Tag: M.W=150-200

Cascioferro, Stella published the artcileSynthesis and biofilm formation reduction of pyrazole-4-carboxamide derivatives in some Staphylococcus aureus strains, Recommanded Product: Ethyl 5-amino-3-methyl-1H-pyrazole-4-carboxylate, the publication is European Journal of Medicinal Chemistry (2016), 58-68, database is CAplus and MEDLINE.

The ability of several N-phenyl-1H-pyrazole-4-carboxamide derivatives and other pyrazoles opportunely modified at the positions 3, 4 and 5, to reduce the formation of the biofilm in some Staphylococcus aureus strains (ATCC 29213, ATCC 25923 and ATCC 6538) were investigated. All the tested compounds were able, although to a different extent, to reduce the biofilm formation of the three bacterial strains considered. Among these, the 1-(2,5-dichlorophenyl)-5-methyl-N-phenyl-1H-pyrazole-4-carboxamide 14 resulted as the best inhibitor of biofilm formation showing an IC₅₀ ranging from 2.3 to 32 μM, against all the three strains of S. aureus. Compound 14 also shows a good protective effect in vivo by improving the survival of wax moth larva (Galleria mellonella) infected with S. aureus ATCC 29213. These findings indicate that 14d is a potential lead compound for the development of new anti-virulence agents against S. aureus infections.

European 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, Recommanded Product: Ethyl 5-amino-3-methyl-1H-pyrazole-4-carboxylate.

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

Yu, Lingbo published the artcileSynthesis of 1-alkyl-4-amino-5-pyrazolecarboxylate and ethyl 1-alkyl-5-amino-4-pyrazolecarboxylate, Product Details of C7H11N3O2, the publication is Zhongguo Haiyang Daxue Xuebao, Ziran Kexueban (2006), 36(3), 54-58, database is CAplus.

Synthetic routes to two kinds of substituted pyrazole derivatives were designed based on an anal. of their structural features. The methods for preparing such heterocyclic intermediates, including an N-alkylation reaction condition are researched. The structures of 1-cyclopentyl-4-nitro-5-propyl-1H-pyrazole-3-carboxylic acid Et ester and 1-cyclopentyl-4-nitro-3-propyl-1H-pyrazole-5-carboxylic acid Et ester were identified by HMBC and INEPT NMR techniques.

Zhongguo Haiyang Daxue Xuebao, Ziran Kexueban 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 C15H21BO3, Product Details of C7H11N3O2.

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

Sakai, Holt A. published the artcileCross-Electrophile Coupling of Unactivated Alkyl Chlorides, Recommanded Product: 4-Chloro-1-methyl-1H-pyrazolo[3,4-b]pyridine, the publication is Journal of the American Chemical Society (2020), 142(27), 11691-11697, database is CAplus and MEDLINE.

Overcoming intrinsic limitations of C(sp³)-Cl bond activation, the development of a novel organosilane reagent Si(TMS)₃(N)R¹R² (R¹ = adamantyl, tert-Bu, i-Pr, n-Bu; R² = H) that can participate in chlorine atom abstraction under mild photocatalytic conditions were reported. In particular, the application of this mechanism to a dual nickel/photoredox catalytic protocol that enables the first cross-electrophile coupling of unactivated alkyl chlorides R³Cl (R³ = cyclohexyl, oxan-4-yl, 4-cyanobutyl, etc.) and aryl chlorides R⁴Cl (R⁴ = pyridin-4-yl, quinolin-3-yl, 2-(methylsulfanyl)pyrimidin-5-yl, etc.) was described. Employing these low-toxicity, abundant, and com. available organochloride building blocks, this methodol. allows access to a broad array of highly functionalized C(sp₂)-C(sp₃) coupled adducts, e.g., I including numerous drug analogs.

Journal of the American Chemical Society published new progress about 1268520-92-8. 1268520-92-8 belongs to pyrazoles-derivatives, auxiliary class Other Aromatic Heterocyclic,Chloride, name is 4-Chloro-1-methyl-1H-pyrazolo[3,4-b]pyridine, and the molecular formula is C7H6ClN3, Recommanded Product: 4-Chloro-1-methyl-1H-pyrazolo[3,4-b]pyridine.

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

Saito, Koji published the artcileFormation of pyrazolo[1,5-a]pyrimidine derivatives. II. Reaction of ethyl ethoxymethylenecyanoacetate with its hydrazino derivatives, Computed Properties of 23286-70-6, the publication is Bulletin of the Chemical Society of Japan (1974), 47(2), 476-80, database is CAplus.

The reaction of ethyl ethoxymethylenecyanoacetate with its hydrazino derivative in the presence of pyridine in EtOH at room temperature gave ethyl (4-ethoxycarbonyl-5-aminopyrazol-1-yl)methylenecyanoacetate (I) and two geometric isomers of ethyl (4-ethoxycarbonylpyrazol-5-ylamino)methylenecyanoacetate (II) I under the same conditions rearranged to II. I and II upon heating cyclized exclusively to the same product, diethyl 7-aminopyrazolo[1,5-a]pyrimidine-3,6-dicarboxylate III.

Bulletin of the Chemical Society of Japan 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

Zhang, Qiangsheng published the artcileThe discovery of SKLB-0335 as a paralog-selective EZH2 covalent inhibitor, COA of Formula: C7H11N3O2, the publication is Chemical Communications (Cambridge, United Kingdom) (2021), 57(24), 3006-3009, database is CAplus and MEDLINE.

By targeting the unique Cys663 of EZH2, SKLB-0335 displayed high paralog-selectivity on EZH2. Biochem. studies showed that SKLB-0335 was covalently bind to EZH2 at its S-adenosylmethionine (SAM) pocket and inhibited H3K27Me3. SKLB-0335 was an effective chem. probe with which to further investigate the specific biol. functions of EZH2.

Chemical Communications (Cambridge, United Kingdom) 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 C7H6N2O2S, COA of Formula: C7H11N3O2.

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

Seki, Kunio published the artcileStudies on hypolipidemic agents. II. Synthesis and pharmacological properties of alkylpyrazole derivatives, Application of 3-Isopropyl-1H-pyrazole-5-carboxylic acid, the publication is Chemical & Pharmaceutical Bulletin (1984), 32(4), 1568-77, database is CAplus and MEDLINE.

Claisen condensation of MeCOR (R = C₁-C₁₇ alkyl) with (CO₂Et)₂ gave enolates RCOCH:C(ONa)CO₂Et, which underwent cyclocondensation with R¹NHNH₂[R¹ = H, Me, (CH₂)_nMe, C₆H₄R²-4; R² = H, Me, Cl, OMe, NH₂; n = 7, 9, 11] to give pyrazoles I (R³ = CO₂H, CO₂Et). Reduction of I (same R, R¹ = H, R² = CO₂Et) gave I (R³ = CH₂OH) and hydrolysis of I (R³ = CO₂Et) gave I (R = CO₂H). The latter compounds were chlorinated and amidated to give I [same R, R¹ = H, R³ = CONHR⁴, R⁴ = CH₂CH₂OH, CH₂CO₂Et, CH(CHMeEt)CO₂Et, H, Bu, decyl]. These pyrazoles (46 compounds) were evaluated for hypolipidemic activity in rats. Homologation of the C-5 alkyl chain led to marked increase in activity, but introduction of other substituents at other sites on the pyrazole ring failed to enhance the activity. The replacement of the pyrazole ring with an isoxazole ring resulted in a marked decrease in activity. I (R = tridecyl, R¹ = H, R² = CO₂H) was as effective as clofibrate in lowering serum triglycerides and cholesterol in rats and showed fairly low toxicity with LD₅₀ = 10.0 g/kg orally in mice.

Chemical & Pharmaceutical Bulletin 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 C48H47FeP, Application of 3-Isopropyl-1H-pyrazole-5-carboxylic acid.

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

Ege, Guenter published the artcileReactions with diazoazoles. Part VI. Unequivocal synthesis of 3-methyl-3H-azolotetrazoles. Correction of the formerly described 3-methylazolotetrazoles in favor of mesoionic 2-methylazolotetrazoles, Recommanded Product: Ethyl 5-amino-3-methyl-1H-pyrazole-4-carboxylate, the publication is Journal of Heterocyclic Chemistry (1983), 20(6), 1629-39, database is CAplus.

3-Methyl-3H-pyrazolo[1,5-d]tetrazoles I (X = CR¹; R = H, R¹ = H, Ph; R = Me, R¹ = CO₂Et) and 3-methyl-6-phenyl-3H-1,2,4-triazolo[1,5-d]tetrazole (I, X = N, R = Ph) have been unequivocally synthesized by annulation of the tetrazole moiety to the pyrazole or 1,2,4-triazole system. The constitution of some N-Me substituted azolotetrazoles, formerly described as I (X = CH, R = Ph; X = CMe, R = CO₂Et; X = N, R = Ph) and 1-methyl-6-phenyl-1H-1,2,4-triazolo[4,3-d]tetrazole, has to be revised to the corresponding mesoionic 2-Me derivatives The structures of I (X = CH, R = Ph; X = CMe R = CO₂Et) and 2-methyl-7-phenyl-2H-pyrazolo[1,5-d]tetrazole have been determined by x-ray analyses. The azapentalenic system is aromatic in all 3 compounds and mesoionic in the case of the 2-methyl-2H-substitution pattern. The Ph and ester substituents are coplanar with the azapentalene system. 3-, 2-, And 1-methylpyrazolo[1,5-d]tetrazoles exhibit different behavior with SnCl₂ or NaOEt. Azolotetrazoles with a Me substituent at N-1, N-2 or N-3 of the tetrazole moiety can be distinguished by a combination of ¹H and ¹³C NMR with respect to the chem. shifts of the N-Me group and the bridgehead C. Results of semiempirical calculations of the pyrazolo[1,5-d]tetrazole anion and of its N-Me derivatives are discussed.

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, Recommanded Product: Ethyl 5-amino-3-methyl-1H-pyrazole-4-carboxylate.

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

Baba, Hideo published the artcileReactions of 伪-cyano-尾-methoxy-尾-alkylacrylic esters with hydrazine and hydroxylamine, Recommanded Product: Ethyl 5-amino-3-methyl-1H-pyrazole-4-carboxylate, the publication is Bulletin of the Chemical Society of Japan (1969), 42(6), 1653-9, database is CAplus.

伪-Cyano-尾-methoxy-尾-alkyl (Me, Et, Pr, Bu, amyl, and iso-Bu) acrylic esters (I) react with hydrazine to give 尾-hydrazino intermediates. The hydrazino group of these intermediates is cyclized preferentially between its terminal NH2 and the cyano group in a neutral or acidic medium to give 5-aminopyrazole derivatives and preferentially between the terminal NH2 and the ester group in the presence of a base to give 5-pyrazolinone derivatives When the 尾-alkyl group of I is isopropyl, tertbutyl, etc., I affords only the 5-pyrazolinone derivatives in the reaction with hydrazine. The reactions of I with hydroxylamine gave 5-aminoisoxazole derivatives, but in the case of the 尾-tert-butyl derivative of I, they gave 5-aminoisoxazole accompanied by the 5-isoxazolinone derivative

Bulletin of the Chemical Society of Japan 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, Recommanded Product: Ethyl 5-amino-3-methyl-1H-pyrazole-4-carboxylate.

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

Vicentini, C. B. published the artcilePotential of pyrazolooxadiazinone derivatives as serine protease inhibitors, Recommanded Product: Ethyl 5-amino-3-methyl-1H-pyrazole-4-carboxylate, the publication is Journal of Enzyme Inhibition (2001), 16(1), 15-34, database is CAplus and MEDLINE.

As a part of an investigation on mol. hybrids as new serine protease inhibitors, the pyrazolo [4,3-c][1,2,5]oxadiazin-3(5H)-one ring system was selected as a model of potential mechanism-based inhibitors. Due to the inherent reactivity of this system an optimal balance between susceptibility to nucleophilic attack and stability in solvents was sought prior to development as therapeutic agents. Substitutions on N5 and C7 of the supporting pyrazole ring with either aliphatic or aromatic groups and the replacement of the carbonyl oxygen on the reactive oxadiazinone ring with sulfur were explored. Two members of this class of inhibitors displayed time-dependent inhibition of human leukocyte elastase (HLE) suggesting mechanism-based inhibition. The observation that HLE generated a product(s) which displayed an identical UV-Visible spectrum to that observed during non-enzymic hydrolysis further supports this proposal. FlexX-based docking of these compounds into a model of HLE active site produced a mol. model of the inhibitor-enzyme interaction.

Journal of Enzyme Inhibition 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 C11H13N3, Recommanded Product: Ethyl 5-amino-3-methyl-1H-pyrazole-4-carboxylate.

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

Qian, Yimin published the artcileDiscovery of Highly Selective and Orally Active Lysophosphatidic Acid Receptor-1 Antagonists with Potent Activity on Human Lung Fibroblasts, Related Products of pyrazoles-derivatives, the publication is Journal of Medicinal Chemistry (2012), 55(17), 7920-7939, database is CAplus and MEDLINE.

Lysophosphatidic acid is a class of bioactive phospholipid that mediates most of its biol. effects through LPA receptors, of which six isoforms have been identified. The recent results from LPA1 knockout mice suggested that blocking LPA1 signaling could provide a potential novel approach for the treatment of idiopathic pulmonary fibrosis. Here, we report the design and synthesis of pyrazole- and triazole-derived carbamates as LPA1-selective and LPA1/3 dual antagonists. In particular, compound I, the most selective LPA1 antagonist reported, inhibited proliferation and contraction of normal human lung fibroblasts (NHLF) following LPA stimulation. Oral dosing of compound I to mice resulted in a dose-dependent reduction of plasma histamine levels in a murine LPA challenge model. Furthermore, we applied our novel antagonists as chem. probes and investigated the contribution of LPA1/2/3 in mediating the pro-fibrotic responses. Our results suggest LPA1 as the major receptor subtype mediating LPA-induced proliferation and contraction of NHLF.

Journal of 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 C4H6BrN3, Related Products of pyrazoles-derivatives.

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