Category: pyrazoles-derivatives

Finar, I. L. published the artcilePreparation and properties of some bipyrazolyls, Application of 1,5-Diphenyl-1H-pyrazole-3-carboxylic acid, the publication is Journal of the Chemical Society (1955), 1205-8, database is CAplus.

The synthesis of 5,5′-dimethyl-1,1′-diphenyl-(I) and 1,1′,5,5′-tetraphenyl-3,3′-bipyrazolyl (II) was repeated, and the 3,5′-isomer (III) of the latter was isolated. Evidence was given for the orientations of these two isomers, and some 4,4′-disubstituted derivatives of I, II, and III were prepared (CO₂Et)₂ (IV) (36.5 g.) and 29 g. dry Me₂CO were added during 25 min. to NaOMe (from 12.5 g. Na) under Et₂O at 0°, the mixture was stirred for 2 days to give 21-38% octane-2,4,5,7-tetraone (V), yellow needles, m. 120-1° (from MeOH). IV (36.5 g.) and 1/2 of 16 g. PhCOMe were similarly treated, the other 1/2 added 4 hrs. later, and the mixture stirred 3 days to give 62-74% 1,6-diphenylhexane-1,3,4,6-tetraone (VI), yellow needles, m. 177-9°. V (3.4 g.) was heated with 4.3 g. PhNHNH₂ in HOAc for 1 hr. to give 3.4 g. I, buff needles, m. 141-2°. VI (47.2 g.) was similarly treated 3-4 hrs. with 34.6 g. PhNHNH₂ to give 35.2 g. II, m. 233°. The filtrate was diluted with H₂O and then crystallized to yield 12.2 g. III, white needles, m. 135-6°. VI (58.8 g.) in HOAc was treated during 2.75 hrs. with 21.6 g. PhNHNH₂ in HOAc, heated for a further 1.25 hrs., and set aside for 2 days to give after fractional crystallization unchanged starting material, II, and 3-(α-benzoylacetyl)-1,5-diphenylpyrazole (VII), yellow needles, m. 164-6.5°. VII on oxidation with alk. KMnO₄ yielded 1,5-diphenylpyrazole-3-carboxylic acid (VIII), m. 185-6°. VII (2.9 g.) and 0.97 g. PhNHNH₂ in HOAc heated 1 hr., and kept at room temperature overnight gave 2.4 g. II and 1 g. III. The infrared spectra of II and III were complex and similar. In general, the lowering of the symmetry as in III increases the number of bands. III in the 1600-650 cm.^-1 region had 25 strong bands. Bischler’s method [Ber. 25, 3143(1892)] of preparing VIII was modified as follows: MeCOCH₂CO₂Et (30 g.) was refluxed 6 hrs. with 5.4 g. Na wire under Et₂O, then 46 g. BzCH₂Br in Et₂O was added to maintain gentle reflux, then refluxed 2 hrs., and set aside overnight to give 56 g. AcCH(CH₂Bz)CO₂Et (IX) as a red oil. IX (12.4 g.) in EtOH was treated in the cold with 4.65 g. PhN₂Cl, and then 16.4 g. NaOAc in H₂O, the mixture set aside 24 hrs. in ice, and the oil which separated heated 15 min. with 6 g. NaOH in a little H₂O to give 6.7 g. VIII. I in CHCl₃ was treated with Br at room temperature to yield 4,4′-dibromo-5,5′-dimethyl-1,1′-diphenyl-3,3′-bipyrazolyl, rods, m. 159-60°. 4,4′-Dibromo-1,1′,5,5′-tetraphenyl-3,3′-bipyrazolyl, plates, m. 272-3°. 4,4′-Dibromo-1,1′,3′,5-tetraphenyl-3,5′-bipyrazolyl, white rosettes, m. 200-1°. II (13.2 g.) in HOAc and 26 cc. concentrated HCl was heated 2 hrs. with 2.4 g. paraformaldehyde to give the 4,4′-bis(chloromethyl) derivative, white needles, (6.2 g.), m. 274-6°. I (3.14 g.) in HOAc was heated 0.5 hrs. with 6.37 g. HgAc₂ to yield 4.8 g. 4,4′-bis(acetoxymercuri) compound (X), white needles, m. 204-4.5° (aqueous HOAc). II (4.38 g.) similarly treated yielded after 5 hrs. refluxing 7.6 g. 4,4′-bis(acetoxymercuri)-1,1′,5,5′-tetraphenyl-3,3′-bipyrazolyl (XI), white powder, m. 271.5°. The mercuri compounds when treated with HOAc and Br at room temperature gave the corresponding 4,4′-di-Br compounds X refluxed with dilute HCl gave I; however, XI had to be refluxed for some time with HOAc containing concentrated HCl before II could be obtained.

Journal of the Chemical Society 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 C16H12N2O2, Application of 1,5-Diphenyl-1H-pyrazole-3-carboxylic acid.

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

Graubaum, Heinz published the artcileAcyl migrations on 3(5)-aminopyrazole, Recommanded Product: 3-Acetamidopyrazole, the publication is Journal fuer Praktische Chemie/Chemiker-Zeitung (1993), 335(7), 585-8, database is CAplus.

3-Aminopyrazole forms 3 isomeric monoacylation products [I–III, R = Me, Et, Ph, 4-Me₂CHC₆H₄, 4-ClC₆H₄], 4 diacylation products and 3 triacylation products by reaction with RNCO. Acetamides IV [R¹ = RNHCO, R = Me, Et, Ph; R¹ = C(:NH)OR², R² = 4-MeOC₆H₄, 4-MeC₆H₄, 4-ClC₆H₄] were obtained from 3-acetylaminopyrazole and RNCO or R²OCN. Acyl migrations are observed depending on the reaction temperature and the structure of the acyl residue.

Journal fuer Praktische Chemie/Chemiker-Zeitung 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, Recommanded Product: 3-Acetamidopyrazole.

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

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

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

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

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

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

Yang, Mengchen published the artcileHighly enantioselective Michael addition of pyrazolin-5-ones to nitroolefins catalyzed by cinchona alkaloid derived 4-methylbenzoylthioureas, SDS of cas: 14580-22-4, the publication is Chirality (2018), 30(9), 1096-1104, database is CAplus and MEDLINE.

Cinchona alkaloid-derived (4-methyl/nitro)benzoylthioureas were synthesized, which smoothly catalyzed the asym. Michael addition of pyrazolin-5-ones to nitroolefins. The results showed that electronic effects of substituents in the benzene ring of benzoylthioureas have subtle influences on their catalytic abilities and electron donating Me group was favored than electron withdrawing nitro group. Preliminary Hartree-Fock calculations revealed that in the catalytic cycle, hydrogen bond energies of the complex formed with 4-methylbenzoylthioureas were about 0.19 to 1.56 kcal/mol higher than with the corresponding 4-nitrobenzoylthioureas. 4-Methylbenzoylthioureas were identified as the most effective catalysts that promoted asym. Michael addition of pyrazolin-5-ones to nitroolefins to give the S- or R-products with high enantioselectivities.

Chirality 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 C4H10BBrO2, SDS of cas: 14580-22-4.

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

Yang, Fan published the artcileHomology modelling of G-coupled protein receptor 109A and docking simulation with pyrazole agonists, Quality Control of 890590-91-7, the publication is Jisuanji Yu Yingyong Huaxue (2016), 33(5), 569-574, database is CAplus.

Niacin receptor G-coupled protein receptor 109A (GPR109A) is an important target protein of the treatment of cardiovascular diseases and disorders of lipid metabolism diseases. Since GPR109A is one membrane protein, the crystal structure of which has not been resolved, there are many challenges to drug design for the receptor. Based on the mouse PUMA-G crystal structure, the three-dimensional structure of GPR109A was built by using the homol. modeling method. The model was evaluated by using the Ramachandran Plot and Profile-3D, and the model was optimized with MMFF94 force field, membrane and method of loop, and finally one stabile model was obtained and 12 sites that might be the active sites in the optimal model were found. SYBYL-X2 software was used to build GPR109A pyrazole agonist drug mols., through the steepest descent method and the Conjugate gradient method to receive the most stable conformation of the small drugs mols. All the agonists were docked into each active site of the protein by Libdock method, receiving the interaction models. We analyzed the distribution of amino acid of each active site, and took 5-methyl-3-carboxylic acid as a reference drug mol. to explore the interaction force with each protein active site. This study has theor. significance in designing G-coupled protein receptor 109A pyrazole agonists.

Jisuanji Yu Yingyong Huaxue published new progress about 890590-91-7. 890590-91-7 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Carboxylic acid, name is 3-Isopropyl-1H-pyrazole-5-carboxylic acid, and the molecular formula is C3H5BN2O2, Quality Control of 890590-91-7.

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