19743-76-1

Usage

Molecular structure

1H-Pyrazolo[3,4-b]pyridine-5-carboxylic acid, 4-chloro-1-phenyl-, ethyl ester is a heterocyclic compound that contains a pyrazolo[3,4-b]pyridine ring with a 4-chloro-1-phenyl group and an ethyl ester functional group attached to it.

Molecular weight

330.76 g/mol

Appearance

It is likely a solid with a specific color that can vary depending on the synthesis method and purity.

Solubility

It may be soluble in common organic solvents such as DMSO, methanol, or ethanol, but its solubility can vary depending on the specific conditions.

Stability

The compound may be stable under standard temperature and pressure conditions, but it may be sensitive to light, heat, or moisture.

Biological activity

As a derivative of pyrazolo[3,4-b]pyridine, 1H-Pyrazolo[3,4-b]pyridine-5-carboxylic acid, 4-chloro-1-phenyl-, ethyl ester may exhibit potential biological and pharmacological activities. Its 4-chloro-1-phenyl group and ethyl ester functional group may contribute to its interactions with biological targets.

Applications

The compound may be used in drug discovery and development, as well as in the study of organic chemistry and chemical biology.

Synthesis

The synthesis of 1H-Pyrazolo[3,4-b]pyridine-5-carboxylic acid, 4-chloro-1-phenyl-, ethyl ester may involve various chemical reactions and techniques, including the formation of the pyrazolo[3,4-b]pyridine ring and the attachment of the 4-chloro-1-phenyl and ethyl ester groups.

Safety

As with any chemical compound, appropriate safety precautions should be taken when handling 1H-Pyrazolo[3,4-b]pyridine-5-carboxylic acid, 4-chloro-1-phenyl-, ethyl ester, including the use of personal protective equipment and proper disposal of waste materials.

Upstream product

• 54844-13-2 carbethoxy-5 dihydro-3,6 oxo-6 phenyl-2 pyrazolo <2,4-b> pyridine 
• 62-53-3 aniline 
• 826-85-7 1-phenylpyrazol-5-amine 
• 37555-99-0 diethyl ethoxymalonate 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 19743-75-0 4-oxo-1-phenyl-4,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester 
• 37799-81-8 diethyl{[(1-phenyl-5-pyrazolyl)-amino]methylene} malonate 

Downstream Products

• 1031442-95-1 ethyl 4-[(4-methylpyridin-2-yl)amino]-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate 
• 1031442-85-9 ethyl 4-(3'-fluorophenylamino)-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate 
• 1031442-82-6 ethyl 4-(3'-methoxyphenylamino)-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate 
• 1031442-80-4 ethyl 4-(4'-chlorophenylamino)-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate 
• 1031442-73-5 ethyl 4-(4'-nitrophenylamino)-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate 
• 1031442-78-0 ethyl 4-(3'-methylphenylamino)-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate 
• 1031442-72-4 ethyl 4-(3'-nitrophenylamino)-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate 
• 1031442-98-4 4-[(4-methylpyridin-2-yl)amino]-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid 

Relevant academic research and scientific papers

Deciphering the robustness of pyrazolo-pyridine carboxylate core structure-based compounds for inhibiting α-synuclein in transgenic C. elegans model of Synucleinopathy

Parkinson's disease (PD), a calamitous neurodegenerative disorder with no cure till date, is closely allied with the misfolding and aggregation of α-Synuclein (α -Syn). Inhibition of α-Syn aggregation is one of the optimistic approaches for the treatment for PD. Here, we carried out hypothesis-driven studies towards synthesising a series of pyrazolo-pyridine carboxylate containing compounds (7a–7m) targeted at reducing deleterious α-Syn aggregation. The target compounds were synthesized through multi-step organic synthesis reactions. From docking studies, compounds 7b, 7g and 7i displayed better interaction with the key residues of α-Syn with values: ?6.8, ?8.9 and ?7.2 Kcal/mol, respectively. In vivo transgenic C. elegans model of Synucleinopathy was used to evaluate the ability of the designed and synthesized compounds to inhibit α-Syn aggregation. These lead compounds 7b, 7g and 7i displayed 1.7, 2.4 and 1.5-fold inhibition of α-Syn with respect to the control. Further, the strategy of employing pyrazolo-pyridine-based compounds worked with success and these scaffolds could be further modified and validated for betterment of endpoints associated with PD.

Synthesis of new conjugates 1H-Pyrazolo[3,4-b]pyridine-phosphoramidate and evaluation against leishmania amazonensis

In this research three series of substituted 1H-pyrazolo[3,4-b]pyridine phosphoramidates were synthesized and characterized by infrared,1H,13C, and31P nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectrometry. The products were obtained in good yields (67-83percent) under mild conditions by nucleophilic aromatic substitution reaction of aminoalkylphosphoramidates over 4-chloro-1H-pyrazolo[3,4-b]pyridines. These compounds were evaluated as antileishmanials against Leishmania amazonensis promastigotes in vitro. Among all, compounds of a series showed expressive antileishmanial activity. Two of them emerged as the most active, with IC50 values of 6.44 ± 1.49 and 12.25 ± 0.68 μM. The cytotoxicity of this series was assessed on murine cells and presented values similar to the reference drug pentamidine.

Mass spectrometry of pyrazolo[3,4-b]pyrido[2′,3′-b]-1,6-naphthyridines and dipyrazolo[3,4-b];3′,4′-h]-1,6-naphthyridines

The mass spectra of several pyrazolo[3,4-b]pyrido[2′,3′-b]-1,6-naphthyridines and dipyrazolo[3,4-b];3′,4′-h]-1,6-naphthyridines are presented. The fragmentation is initiated by the elimination of CO molecule [m/z 28] followed by other fragments, such as h

Mass spectrometry of heterocyclic compounds: Benzo[b]pyrazolo[3,4-b]-1,6-naphthyridines

The mass spectra of a number of benzo[b]pyrazolo[3,4-b]-1,6-naphthyridines are presented. The fragmentation involves elimination of CO molecule followed by other fragments, such as halogen (Cl, Br) or halogen acids (HCl, HBr) and HCN, etc.

Design, synthesis and anti-P. falciparum activity of pyrazolopyridine–sulfonamide derivatives

Ten 1-phenyl-1H-pyrazolo[3,4-b]pyridine derivatives connected by a linker group to benzenesulfonamide moieties with different substituents in the 4-position were synthesized and assayed against Plasmodium falciparum. These ten compounds exhibited activity in vitro against the chloroquine-resistant clone W2 with IC50values ranging from 3.46 to 9.30 μM. The most active derivatives with substituent R2= Cl or CH3at the benzenesulfonamide moiety exhibited the lowest IC50. Compounds with an R1= CO2Et substituent at the 5-position of the 1H-pyrazolo[3,4-b]pyridine ring presented lower activity than those with a CN substituent. The 1H-pyrazolo[3,4-b]pyridine system appears to be promising for further studies as an antimalarial for overcoming the burden of resistance in P. falciparum.

Pyrazolopyridines as a novel structural class of potent and selective PDE4 inhibitors

Optimisation of a high-throughput screening hit resulted in the discovery of 4-(substituted amino)-1-alkyl-pyrazolo[3,4-b]pyridine-5-carboxamides as potent and selective inhibitors of Phosphodiesterase 4 (PDE4). Herein, we describe early SAR studies around this novel template highlighting preferred substituents and rationalization of SAR through X-ray crystal structures of analogues bound to the PDE4 active site. Pyrazolopyridine 20a was found to be a potent and selective PDE4 inhibitor which also inhibits LPS induced TNF-α production from isolated human peripheral blood mononuclear cells and has an encouraging rat PK profile suitable for oral dosing.

Synthesis and SAR of bicyclic heteroaryl hydroxamic acid MMP and TACE inhibitors

Potent and selective bicyclic heteroaryl hydroxamic acid MMP and TACE inhibitors were synthesized by a novel convergent route. Selectivity and efficacy versus MMPs and TACE could be controlled by appropriate substitution on the scaffolds and by variation of the P1′ group. Select compounds were found to be effective in in vivo models of arthritis.

Preparation and use of acetylenic ortho-sulfonamido and phosphinic acid amido bicyclic heteroaryl hydroxamic acids as TACE inhibitors

Compounds of the formula which are useful in disease conditions mediated by TNF-α, such as rheumatoid arthritis, osteoarthritis, sepsis, AIDS, ulcerative colitis, multiple sclerosis, Crohn's disease and degenerative cartilage loss.

New tetracyclic heteroaromatic ring system 3H-benzo[b]pyrazolo[3, 4-h]-1, 6-naphthyridines

Various derivatives of the tetracyclic ring system 3H-Benzo[b]pyrazolo[3,4-h]-1,6-naphthyridine were prepared from 4-anilino-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acids by intramolecular cyclization employing phophoryl chloride. 1H NMR spectra of the various derivatives were recorder.

ACETYLENIC ORTHO-SULFONAMIDO AND PHOSPHINIC ACID AMIDO BICYCLIC HETEROARYL HYDROXAMIC ACIDS AS TACE INHIBITORS

Compounds of the formula are provided wherein P and Q are provided that when P is Q is and vice versa; which are useful in disease conditions mediated by TNF- alpha , such as rheumatoid arthritis, osteoarthritis, sepsis, AIDS, ulcerative colitis, multiple sclerosis, Crohn's disease and degenerative cartilage loss.