Day: December 2, 2022

Venturella, Pietro published the artcileReactivity of the flavanone nucleus. II. Effect of substituents on the reaction with phenylhydrazine, Computed Properties of 13599-22-9, the publication is Annali di Chimica (Rome, Italy) (1961), 759-68, database is CAplus.

cf. CA 55, 15467b. Substituents in the flavanone nucleus do not particularly affect the conversion of their phenylhydrazones into pyrazoline derivatives The possibility to isolate the intermediate phenylhydrazones depends on the nature and the position of the substituents. The appropriate flavanone (0.5 g.) in 10 cc. 95% EtOH refluxed 1 hr. with 0.3 g. PhNHNH₂, kept some time, and diluted with H₂O gave the corresponding phenylhydrazone. In this manner were prepared the following compounds: 2-(p-methoxyphenyl)flavanone phenylhydrazone (I); 2-[3,4-(CH₂O₂)C₆H₃] analog (II) of I, m. 127-8°; 2-(3,4-methyl-enedioxyphenyl)-5,6,8-trimethoxyflavanone phenylhydrazone (III) (without EtOH), m. 129-31°; 2-Ph analog of III; 2-phenyl-6-methoxyflavanone phenylhydrazone (IV); and the 5,6-di-MeO analog of IV, needles, m. 118-20°. The appropriate flavanone (0.5 g.) and excess PhNHNH₂ heated a few min. in a test tube over a free flame, cooled, dissolved in AcOH, and poured into H₂O gave the corresponding 3,5-diarylpyrazoline (V). The appropriate flavanone (0.5 g.) in 5 cc. AcOH refluxed 1 hr. with 0.3 g. PhNHNH₂, cooled, and diluted with H₂O gave the corresponding V. The appropriate chalcone (0.2 g.) and PhNHNH₂ heated a few min. in a test tube over a free flame, dissolved in AcOH, and poured into H₂O gave the corresponding V. The appropriate phenylhydrazone refluxed 1 hr. with AcOH gave the corresponding V. The appropriate V refluxed with Ac₂O and NaOAc gave the corresponding acetate which fluoresces in EtOH intensely blue-green. By these methods were prepared the following V and their acetates (3- and 5-aryl group, crystal form, and m.p., and m.p. of acetate given): o-HOC₆H₄, p-MeOC₆H₄ (Va), needles, 168-9°, 132-3°; o-HOC₆H₄, 3,4-(CH₂O₂)C₆H₃ (VI), needles, 145-6°, 116-17°; 2,3,5,6-HO(MeO)₃C₆H, 3,4-(CH₂O₂)C₆H₃ (VIa), needles, 185-6°, 195-6°, 2,3,5,6-HO(MeO)₃C₆H, Ph (VII), yellow-green plates, 193-4°, 132-3°; 2,5-HO(MeO)C₆H₃, Ph (VIII), needles, 150-1°, 114-15°; 2,5,6-HO(MeO)₂C₆H₂, Ph (IX), yellow plates, 147-8°, 147°, VII or VIII or IX (1 g.) in 30 cc. refluxing 5% aqueous NaOH treated gradually with 6.5 g. KMnO₄ in 70 cc. H₂O, refluxed 3 hrs., and worked up gave 1,5-diphenyl-3-pyrazolecarboxylic acid, m. 183-5° (EtOH). Va or VI, or Via oxidized similarly with 8 g. KMnO₄ in 100 cc. H₂O gave 1-phenyl-3,5-pyrazoledicarboxylic acid, platelets, m. 265-6° (H₂O). The ultraviolet absorption spectra of the various pyrazolines, and II, III, and V, and the infrared absorption spectra of VI and its acetate are recorded.

Annali di Chimica (Rome, Italy) published new progress about 13599-22-9. 13599-22-9 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Carboxylic acid,Benzene, name is 1,5-Diphenyl-1H-pyrazole-3-carboxylic acid, and the molecular formula is C12H10O4S, Computed Properties of 13599-22-9.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

van Alphen, J. published the artcileThe reaction between α-halogen ketones and derivatives of phenylhydrazine. I. The reactivity of the N:NC:C group in α-phenylazocrotonic acid esters, Application of 1-(2-Chlorophenyl)-3-methyl-5-pyrazolone, the publication is Recueil des Travaux Chimiques des Pays-Bas et de la Belgique (1945), 109-14, database is CAplus.

α-Phenylazocrotonic acid (I) Et ester, prepared from 16.5 g. ClCH₂CO₂Et (II) in 60 ml. EtOH mixed with cooling with 10.8 g. PhNHNH₂ in 100 ml. EtOH and 13.6 g. crystallized NaOAc in 30 ml. H₂O, seps. as red needles, m. 51°. After a long time 1-phenyl-3-methyl-4-phenylazo-5-pyrazolone (III), m. 158°, seps. from the mother liquor. I Me ester, prepared in the same manner, m. 46° (from EtOH). When the Et ester was ozonized in CHCl₃ at 0°, then decomposed with ice and CaCO₃, the CHCl₃ layer contained an oil which was reduced in EtOH with Al-Hg, yielding PhNHNHAc, thus proving the structure of I. Reduction of I (Raney Ni, H) yielded 4,4′-bi[1-phenyl-3-methylpyrazolone] (IV), which, boiled with FeCl₃, gave the characteristic blue color of “pyrazolone blue” in CHCl₃. I reduced in EtOH (Al-Hg) yielded 1-phenyl-3-methyl-5-pyrazolone (V). Bromination of I yielded tars. Bromination in small amounts in Et₂O yielded 1-(4-bromophenyl)-3-methyl-4-bromo-5-pyrazolone, m. 171°. Me ester of I yielded the same product. Et ester of I reacted in dry Et₂O with HCl to give a salt which, boiled with H₂O, yielded 1-phenyl-3-methyl-4-chloro-5-pyrazolone (VI), m. 153°. Me ester of I yielded the same product. Heating VI with PhNHNH₂ yielded III. That the Cl had not entered the ring was shown by the preparation of 1-(4-chlorophenyl)-3-methyl-5-pyrazolone, m. 168°, and 1-(2-chlorophenyl)-3-methyl-5-pyrazolone, m. 109°. Et acetoacetate p-chlorphenylhydrazone, yellow needles, m. 111°. PhMgBr added to I gave a complex mixture of unidentifiable products. I does not add to maleic anhydride.

Recueil des Travaux Chimiques des Pays-Bas et de la Belgique published new progress about 14580-22-4. 14580-22-4 belongs to pyrazoles-derivatives, auxiliary class Organic Pigment, name is 1-(2-Chlorophenyl)-3-methyl-5-pyrazolone, and the molecular formula is C25H47NO8, Application of 1-(2-Chlorophenyl)-3-methyl-5-pyrazolone.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Valecha, Sheela M. published the artcileSynthesis and characterization of manganese (II), cobalt (II), nickel (II), copper (II) and zinc (II) mixed ligand complexes with [(1-phenyl-3-methyl-5-hydroxopyrazol-4-yl) phenylimino]2′,3′ dimethylaniline and 2-hydroxy-1-naphthaldehyde, Application In Synthesis of 4551-69-3, the publication is Acta Chimica Pharmaceutica & Indica (2015), 5(1), 16-21, database is CAplus.

Mixed ligand complexes of the type [MLL′] where M = Mn (II), Co (II), Ni (II), Cu (II), Zn (II) HL = [(1-phenyl-3-methyl-5-hydroxopyrazol-4-yl)phenylimino]2,3-dimethylaniline; (HPMPZP)dma. HL′= 2-hydroxy-1-naphaldehyde; (HNA), have been synthesized and characterized on the basis of elemental anal., conductivity measurements, magnetic, electronic and infra red spectral studies. The complexes confirm to 1:1:1 stoichiometry and are non electrolytes. The schiff base HL act as a monovalent bidentate ligand co-ordinating through azomethine nitrogen and phenolic oxygen. On the basis of electronic spectra, IR spectra and magnetic moment measurements; six coordinated octahedral structures have been proposed for the complexes. Thermal studies revealed the presence of two coordinated water mols. The shiff base and mixed ligand complexes have been tested for their antibacterial activity against the Escherichia coli, Bacillus substilis, staphylococcus aureus.

Acta Chimica Pharmaceutica & Indica published new progress about 4551-69-3. 4551-69-3 belongs to pyrazoles-derivatives, auxiliary class Benzenes, name is 4-Benzoyl-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, and the molecular formula is C24H12, Application In Synthesis of 4551-69-3.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Tomasik, Z. published the artcile1-o-Chlorophenyl-3-methyl-5-pyrazolone and its derivatives, SDS of cas: 14580-22-4, the publication is Roczniki Chemii (1928), 345-8, database is CAplus.

o-ClC₆H₄NHNH₂ condenses with AcCH₂CO₂Et to yield 1-o-chlorophenyl-3-methyl-5-pyrazolone, m. 199° (4-benzylidene derivative, m. 167°; 4-o-nitrobenzylidene derivative, m. 160°), which when condensed with o-O₂NC₆H₄CHO yields o-nitrophenylbis-[1-o-chlorophenyl-3-methyl-5-pyrazolonyl]methane, m. 249°.

Roczniki Chemii published new progress about 14580-22-4. 14580-22-4 belongs to pyrazoles-derivatives, auxiliary class Organic Pigment, name is 1-(2-Chlorophenyl)-3-methyl-5-pyrazolone, and the molecular formula is C13H10O3, SDS of cas: 14580-22-4.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Shibamoto, Takayuki published the artcileA Novel Gas Chromatographic Method for Determination of Malondialdehyde from Oxidized DNA, SDS of cas: 930-36-9, the publication is Methods in Molecular Biology (New York, NY, United States) (2015), 49-62, database is CAplus and MEDLINE.

Malondialdehyde (MA) is known to form from various lipids upon oxidation as one of secondary oxidation products. Determination of MA formed from lipid peroxidation has been used to examine occurrence of oxidative damages associated with many diseases, such as cancer, Alzheimer’s, arthritis, inflammation, diabetes, atherosclerosis, and AIDS as well as aging. Anal. of MA is, however, extremely difficult because it is highly reactive and readily polymerized and forming adducts with biol. substances such as proteins, phospholipids, and DNA (Shibamoto, J Pharm Biomed Anal 41:12-25, 2002). Gas chromatog. method using stable derivative, 1-methylpyrazole was advanced and has been successfully used to analyze MA in various lipids and lipid-rich foods. This method was also applied to determine MA formed from DNA and related compounds The amounts found in oxidized 2-deoxyribonucleotides were 213.8 nmol/16 mmol in 2-deoxyguanosine, 130.6 nmol/16 mmol in 2-deoxycytidine, 85.1 nmol/16 mmol in 2-deoxyadenosine, and 84.5 nmol/16 mmol in thymidine. When the antioxidant activity of flavonoids and anthocyanins against calf thymus DNA oxidized with Fenton’s reagent was examined using this newly developed gas chromatog. method, antioxidant activity of flavonoids and anthocyanins ranged from 48.5% (catechin) to 29.9% (apigenin) and from 45.0% (callistephin) to 10.2% (cyaniding), resp.

Methods in Molecular Biology (New York, NY, United States) published new progress about 930-36-9. 930-36-9 belongs to pyrazoles-derivatives, auxiliary class Pyrazole, name is 1-Methylpyrazole, and the molecular formula is C3H5F3O, SDS of cas: 930-36-9.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Roy, Sutapa published the artcileSynthesis, characterization and 3-D molecular modeling of some oxovanadium(IV) complexes involving O₂N₂ donor core, SDS of cas: 4551-69-3, the publication is Journal of Pharmacy and Chemistry (2014), 8(4), 9-13, database is CAplus.

In view of the wide application of vanadium complexes, oxovanadium(IV) complexes involving pyrazolone-based aroylhydrazone and 8-hydroxyquinoline were synthesized and characterized by different physicochem. studies such as elemental anal., molar conductance, magnetic measurements, IR, TGA, ESR, mass and electronic spectral studies. The overall exptl. data based from all the studies presented suggests the complexes under present investigation are [VO(L)(8-hq)(H₂O)], where LH- pyrazolone-based aroylhydrazone and 8-hqH = 8-hydroxyquinoline, involving a monobasic didentate (O,N) donor ligand. An octahedral structure with axial oxo groups are proposed for these complexes.

Journal of Pharmacy and Chemistry published new progress about 4551-69-3. 4551-69-3 belongs to pyrazoles-derivatives, auxiliary class Benzenes, name is 4-Benzoyl-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, and the molecular formula is C17H14N2O2, SDS of cas: 4551-69-3.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Makisumi, Yasuo published the artcileAzaindolizine compounds. X. Synthesis of 5,7-disubstituted pyrazolo[1,5-a]pyrimidines, Safety of 3-Acetamidopyrazole, the publication is Chemical & Pharmaceutical Bulletin (1962), 612-20, database is CAplus.

cf. CA 57, 16606b. The title compounds (I) were prepared in general by condensing AcCH₂CO₂Et (II), CH₂Ac₂ (III), NCCH₂CO₂Et (IV), and CH₂(CO₂Et)₂ (V) separately with 5-amino-pyrazole (VI), its 1-Ph derivative (VII), its 4-EtO₂C derivative (VIII), and its 4-NC. derivative (IX). II kept overnight at room temperature with VI, VII, or VIII in the absence of solvent gave the corresponding 5-EtO₂CCH:CMeNH derivatives (X-XII) of pyrazole, m. 102°, 80-1°, and 175-6°, resp. On the other hand, refluxing II with VI or VIII 2-2.5 hrs. in AcOH gave the cyclized compounds (Ia, R = H and EtO₂C), m. 298-9° and 218-20°, resp., whereas refluxing II 4 hrs. with VII in AcOH gave the different cyclized compound (XIII), m. 188-9°. Ia (R = H and EtO₂C) and XIII were formed also by refluxing X-XII 2-3 hrs. with AcOH. Ia (R = EtO₂C) was also formed by refluxing XI 10 hrs. with Na in EtOH, and Ia (R = H) was prepared by refluxing VI 3 hrs. with II in EtOH containing anhydrous ZnCl₂. Hydrolysis of 0.5 g. Ia (R = EtO₂C) by heating 2 hrs. on a steam bath with 10% NaOH yielded 0.45 g. corresponding free acid, m. 296-7° (decomposition), and this (0.5 g.) was successfully decarboxylated by refluxing 3 hrs. with 40% H₂SO₄ to yield 0.32 g. Ia (R = H). Also, 0.94 g. IX refluxed 2.5 hrs. with II in AcOH yielded 1.5 g. Ia (R = cyano), m. 313° (decomposition), and this (0.5 g.) hydrolyzed and decarboxylated by refluxing 4 hrs. with 40% H₂SO₄ also yielded 0.4 g. Ia (R = H). Refluxing III (in place of II) with VI or VIII 10-12 hrs. in EtOH containing 3 drops piperidine, removing the solvent, and purifying the residue by Al₂O₃ chromatography gave, resp., Ib (R = H), m. 40-40.5°, and Ib (R = EtO₂C), m. 107-7.5°. The latter, like Ia (R = EtO₂C) was hydrolyzed to the corresponding free acid, m. 178-9°, which was decarboxylated either by heating 20 min. at 200° without solvent or by refluxing with 40% H₂SO₄ to give Ib (R = H), formed likewise by refluxing the ester, Ib (R = EtO₂C), itself with 40% H₂SO₄. Use of IV (in place of II or III) with VI or VIII in EtOH containing Na gave, resp., Ic (R = H), m. 306° (decomposition), and Ic (R = EtO₂C), m. 236-7°, which was hydrolyzed to the free acid, m. 296° (decomposition), and this was decarboxylated by heating in vacuo at 260-70° to give Ic (R = H). However, heating IV with VI 2 hrs. at 160-70° in the absence of solvent gave the noncyclized 5-(2-cyanoacetamido)-pyrazole (XVI), m. 211-12° (decomposition), and this was cyclized to Ic (R = H) by heating 5 hrs. on a steam bath in AcOH. Finally, V (in place of II) with VI or VIII in EtOH containing Na gave, resp., Id (R = H), m. 239-40° (decomposition), and Id (R = EtO₂C), m. 186-7° (decomposition), which also was hydrolyzed to the corresponding acid, m. 229° (decomposition), and this heated 5 min. at 235° was not only decarboxylated but also decomposed to give 5-acetamidopyrazole (XV), m. 223-4°, identical with the product obtained by refluxing VI 1 hr. with AcOH. However, heating VI 15 min. on a steam bath with Ac₂O gave 1-acetyl-5-acetamidopyrazole, m. 190.5-1.5°, which was readily converted to XV by heating with H₂O. In support of the structures, ultraviolet absorption curves were shown for Ia (R = H, EtO₂C, and CN), X-XII, Ic (R = H), Id (R = H), XIV, and XV, and both infrared and ultraviolet absorption data were reported for most of the compounds The infrared spectra of I showed that the 5- or 7-HO groups were mainly in the lactam form, whereas the 5- or 7-H₂N groups kept the amino form in neutral medium, thus showing analogy with pyrimidine derivatives

Chemical & Pharmaceutical Bulletin published new progress about 3553-12-6. 3553-12-6 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Amine,Amide, name is 3-Acetamidopyrazole, and the molecular formula is C5H7N3O, Safety of 3-Acetamidopyrazole.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Lugovkin, B. P. published the artcileSynthesis of 3-indolyl(1-aryl-3-methylpyrazol-5-on-4-yl)methanephosphonates, Formula: C10H9ClN2O, the publication is Zhurnal Obshchei Khimii (1973), 43(6), 1261-3, database is CAplus.

Indole-3-carboxaldehyde reacted with 1-aryl-3-methyl-5-pyrazolones to form the 4-indoleninylpyrazolone analogs which with (RO)2PHO in the presence of RONa catalyst gave title compounds I (Ar = Ph, p-tolyl, o-, p-ClC6H4; (R = Me, Et).

Zhurnal Obshchei Khimii published new progress about 14580-22-4. 14580-22-4 belongs to pyrazoles-derivatives, auxiliary class Organic Pigment, name is 1-(2-Chlorophenyl)-3-methyl-5-pyrazolone, and the molecular formula is C10H9ClN2O, Formula: C10H9ClN2O.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Ludington, Jennifer L. published the artcileVirtual Fragment Preparation for Computational Fragment-Based Drug Design, Category: pyrazoles-derivatives, the publication is Methods in Molecular Biology (New York, NY, United States) (2015), 31-41, database is CAplus and MEDLINE.

Fragment-based drug design (FBDD) has become an important component of the drug discovery process. The use of fragments can accelerate both the search for a hit mol. and the development of that hit into a lead mol. for clin. testing. In addition to exptl. methodologies for FBDD such as NMR and X-ray Crystallog. screens, computational techniques are playing an increasingly important role. The success of the computational simulations is due in large part to how the database of virtual fragments is prepared In order to prepare the fragments appropriately it is necessary to understand how FBDD differs from other approaches and the issues inherent in building up mols. from smaller fragment pieces. The ultimate goal of these calculations is to link two or more simulated fragments into a mol. that has an exptl. binding affinity consistent with the additive predicted binding affinities of the virtual fragments. Computationally predicting binding affinities is a complex process, with many opportunities for introducing error. Therefore, care should be taken with the fragment preparation procedure to avoid introducing addnl. inaccuracies.This chapter is focused on the preparation process used to create a virtual fragment database. Several key issues of fragment preparation which affect the accuracy of binding affinity predictions are discussed. The first issue is the selection of the two-dimensional at. structure of the virtual fragment. Although the particular usage of the fragment can affect this choice (i.e., whether the fragment will be used for calibration, binding site characterization, hit identification, or lead optimization), general factors such as synthetic accessibility, size, and flexibility are major considerations in selecting the 2D structure. Other aspects of preparing the virtual fragments for simulation are the generation of three-dimensional conformations and the assignment of the associated at. point charges.

Methods in Molecular Biology (New York, NY, United States) published new progress about 930-36-9. 930-36-9 belongs to pyrazoles-derivatives, auxiliary class Pyrazole, name is 1-Methylpyrazole, and the molecular formula is C4H6N2, Category: pyrazoles-derivatives.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Huppatz, John L. published the artcileSystemic fungicides. The synthesis of pyrazolo[1,5-a]pyrimidine analogs of carboxin, SDS of cas: 23286-70-6, the publication is Australian Journal of Chemistry (1985), 38(1), 221-30, database is CAplus.

Pyrazolo[1,5-a]pyrimidines I (R = H, Me, HO, Cl, Me₂N; R¹ = H, Me, Pr, HO, Cl) and II (R² = H, Br; R³ = CONHPh, CO₂Et, CO₂H, NO₂), structural analogs of the systemic fungicide carboxin, were prepared A common intermediate incorporating structural features desirable for fungicidal activity, pyrazole-4-carboxamide III, was used to prepare pyrazolo[1,5-a]pyrimidines variously substituted in positions 5 and 7 of the ring system. Bromination of I (R = R¹ = H) occurred preferentially in the Ph ring and II (R² = Br; R³ = CO₂Et) was prepared by bromination of II (R² = H; R³ = CO₂Et) (IV). Attempted nitration of the ester IV resulted in displacement of the ethoxycarbonyl substituent by a nitro group. The simplest pyrazolo[1,5-a]pyrimidine I (R = R¹ = H) showed a high level of fungicidal activity in fungal growth assays of Basidiomycete species, but compounds substituted in the pyrimidine ring were inactive.

Australian Journal of Chemistry published new progress about 23286-70-6. 23286-70-6 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Amine,Ester, name is Ethyl 5-amino-3-methyl-1H-pyrazole-4-carboxylate, and the molecular formula is C7H11N3O2, SDS of cas: 23286-70-6.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics