Showing papers on "Pyrazole published in 1985"

Selective induction of coumarin 7-hydroxylase by pyrazole in D2 mice.

Abstract: Pyrazole, was given to DBA/2N (D2), C57BL/6N (B6) and AKR/N mice to study its effects on hepatic drug metabolism. A decrease in the total amount of microsomal cytochrome P-450 as well as in the activities of ethylmorphine demethylase and benzo[a]pyrene hydroxylase was found. On the other hand ethoxycoumarin de-ethylase was increased 1.5-2.5-fold (depending on the strain of mouse) and coumarin 7-hydroxylase as much as sevenfold (but only in D2 mice) after pyrazole treatment. This increase was much higher than that caused by phenobarbital, the only well known inducer of coumarin 7-hydroxylase. By reconstituting the mono-oxygenase complex after purification of cytochrome P-450 we found a 40-fold increase in coumarin 7-hydroxylase and eightfold increase in ethoxycoumarin de-ethylase after pyrazole treatment. This was found only in D2 mice. An antibody previously developed against a cytochrome P-450 fraction from the the D2 strain with a high coumarin 7-hydroxylase activity inhibited the microsomal coumarin 7-hydroxylase almost 100% after pyrazole pretreatment of the animals. In the case of control or phenobarbital-treated mice the inhibition was somewhat weaker. With the reconstituted mono-oxygenase complex the inhibition of coumarin 7-hydroxylase was almost 100% both for control and pyrazole-treated D2 mice. The data indicate that pyrazole causes an induction of the microsomal monooxygenase complex different from that caused by phenobarbital or 3-methylcholanthrene and selective for coumarin 7-hydroxylation or 7-ethoxycoumarin de-ethylation. This induction was strong in D2, weak in B6 and absent in AKR/N mice.

Transition-metal co-ordination compounds of a novel aniline-based pyrazole derivative. X-Ray crystal structures of [NN-bis(3,5-dimethylpyrazol-1-ylmethyl) aminobenzene]-dichlorocobalt(II) and -dibromocopper(II)

Abstract: The synthesis and characterization of transition-metal co-ordination compounds containing the newly synthesized ligand NN-bis(3,5-dimethylpyrazol-1 -ylmethyl)aminobenzene (bdmpab) are described The compounds have the general formulae [M (bdmpab)X2](M = Co, Cu, or Zn; X = Cl or Brand M = Co; X = SCN or NO3) and [Cu2(bdmpab)(SCN)3] and have been characterized by several spectroscopic methods and analytical techniques In some compounds (viz M = Co or Zn; X = Cl or Br and M = Co; X = SCN or NO3) bdmpab acts as a bidentate ligand and in others (viz M = Cu; X = Cl, Br, or SCN) as a tridentate ligand In all compounds the anions are also bonded Because of the flexible character of the ligand the preference of the transition-metal ions for specific co-ordination geometries is reflected in the resulting co-ordination compounds To prove the chelating nature of the ligand, and in particular to find out whether or not the aniline nitrogen is co-ordinated, the crystal structures of two representative examples have been determined [Co(bdmpab)Cl2] crystallises in space group Pbca, with a= 8713(2), b= 17252(4), c= 27626(7)A, and Z= 8 Standard least-squares refinement gave R= 0031 (R′= 0028) The cobalt atom has a CoN2Cl2chromophore in a distorted tetrahedral geometry Co–N distances are 2038(2) and 2044(2)A for the pyrazole nitrogens The Co ⋯ N contact of 3854(2)A for the aniline nitrogen is considered as non-co-ordinating Co–Cl distances are 22434(8) and 22266(8)A [Cu(bdmpab)Br2] crystallises in space group P21/n, with a= 8742(3), b= 29408(5), c= 8522(1)A, β= 10777(2)°, and Z= 4 Standard least-squares refinement gave R= 0025 (R′= 0026) The copper atom has a CuN3Br2 chromophore in a distorted trigonal-bipyramidal geometry The pyrazole nitrogens occupy the axial positions Cu-N distances are 1988(5) and 1981(5)A for the pyrazole nitrogens and 2423(1)A for the aniline nitrogen Cu–Br distances are 2454(1) and 2414(1)A

Herbicidal 4-benzoyl-1-methyl-5-hydroxypyrazoles

Abstract: Pyrazole derivatives, selective herbicidal compositions containing said derivatives and the use of said derivatives are provided. The pyrazole derivatives having selective herbicidal activity are represented by the formula I: ##STR1## wherein, X denotes a halogen, nitro or methanesulfonyl, Y denotes hydrogen, a lower alkyl or a halogen, Z denotes a halogen or methanesulfonyl, and R denotes hydrogen; an organic acid residue; a lower alkynyl; a lower alkyl or a lower alkenyl which may be substituted by a halogen, hydroxy, cyano or an alkoxycarbonyl; or a benzyl which may be substituted by a halogen, nitro or a lower alkyl.

Insecticidal n-aryl-3-aryl-4,5-dihydro-1h-pyrazole-1-carboxamides

Abstract: This invention relates to N-aryl-3-aryl-4,5-dihydro-1H-pyrazole-1-carboxamide compounds which are useful as pesticides, compositions containing those compounds, methods of controlling pests and processes for preparing these compounds.

Selective sequential demasking of the ester functions of 1-methyl-3,4,5-tris(methoxycarbonyl)pyrazole

Abstract: La deprotection par hydrolyse basique des fonctions esters du compose du titre se fait dans l'ordre 5, 4, 3; elle est etudiee par l'addition d'une amine apres chaque hydrolyse d'un ester et on obtient finalement le methoxy-2' ethylamide-3 phenylamide-5 propylamide-4 de l'acide methyl-1 pyrazoletricarboxylique-3,4,5 (les amines ont ete ajoutees dans l'ordre aniline, propylamine et methoxy-2 ethylamine)

Interaction of pyrazole and 4-methylpyrazole with hepatic microsomes: effect on cytochrome P-450 content, microsomal oxidation of alcohols, and binding spectra

Abstract: Microsomes isolated from rats treated with either pyrazole or 4 methylpyrazoie, potent inhibitors of alcohol dehydrogenase, cata lyzed the oxidation of ethanol and 2-butanoJ at rates 2–3-fold highe than saline controls. Time course experiments and dose-response experiments indicated that an increase in the microsomal oxidatioi of alcohols could be observed 24 hr after a single treatment with 200 mg/kg body weight of either pyrazole or 4-methylpyrazole, and after 2 or 3 days of treatment with 50 mg/kg of either of these compounds. The pyrazole treatment did not change the activity of NADPH-cytochrome P-450 reductase, the content of cytochrome P-450, or the oxidation of aminopyrine. Hence, microsomal oxidatior of alcohols was increased by the pyrazole treatment whether results were expressed “per mg of protein” or “per nmol of P-450.” Microsomes from the pyrazole-treated rats displayed an increase in binding spectrum with ethanol as the substrate as compared to controls as well as type 2 binding spectrum with dimethyl sulfoxide and 2-butanol. These results suggest the possibility that pyrazole ma) induce an alcohol-preferring P-450 isozyme. By contrast, the 4-methylpyrazoie treatment, besides increasing the oxidation of alcohols, also increased the oxidation of aminopyrine and the content of cytochrome P-450. The increase in the oxidation of alcohols arte aminopyrine was primarily due to the increase in content of P-45C produced by the 4-methylpyrazole treatment Binding spectra wrtti dimethyl sulfoxide and 2-butanol were also observed after 4-methylpyrazole treatment; however, the 2-butanol-binding spectrum was a modified type I spectrum, not type 2. Taken as a whole, these results indicate that pyrazole and 4-methylpyrazole treatment can affect the microsomal mixed function oxidase system and the oxidation of alcohols by microsomes, and that there are differences in the interaction of these compounds with microsomes.

Synthesis of macrobicyclic ligands containing pyrazole subunits: the N,N′-bipyrazolyl cryptand

Abstract: The pyrazolyl cryptands [bpz.bpz.bpz](1) and [2.2.bpz](2) have been obtained in a one-step, non high-dilution macrobicyclization reaction, from a 1,1′-bipyrazole derivative; similarly, tripodal ligands (7)–(9) with pyrazole structure are described.

C-nucleoside studies. Part 18. The synthesis of C-Nucleoside analogues of the antiviral agent (S)-9-(2,3-Dihydroxypropyl)adenine

Abstract: 1-Methylsulphonyl-3-(1-O-methylsulphonyl-2,3-O-isopropylidene-D-erythro-trihydroxypropyl)-pyrazole (22), available in 56% overall yield from 1,2:5,6-di-O-isopropylidene-3-O-p-tolylsulphonyl-α-D-allofuranose (15), was treated with sodium borohydride to give 3(5)-[(S)-2,3-O-isopropylidene-dihydroxypropyl]pyrazole (23) in 90% yield. This was elaborated into 4-amino-3(5)-cyano-5(3)-[(S)-2,3-di-O-acetyldihydroxypropyl] pyrazole (30), which on treatment with formamidine acetate in refluxing ethanol, followed by sodium methoxide in methanol, gave 7-amino-3-[(S)-2,3-dihydroxy-propyl] pyrazolo[4,3-d]pyrimidine (6), a C-nucleoside analogue of the potent antiviral agent (S)-9-(2,3-dihydroxypropyl)adenine (3). Treatment of (6) with nitrous acid formed 3-[(S)-2,3-dihydroxy-propyl]pyrazolo[4,3-d]pyrimidin-7(6H)-one (7), an analogue of (3) containing the chromophore of formycin B.Treatment of (30) with nitrous acid, basification, and photolysis of the resultant diazopyrazole in aqueous acetone yielded 3(5)-cyano-5(3)-[(S)-2,3-di-O-acetyldihydroxypropyl]-4-hydroxypyrazole (33) in 67% yield. Two further steps gave the pyrazofurin analogue 5(3)-carbamoyl-3(5)-[(S)-2,3-dihydroxypropyl]-4-hydroxypyrazole (8).

Compositions comprising imidazole, pyrazole or derivatives thereof for removing undesirable organic matter from a surface

Abstract: A method of removing undesirable organic matter, such as food soil, paint, or the like, comprises contacting the organic matter with imidazole, pyrazole, an alkyl or aryl substituted imidazole, an alkyl or aryl substituted pyrazole, or a mixture of two or more thereof. Compositions containing these compounds as the active ingredient are also disclosed.

Eine neue Synthese von 4,5‐Dihydroxy‐pyrazolen

Abstract: A New Synthesis of 4,5-Dihydroxy-pyrazoles 1-Aryl-pyrazolin-5-ones 1 are converted by Knoevenagel condensation with acetone or by reaction with 2,2-dimethyl-1,3-dioxolane 6 to 1-aryl-4-isopropyliden-pyrazolin-5-ones 2. The compounds 2 are epoxidized by hydrogen peroxide forming the spiro-epoxides 3, which can be cleaved to 4,5-dihydroxy-pyrazoles 4 under acidic conditions. 4-Acetoxy-5-hydroxy-pyrazoles 13 are formed directly, when 3 are cleaved in presence of acetic anhydride. The 3,3′,3′-trimethyl-1-(4-nitro-phenyl)-pyrazolin-4-spiro-2′-oxiran-5-one 3b undergoes rearrangement to the 1,3-dioxolo[4,5-c]pyrazole 12.

Oxidation of the dioximes of 1,3-diketones with lead tetra-acetate

Abstract: The oxidation of dioximes of aliphatic and cyclic 1,3-diketones with lead tetra-acetate has been investigated. The formation of pyrazole and pyrazoline 1,2-dioxides in moderate yields has been established. A general reaction scheme is proposed.

N-aryl-3-aryl-4,5-dihydro-1H-pyrazole-1-carboxamides, processes for their production, insecticidal compositions containing them and methods for combatting insects

Abstract: Compounds of the general formula: which are N-aryl-3-aryl-4,5-dihydro-1H-pyrazole-1-carboxamides and agronomically acceptable salts thereof are pesticidally, especially insecticidally active. They are provided in Insecticidal compositions together with agronomically acceptable carriers or diluents and may be applied to insects or to loci to be freed or protected to attack by insects. The compounds may be prepared from 1-substituted-4,5-dihydro-1H-pyrazoles which may also be 4-monosubstituted by deprotonation and subsequent alkylation or acylation or from beta-dicarbonyl compounds by reaction with hydrazine and formaldehyde and subsequently aryl isocyanate followed by optional treatment with base and alkylation or acylation.

5-substituted-1-benzyl-1h-pyrazole(3,4-b)pyrazine derivative and antitumor agent containing said compound

Abstract: NEW MATERIAL:A compound expressed by formula I (R is lower alkyl, lower alkyl substituted by phenyl, phenyl or phenyl substituted by one or more halogen or lower alkyl) EXAMPLE:5-Butylamino-1-benzyl-1H-pyrazolo[3,4-b]pyrazine USE:An antitumor agent, having improved antitumor action, and capable of suppressing the multiplication of cancerated cells PREPARATION:Ethyl ethoxymethylene cyanoacetate is reacted with benzyl hydrazine to give ethyl 5-amino-1-benzyl-pyrazole-4-carboxylate expressed by formula II, which is then hydrolyzed under alkaline conditions and decarbonated to afford a compound expressed by formula III The resultant compound expressed by formula III is then reacted with isoamyl nitrite and catalylically reduced to give a compound expressed by formula IV, which is reacted with glyoxylic acid to afford a compound expressed by formula V The resultant compound expressed by formula V is then reacted with phosphorus oxychloride and an amine expressed by the formula R-NH2 one after another to give the aimed compound expressed by formula I