3,5-Diaryl-1H-pyrazolo[3,4-b]pyridines as potent tubulin polymerization inhibitors: Rational design, synthesis and biological evaluation

“On Water” Palladium Catalyzed Direct Arylation of 1H-Indazole and 1H-7-Azaindazole

“…After succeeding in developing a “greener” pathway to synthesize C3-arylated 1 H -indazole, we extended the methodology to prepare C3-arylated pyrazolo[3,4- b ]pyridine, also known as azaindazole, which is an 1 H -indazole isostere and is often used as a key pharmacophore in drug design [ 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 54 , 55 , 56 , 57 ]. Despite the enormous biological interest of C3-arylated pyrazolo [3,4- b ]pyridines, only one work has been reported by Lavard and Popowycz [ 38 ], addressing the functionalization of this motif via direct arylation.…”

“…Although this reported method is efficient, it is relatively energywasting, using heating at 160 °C for a long period of 3 days and organic solvent. For this reason, we decided to test our conditions developed to prepare C3-arylated pyrazolo[3,4-b]pyridine using the After succeeding in developing a "greener" pathway to synthesize C3-arylated 1H-indazole, we extended the methodology to prepare C3-arylated pyrazolo [3,4-b]pyridine, also known as azaindazole, which is an 1H-indazole isostere and is often used as a key pharmacophore in drug design [42][43][44][45][46][47][48][49][50][51][52][53][54][55][56][57]. Despite the enormous biological interest of C3-arylated pyrazolo [3,4- one work has been reported by Lavard and Popowycz [38], addressing the functionalization of this motif via direct arylation.…”

Crystal structure analysis of ethyl 6-(4-methoxyphenyl)-1-methyl-4-methylsulfanyl-3-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

“…Among pyrazolopyridines, pyrazolo [3,4-b]pyridines are medicinally important because of the ease of combinatorial library synthesis, adherence to the Lipinski rule and favourable ADMET properties. (Chauhan & Kumar, 2013;Zhai et al, 2019). Based on the importance of pyrazolo[3,4-b]pyridinecontaining molecules, we have undertaken a single-crystal X-ray diffraction study of the title compound.…”

Modular Synthesis and Antiproliferative Activity of New Dihydro-1H-pyrazolo[1,3-b]pyridine Embelin Derivatives

“…Pyrazoles are very attractive nitrogenated scaffolds since molecules having pyrazoles fused to other heterocycles such as dihydro-1 H -pyrazolo[1,3- b ]pyridines and pyrazolo[3,4- b ]pyridines have raised great interest due to the biological activities that they exhibit. Figure 1 shows some examples of antitumoral compounds that exhibit this type of structure such as spirooxindoles ( A ) with cytotoxic activity against triple-negative breast cancer MDA-MB-231 cell line [ 7 ], compound ( B ) with potent and selective inhibitory activity against FGFR kinase [ 8 ] and compound ( C ) as potent tubulin polymerization inhibition [ 9 ].…”