Methods for the synthesis of 1H-pyrazolo[3,4-b]pyridine derivatives

Smolobochkin, Аndrey V.; Газизов, А. С.; Garifzyanov, A. R.; Бурилов, А. Р.; Пудовик, М. А.

doi:10.1007/s11172-022-3487-1

Cited by 7 publications

(12 citation statements)

References 49 publications

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“…Upon a literature search for the optimum way to accomplish the synthesis of pyrazolo[3,4-b]pyridines [ 24 , 25 ], we have decided to prepare the target compounds by using commercial phenylhydrazine ( 1a ) or 3-fluorophenylhydrazine ( 1b ) as starting materials ( Scheme 1 ). Each hydrazine was converted to the corresponding pyrazole-4-carbonitriles ( 2a , b ) [ 26 , 27 ], and then, upon hydrolysis and subsequent decarboxylation, converted to the pyrazoles 3a , b following a previously reported methodology [ 20 , 28 ].…”

Section: Resultsmentioning

confidence: 99%

Discovery of New 1,4,6-Trisubstituted-1H-pyrazolo[3,4-b]pyridines with Anti-Tumor Efficacy in Mouse Model of Breast Cancer

et al. 2023

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Purine analogues are important therapeutic tools due to their affinity to enzymes or receptors that are involved in critical biological processes. In this study, new 1,4,6-trisubstituted pyrazolo[3,4-b]pyridines were designed and synthesized, and their cytotoxic potential was been studied. The new derivatives were prepared through suitable arylhydrazines, and upon successive conversion first to aminopyrazoles, they were converted then to 1,6-disubstituted pyrazolo[3,4-b]pyridine-4-ones; this served as the starting point for the synthesis of the target compounds. The cytotoxic activity of the derivatives was evaluated against several human and murine cancer cell lines. Substantial structure activity relationships (SARs) could be extracted, mainly concerning the 4-alkylaminoethyl ethers, which showed potent in vitro antiproliferative activity in the low μM level (0.75–4.15 μΜ) without affecting the proliferation of normal cells. The most potent analogues underwent in vivo evaluation and were found to inhibit tumor growth in vivo in an orthotopic breast cancer mouse model. The novel compounds exhibited no systemic toxicity; they affected only the implanted tumors and did not interfere with the immune system of the animals. Our results revealed a very potent novel compound which could be an ideal lead for the discovery of promising anti-tumor agents, and could also be further explored for combination treatments with immunotherapeutic drugs.

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Section: Resultsmentioning

confidence: 99%

Discovery of New 1,4,6-Trisubstituted-1H-pyrazolo[3,4-b]pyridines with Anti-Tumor Efficacy in Mouse Model of Breast Cancer

et al. 2023

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“…The structure of the obtained compound 5a was confirmed by 2D NMR spectroscopy data (Figure 2). The NMR signals were assigned on the basis of 1 H, 13 Supporting Information). The presence of the fused pyrrolidine ring is supported by the cross-peak between methyne protons H-C7 and H-C6 and C10 carbon atom in the HMBC ( 1 H-13 C) spectrum.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…The 1 H and 13 C NMR spectra were recorded on a Bruker Avance 600 spectrometer at operating frequency (600 MHz and 150 MHz, respectively) with respect to the residual proton signals of deuterated solvents (DMSO-d 6 , CD 3 OD, CDCl 3 ). The 19 F NMR spectra were recorded on a Bruker Avance III HD 700 (658.71 MHz) spectrometer at room temperature, and chemical shifts are given in ppm relative to CFCl 3 .…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…1 H NMR (DMSO-d 6 , 600 MHz): δ 8.93 (s, 1H), 7.64 (s, 1H), 7.57 (d, 2H, J = 8.2 Hz), 7.33 (d, 2H, J = 8.2 Hz), 4.35−4.18 (m, 2H), 3.21−3.08 (m, 2H), 2.64 (q, 2H, J = 7.6 Hz), 1.20 (t, 3H, J = 7.6 Hz). 13 C{ 1 H} NMR (DMSO-d 6 , 150 MHz): δ 159.4 (q, J = 32. 2 Hz),173.7,148.2,142.1,138.7,133.0,131.6,129.6,117.8 (q,J = 297.8 Hz),55.6,29.1,27.1,16.1.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…Due to the wide application in medical practice, a sufficient number of the methods for the synthesis of pyrazolopyridines was developed. , A multicomponent reaction of ketone with a free α-methylene group, aminopyrazole, and usually aromatic aldehyde is a widespread method. The first stage of reaction is the Knoevenagel reaction of aldehyde with ketone, while the formed adduct reacts with pyrazole-5-amine to afford pyrazolopyridine (Scheme a).…”

Section: Introductionmentioning

confidence: 99%

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One-Step Synthesis of Functionalized Pyrazolo[3,4-b]pyridines via Ring Opening of the Pyrrolinium Ion

et al. 2023

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Herein, we report a highly regioselective one-pot synthesis of pyrazolo [3,4-b]pyridines via the reaction of 3-arylidene-1-pyrrolines with aminopyrazoles. The reaction proceeds through the sequential nucleophilic addition/electrophilic substitution/C−N bond cleavage and provides easy access to pyrazolo[3,4-b]pyridine derivatives featuring a primary amino group. Moreover, the reaction can be terminated at the electrophilic substitution stage, thus providing convenient entry to the hardly accessible pyrazolopyrrolopyridine scaffold.

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Intramolecular reductive Heck reaction in the synthesis of 3,3-disubstituted isoindolin-1-ones

Ashatkina,

Reznikov,

Vostrukhina

et al. 2023

Russ Chem Bull

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Methods for the synthesis of 1H-pyrazolo[3,4-b]pyridine derivatives

Cited by 7 publications

References 49 publications

Discovery of New 1,4,6-Trisubstituted-1H-pyrazolo[3,4-b]pyridines with Anti-Tumor Efficacy in Mouse Model of Breast Cancer

Discovery of New 1,4,6-Trisubstituted-1H-pyrazolo[3,4-b]pyridines with Anti-Tumor Efficacy in Mouse Model of Breast Cancer

One-Step Synthesis of Functionalized Pyrazolo[3,4-b]pyridines via Ring Opening of the Pyrrolinium Ion

Intramolecular reductive Heck reaction in the synthesis of 3,3-disubstituted isoindolin-1-ones

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