Synthesis of Chromone-Related Pyrazole Compounds

Abstract

Chromones, six-membered oxygen heterocycles, and pyrazoles, five-membered two-adjacent-nitrogen-containing heterocycles, represent two important classes of biologically active compounds. Certain derivatives of these scaffolds play an important role in medicinal chemistry and have been extensively used as versatile building blocks in organic synthesis. In this context, we will discuss the most relevant advances on the chemistry that involves both chromone and pyrazole rings. The methods reviewed include the synthesis of chromone-pyrazole dyads, synthesis of chromone-pyrazole-fused compounds, and chromones as starting materials in the synthesis of 3(5)-(2-hydroxyaryl)pyrazoles, among others. This review will cover the literature on the chromone and pyrazole dual chemistry and their outcomes in the 21st century.

Pyrazoles as Key Scaffolds for the Development of Fluorine-18-Labeled Radiotracers for Positron Emission Tomography (PET)

“…Abdel-Maksoud et al have demonstrated antitumoral activity of several compounds with a pyrazole and sulfonamide moieties [19]; antibacterial and antifungal activity of pyrazole was demonstrated by Chowdary et al [20]. Pyrazoles also showed good activity as monoamine oxidase inhibitors, antidepressant and anticonvulsant agents [21], as BRAF inhibitors [22] and DNA gyrase inhibitors [23] and present antileishmanial, anti-inflammatory, analgesic, antidiabetic and cannabinoid activity; cyclin-dependent kinase and tissue-nonspecific alkaline phosphatase inhibitory activity and moderate antihepatotoxic activity, among others [9,11,[24][25][26][27][28][29]. In 2013, Prabhu et.…”

“…Cortivazol(27) and related [ 18 F]arylpyrazolo steroids 28-29 as potential glucocorticoid receptor ligands for PET imaging [54,55]. 2.1.6.…”

“…Cortivazol(27) and related [ 18 F]arylpyrazolo steroids 28-29 as potential glucocorticoid receptor ligands for PET imaging [54,55]. Later, Würst et al used the 2 -(4-fluorophenyl)-21-[ 18 F]fluoro-20-oxo-11β,17α-dihydroxypregn-4-eno[3,2-c]pyrazole (29) (Figure 11) as a ligand for studying brain GRs.…”

Styrylpyrazoles: Properties, Synthesis and Transformations

“…Pyrazole and its derivatives occupy a prime place in medicinal chemistry because they are present in several drugs with real medicinal applications, such as celecoxib (Celebrex ® ), sildenafil (Viagra ® ), rimonabant, lonazolac, fomepizole, penthiopyrad, doramapimod, sulfaphenazole and in several remarkable compounds with a wide range of pharmacological activities, namely anticancer [3], analgesic, anti-inflammatory and antioxidant [4][5][6][7], antibacterial and antifungal [8,9] antipyretic, antidepressant and anticonvulsant [10,11], antidiabetic [12] and cannabinoid activities [13,14], among Pyrazole and its derivatives occupy a prime place in medicinal chemistry because they are present in several drugs with real medicinal applications, such as celecoxib (Celebrex ® ), sildenafil (Viagra ® ), rimonabant, lonazolac, fomepizole, penthiopyrad, doramapimod, sulfaphenazole and in several remarkable compounds with a wide range of pharmacological activities, namely anticancer [3], analgesic, anti-inflammatory and antioxidant [4][5][6][7], antibacterial and antifungal [8,9] antipyretic, antidepressant and anticonvulsant [10,11], antidiabetic [12] and cannabinoid activities [13,14], among others [15][16][17][18][19][20][21]. Along with the medicinal applications, pyrazoles are also useful as agrochemicals, such as herbicides, others [15][16][17][18][19][20]…”

“…Pyrazole and its derivatives occupy a prime place in medicinal chemistry because they are present in several drugs with real medicinal applications, such as celecoxib (Celebrex ® ), sildenafil (Viagra ® ), rimonabant, lonazolac, fomepizole, penthiopyrad, doramapimod, sulfaphenazole and in several remarkable compounds with a wide range of pharmacological activities, namely anticancer [ 3 ], analgesic, anti-inflammatory and antioxidant [ 4 , 5 , 6 , 7 ], antibacterial and antifungal [ 8 , 9 ] antipyretic, antidepressant and anticonvulsant [ 10 , 11 ], antidiabetic [ 12 ] and cannabinoid activities [ 13 , 14 ], among others [ 15 , 16 , 17 , 18 , 19 , 20 , 21 ]. Along with the medicinal applications, pyrazoles are also useful as agrochemicals, such as herbicides, fungicides, and insecticides [ 22 ] and possess other applications, such as dyestuffs, sunscreen materials [ 23 , 24 ], analytical reagents and pluripotent ligands in coordination chemistry [ 25 , 26 ].…”