Showing papers on "Pyrazoline published in 2006"

Synthesis, structure, and in vitro antitumor activity of some glycoside derivatives of ferrocenyl-chalcones and ferrocenyl-pyrazolines.

Abstract: Some new glycosides of 3-ferrocenyl-1-(4'-hydroxyphenyl)-prop-2-en-1-one were prepared and transformed into the corresponding pyrazoline and pyrazole derivatives. Using methyl-hydrazine, formation of regioisomers was observed. DDQ was found to be a mild and efficient reagent for the pyrazoline-pyrazole dehydroaromatization process. The structure of the new compounds was proved by IR and NMR spectroscopy. The in vitro antitumor activity of the substances was investigated against human leukemia (HL-60) cells by the MTT method. Among these new compounds some chalcone derivatives (3 a, 3 b, 5 a, and 5 b) showed attractive in vitro antitumor effects on human leukemia cells. These molecules contained ferrocenyl moieties and a p-hydroxy-phenolic ring or a size-independent apolar substitution of that.

Synthesis, biological evaluation and 3D-QSAR of 1,3,5-trisubstituted-4,5-dihydro-(1H)-pyrazole derivatives as potent and highly selective monoamine oxidase A inhibitors.

Abstract: The present report provides a extended study of the chemistry, the inhibitory activity against monoamino oxidases (MAO), and molecular modeling including the 3D-QSAR hypothesis of 1,3,5-trisubstituted-4,5-dihydro-(1H)-pyrazole derivatives. Four series of about eighty novel pyrazoline derivatives were prepared and investigated for their ability to inhibit the activity of the A and B isoforms of MAO selectively. Most of the new synthesized compounds proved more reversible, potent, and selective inhibitors of MAO-A than of MAO-B, and could be taken into account to develop the search further in this field, knowing that reversible and selective MAO-A inhibitors are used as antidepressant and antianxiety drug. The 30 most active compounds show inhibitory activity on MAO-A in the 8.6 x 10(-8) - 9.0 x 10(-9)M range. Moreover, it should be pointed out that for most of them a high IC(50) > or = 10(-9)M value is associated with a high A-selectivity (Selectivity Index MAO-B/MAO-A in the 10,000-16,250 range). Furthermore, due to the presence of a chiral centre at the C5 position of the pyrazole moiety, we performed the semi-preparative chromatographic enantioseparation of the most potent, selective, and chiral compounds. The separated enantiomers were then submitted to in vitro biological evaluation, and from the results of these experiments it has been possible to point out a difference in inhibiting the two isoforms selectively between the racemic mixture and the single enantiomers. The molecular modeling work was carried out combining the Glide docking approach with CoMFA with the aim to rationalize the structure-activity relationships of each pyrazoline inhibitor toward MAO-A and MAO-B isoforms and to derive a suitable selectivity model.

Synthesis of some new testosterone derivatives fused with substituted pyrazoline ring as promising 5alpha-reductase inhibitors.

Abstract: Condensation of 3beta-hydroxy-16-[(4-chlorophenyl)methylene]androst-5-en-17-one (1) with hydrazine hydrate in acetic acid afforded N-acetyl pyrazoline derivative 2, while condensation of 1 with semicarbazide afforded compound 3. Also, compound 1 was treated with hydrazine hydrate in absolute methanol or ethanol to afford the corresponding alpha-methoxy (4) and alpha-ethoxy (5) derivatives, which were cyclized with etherated boron trifluoride to the pyrazoline derivative 6. The latter could be prepared directly by refluxing 1 with hydrazine hydrate in dioxane. Oxidation of compound 6 with Oppenour or Moffat oxidizing agents yielded 3-oxo-derivatives 7 and 8, respectively. On the other hand, condensation of compound 1 with substituted hydrazines, gave the corresponding 3beta-hydroxyandrostenopyrazolines 9a,b, which were oxidized using the Moffat method to give 3-oxo-androstenopyrazolines 10a,b, which were condensed with ethylene triphenyl-phosphorane in DMSO to yield 3-ethylene androstenopyrazolines 11a,b. Dehydrogenation of 9a,b with Wettestein oxidation afforded Delta4,6-diene-3-one analogues 12a,b, which were treated with chloranil to yield Delta(4,6,8(14))-tri-ene-3-one analogues 13a,b. Oppenour oxidation of 9a,b afforded Delta4-ene-3-one analogues 14a,b, which were treated with dichlorodicyanoquinone (DDQ) in dioxane to give Delta1,4,6-triene-3-one analogues 15a,b. Pharmacological screening showed that many of these compounds inhibit 5alpha-reductase activity.

Synthesis, spectral and antimicrobial studies of diorganotin(IV)3(2'-hydroxyphenyl)-5-(4-substituted phenyl) pyrazolinates

Abstract: Diorganotin(IV) dipyrazolinates of the type R 2 Sn(C 15 H 12 N 2 OX) 2 [where C 15 H 12 N 2 OX = 3(2'-Hydroxyphenyl)-5(4-X-phenyl)pyrazoline {where X = H (a); CH 3 (b); OCH 3 (c); Cl (d) and R = Me, Pr" and Ph}] have been synthesized by the reaction of R 2 SnCl 2 with sodium salt of pyrazolines in 1:2 molar ratio, in anhydrous benzene. These newly synthesized derivatives have been characterized by elemental analysis (C, H, N, Cl and Sn), molecular weight measurement as well as spectral [IR and multinuclear NMR ( 1 H, 13 C and 119 Sn)] studies. The bidentate behaviour of the pyrazoline ligands was confirmed by IR, 1 H and 13 C NMR spectral data. A distorted trans-octahedral structure around tin(IV) atom for R 2 Sn(C 15 H 12 N 2 OX) 2 has been suggested. The free pyrazoline and diorganotin(IV) dipyrazolinates have also been screened for their antibacterial and antifungal activities. Some diorganotin(IV) dipyrazolinates exhibit higher antibacterial and antifungal effect than free ligand and some of the antibiotics.

Contact allergy to an optical whitener, “cpy”, in washing powders

Abstract: SUMMARY— In 16 months contact dermatitis from an optical whitener, Tinopal CH 3566, was diagnosed in 167 patients at the Finsen Institute The dermatitis presented as a textile dermatitis Since “Tinopal” covers a wide range of chemically unrelated optical whiteners, the designation “CPY” is introduced for the particular pyrazoline derivative implicated in this dermatitis This product sensitized 16 of 20 animals in the guinea-pig maximization test: this rates this optical whitener as a strong sensitizer The result of patch testing in some of the patients with a number of pyrazoline derivatives points to the 4-position in the pyrazoline ring and the para-position in the l-benzyl-ring as key positions Benzylsalicylate evoked a positive reaction in 16 of 88 patients Seven of 13 patients showed a positive patch test to “Nylon” washed in a detergent containing the brightener

5(R)-Substituted Pyrazoline Compounds, their Preparation and Use as Medicaments

Abstract: The present invention relates to substituted pyrazoline compounds, methods for their preparation, medicaments comprising these compounds as well as their use for the preparation of a medicament for the treatment of humans and animals.

Amorphous phase of a substituted pyrazoline, its preparation and use as medicament

Abstract: The present invention relates to an amorphous phase of (rac)-N-piperidinyl-5-(4- chlorophenyl)-1-(2,4-dichlorophenyl)-4,5-dihydro-1 H-pyrazole-3-carboxamide, methods for its preparation, medicaments comprising this compound as well as their use for the preparation of a medicament for the treatment of humans and animals.

Cycloalkane-substituted pyrazoline compounds, their preparation and use as medicaments

Abstract: The present invention relates to Cycloalkane-substituted substituted pyrazoline compounds, methods for their preparation, medicaments comprising these compounds as well as their use for the preparation of a medicament for the treatment of humans and animals.

4,5-dihydro-(1h)-pyrazole derivatives as cannabinoid cb1 receptor modulators

Abstract: This invention is directed to 4,5-dihydro -(1 H)-pyrazole (pyrazoline) derivatives as cannabinoid CB1 receptor modulators, to pharmaceutical compositions containing these compounds, to methods for the preparation of these compounds, methods for preparing novel intermediates useful for their synthesis, and methods for preparing compositions. The invention also relates to the uses of such compounds and compositions, particularly their use in administering them to patients to achieve a therapeutic effect in disorders in which CB1 receptors are involved, or that can be treated via manipulation of those receptors. The compounds have the general formula (I) wherein the symbols have the meanings given in the specification.

Prodrugs of pyrazoline compounds, their preparation and use as medicaments

Abstract: The present invention relates to prodrugs of pyrazoline compounds of formula I, methods for their preparation, medicaments comprising these compounds as well as their use for the preparation of a medicament for the treatment of humans and animals.

Substituted pyrazoline compounds, their preparation and use as medicaments

Abstract: The present invention relates to substituted pyrazoline compounds, methods for their preparation, medicaments comprising these compounds as well as their use for the preparation of a medicament for the treatment of humans and animals.

4-Substituted Pyrazoline Compounds, their Preparation and Use as Medicaments

Abstract: The present invention relates to 4-substituted pyrazoline compounds, methods for their preparation, medicaments comprising these compounds as well as their use for the preparation of a medicament for the treatment of humans and animals.

Recyclization of 7-Fluoroalkyl-4,7-dihydroazolo[5,1-c]triazines into 5-(Pyrazolinylhydrazono)azoles in the Reactions with Hydrazides and Thiosemicarbazide

Abstract: 7-Fluoroalkyl-4,7-dihydroazolo[5,1-c][1,2,4]triazines react with hydrazides and thiosemicarbazide to form 5-(5-hydroxy-5-polyfluoroalkyl-2-pyrazoline-4-ylhydrazono)azoles as a result of triazine ring opening at bond C-7-N-8 and followed by regio-selective condensation.

1‐N‐Substituted Thiocarbamoyl‐3‐phenyl‐2‐pyrazolines: Synthesis and in vitro Antiamoebic Activities.

Abstract: The title compounds were prepared by reaction of Mannich bases with various N-4 substituted thiosemicarbazides. The chemical structures of the compounds were proved by means of their UV, IR, 1H NMR, 13C NMR spectroscopic data and elemental analyses. The in vitro antiamoebic activities of these compounds were evaluated by microdilution method against HM1:IMSS strain of Entamoeba histolytica and compared with the standard drug, metronidazole. It was concluded that 3-chloro and 3-bromo substituents on the phenyl ring at position 3 of the pyrazoline ring enhanced the antiamoebic activity. Compounds 9, 17, 18, 20 and 21 showed less IC50 value than metronidazole.

Synthesis of chlorins linked with pyrazoline by 1,3-dipolar diazomethane cycloaddition reaction

Abstract: Chlorins and bacteriochlorins, occurred in natural systems as a class of tetrapyrrolic macrocycles, have gained much interests in recent years because of their unique optical and photochemical properties. They can be utilized as the second generation photosensitizers for photodynamic therapy (PDT) of cancer and as models for photosynthetic reaction centers. Among the chlorophyll derivatives, pheophorbide, pyropheophorbide, purpurin and N-alkylimide of purpurin18 have been reported as potent photosensitizers with significant anticancer activity. Their derivatives were usually prepared by chemical modification of peripheral functional groups, particularly the vinyl group at 3-position. Our interest in the synthesis of chlorins as potential photosensitizers for PDT led us to explore new strategies for vinyl functionalization of pheophorbide-a by 1,3-dipolar cycloaddition methodology with diazomethane. 1,3-Dipolar [3+2] cycloaddition is an effective method for the synthesis of five-membered heterocycles. It is well known that diazomethane is a reactive reagent for 1,3dipolar cycloaddition with olefin to furnish pyrazoline derivatives, which serve as useful building blocks in the synthesis of various compounds through chemical transformation and/or ring cleavage. In the present work, the novel pyrazolinyl chlorins, promising versatile starting materials for further application by chemical transformation of pyrazoline ring for constructing new structure of chlorin, were synthesized by 1,3-dipolar cycloaddition reaction with chlorin and diazomethane. It was found that the vinyl group of pheophorbide-a 1, extracted from the alga Spirulina maxima, reacts slowly over a period of 3 days with ethereal

Conversion of 2-pyrazolines to pyrazoles using bromine

Abstract: This invention relates to a method for preparing a compound of Formula 1 wherein L, R1, R2 and X are as defined in the disclosure, comprising contacting a 2 pyrazoline of Formula 2 with bromine at a temperature of at least about 80°C. (Formula 1) (Formula 2). This invention also discloses preparation of a compound of Formula 3 wherein X, Z, R5, R6, R7, R8a, R8b and n are as defined in the disclosure, using a compound of Formula 1a wherein R10 is as defined in the disclosure, prepared by the aforesaid method for preparing a compound of Formula 1. (Formula 3) (Formula 4).

Reaction of 2′‐Hydroxy‐5′‐acetamido Chalcones with Dimethyl Sulfoxide‐Iodine, Pyridine‐Mercuric(II) Acetate and Triethanolamine.

Abstract: Reaction of 2'-hydroxy-5'-acetamido chalcones 5a-d with catalytic amount of iodine in DMSO affords flavone 6a-d, molar amount of mercuric (II) acetate in pyridine gives aurones 7a-d while with phenylhydrazine and hydrazine hydrate gives pyrazoline 8a-h in triethanolamine medium.

4-p-Anisyl-1,2′-diphenyl-3-p-tolyl-2′,3′-dihydrospiro­[2-pyrazoline-5,3′-isoquinolin]-4′(1′H)-one

Abstract: In the title compound, C37H31N3O2, the piperidine ring adopts a half-chair conformation. The mol­ecule is stabilized by intra­molecular C—H⋯N bonds and mol­ecules are connected via C—H⋯O hydrogen-bonding inter­actions.

Salts of substituted pyrazoline compounds, their preparation and use as medicaments

Abstract: The present invention relates to salts of substituted pyrazoline compounds, methods for their preparation, medicaments comprising these compounds as well as their use for the preparation of a medicament for the treatment of humans and animals.

4,5-dihydr0-1h-pyrazole derivatives, their preparation and use as medicaments

Abstract: The present invention relates to 4-substituted pyrazoline compounds of formula (I), methods for their preparation, medicaments comprising these compounds as well as their use for the preparation of a medicament for the treatment of humans and animals.

New light-absorbing material

Abstract: PROBLEM TO BE SOLVED: To provide a new light-shielding agent and a fluorescent light-detecting agent which are each applied to metal foil-containing laminates and have each strong absorbability in near UV ray portion to visible short wavelength portion. SOLUTION: This light-shielding agent and the fluorescent light-detecting agent each contains a pyrazoline compound represented by the general formula (I) [R 1 to R 5 are each H, a halogen, a 1 to 8C alkyl, a 1 to 8C alkoxy, amino or a 1 to 8C alkyl group-having alkylamino or dialkylamino; X is O, S or a secondary amine which may be alkylated; (n) is an integer of 0 or 1]. COPYRIGHT: (C)2006,JPO&NCIPI