]furan derivatives 6-10 were prepared and their leukotriene B(4) inhibitory activity was evaluated. We found that several compounds showed strong inhibition of calcium mobilization in CHO cells overexpressing human BLT(1) and BLT(2) receptors. Among them, 3-(4-chlorophenyl)-2-[5-formyl-2-[(dimethylamino)methyleneamino]thiazol-4-yl]-5-methoxybenzo[b]furan 9b showed the most potent and selective inhibition for the human BLT(2) receptor, and its IC(50) value was smaller than that of the selected positive control compound, ZK-158252.     

1-[2′,4′-二氟-(1,1′-联苯)-4-基苯基甲基]-咪唑的合成

以2,4-二氟联苯为起始原料,经酰化反应制得2′,4′-二氟-(1,1′-联苯)-4-基苯基甲酮(2);2经NaBH4还原得2′,4′-二氟-(1,1′-联苯)-4-基苯基甲醇(3);3经氯代得2′,4′-二氟-(1,1′-联苯)-4-基苯基氯甲烷(4);4与咪唑发生亲核取代反应合成了1-[2′,4′-二氟-(1,1′-联苯)-4-基苯基甲基]-咪唑(5). 2～5为新化合物,其结构经1H NMR, IR, MS和元素分析确证.     

4-(o-Carboxyphenylamino)pyrimidines

2-Chloro-4-(o-carboxyphenylamino)pyrimidines were synthesized by reaction of 2,4-dichloro-pyrimidines with anthranilic acid in aqueous media in the presence of hydrochloric acid. A number of their derivatives-2-hydroxy-, 2-methoxy-, and 2-amino-4-(o-carboxyphenyl-amino)pyrimidines -were obtained.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1252–1254, September, 1977.     

Halogen-substituted 2-(2′-arenesulfonylaminophenyl)-4h-1,3-benzoxaz-4-ones

Chloro- and bromo-substituted 2-(2-tosylaminophenyl)-4H-1,3-benzoxaz-4-ones and 2-(2-tosylaminophenyl)-4H-naphtho[2,3-d]-1,3-oxaz-4-ones, their absorption spectra at room temperature, and their luminescence spectra at 77 deg K are described.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1597–1601, December, 1970.     

Synthesis of 4-(4-phenyl-3-pyrazolyl)-4H-1,2,4-triazoles

4-(4-PhenyI-3-pyrazolyl)-4H-1,2,4-triazoles and 4-phenyl-5-(4H-1,2,4-triazol4-yl)-3-pyrazolols were prepared by the reaction of formylhydrazine on α-phenyl-α-cyanoacetaldehydes and ethyl α-phenyl-α-cyanoacetates.     

Synthesis of 5-(3,4,5-trimethoxyphenyl)-4-substituted aryl-3-hydrazino-carbonylmethylthio-4H-1,2,4-triazoles as possible antiinflammatory agents

A series of 5-(3,4,5-trimethoxyphenyl)-4-substituted aryl-3-hydrazinocarbonylmethylthio-4H-1,2,4-triazoles were synthesized and evaluated for their antiprotolytic and antiinflammatory activities.     

Synthesis of 5-Substituted-3-[(2’R,4’R)-4’-Hydroxy-2’-hydroxymethyltetrahydrofuran-4’-yl]-1,2,4-oxadiazoles and Their Epimers

The syntheses of 5-substituted-3-[( 2' R, 4' R)-4 ' -hydroxy-2 ' -hydroxymethyltetra-hydrofuran-4' -yl]D-1 ,2, 4-oxadiazoles and their epimers were accomplished with the aid of th construction of 1,2, 4-oxadiazoles by condensation of O-acylated cyanohydrins with hydroxylamine via intramolecular transacylation and subsequent cyclization.     

1-(1-aryl-3-ethylthiocarbamido)-4-arylaminothiocarbonyl)- piperazines as possible anticonvulsants

Several 1-(1-aryl-3-ethylthiocarbamido)-4-(arylaminothiocarbonyl)piperazines were synthesized as possible anticonvulsants. These 1,4-disubstituted piperazines were characterized by their sharp melting points and elemental and spectral analyses.