Tag: M.W=150-200

Pfeiffer, Wolf Diethard published the artcileSelective pyrazole synthesis by the means of ultrasonic radiation, Name: Ethyl 5-amino-3-methyl-1H-pyrazole-4-carboxylate, the publication is Zeitschrift fuer Chemie (1987), 27(8), 296-7, database is CAplus.

Pyrazoles I (R = NH₂, NHNH₂, NHMe, NHCHMe₂, NHCMe₃, NHPh, NHAc, NMe₂, Ph, Bz, SMe, R¹ = R² = Ph; R = NH₂, R¹ = CO₂Et, R² = Me) were prepared in 80-90% yields by ultrasonic radiation mediated selective desulfuration or deselenylation-ring contraction reaction of resp. 1,3,4-thiadiazines or 1,3,4-selenadiazines.

Zeitschrift fuer Chemie 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, Name: Ethyl 5-amino-3-methyl-1H-pyrazole-4-carboxylate.

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

Baraldi, Pier Giovanni published the artcileSynthesis, antibacterial activity and structure-activity relationships of N-substituted 4-diazopyrazole-5-carboxamides. 2, Product Details of C7H10N2O2, the publication is Farmaco (1991), 46(11), 1337-50, database is CAplus and MEDLINE.

A series of 4-diazopyrazole-5-carboxamides were synthesized and their antibacterial activity against a number of Gram-neg. and Gram-pos. strains was tested. Some of the compounds were quite active and the whole set was allowed to further study the SAR of the class. Substituents in position 5 affect Gram-neg. and Gram-pos. activities via bulk and electronic properties resp.; position 3 mostly affects the Gram-neg. activity, while the presence of the charged diazo group in position 4 is crucial for both antibacterial activities.

Farmaco 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 C7H10N2O2, Product Details of C7H10N2O2.

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

Dhankhar, Priyanka published the artcilePhotoluminescent report on red light emitting europium(III) complexes with heterocyclic acid, Category: pyrazoles-derivatives, the publication is Spectroscopy Letters (2020), 53(4), 256-269, database is CAplus.

Five luminescent europium (III) carboxylate complexes have been synthesized by using ligand 3-isopropylpyrazole-5-carboxylic acid as primary ligand and 4,4′-dimethyl-2,2′-bipyridyl, 2,2′-bipyridyl, 5,6-dimethyl-1,10-phenanthroline and 1,10-phenanthroline as secondary ligands and characterized through various techniques. These complexes exhibit excellent thermal stability and characteristic europium centered photoemission spectra under the excitation of UV light. Luminescence decay curves, Judd-Ofelt anal., internal quantum efficiency and energy transfer mechanism have also been discussed. The color coordinates and color purity are calculated to investigate red emission of the complexes. The study results reveal that these complexes can be potentially used as red light emitting materials in various optoelectronic devices.

Spectroscopy Letters 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 C7H10N2O2, Category: pyrazoles-derivatives.

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

Nitu, Sabina published the artcileAzoic compounds obtained from 1H-5-amino-4-ethoxycarbonyl-3-methyl-pyrazole and phenols or phenolic derivatives, Category: pyrazoles-derivatives, the publication is Revista de Chimie (Bucharest, Romania) (2008), 59(12), 1352-1354, database is CAplus.

The coupling of 1H-4-ethoxycarbonyl-3-methyl-pyrazol-5-yldiazonium chloride with phenols and Ph ethers I (R¹ = H, Me, PhCH₂; R² = 4-Me, 3-MeO, 2,4-F₂, etc.) affords the corresponding arylazopyrazoles II which were characterized by TLC, IR, VIS and NMR spectroscopy. The similar reaction with 4-hydroxybenzoic acid was accompanied by decarboxylation to give (4-hydroxyphenyl)azo derivatives

Revista de Chimie (Bucharest, Romania) 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, Category: pyrazoles-derivatives.

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

Beyer, Hans published the artcileThiazoles. XXVIII. 2,2′-Dithiazolylamine and its nitration products, Category: pyrazoles-derivatives, the publication is Chemische Berichte (1956), 1602-8, database is CAplus.

cf. C.A. 51, 2813c. 4,4′-Di- and 4,4′,5,5′-tetrasubstituted 2,2′-dithiazolylamines have been prepared Heating 4.5 g. dithiobiuret (I) and 11 g. CH₂ClCHClOEt in 80 cc. 60% EtOH 1 hr. on a water bath, adding 30 cc. 5% HCl, decomposing the precipitated HCl salt with NaOAc, and concentrating the solution to 10 cc. yield 64% 2,2′-dithiazolylamine (II), yellow leaflets, m. 215°, which is also obtained in 75% yield when 6.8 g. I and 7.8 g. CH₂ClCHO is heated 1 hr. on a water bath and the precipitated II.HCl is treated with NaOAc (HCl salt, needles, m. 214°; N-Ac derivative, small rods, m. 121-2°). Heating an intimate mixture of 11.4 g. 2-amino-4-methylthiazole (III) and 15 g. III.HCl 0.5 hr. at 200°, extracting the powd. melt with boiling H₂O, and recrystallizing the residue from 2N HCL give 30% 4,4′-dimethyl-2,2′-dithiazolylamine (IV).HCl, yellow needles, m. 276-8° (decomposition), which, with NaOAc, yields IV, needles, m. 153-4°, also obtained in 70% yield on heating 5.4 g. I with 11.1 g. AcCH₂Cl in 50 cc. EtOH 2 hrs. on a water bath. Heating a mixture of 17.6 g. 2-amino-4-phenylthiazole (V) and 21.5 g. V.HBr 1 hr. at 200°, extracting the powd. melt with hot H₂O and C₆H₆, and recrystallizing the residue from Me₂CO yield 85% 4,4′-diphenyl-2,2′-dithiazolylamine (VI), yellow rhombs, m. 219-21°, also obtained in 93% yield on mixing 2.7 g. I and 8 g. PhCOCH₂Cl, each dissolved in 25 cc. EtOH (N-Ac derivative of VI, needles or leaflets, m. 138°; N-Bz derivative, needles, m. 165-7°). Treating 3.3 g. VI in 150 cc. AcOH with solid NaNO₂ in small portions with cooling gives 72% 4,4′-diphenyl-2,2′-dithiazolylnitrosamine, red-brown cubes, m. 228-9° (decomposition), crystallizing from C₅H₅N with 1 mol. C₅H₅N, red rods, losing its C₅H₅N on heating at 200°. Treating 5.5 g. 2-amino-4,5-dimethylthiazole-HCl with 0.66 g. solid NaOH 15 min. at 220° yields 53% 4,4′,5,5′-tetramethyl-2,2′-dithiazolylamine, rhombs, m. 215-16°, which is also obtained in 78% yield when 1.3 g. I and 2.8 g. AcCHClMe is refluxed 0.5 hr. in 10 cc. MeOH. Fusing 29.3 g. 2-amino-4,5-diphenylthiazole (VII).HCl (or HBr) and 25.7 g. VII 0.5 hr. at 220° and triturating the melt with hot H₂O give 40% (or 70%) 4,4′,5,5′-tetraphenyl-2,2′-dithiazolylamine, rhombic leaflets, m. 208-9°, which is also obtained in 60% yield when 1.3 g. I and 3.2 g. desyl chloride is refluxed 1 hr. in 20 cc. EtOH (Ac derivative, platelets, m. 213-15°). Refluxing 1.7 g. 4-methyl-2-thiazolylthiourea and 2 g. PhCOCH₂Br in 50 cc. EtOH 1 hr. yields 90% 4-methyl-4′-phenyl-2,2′-dithiazolylamine, needles, m. 245°. Heating 2.6 g. I and 9.6 g. m-O₂NC₆H₄COCH₂Br in 100 cc. EtOH 1 hr. on a water bath gives 85% 4,4′-bis(m-nitrophenyl)-2,2′-dithiazolylamine (VIII), yellow needles, m. 252-3° [N-Ac derivative, yellow needles, m. 296-8° (decomposition)]. Heating 4.5 g. I and 9.6 g. CH₂ClCHClOEt in 50 cc. EtOH 1 hr. on a water bath gives 29.2% 2-thiazolylthiourea-HCl, clusters of felted needles, m. 203-4° (decomposition); from the mother liquor 3.5 g. II is isolated. Heating 5.4 g. I and 7.4 g. CH₂ClOMe 1 hr. on a water bath gives a mixture of 4-methyl-2-thiazolylthiourea (IX).HCl and IV.HCl which are separated by fractional crystallization from EtOH. Decomposition of IX.HCl with NaOAc gives IX, small rods, m. 174-5°. Treating 1.8 g. II in 25 cc. concentrated H₂SO₄ at -5° dropwise with 2 cc. concentrated HNO₃ in 10 cc. concentrated H₂SO₄ and, after 2 hrs., pouring the mixture onto ice yield 85% 5,5′-dinitro-4,4′-dimethyl-2,2′-dithiazolylamine, small orange-red rods, decompose 233°; it dissolves in alc. NaOH with a deep red color. Similar nitration of 3.6 g. VI in 150 cc. boiling Me₂CO with 10 cc. concentrated H₂SO₄ and concentrated HNO₃ (1:1) gives 86% 5,5′-dinitro-4,4′-diphenyl-2,2′-thiazolylamine (X), orange-red leaflets, m. 229-31° (decomposition); it crystallizes with 1 mole C₅H₅N, deep red rods. Adding Zn dust in small portions to 4.25 g. X in 25 cc. Ac₂O and 10 cc. AcOH, refluxing the mixture 0.5 hr., pouring the filtered solution into H₂O, and recrystallizing the precipitate from AcOH yield 5,5′-diamino-4,4′-diphenyl-2,2′-dithiazolylamine pentaacetate, rhombs, m. 208-9°. Treating 11.4 g. VIII with 100 cc. concentrated HNO₃ and warming the mixture on a water bath give 2.1 g. O₂NC₆H₄CO₂H, m. 141-2°; similarly, X yields BzOH.

Chemische Berichte 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, Category: pyrazoles-derivatives.

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

Wilde, Richard G. published the artcileACAT inhibitors derived from hetero-Diels-Alder cycloadducts of thioaldehydes, Recommanded Product: 4-Bromo-1-methyl-1H-pyrazol-5-amine, the publication is Bioorganic & Medicinal Chemistry (1996), 4(9), 1493-1513, database is CAplus and MEDLINE.

Acyl-CoA:cholesterol acyltransferase (ACAT) is the enzyme largely responsible for intracellular cholesterol esterification. A systemic inhibitor of ACAT is believed to be able to slow or even reverse the atherosclerotic process. Towards that goal, a series of cyclic sulfides, derived from the hetero-Diels-Alder reaction of thioaldehydes with 1,3-dienes, and bearing carboxamide substituents, were prepared and evaluated for in vitro (in several tissues and species) and ex vivo ACAT inhibition. The most active compounds were thiopyrans I [R¹ = pentyl, octyl]. Minor changes in structure had a significant effect in optimization of the biol. activity of this series of compounds

Bioorganic & Medicinal Chemistry published new progress about 105675-85-2. 105675-85-2 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Bromide,Amine, name is 4-Bromo-1-methyl-1H-pyrazol-5-amine, and the molecular formula is C10H9ClN2O, Recommanded Product: 4-Bromo-1-methyl-1H-pyrazol-5-amine.

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

Li, Zhaosha published the artcileEffects of pyrazole partial agonists on HCA₂-mediated flushing and VLDL-triglyceride levels in mice, Formula: C7H10N2O2, the publication is British Journal of Pharmacology (2012), 167(4), 818-825, database is CAplus and MEDLINE.

Background and Purpose Niacin can effectively treat dyslipidemic disorders. However, its clin. use is limited due to the cutaneous flushing mediated by the nicotinic acid receptor HCA₂. In the current study, we evaluated two partial agonists for HCA₂, LUF6281 and LUF6283, with respect to their anti-dyslipidemic potential and cutaneous flushing effect. Exptl. Approach In vitro potency and efficacy studies with niacin and the two HCA₂ partial agonists were performed using HEK293T cells stably expressing human HCA₂. Normolipidemic C57BL/6 mice received either niacin or the HCA₂ partial agonists (400 mg·kg^-1·day^-1) once a day for 4 wk for evaluation of their effects in vivo. Key Results Radioligand competitive binding assay showed K_i values for LUF6281 and LUF6283 of 3 and 0.55 μM. [³⁵S]-GTPγS binding revealed the rank order of their potency as niacin > LUF6283 > LUF6281. All three compounds reduced plasma VLDL-triglyceride concentrations similarly, while LUF6281 and LUF6283, in contrast to niacin, did not also exhibit the unwanted flushing side effect in C57BL/6 mice. Niacin reduced the expression of lipolytic genes HSL and ATGL in adipose tissue by 50%, whereas LUF6281 and LUF6283 unexpectedly did not. In contrast, the decrease in VLDL-triglyceride concentration induced by LUF6281 and LUF6283 was associated with a parallel >40% reduced expression of APOB within the liver. Conclusions and Implications The current study identifies LUF6281 and LUF6283, two HCA₂ partial agonists of the pyrazole class, as promising drug candidates to achieve the beneficial lipid lowering effect of niacin without producing the unwanted flushing side effect.

British Journal of Pharmacology 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 C7H10N2O2, Formula: C7H10N2O2.

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

Burca, Ion published the artcile5-((8-Hydroxyquinolin-5-yl)diazenyl)-3-methyl-1H-pyrazole-4-carboxylic acid, HPLC of Formula: 23286-70-6, the publication is Molbank (2021), M1238, database is CAplus.

A new azo compound I was prepared via the azo coupling reaction between 4-(ethoxycarbonyl)-3-methyl-1H-pyrazole-5-diazonium chloride II and 8-hydroxyquinoline (oxine). The ester functional group of the obtained compound I was hydrolyzed and thus a new chem. structure with a carboxylic functional group III was resulted. The structures of the new compounds were fully characterized by: UV-Vis, FT-IR, 1D and 2D NMR spectroscopy, and HRMS spectrometry.

Molbank 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, HPLC of Formula: 23286-70-6.

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

De Ninno, Michael P. published the artcileThe discovery of potent, selective, and orally bioavailable PDE9 inhibitors as potential hypoglycemic agents, Recommanded Product: 3-Isopropyl-1H-pyrazole-5-carboxylic acid, the publication is Bioorganic & Medicinal Chemistry Letters (2009), 19(9), 2537-2541, database is CAplus and MEDLINE.

Starting from a non-selective pyrazolopyrimidone lead, the sequential use of parallel medicinal chem. and directed synthesis led to the discovery of potent, highly selective, and orally bioavailable PDE9 inhibitors. The availability of these tools allowed for a thorough evaluation of the therapeutic potential of PDE9 inhibition.

Bioorganic & Medicinal Chemistry Letters 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 C7H10N2O2, Recommanded Product: 3-Isopropyl-1H-pyrazole-5-carboxylic acid.

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

Kettle, Jason G. published the artcileDiscovery of N-(4-{[5-Fluoro-7-(2-methoxyethoxy)quinazolin-4-yl]amino}phenyl)-2-[4-(propan-2-yl)-1H-1,2,3-triazol-1-yl]acetamide (AZD3229), a Potent Pan-KIT Mutant Inhibitor for the Treatment of Gastrointestinal Stromal Tumors, COA of Formula: C7H10N2O2, the publication is Journal of Medicinal Chemistry (2018), 61(19), 8797-8810, database is CAplus and MEDLINE.

While the treatment of gastrointestinal stromal tumors (GISTs) has been revolutionized by the application of targeted tyrosine kinase inhibitors capable of inhibiting KIT-driven proliferation, diverse mutations to this kinase drive resistance to established therapies. Here we describe the identification of potent pan-KIT mutant kinase inhibitors that can be dosed without being limited by the tolerability issues seen with multitargeted agents. This effort focused on identification and optimization of an existing kinase scaffold through the use of structure-based design. Starting from a series of previously reported phenoxyquinazoline and quinoline based inhibitors of the tyrosine kinase PDGFRα, potency against a diverse panel of mutant KIT driven Ba/F3 cell lines was optimized, with a particular focus on reducing activity against a KDR driven cell model in order to limit the potential for hypertension commonly seen in second and third line GIST therapies. AZD3229 demonstrates potent single digit nM growth inhibition across a broad cell panel, with good margin to KDR-driven effects. Selectivity over KDR can be rationalized predominantly by the interaction of water mols. with the protein and ligand in the active site, and its kinome selectivity is similar to the best of the approved GIST agents. This compound demonstrates excellent cross-species pharmacokinetics, shows strong pharmacodynamic inhibition of target, and is active in several in vivo models of GIST.

Journal of Medicinal Chemistry 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 C7H10N2O2, COA of Formula: C7H10N2O2.

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