Category: 23286-70-6

Guccione, Salvatore published the artcileSynthesis of 3-methyl-substituted pyrazolotriazolopyrimidin-4-one and pyrazolothiazolopyrimidin-4-one derivatives, SDS of cas: 23286-70-6, the publication is Journal of Heterocyclic Chemistry (1996), 33(2), 459-463, database is CAplus.

As a part of a research on anti-inflammatory analgesic compounds 3-Me substituted pyrazolotriazolopyrimidin-4-one derivatives (R = Ph, 4-chlorophenyl) and pyrazolothiazolopyrimidin-4-one derivatives II (R¹ = H, Br) were prepared by previously reported procedures. None of the compounds showed improved activity when compared with the previously reported unsubstituted analogs.

Journal of Heterocyclic 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

Mikami, Satoshi published the artcileDiscovery of an Orally Bioavailable, Brain-Penetrating, in Vivo Active Phosphodiesterase 2A Inhibitor Lead Series for the Treatment of Cognitive Disorders, Application In Synthesis of 23286-70-6, the publication is Journal of Medicinal Chemistry (2017), 60(18), 7658-7676, database is CAplus and MEDLINE.

Herein, the authors describe the discovery of a potent, selective, brain-penetrating, in vivo active phosphodiesterase (PDE) 2A inhibitor lead series. To identify high-quality leads suitable for optimization and enable validation of the physiol. function of PDE2A in vivo, structural modifications of the high-throughput screening hit were performed. The lead generation efforts revealed three key potency-enhancing functionalities with minimal increases in mol. weight (MW) and no change in topol. polar surface area (TPSA). Combining these structural elements led to the identification of 6-methyl-N-((1R)-1-(4-(trifluoromethoxy)phenyl)propyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (38a), a mol. with the desired balance of preclin. properties. Further characterization by cocrystal structure anal. of (38a) bound to PDE2A uncovered a unique binding mode and provided insights into its observed potency and PDE selectivity. Compound (38a) significantly elevated 3′,5′-cGMP levels in mouse brain following oral administration, thus validating this compound as a useful pharmacol. tool and an attractive lead for future optimization.

Journal of Medicinal 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, Application In Synthesis of 23286-70-6.

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

Gharbi, Rafik published the artcileA convenient synthesis of a novel fused tetracyclic heterocoumarin, Application of Ethyl 5-amino-3-methyl-1H-pyrazole-4-carboxylate, the publication is Journal of Heterocyclic Chemistry (2005), 42(1), 169-172, database is CAplus.

New tetracyclic 6H-[1]benzopyrano[3,4-e]pyrazolo[1,5-a]pyrimidin-6-ones (I, R¹ = H, Me, Et; R² = CN, CO₂Et) have been synthesized through the condensation under acidic conditions of [1]benzopyrano[4,3-c][1,5]benzodiazepin-7(8H)-one (II) and a series of 3,4-disubstituted 5-amino-1H-pyrazoles (III).

Journal of Heterocyclic 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, Application of Ethyl 5-amino-3-methyl-1H-pyrazole-4-carboxylate.

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

Daidone, G. published the artcileNew N-pyrazolyl salicylamides with antifungal activity, Category: pyrazoles-derivatives, the publication is Farmaco, Edizione Scientifica (1985), 40(9), 683-94, database is CAplus and MEDLINE.

Nine pyrazolyl salicylamides I [R = H or Ph; R¹ and R³ = H or Me; R² = H, Ph, CN, or CO₂Et; R¹R² = (CH₂)₄], as well as II (R = R¹ = R⁴ = H, R² = CO₂Et) [98817-30-2], II (R = R⁴ = H, R² = Me, R³ = CO₂Et) [98817-31-3], II (R = H) [98817-32-4], and (R = Me) [98817-33-5], were prepared and tested in vitro against Cryptococcus neoformans and Candida albicans. All compounds, with the exception of I (R = Ph, R¹ = R² = H, R³ = Me) [98817-34-6], were active. I (R = Ph, R¹ = Me, R² = R³ = H) [70803-10-0] was the most active.

Farmaco, Edizione Scientifica 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

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

Beyer, Hans published the artcileThiazoles. XXIX. The condensation products of thiosemicarbazide with ethyl α-chloroacetoacetate and a novel ring contraction of 2-amino-5-methyl-6-carbethoxy-1,3,4-thiadiazine to 3-methyl-4-carbethoxy-5-aminopyrazole, Synthetic Route of 23286-70-6, the publication is Chemische Berichte (1956), 1652-8, database is CAplus.

On condensation of AcCHClCO₂Et (I) with H₂NNHCSNH₂ (II), 4-methyl-5-carbethoxy-2-thiazolylhydrazine (III), MeC(:NNHCSNH₂)CHClCO₂Et (IV), or 3-amino-4-methyl-5-carbethoxy-2-thiazolone imide (V) is formed, depending upon the pH and temperature Refluxing 13.3 g. 1-acetylthiosemicarbazide and 8.5 g. NaOAc in 75 cc. absolute EtOH in a CO₂ atm., adding dropwise within 15 min. 16.5 g. I in 25 cc. absolute EtOH, and refluxing the mixture another hr. yield 96% N’-acetyl-N-(4-methyl-5-carbethoxy-2-thiazolyl)hydrazine (VI), fine needles, m. 227°, which (12.2 g.), refluxed in 75 cc. absolute EtOH 1 hr. with 5.3 cc. concentrated HCl, gives 88% III.HCl, needles, m. 189-90°. III.HCl is also formed in 80% yield when 4.1 g. I in 3 cc. EtOH is added (15 min.) to 2.28 g. II in 20 cc. EtOH at 50° (free III, liberated with NaOAc, 100%, leaflets, m. 186°; di-Ac derivative, prepared by heating 2.01 g. III or 2.43 g. VI with 15 cc. Ac₂O 20 min. on a water bath, 84%, needles, m. 198°; tri-Ac derivative, prepared by heating 2.01 g. III 15 min. in 10 cc. Ac₂O containing 5 drops concentrated H₂SO₄, prisms, m. 131°; monoformyl derivative, prepared by refluxing 2.01 g. III 1 hr. with 10 cc. 98% HCO₂H, 92%, fine needles, m. 205°). Boiling 2.01 g. III 15 min. in 25 cc. Me₂CO yields 92% acetone (4-methyl-5-carbethoxy-2-thiazolyl)hydrazone, silky needles, m. 143°; PhCOMe derivative, 95%, m. 118°. Adding dropwise (1 hr.) 16.4 g. I to 9.1 g. II in 50 cc. 2N HCl at 0° yields 100% IV, also formed in 78% yield by mixing the 2 reagents in alc. solution without HCl; IV decompose on storage. Adding at 70° 9.5 g. IV to 60 cc. PrOH and bringing the mixture quickly to the boil give 74% 2-amino-5-methyl-6-carbethoxy-1,3,4-thiadiazine-HCl, decompose about 90° [free base (VII), liberated with saturated NaOAc solution, fine yellow needles, decompose above 80°; after 2-3 days it decompose with the formation of 3-methyl-4-carbethoxy-5-aminopyrazole (VIII)]. Heating VII or IV with the calculated amount of p-O₂NC₆H₄CHO (IX) in EtOH yields 40% IX (4-methyl-5-carbethoxy-2-thiazolyl)hydrazone, yellow needles, m. 244°; BzH analog, pale yellow leaflets, m. 189°, is prepared by treating III.HCl in 2N HCl with BzH and NaOAc, or in 93% yield by condensation of equimolar amounts of III and BzH. Heating 7.2 g. VII.HCl in 50 cc. concentrated HCl 15-20 min. on a water bath and concentrating the filtered solution to 1/3 its volume yield 66% V.HCl, fine needles, m. 242-4° (decomposition), which is also formed in 43% yield when 8.2 g. I is added to 4.6 g. II in 30 cc. hot concentrated HCl and the solution concentrated to 0.5 its volume (free V, needles, m. 130°; di-Ac derivative, prisms, m. 107-8°). Adding 1.28 g. NaNO₂ in H₂O to 2.4 g. V.HCl in 25 cc. 2N HCl at 0° and pouring the ice-cooled solution into 1.2 g. PhNMe₂ in dilute HCl give 2-(p-dimethylaminophenylazo)-4-methyl-5-carbethoxythiazole (X).HCl, deep blue crystals, from which NH₄OH liberates the free X, red-brown leaflets, m. 205°; X is also obtained in 43% yield when 3.7 g. 2-amino-4-methyl-5-carbethoxythiazole is diazotized at 0° and the diazonium solution is treated with 2.4 g. PhNMe₂. Refluxing 9.5 g. VII.HCl 1 hr. in 50 cc. 2N alc. HCl and filtering off the S formed yield 80% VIII.HCl, m. 187-9° [free base, leaflets containing 1 mole H₂O, m. 69°, m. 113° (H₂O-free); nitrate, prisms, m. 197-8° (decomposition); mono-Ac derivative, prisms, m. 91°]. Treating 4.1 g. VIII.HCl in 15 cc. H₂O and 3 cc. concentrated HCl at 0° with 1.38 g. NaNO₂ in 7 cc. H₂O, pouring the diazonium solution into ice cold 30% H₃PO₂, keeping the mixture overnight at 0°, and adding saturated NaOAc solution give 3-methyl-4-carbethoxypyrazole-H₂O, m. 46° (HCl salt, needles, sinters 145°, m. 160°). Diazotizing 2.5 g. VIII.HCl, adding the diazonium solution to 1.2 g. PhNMe₂ in dilute HCl, and then adding NaOAc give 70% 3-methyl-4-carbethoxy-5-(p-dimethylaminophenylazo)pyrazole, stout orange prisms, m. 172°.

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, Synthetic Route of 23286-70-6.

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

Lu, Xiaoyun published the artcileDiscovery of new chemical entities as potential leads against Mycobacterium tuberculosis, Product Details of C7H11N3O2, the publication is Bioorganic & Medicinal Chemistry Letters (2016), 26(24), 5916-5919, database is CAplus and MEDLINE.

A series of biheterocyclic (1H-indole, benzofuran, pyrazolo[1,5-a]pyrimidine, pyrazolo[1,5-a]pyrimidin-5(4H)-one, imidazo[2,1-b]thiazole, and pyrazolo[5,1-b]thiazole) derivatives were synthesized and evaluated for their anti-tubercular activities. The imidazo[2,1-b]thiazoles and pyrazolo[5,1-b]thiazoles exhibited promising anti-tubercular activity in varying degrees. Especially, the 2,6-dimethylpyrazolo[5,1-b]thiazole exhibited strong suppressing function against H37Ra strain with MIC value of 0.03 μg/mL. This compound also displayed good pharmacokinetic profiles with oral bioavailability (F) of 41.7% and a half-life of 13.4 h. Furthermore, this compound significantly reduced the bacterial burden in an autoluminescent H37Ra infected mouse model, suggesting its promising potential for development of anti-tubercular drugs.

Bioorganic & Medicinal Chemistry Letters 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, Product Details of C7H11N3O2.

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

Bercean, Vasile-Nicolae published the artcileAzo compounds derived from 1H-5-amino-4-ethoxycarbonyl-3-methyl-pyrazole and phenols or phenolic derivatives and possibilities of their cyclization to pyrazolo[5,1-c]benzo[1,2-e][1,2,4]triazines, Computed Properties of 23286-70-6, the publication is Revista de Chimie (Bucharest, Romania) (2011), 62(2), 154-157, database is CAplus.

The coupling reaction of 1H-4-ethoxycarbonyl-3-methylpyrazol-5-yldiazonium chloride with phenols and phenolic derivatives led to 1H-5-arylazo-4-ethoxycarbonyl-3-methylpyrazoles. Cyclization of one of the latter compounds, [1H-4-ethoxycarbonyl-5-(4,6-dimethoxy-2-hydroxyphenylazo)-3-methylpyrazole] gave the corresponding pyrazolo[5,1-c]benzo[1,2-e][1,2,4]triazine.

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, Computed Properties of 23286-70-6.

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

Bercean, Vasile-Nicolae published the artcileNew azo compounds derived from 1H-5-amino-4-ethoxycarbonyl-3-methyl-pyrazole and 3-mono- or 1,3-disubstituted pyrazol-5-ones, Synthetic Route of 23286-70-6, the publication is Revista de Chimie (Bucharest, Romania) (2010), 61(4), 364-367, database is CAplus.

Pyrazole-derived azo compounds were designed, and the synthesis of the target compounds was achieved by a coupling reaction of 3-amino-5-methyl-1H-pyrazole-4-carboxylic acid Et ester (I) with pyrazolone derivatives The products thus obtained were confirmed by MS, IR, UV-VIS, ¹H-NMR, and ¹³C-NMR, and existed in multiple tautomeric forms.

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, Synthetic Route of 23286-70-6.

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

Gavrilenko, B. B. published the artcileReaction of enamines with hydrazine, Safety of Ethyl 5-amino-3-methyl-1H-pyrazole-4-carboxylate, the publication is Zhurnal Organicheskoi Khimii (1974), 10(3), 601-4, database is CAplus.

RR1C:C(NH2)NHNH2 (I; R = CO2Me, CO2Et, CO2Pr, CO2Ph, R1 = CO2Me, CO2Et, CN) were obtained in 78-90% yields by boiling RR1C:C(CCl3)NH2 on a water bath 3-5 min. Pyrazoles (II; R1 = CO2Et, CO2Pr, CO2Ph) were obtained in 80-95% yields by cyclization of the appropriate I (R = CN) in DMF containing N2H4.H2O. Analogous obtained were 70-98% pyrazoles (III; R1 = H, CO2Et,R3 = Me). Acylaminopyrazoles (IV; R1 = H, CO2Et, CO2Pr,R3 = Me, Ph, NH2, AcNH) were addnl. obtained in 78-96% yields.

Zhurnal Organicheskoi Khimii 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, Safety of Ethyl 5-amino-3-methyl-1H-pyrazole-4-carboxylate.

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