Facile Synthesis of Pyrazolo[3,4‐c]pyrazoles Bearing Coumarine Ring as Anticancer Agents

Abstract

In the present study, 2‐(2‐oxo‐2H‐chromene‐3‐carbonyl)‐5‐phenyl‐2,4‐dihydro‐3H‐pyrazol‐3‐one was prepared and reacted with various hydrazonoyl halides to give a series of 2‐(2‐oxo‐2H‐chromene‐3‐carbonyl)‐5‐phenyl‐4‐((2‐phenylhydrazono)methyl)‐2,4‐dihydro‐3H‐pyrazol‐3‐one in good yield. Cyclization of the latter hydrazone with POCl3 yielded the respective 3‐(3‐phenyl‐ 4,6‐disubstituted‐1,6‐dihydropyrazolo[3,4‐c]pyrazole‐1‐carbonyl)‐2H‐chromen‐2‐ones. The structures of the newly synthesized compounds were established on the basis of spectroscopic evidences and their alternative syntheses. The newly synthesized compounds were evaluated for their antitumor activities against hepatocellular carcinoma (HepG2) cell line and the results revealed promising activities of compounds 4e, 4c, and 4d with IC50 equal 0.92 ± 0.22, 1.43 ± 0.19, and 2.17 ± 0.21 μM, respectively.

Synthesis, Crystal Structure, Antifungal Activity, and Docking Study of Difluoromethyl Pyrazole Derivatives

“…In the recent years, lots of succinate dehydrogenase inhibitors contain pyrazole motif , such as penthiopyrad, sedaxane, pydiflumetofen, bixafen, isopyrazam, and pyrapropoyne fluxapyroxad. Chemists are very interested in pyrazole because of its unique biological activity, such as antimicrobial , DPPH radical scavenging , anticancer , antifungal , anti‐inflammatory , nematicidal , and cholinesterases inhibitory activities. On the other hand, urea structure also is an important skeleton in bioactive molecules.…”

Fe3O4@SiO2@D‐NHCS‐Tr as an efficient and reusable catalyst for the synthesis of indol‐3‐yl‐4H‐chromene via a multi‐component reaction under solvent‐free conditions

“…Indole is a heterocyclic compound found in many natural buildings and also in the chemical structure of many pharmaceutical and agricultural compounds. 3-Substituted indoles are important structures found in many drugs with properties such as anti-cancer, antitumor, anti-inflammatory, analgesic, and anti-fever [17][18][19][20][21][22][23][24][25][26][27].…”

Access and modulation of substituted 1-methyl-1,6-dihydropyrazolo[3,4-c]pyrazoles

“…Among this group, the pyrazolo [3,4-c]pyrazole nucleus stands out from the little attention it was given, despite previous reports of interesting biologically activities. [3][4][5][6][7] Differences in the distribution of ring electron densities and in spatial orientation between [5:5] bicyclic aromatic rings and their [6:5] and [6:6] analogs could explain these interesting therapeutic effects. 8 The synthesis of this bicyclic scaffold are scarcely found in the literature and are almost exclusively based on an existing pyrazole motif.…”