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