M.W=100-150 | Page 27 of 51 | pyrazoles-derivatives

Hartz, Richard A.’s team published research in Journal of Medicinal Chemistry in 64 | CAS: 763120-58-7

Journal of Medicinal Chemistry published new progress about 763120-58-7. 763120-58-7 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Boronic acid and ester,Boronic Acids,Boronic acid and ester, name is 1H-Pyrazole-4-boronic acid, and the molecular formula is C3H5BN2O2, Application of 1H-Pyrazole-4-boronic acid.

Hartz, Richard A. published the artcileDiscovery, Structure-Activity Relationships, and In Vivo Evaluation of Novel Aryl Amides as Brain Penetrant Adaptor Protein 2-Associated Kinase 1 (AAK1) Inhibitors for the Treatment of Neuropathic Pain, Application of 1H-Pyrazole-4-boronic acid, the publication is Journal of Medicinal Chemistry (2021), 64(15), 11090-11128, database is CAplus and MEDLINE.

Effective treatment of chronic pain, in particular neuropathic pain, without the side effects that often accompany currently available treatment options is an area of significant unmet medical need. A phenotypic screen of mouse gene knockouts led to the discovery that adaptor protein 2-associated kinase 1 (AAK1) is a potential therapeutic target for neuropathic pain. The synthesis and optimization of structure-activity relationships of a series of aryl amide-based AAK1 inhibitors led to the identification of 59, a brain penetrant, AAK1-selective inhibitor that proved to be a valuable tool compound Compound 59 was evaluated in mice for the inhibition of μ2 phosphorylation. Studies conducted with 59 in pain models demonstrated that this compound was efficacious in the phase II formalin model for persistent pain and the chronic-constriction-injury-induced model for neuropathic pain in rats. These results suggest that AAK1 inhibition is a promising approach for the treatment of neuropathic pain.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Fukuzumi, Takeo’s team published research in Bulletin of the Chemical Society of Japan in 87 | CAS: 763120-58-7

Bulletin of the Chemical Society of Japan published new progress about 763120-58-7. 763120-58-7 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Boronic acid and ester,Boronic Acids,Boronic acid and ester, name is 1H-Pyrazole-4-boronic acid, and the molecular formula is C3H5BN2O2, SDS of cas: 763120-58-7.

Fukuzumi, Takeo published the artcileSynthesis of 8-substituted adenine and adenosine libraries and the binding to pre-miR-29a, SDS of cas: 763120-58-7, the publication is Bulletin of the Chemical Society of Japan (2014), 87(9), 1013-1015, database is CAplus.

A small chem. library of 8-substituted adenine and adenosine derivatives was synthesized and examined for binding to pre-miR-29a. We found that one compound showed the affinity with 61 nM of K_d and a 10-fold stronger binding than the double-stranded RNA.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Borthwick, Jennifer A.’s team published research in Journal of Medicinal Chemistry in 59 | CAS: 724710-02-5

Journal of Medicinal Chemistry published new progress about 724710-02-5. 724710-02-5 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Boronic acid and ester,Pyrazole,Boronic Acids,Boronic acid and ester, name is (1H-Pyrazol-5-yl)boronic acid, and the molecular formula is C3H5BN2O2, Synthetic Route of 724710-02-5.

Borthwick, Jennifer A. published the artcileStructurally Diverse Mitochondrial Branched Chain Aminotransferase (BCATm) Leads with Varying Binding Modes Identified by Fragment Screening, Synthetic Route of 724710-02-5, the publication is Journal of Medicinal Chemistry (2016), 59(6), 2452-2467, database is CAplus and MEDLINE.

Inhibitors of mitochondrial branched chain aminotransferase (BCATm), identified using fragment screening, are described. This was carried out using a combination of STD-NMR, thermal melt (T_m), and biochem. assays to identify compounds that bound to BCATm, which were subsequently progressed to X-ray crystallog., where a number of exemplars showed significant diversity in their binding modes. The hits identified were supplemented by searching and screening of addnl. analogs, which enabled the gathering of further X-ray data where the original hits had not produced liganded structures. The fragment hits were optimized using structure-based design, with some transfer of information between series, which enabled the identification of ligand efficient lead mols. with micromolar levels of inhibition, cellular activity, and good solubility

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Andrews, Martin J. I.’s team published research in Bioorganic & Medicinal Chemistry Letters in 22 | CAS: 763120-58-7

Bioorganic & Medicinal Chemistry Letters published new progress about 763120-58-7. 763120-58-7 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Boronic acid and ester,Boronic Acids,Boronic acid and ester, name is 1H-Pyrazole-4-boronic acid, and the molecular formula is C3H5BN2O2, Safety of 1H-Pyrazole-4-boronic acid.

Andrews, Martin J. I. published the artcileDiscovery of a series of imidazopyrazine small molecule inhibitors of the kinase MAPKAPK5, that show activity using in vitro and in vivo models of rheumatoid arthritis, Safety of 1H-Pyrazole-4-boronic acid, the publication is Bioorganic & Medicinal Chemistry Letters (2012), 22(6), 2266-2270, database is CAplus and MEDLINE.

MAPKAPK5 has been proposed to play a role in regulation of matrix metalloprotease expression and so to be a potential target for intervention in rheumatoid arthritis. We present here the identification of a series of compounds against this target which are effective in both biochem. and cell assays. The expansion of the series is described, along with early SAR and pharmacokinetics for some representative compounds

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Magalhaes, Joana’s team published research in Journal of Chemical Information and Modeling in 58 | CAS: 763120-58-7

Journal of Chemical Information and Modeling published new progress about 763120-58-7. 763120-58-7 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Boronic acid and ester,Boronic Acids,Boronic acid and ester, name is 1H-Pyrazole-4-boronic acid, and the molecular formula is C3H5BN2O2, Application In Synthesis of 763120-58-7.

Magalhaes, Joana published the artcileIntegration of Enhanced Sampling Methods with Saturation Transfer Difference Experiments to Identify Protein Druggable Pockets, Application In Synthesis of 763120-58-7, the publication is Journal of Chemical Information and Modeling (2018), 58(3), 710-723, database is CAplus and MEDLINE.

Saturation transfer difference (STD) is an NMR technique conventionally applied in drug discovery to identify ligand moieties relevant for binding to protein cavities. This is important to direct medicinal chem. efforts in small-mol. optimization processes. However, STD does not provide any structural details about the ligand-target complex under investigation. Herein, we report the application of a new integrated approach, which combines enhanced sampling methods with STD experiments, for the characterization of ligand-target complexes that are instrumental for drug design purposes. As an example, we have studied the interaction between StOASS-A, a potential antibacterial target, and an inhibitor previously reported. This approach allowed us to consider the ligand-target complex from a dynamic point of view, revealing the presence of an accessory subpocket which can be exploited to design novel StOASS-A inhibitors. As a proof of concept, a small library of derivatives was designed and evaluated in vitro, displaying the expected activity.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Taylor, Edward C.’s team published research in Journal of Organic Chemistry in 1966 | CAS: 54385-49-8

Journal of Organic Chemistry published new progress in CAplus about 54385-49-8, 54385-49-8 belongs to class pyrazoles-derivatives, name is 5-Amino-1H-pyrazole-3,4-dicarbonitrile, and the molecular formula is C5H3N5, SDS of cas: 54385-49-8.

Taylor, Edward C. published the artcile3-Cyano-4-aminopyrazolo[3,4-d]pyrimidine, an azalog of the aglycone of toyocamycin, SDS of cas: 54385-49-8, the main research area is .

cf. CA 63, 602a. Condensation of (NC)2C:C(CN)2 with H2NC(:NH)NH2.HCl followed by hydrolysis gave a good yield of 5-aminopyrazole-3,4-dicarbonitrile (I, R = NH2) (II). Reaction of II with HC(OEt)3 under anhydrous conditions by refluxing 7 h., isolation of the intermediate I (R = N:CHOEt) (III), and treatment with alc. NH3 gave 83% yield of the desired aglycon analog (IV, R = CN) (V). III recrystallized from C5H5N-petroleum ether without special precautions against moisture gave I (R = NHCHO). V refluxed 24 h. in 10% aqueous NaOH and acidified with 9% aqueous HCl gave the acid IV (R = CO2H), sublimed in vacuo to 4-aminopyrazolo[3,4-d] pyrimidine IV (R = H). V in 8% aqueous HCl stirred at 0° with addition of aqueous NaNO2, the mixture boiled and the isolated product recrystallized gave 3-cyano-4(5H)-pyrazolo[3,4-d]pyrimidinone.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Shakir, Mohammed’s team published research in Transition Metal Chemistry (Dordrecht, Netherlands) in 1993-02-28 | CAS: 54385-49-8

Transition Metal Chemistry (Dordrecht, Netherlands) published new progress about transition metal aminocyanopyrazole complex; pyrazole dicyanoamino transition metal complex; cyanoaminopyrazole transition metal complex. 54385-49-8 belongs to class pyrazoles-derivatives, name is 5-Amino-1H-pyrazole-3,4-dicarbonitrile, and the molecular formula is C5H3N5, Synthetic Route of 54385-49-8.

Shakir, Mohammed published the artcile3,4-Dicyano-5-aminopyrazole complexes of anhydrous divalent transition metal chlorides and their triphenylphosphine derivatives, Synthetic Route of 54385-49-8, the main research area is transition metal aminocyanopyrazole complex; pyrazole dicyanoamino transition metal complex; cyanoaminopyrazole transition metal complex.

3,4-Dicyano-5-aminopyrazole (L) reacts either with anhydrous MCl2 or with [M(PPh3)2Cl2] to yield ML4Cl2 (M = Cr, Mn, Fe, Co, Ni, Cu, Zn, Cd, Hg), whose monomeric and covalent natures were confirmed by their solubility in most nonpolar solvents and their low elec. conductivities. The bonding mode of substituted pyrazole is inferred from the position of the ν(C:N) band in the IR spectra. The electronic spectra and the magnetic moments of these compounds were recorded.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Hecht, Sidney M.’s team published research in Journal of Organic Chemistry in 1975 | CAS: 54385-49-8

Journal of Organic Chemistry published new progress about Tautomers. 54385-49-8 belongs to class pyrazoles-derivatives, name is 5-Amino-1H-pyrazole-3,4-dicarbonitrile, and the molecular formula is C5H3N5, Recommanded Product: 5-Amino-1H-pyrazole-3,4-dicarbonitrile.

Hecht, Sidney M. published the artcileStructure determination of the N-methyl isomers of 5-amino-3,4-dicyanopyrazole and certain related pyrazolo[3,4-d]pyrimidines, Recommanded Product: 5-Amino-1H-pyrazole-3,4-dicarbonitrile, the main research area is pyrazoledicarbonitrile amino tautomerism; tautomerism aminopyrazoledicarbonitrile; pyrazolopyrimidine structure.

Addnl. data considered in abstracting and indexing are available from a source cited in the original document. The position of N substitution of 4-aminopyrazolo[3, 4-d]pyrimidine derivatives was studied by chem. and spectroscopic techniques, and structures were assigned to the pyrazole precursors of these compounds The more abundant pyrazole resulting from treatment of tetracyanoethylene with MeNHNH2 was 3-amino-4, 5-dicyano-1-methylpyrazole (I) on the basis of its conversion to a pyrazolo[3,4-d]pyrimidine identical with authentic 4-amino-2-methylpyrazolo[3,4-d]pyrimidine, rather than with the authentic 1-methyl isomer. The assigned structure was verified by x-ray crystallog. determination of I. Because I was not expected to be the more abundant pyrazole, a mechanism was proposed to account for its formation. 13C NMR and uv data for 3-amino-4,5-dicyanopyrazole indicated that 5-amino-3,4-dicyano-1H-pyrazole was the major tautomer.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Earl, Robert A.’s team published research in Journal of Organic Chemistry in 1975 | CAS: 54385-49-8

Journal of Organic Chemistry published new progress about Methylation. 54385-49-8 belongs to class pyrazoles-derivatives, name is 5-Amino-1H-pyrazole-3,4-dicarbonitrile, and the molecular formula is C5H3N5, SDS of cas: 54385-49-8.

Earl, Robert A. published the artcileChemical and carbon-13 nuclear magnetic resonance reinvestigation of the N-methyl isomers obtained by direct methylation of 5-amino-3,4-dicyanopyrazole and the synthesis of certain pyrazolo[3,4-d]pyrimidines, SDS of cas: 54385-49-8, the main research area is pyrazole amino dicyano methylation; methylation aminodicyanopyrazole; pyrazolopyrimidine amino methyl.

The structural assignments for the isomeric N-1- and N-2-methyl derivatives of 5-amino-3,4-dicyanopyrazole obtained by direct methylation by C. L. Dickenson et. al (1964) were reinvestigated. The higher melting isomer was annulated to give 4-amino-3-cyano-1-methylpyrazolo[3,4-d]pyrimidine (I, R = CN), which with alkaline peroxide gave I (R = CONH2). Hydrolysis of I (R = CONH2) under more vigorous conditions gave I (R = CO2H), which was decarboxylated in hot sulfolane to give I (R = H). This established the structure of the N-methylpyrazole as 5-amino-3,4-dicyano-1-methylpyrazole and reversed the structural assignment previously reported. A similar reaction sequence converted the lower melting isomer into 4-amino-2-methylpyrazolo[3,4-d]pyrimidine (II) and established the structure as 5-amino-3,4-dicyano-2-methylpyrazole.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Hassan, Alaa A.’s team published research in ARKIVOC (Gainesville, FL, United States) in 2003 | CAS: 54385-49-8

ARKIVOC (Gainesville, FL, United States) published new progress about Cyclization. 54385-49-8 belongs to class pyrazoles-derivatives, name is 5-Amino-1H-pyrazole-3,4-dicarbonitrile, and the molecular formula is C5H3N5, COA of Formula: C5H3N5.

Hassan, Alaa A. published the artcilePyrazole, pyrazolo[1,2-c]-1,3,4-thiadiazole and thiadiazepine derivatives from thiosemicarbazides, COA of Formula: C5H3N5, the main research area is thiosemicarbazide tetracyanoethene cyclization; pyrazole derivative preparation; pyrazolothiadiazole derivative preparation; thiadiazepine derivative preparation.

Thiosemicarbazides RNHCSNHNH2 [R = Ph, Bn, allyl] reacted with tetracyanoethene in Et acetate with admission of air to form the 7-amino-2-organylimino-2,3-dihydro-1,3,4-thiadiazepine-5,6-dicarbonitriles I [ R = Ph, Bn], 7-amino-1-organylimino-3-oxopyrazolo[1,2-c]-1,3,4-thiadiazole-5,5,6-tricarbonitriles II, 7-amino-1-organyl-iminopyrazolo[1,2-c]-1,3,4-thiadiazole-3,3,5,5,6-pentacarbonitriles III and 3-amino-1H-pyrazole-4,5-dicarbonitrile (IV) in moderate yields. Rationales for the observed conversations are presented.

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics