pyrazoles-derivatives

Mah, Shinmee team published research in Journal of Medicinal Chemistry in 2018 | 269410-08-4

Quality Control of 269410-08-4, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole, also known as 4-Pyrazoleboronic acid pinacol ester , is a useful research compound. Its molecular formula is C9H15BN2O2 and its molecular weight is 194.04 g/mol. The purity is usually 95%.

4-Pyrazoleboronic acid pinacol ester is a useful reagent for Suzuki-Miyaura cross-couplings as well as Ruthenium-catalyzed asymmetric hydrogenation. 4-Pyrazoleboronic acid pinacol ester is also a useful reagent for preparing VEGF, Aurora, RHO (ROCK), Janus Kinase 2, c-MET, ALK, S-nitrsoflutathione reductase, CDC7, Acetyl-CoA carboxylase inhibitors.

4-Pyrazoleboronic acid pinacol ester is used in the preparation of Rho kinase (ROCK) inhibitors as wella s other biologically active compounds.

4-Pyrazoleboronic acid pinacol ester is an organic compound that is the product of a bifunctional coupling reaction between 4-pyrazolecarboxylic acid and pinacol. It has been shown to inhibit protein S6 kinase, which is involved in the regulation of cell growth and proliferation. This compound has also been shown to be effective against cancer cells, including those that are resistant to conventional chemotherapeutic drugs. 4-Pyrazoleboronic acid pinacol ester may also be used as a precursor for other compounds with pharmaceutical activity., 269410-08-4.

Pyrazoles are synthesized by the reaction of α,β-unsaturated aldehydes with hydrazine and subsequent dehydrogenation. 269410-08-4, formula is C9H15BN2O2, Name is 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole. Substituted pyrazoles are prepared by condensation of 1,3-diketones with hydrazine (Knorr-type reactions). For example, acetylacetone and hydrazine gives 3,5-dimethylpyrazole. Quality Control of 269410-08-4.

Mah, Shinmee;Park, Jung Hee;Jung, Hoi-Yun;Ahn, Kukcheol;Choi, Soyeon;Tae, Hyun Seop;Jung, Kyung Hee;Rho, Jin Kyung;Lee, Jae Cheol;Passerini, Carlo Gambacorti;Fontana, Diletta;Hong, Soon-Sun;Hong, Sungwoo research published 《 Correction to Identification of 4-Phenoxyquinoline Based Inhibitors for L1196M Mutant of Anaplastic Lymphoma Kinase by Structure-Based Design [Erratum to document cited in CA168:042070]》, the research content is summarized as follows. Two authors (Carlo GambacortiPasserini and Diletta Fontana)and their affiliation (Departmentof Health Science, University of Milano-Bicocca,via Cadore,48,20900 Monza, Italy) have been added. The following sentence was added to the acknowledgments: “All Ba/F3 ALK WT and mutant cell lines were kindly provided by University of Milano-Bicocca (UNIMIB)”.

4-Pyrazoleboronic acid pinacol ester is used in the preparation of Rho kinase (ROCK) inhibitors as wella s other biologically active compounds.

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

Mah, Shinmee team published research in Journal of Medicinal Chemistry in 2017 | 269410-08-4

Application of C9H15BN2O2, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole, also known as 4-Pyrazoleboronic acid pinacol ester , is a useful research compound. Its molecular formula is C9H15BN2O2 and its molecular weight is 194.04 g/mol. The purity is usually 95%.

4-Pyrazoleboronic acid pinacol ester is used in the preparation of Rho kinase (ROCK) inhibitors as wella s other biologically active compounds.

Mah, Shinmee;Park, Jung Hee;Jung, Hoi-Yun;Ahn, Kukcheol;Choi, Soyeon;Tae, Hyun Seop;Jung, Kyung Hee;Rho, Jin Kyung;Lee, Jae Cheol;Hong, Soon-Sun;Hong, Sungwoo research published 《 Identification of 4-Phenoxyquinoline Based Inhibitors for L1196M Mutant of Anaplastic Lymphoma Kinase by Structure-Based Design》, the research content is summarized as follows. Dysregulation of anaplastic lymphoma kinase (ALK) has been detected in nonsmall cell lung cancer (NSCLC) in the form of EML4-ALK fusion. Secondary mutations opposing activity of the first-generation ALK inhibitor crizotinib came into existence, requiring mutation-targeting drug discovery for the powerful second-line treatment. In this study, we report 4-phenoxyquinoline-based inhibitors that overcome crizotinib resistance to ALK L1196M, discovered by the fragment-growing strategy. The protonation of 4-aminoquinoline core could interrupt the ability the N atom of quinoline to act as a hydrogen bond acceptor; therefore, the pK_a and calculated ionization pH values of relevant pyridine-based core moieties were carefully analyzed. The replacement of amine linkage with ether resulted in single-digit nanomolar range inhibitors. The inhibitors exhibited significant antiproliferative effects on H2228 CR crizotinib-resistant cells by decreasing PI3K/AKT and MAPK signaling. This work constitutes the first example for systematic investigation of the effect of ionization pH on activity in this system.

4-Pyrazoleboronic acid pinacol ester is used in the preparation of Rho kinase (ROCK) inhibitors as wella s other biologically active compounds.

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

Ma, Chenyang team published research in Dalton Transactions in 2021 | 2075-46-9

Name: 4-Nitro-1H-pyrazole, 4-Nitro-1H-pyrazole, also known as 4-Nitropyrazole, is a useful research compound. Its molecular formula is C3H3N3O2 and its molecular weight is 113.08 g/mol. The purity is usually 95%.

4-Nitropyrazole, is a building block for the synthesis of various pharmaceutical compounds, including inhibitors, and therapeutic agents. It can be used for the synthesis of highly selective, brain-penetrant aminopyrazole LRRK2 Inhibitor, as a potentially viable treatment for Parkinson’s disease., 2075-46-9.

Pyrazole is an organic compound with the formula C3H3N2H. It is a heterocycle characterized by a 5-membered ring of three carbon atoms and two adjacent nitrogen atoms, which are in ortho-substitution. 2075-46-9, formula is C3H3N3O2, Name is 4-Nitro-1H-pyrazole. Pyrazoles are a class of compounds that have the ring C3N2 with adjacent nitrogen atoms.Notable drugs containing a pyrazole ring are celecoxib (celebrex) and the anabolic steroid stanozolol. Name: 4-Nitro-1H-pyrazole.

Ma, Chenyang;Besson, Claire research published 《 Precise control of the degree and regioselectivity of functionalization in nitro- and amino-functionalized di(trispyrazolylborato)iron(II) spin crossover complexes》, the research content is summarized as follows. Di(trispyrazolylborato)iron(II) ([Tp₂Fe]) complexes represent one of the most robust classes of spin-crossover complexes. Their stability renders them particularly suitable for integration in nanoscale devices, e.g. as sensors or information storage units. While prior studies of the functionalization of those derivatives have been focused on the electronic and steric effects of alkyl and -CF₃ groups in position 3, a pyrazole exchange reaction between nitropyrazole and either trispyrazolylborate or its iron complex allows the regioselective installation of nitro substituents in positions 3, 4 and 5 of the [Tp₂Fe] complexes. The degree of substitution can be varied from 1 to 4 functionalized pyrazoles per complex. The amine-functionalized analogs are accessed by reduction of the nitro analogs under hydrogen transfer conditions. With the exception of di- and tetra-3-NO₂ substituted complexes, all derivatives display spin crossover properties in the solid state, with transition temperatures ranging from 180 to 380 K and showing different degrees of abruptness but no hysteresis. The Slichter-Drickamer model was used to extract the empirical thermodn. transition parameters, allowing a systematic investigation of the influence of stoichiometry, position, and electronic nature of the substitution on the magnetic properties of the complexes. The steric effects dominate for substitution in position 3 but the electronic effects are significant for the other positions.

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

Lyu, Jiyuan team published research in Journal of Organic Chemistry in 2020 | 2075-46-9

2075-46-9, 4-Nitro-1H-pyrazole, also known as 4-Nitropyrazole, is a useful research compound. Its molecular formula is C3H3N3O2 and its molecular weight is 113.08 g/mol. The purity is usually 95%.

Pyrazoles are synthesized by the reaction of α,β-unsaturated aldehydes with hydrazine and subsequent dehydrogenation. 2075-46-9, formula is C3H3N3O2, Name is 4-Nitro-1H-pyrazole. Substituted pyrazoles are prepared by condensation of 1,3-diketones with hydrazine (Knorr-type reactions). For example, acetylacetone and hydrazine gives 3,5-dimethylpyrazole. Application In Synthesis of 2075-46-9.

Lyu, Jiyuan;Claraz, Aurelie;Vitale, Maxime R.;Allain, Clemence;Masson, Geraldine research published 《 Preparation of Chiral Photosensitive Organocatalysts and Their Application for the Enantioselective Synthesis of 1,2-Diamines》, the research content is summarized as follows. Chiral phosphoric acid based organocatalysis and visible-light photocatalysis have both emerged as promising technologies for the sustainable production of fine chems. In this context, we have envisioned the design and the synthesis of a new class of chimeric catalytic entities that would feature both catalytic capabilities. Given their multitask nature, such catalysts would be particularly attractive for the development of new catalytic transformations, tandem processes in particular. Toward this goal, several BINOL-based chiral phosphoric acid backbones presenting one or two visible-light-sensitive thioxanthone moieties have been prepared and studied. The utility of these new photoactive chiral organocatalysts is then demonstrated in the enantioselective tandem three-component electrophilic amination of enecarbamates. Of note, the C₁-sym. organo/photocatalyst has shown a better catalytic activity than those presenting a C₂ symmetry.

2075-46-9, 4-Nitro-1H-pyrazole, also known as 4-Nitropyrazole, is a useful research compound. Its molecular formula is C3H3N3O2 and its molecular weight is 113.08 g/mol. The purity is usually 95%.

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

Chen, Bei et al. published their patent in 2009 |CAS: 85426-79-5

The Article related to preparation pyrimidine derivative therapeutic kinase inhibitor, pyrimidine derivative treatment proliferative disorder immune disorder infection, Heterocyclic Compounds (More Than One Hetero Atom): Pyrimidines and Quinazolines and other aspects.Computed Properties of 85426-79-5

On October 15, 2009, Chen, Bei; Jiang, Tao; Marsilje, Thomas H.; Michellys, Pierre-Yves; Nguyen, Truc Ngoc; Pei, Wei; Wu, Baogen; Gao, Zhaobo; Ge, Yonghui; Huang, Chen; Li, Yuncheng published a patent.Computed Properties of 85426-79-5 The title of the patent was Preparation of pyrimidine derivatives as protein kinase inhibitors for treating proliferative disorders, immune disorders, and infections. And the patent contained the following:

The invention relates to pyrimidine derivatives having Formula I or II (wherein R1 and R2 are H, C1-6 alkyl or halo-substituted C1-6 alkyl; R3 is halo, C1-6 alkyl, or a halo-substituted C1-6 alkyl; R4 is H; alternatively, R3 and R4 together form part of a ring; R5, R6 and R8 are independently C1-6 alkyl, C1-6 alkoxy, C2-6 alkenyl or C2-6 alkynyl, each optionally substituted; R7 is sulfamoyl, carbamoyl, etc.; R9 is -L-S(O)2R18, -L-S(O)2NRR17, etc.; R is H or C1-6alkyl; R17 and R18 are independently C1-6 alkyl, halo-substituted C1-6 alkyl, etc.; L is (CR2)1-4 or a bond; n = 1-2) and methods for using such compounds as kinase inhibitors for disease treatment. For example, the compounds of the invention may be used to treat, ameliorate or prevent a condition which responds to inhibition of anaplastic lymphoma kinase (ALK) activity, c-ros oncogene (ROS), insulin-like growth factor (IGF-IR), and/or insulin receptor (InsR) kinase activity or a combination thereof. Synthetic procedures for preparing the pyrimidines of the invention are claimed as are compositions containing them. Example compound III, prepared in a multistep synthesis that culminated in the reaction of corresponding pipieridine intermediate with dimethylamino acetyl halide, had an IC50 of 0.026 μM in an ALK assay. The experimental process involved the reaction of 4-Chloro-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidine(cas: 85426-79-5).Computed Properties of 85426-79-5

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

Jung, Chan Seong et al. published their patent in 2013 |CAS: 85426-79-5

The Article related to pyrazolopyrimidine preparation nitric oxide generation inhibition, cerebral nerve disease treatment pyrazolopyrimidine nitric oxide generation inhibition, Heterocyclic Compounds (More Than One Hetero Atom): Pyrimidines and Quinazolines and other aspects.Application of 85426-79-5

On October 14, 2013, Jung, Chan Seong; Kim, Dong Jin; Park, Gi Deok; Kim, Yun Gyeong; Pyo, Jeong In; Kim, Hyeon Tae; Hwang, On Yu; Azam, Sharif Mohammed Shafioul; Song, Chi Man; Kim, Yeong Su published a patent.Application of 85426-79-5 The title of the patent was Preparation of pyrazolopyrimidine derivatives for inhibiting nitric oxide generation. And the patent contained the following:

Disclosed are pyrazolopyrimidine derivatives, e.g., I [R1 = H, (un)substituted alkyl, (un)substituted aryl, etc.; R2 = H, halo, (un)substituted alkoxy, etc.; X1 = H, halo or (un)substituted aryl; or pharmaceutically acceptable salts thereof]. For example, compound II was prepared by following general procedure: reaction of 4-chloro-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidine with an amine (1.1 equiv) [dioxane, reflux temperature, 8 h]. Compound II [NR2 = piperidn-1-ylethylamino] showed 102±6% inhibition at 20 μM for NO generation. Title compounds are claimed useful for the treatment of Parkinson disease, Alzheimer disease, Hungtinton disease, etc. The experimental process involved the reaction of 4-Chloro-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidine(cas: 85426-79-5).Application of 85426-79-5

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

Chappie, Thomas Allen et al. published their patent in 2017 |CAS: 153597-59-2

The Article related to pyrazolooxazinecarboxamide preparation pde4 inhibitor, Heterocyclic Compounds (More Than One Hetero Atom): Oxazines (Including Morpholine) and other aspects.Reference of Ethyl 6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxylate

On August 31, 2017, Chappie, Thomas Allen; Patel, Nandini Chaturbhai; Verhoest, Patrick Robert; Helal, Christopher John; Sciabola, Simone; Lachapelle, Erik Alphie; Wager, Travis T.; Hayward, Matthew Merrill published a patent.Reference of Ethyl 6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxylate The title of the patent was 6,7-Dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide compounds as PDE4 inhibitors and their preparation. And the patent contained the following:

The invention is directed to PDE4B inhibitors of formula Ior a pharmaceutically acceptable salt thereof. The invention is also directed to pharmaceutical compositions comprising the compounds, methods of treatment using the compounds, and methods of preparing the compounds Compounds of formula I wherein R1 is (un)substituted C3-8 cycloalkyl, (un)substituted C6-10 aryl, (un)substituted 5- to 10-membered heteroaryl, etc.; R2 and R3 are independently H, (un)substituted C1-6 alkyl, (un)substituted C3-8 cycloalkyl, (un)substituted C6-10 aryl, etc.; n is 0, 1, 2 and 3; each R4 is independently halo, CN, OH, SF5, NO2, etc.; and pharmaceutically acceptable salts thereof, are claimed. Example compound II was prepared by cross-coupling of azetidin-1-yl(3-bromo-6,7-dihydro-5H-pyrazolo[5,1-b]oxazin-2-yl)methanol with 4-chloro-2-methylphenylboronic acid. The invention compounds were evaluated for their PDE4 inhibitory activity. From the assay, it was determined that compound II exhibited IC50 values of 211 nM, 241 nM and 653 nM towards PDE4B1, PDE4A3 and PDE4C1, resp. The experimental process involved the reaction of Ethyl 6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxylate(cas: 153597-59-2).Reference of Ethyl 6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxylate

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

Abela, Alexander Russell et al. published their patent in 2021 |CAS: 215610-30-3

The Article related to macrocycle preparation cftr modulator cystic fibrosis, Heterocyclic Compounds (More Than One Hetero Atom): Eight- and Higher-Membered Rings and other aspects.SDS of cas: 215610-30-3

On February 18, 2021, Abela, Alexander Russell; Anderson, Corey Don; Bookser, Brett C.; Busch, Brett B.; Clemens, Jeremy J.; Cleveland, Thomas; Coon, Timothy Richard; Frieman, Bryan; Ghirmai, Senait G.; Gulevich, Anton V.; Hadida Ruah, Sara Sabina; Ishihara, Yoshihiro; Khatuya, Haripada; McCartney, Jason; Miller, Mark Thomas; Paraselli, Prasuna; Pierre, Fabrice; Termin, Andreas; Swift, Sara E.; Uy, Johnny; Vogel, Carl V.; Zhou, Jinglan; Grootenhuis, Peter published a patent.SDS of cas: 215610-30-3 The title of the patent was Macrocycles as modulators of cystic fibrosis transmembrane conductance regulator and preparation. And the patent contained the following:

This disclosure provides compounds of formula I as modulators of Cystic Fibrosis Transmembrane Conductance Regulator (CFTR), pharmaceutical compositions containing at least one such modulator, methods of treatment of cystic fibrosis using such modulators and pharmaceutical compositions, and processes for making such modulators. Compound I, wherein ring A is a Ph, indole, 5-membered hetereoaryl ring, etc.; ring B is Ph, pyridinyl and pyrimidinyl ring; X is O, NH and N(C1-6 alkyl); each R1 is independently C1-6 alkyl, C1-6 alkoxyl,C1-6 haloalkyl; m is 0, 1, 2, 3 and 4; each R2 is independently halo, cyano, (un)substituted C1-6 alkyl; n is 0, 1 and 2; R0 is H, halo, cyano, etc.; each R3 is (un)substituted C1-6 alkyl and two R3 are joined to form C3-6 cycloaklyl ring; Z is a divalent linker (L)r wherein r is 1, 2, 3, 4, 5 and 6; each L is independently C(R8)(R9), O, NRb, etc.; each R8 and R9 is independently H, halo, C1-6 haloalkyl, etc.; and tautomers, deuterated derivatives and pharmaceutically acceptable salts thereof, are claimed. Compound II was prepared using a multi-step procedure (procedure given). Compound II was tested for CFTR modulatory activity giving an EC50 of <1μM. Compounds of the invention were tested for their CFTR modulatory activity (data given). The experimental process involved the reaction of 5-Methoxy-1H-pyrazole(cas: 215610-30-3).SDS of cas: 215610-30-3

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

Tang, Xinxing et al. published their patent in 2021 |CAS: 215610-30-3

The Article related to heteroaromatic macrocyclic ether preparation cancer ros1 alk kinase inhibitor, Heterocyclic Compounds (More Than One Hetero Atom): Eight- and Higher-Membered Rings and other aspects.Formula: C4H6N2O

On November 11, 2021, Tang, Xinxing; Horan, Joshua Courtney; Mente, Scot Richard; Pelish, Henry Efrem; Shair, Matthew D.; Tangpeerachaikul, Anupong published a patent.Formula: C4H6N2O The title of the patent was Preparation of heteroaromatic macrocyclic ether chemotherapeutic agents for treatment of cancer. And the patent contained the following:

Disclosed are heterocyclic heteroaromatic macrocyclic ether compounds of formula I useful alone or in combination addnl. tyrosine kinase inhibitors for the treatment or prevention of cancer. Compounds of formula I [wherein Q = CH or N; Z = CR5 or N; X = 5-membered heteroarylene, comprising 1 to 3 heteroatoms selected from N, O, and S, wherein the 5-membered heteroarylene is substituted with 0, 1, or 2 occurrences of R2, with proviso; Y = 5- to 6-membered heteroarylene, comprising 1 to 3 heteroatoms selected from N, O, and S, wherein the heteroarylene is substituted with 0, 1, or 2 occurrences of R3; R1 = H, Me, and hydroxymethyl; each R2 and R3 independently = H, CN, halo, C1-4alkoxy, etc.; R4 and R5 independently = H or F] and pharmaceutically acceptable salts and pharmaceutical compositions thereof, are claimed and exemplified. Example compound II was prepared from a multistep synthesis (preparation given). Exemplified I were evaluated for inhibition of mutant and wild-type ROS1 and ALK kinases from which II demonstrated apparent inhibitory constants of <50 nM for each kinase. The experimental process involved the reaction of 5-Methoxy-1H-pyrazole(cas: 215610-30-3).Formula: C4H6N2O

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

Horan, Joshua Courtney et al. published their patent in 2021 |CAS: 215610-30-3

On November 11, 2021, Horan, Joshua Courtney; Mente, Scot Richard; Pelish, Henry Efrem; Shair, Matthew D.; Tang, Xinxing; Tangpeerachaikul, Anupong published a patent.Related Products of 215610-30-3 The title of the patent was Preparation of heteroaromatic macrocyclic ether chemotherapeutic agents for treatment of cancer. And the patent contained the following:

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