Category: pyridazine

Synthesis of polyfunctional fluoro-quinoline and fluoro-pyridopyrimidinone derivatives was written by Heeran, Darren;Murray, Ben J.;Qiu, Sili;Martin, Sophie J.;Skelton, Robert M.;Dodds, Kiera R.;Yufit, Dmitry S.;Sandford, Graham. And the article was included in Journal of Fluorine Chemistry in 2021.Electric Literature of C4H5N3 This article mentions the following:

2-Fluoromalonic acid is a useful building block for the synthesis of selectively fluorinated heterocycles. In the presence of phosphoryl chloride, chlorinated fluoroquinolines and fluoro-pyridopyrimidinones were prepared in a single step by an efficient tandem chlorination-cyclisation process. Functionalisation by Suzuki cross-coupling or S_NAr processes allowed for the rapid construction of a small library of 30 novel polysubstituted selectively fluorinated quinoline and pyridopyrimidinone derivatives in high yields and bearing a diverse range of substituents. In the experiment, the researchers used many compounds, for example, 3-Aminopyridazine (cas: 5469-70-5Electric Literature of C4H5N3).

3-Aminopyridazine (cas: 5469-70-5) belongs to pyridazine derivatives. The pyridazine structure is a popular pharmacophore which is found within a number of herbicides such as credazine, pyridafol and pyridate. Pyridazine and derivatives coordinate readily with transition metals to form complexes and catalysts with synthetic utility.Electric Literature of C4H5N3

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Synthesis of 3,6-dichloro-4-pyridazinecarboxylic acid was written by Yao, Zhuanle;Shi, Qiang;Fan, Xuezhong;Wang, Rongbing. And the article was included in Yingyong Huagong in 2009.HPLC of Formula: 5754-18-7 This article mentions the following:

The synthesis of the target compound was achieved (52% yield, 98% purity) using hydrazine dihydrochloride and citraconic anhydride (3-methyl-2,5-furandione) as starting materials, the product structure thus obtained was confirmed by IR and ¹H-NMR, factors affecting product formation were determined and optimized reaction conditions were confirmed. In the experiment, the researchers used many compounds, for example, 1,2-Dihydro-4-methyl-3,6-pyridazinedione (cas: 5754-18-7HPLC of Formula: 5754-18-7).

1,2-Dihydro-4-methyl-3,6-pyridazinedione (cas: 5754-18-7) belongs to pyridazine derivatives. Pyridazines is a six-membered nitrogen-containing significant heterocycle. It has received considerable interest because of its useful applications as natural products, pharmaceuticals, and various bioactive molecules. The unsubstituted pyridazines are more resistant to eletrophilic substitution due to the nature of withdrawal of electron density from the ring by two heteroatoms, while the related electron deficiency of the ring makes pyridazine more easily attacked by nucleophiles.HPLC of Formula: 5754-18-7

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Application of Atypical Acetyl-lysine Methyl Mimetics in the Development of Selective Inhibitors of the Bromodomain-Containing Protein 7 (BRD7)/Bromodomain-Containing Protein 9 (BRD9) Bromodomains was written by Clegg, Michael A.;Bamborough, Paul;Chung, Chun-wa;Craggs, Peter D.;Gordon, Laurie;Grandi, Paola;Leveridge, Melanie;Lindon, Matthew;Liwicki, Gemma M.;Michon, Anne-Marie;Molnar, Judit;Rioja, Inmaculada;Soden, Peter E.;Theodoulou, Natalie H.;Werner, Thilo;Tomkinson, Nicholas C. O.;Prinjha, Rab K.;Humphreys, Philip G.. And the article was included in Journal of Medicinal Chemistry in 2020.Product Details of 823-58-5 This article mentions the following:

Non-BET bromodomain-containing proteins have become attractive targets for the development of novel therapeutics targeting epigenetic pathways. To help facilitate the target validation of this class of proteins, structurally diverse small-mol. ligands and methodologies to produce selective inhibitors in a predictable fashion are in high demand. Herein, we report the development and application of atypical acetyl-lysine (KAc) Me mimetics to take advantage of the differential stability of conserved water mols. in the bromodomain binding site. Discovery of the Bu group as an atypical KAc Me mimetic allowed generation of 31 (GSK6776) as a soluble, permeable, and selective BRD7/9 inhibitor from a pyridazinone template. The Bu group was then used to enhance the bromodomain selectivity of an existing BRD9 inhibitor and to transform pan-bromodomain inhibitors into BRD7/9 selective compounds Finally, a solvent-exposed vector was defined from the pyridazinone template to enable bifunctional mol. synthesis, and affinity enrichment chemoproteomic experiments were used to confirm several of the endogenous protein partners of BRD7 and BRD9, which form part of the chromatin remodeling PBAF and BAF complexes, resp. In the experiment, the researchers used many compounds, for example, 4-Amino-3,6-dichloropyridazine (cas: 823-58-5Product Details of 823-58-5).

4-Amino-3,6-dichloropyridazine (cas: 823-58-5) belongs to pyridazine derivatives. The pyridazine structure is a popular pharmacophore which is found within a number of herbicides such as credazine, pyridafol and pyridate. The unsubstituted pyridazines are more resistant to eletrophilic substitution due to the nature of withdrawal of electron density from the ring by two heteroatoms, while the related electron deficiency of the ring makes pyridazine more easily attacked by nucleophiles.Product Details of 823-58-5

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Synthesis of 1,2-diazine derivatives. VII. Substitution reaction of 3,6-dichloro-4-methylpyridazine was written by Mori, Kazuo. And the article was included in Yakugaku Zasshi in 1962.SDS of cas: 89640-81-3 This article mentions the following:

3,6-Dichloro-4-methylpyridazine (I) (30 g.) and 100 ml. 28% NH₄OH in a sealed tube heated 20-4 hrs. at 120-40° and the product filtered off gave 3-chloro-4-methyl-6-aminopyridazine (II), m. 190-2° (EtOH) and the mother liquor gave the 5-Me analog (III) of II, m. 111-13° (hexane). MeONa (25 g. Na and 1.2 l. MeOH) and 163 g. I refluxed 7 hrs., 0.7 l. MeOH removed, the residue kept overnight, and the product filtered off gave 59 g. 3-chloro-4-methyl-6-methoxypyridazine (IV), m. 112-16° (MeOH), and the mother liquor gave 91 g. 5-Me analog (V) of IV, m. 68-70° (hexane). II (2.4 g.) and MeONa (0.5 g. Na and 50 ml. MeOH) in a sealed tube heated 12 hrs. at 165°, the MeOH removed, and the residue extracted with CHCl₃ gave 1.5 g. 3-methoxy-4-methyl-6-amino- pyridazine, m. 83-5°. Catalytic reduction of 1 g. II or III in 100 ml. EtOH with 10% Pd-C gave 4-methyl-3-aminopyridazine- HCl, m. 264° (decomposition), or the 5-Me analog, m. 194° (decomposition). IV (2 g.), 80 ml. 28% NH₄OH, and a small amount of bronze powder in a sealed tube heated 50 hrs. at 130-60° and the solution concentrated gave 4-methyl-6-amino-3-pyridazinol, m. 213°. IV (3 g.) and 100 ml. 28% NH₄OH in a sealed tube heated 28 hrs. at 130-50° and the product concentrated gave 2 g. 4-methyl-6-chloro-3- pyridazinol (VI), m. 171°. Similarly, 2.3 g. V gave 1.5 g. 5-Me analog (VII) of VI, m. 227°. Catalytic reduction of VI gave 4-methyl- 3-pyridazinol, m. 157-8° and that of VII gave 5-methyl-3-pyridazinol, m. 154°. Catalytic reduction of IV gave 3-methoxy-4- methylpyridazine-HCl, m. 150° (decomposition). I (20 g.) and 80 ml. 40% Me₂NH in a sealed tube heated 8 hrs. at 130° gave 4(or 5)-methyl-3-chloro-6-dimethylaminopyridazine, m. 126°. Oxidation of 13 g. I with K₂Cr₂O₇ gave 11 g. 3-hydroxy-6-chloro-4-pyrid- azinecarboxylic acid (VIII), m. 210° (decomposition) (H₂O). Similarly, oxidation of VII with CrO₃ gave the 5-CO₂H analog (IX) of VIII, m. 245° (decomposition). VIII (1.5 g.) in 20 ml. MeOH and several drops H₂SO₄ refluxed 5-8 hrs. and the product recrystallized (H₂O) gave the Me ester of VIII, m. 132°. Similarly was prepared the Me ester of IX, m. 99-101°. Catalytic reduction of 2.5 g. VIII in 80 ml. MeOH with Pd-C gave Me 3-hydroxy-4-pyridazinecarboxylate (X), m. 159°. Similarly, IX yielded the 5-C0₂Me analog of X, m. 163°. In the experiment, the researchers used many compounds, for example, Methyl 6-oxo-1,6-dihydropyridazine-4-carboxylate (cas: 89640-81-3SDS of cas: 89640-81-3).

Methyl 6-oxo-1,6-dihydropyridazine-4-carboxylate (cas: 89640-81-3) belongs to pyridazine derivatives. Pyridazine-based compounds continued to be a great source of biologically active compounds as evidenced by the number of publications which emerged in 2021. The unsubstituted pyridazines are more resistant to eletrophilic substitution due to the nature of withdrawal of electron density from the ring by two heteroatoms, while the related electron deficiency of the ring makes pyridazine more easily attacked by nucleophiles.SDS of cas: 89640-81-3

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Quantitative Characterization of Bivalent Probes for a Dual Bromodomain Protein, Transcription Initiation Factor TFIID Subunit 1 was written by Suh, Junghyun L.;Watts, Brian;Stuckey, Jacob I.;Norris-Drouin, Jacqueline L.;Cholensky, Stephanie H.;Dickson, Bradley M.;An, Yi;Mathea, Sebastian;Salah, Eidarus;Knapp, Stefan;Khan, Abid;Adams, Alexander T.;Strahl, Brian D.;Sagum, Cari A.;Bedford, Mark T.;James, Lindsey I.;Kireev, Dmitri B.;Frye, Stephen V.. And the article was included in Biochemistry in 2018.HPLC of Formula: 823-58-5 This article mentions the following:

Multivalent binding is an efficient means to enhance the affinity and specificity of chem. probes targeting multidomain proteins in order to study their function and role in disease. While the theory of multivalent binding is straightforward, phys. and structural characterization of bivalent binding encounters multiple tech. difficulties. We present a case study where a combination of exptl. techniques and computational simulations was used to comprehensively characterize the binding and structure-affinity relationships for a series of Bromosporine-based bivalent bromodomain ligands with a bivalent protein, Transcription Initiation Factor TFIID subunit 1 (TAF1). Exptl. techniques-Isothermal Titration Calorimetry, X-ray Crystallog., CD, Size Exclusion Chromatog.-Multi-Angle Light Scattering, and Surface Plasmon Resonance-were used to determine structures, binding affinities, and kinetics of monovalent ligands and bivalent ligands with varying linker lengths. The exptl. data for monomeric ligands were fed into explicit computational simulations, in which both ligand and protein species were present in a broad range of concentrations, and in up to a 100 s time regime, to match exptl. conditions. These simulations provided accurate estimates for apparent affinities (in good agreement with exptl. data), individual dissociation microconstants and other microscopic details for each type of protein-ligand complex. We conclude that the expected efficiency of bivalent ligands in a cellular context is difficult to estimate by a single technique in vitro, due to higher order associations favored at the concentrations used, and other complicating processes. Rather, a combination of structural, biophys., and computational approaches should be utilized to estimate and characterize multivalent interactions. In the experiment, the researchers used many compounds, for example, 4-Amino-3,6-dichloropyridazine (cas: 823-58-5HPLC of Formula: 823-58-5).

4-Amino-3,6-dichloropyridazine (cas: 823-58-5) belongs to pyridazine derivatives. Pyridazine-based compounds continued to be a great source of biologically active compounds as evidenced by the number of publications which emerged in 2021. The activity depends upon the changes of substituted groups in the pyridazine ring system resulting in different biological activities. In addition, the natural pyrimidine bases uracil, thymine, and cytosine, which are constituents of the nucleic acids, are found to be the most important naturally occurring diazines.HPLC of Formula: 823-58-5

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Sulfonamides as Selective Na_V1.7 Inhibitors: Optimizing Potency and Pharmacokinetics While Mitigating Metabolic Liabilities was written by Weiss, Matthew M.;Dineen, Thomas A.;Marx, Isaac E.;Altmann, Steven;Boezio, Alessandro;Bregman, Howard;Chu-Moyer, Margaret;DiMauro, Erin F.;Feric Bojic, Elma;Foti, Robert S.;Gao, Hua;Graceffa, Russell;Gunaydin, Hakan;Guzman-Perez, Angel;Huang, Hongbing;Huang, Liyue;Jarosh, Michael;Kornecook, Thomas;Kreiman, Charles R.;Ligutti, Joseph;La, Daniel S.;Lin, Min-Hwa Jasmine;Liu, Dong;Moyer, Bryan D.;Nguyen, Hanh N.;Peterson, Emily A.;Rose, Paul E.;Taborn, Kristin;Youngblood, Beth D.;Yu, Violeta;Fremeau, Robert T.. And the article was included in Journal of Medicinal Chemistry in 2017.Recommanded Product: 3-Aminopyridazine This article mentions the following:

Several reports have recently emerged regarding the identification of heteroarylsulfonamides as Na_V1.7 inhibitors that demonstrate high levels of selectivity over other Na_V isoforms. The optimization of a series of internal Na_V1.7 leads that address a number of metabolic liabilities including bioactivation, PXR activation, as well as CYP3A4 induction and inhibition led to the identification of potent and selective inhibitors that demonstrated favorable pharmacokinetic profiles and were devoid of the aforementioned liabilities. The key to achieving this within a series prone to transporter-mediated clearance was the identification of a small range of optimal cLogD values and the discovery of subtle PXR SAR that was not lipophilicity dependent. This enabled the identification of compound 20, which was advanced into a target engagement pharmacodynamic model where it exhibited robust reversal of histamine-induced scratching bouts in mice. In the experiment, the researchers used many compounds, for example, 3-Aminopyridazine (cas: 5469-70-5Recommanded Product: 3-Aminopyridazine).

3-Aminopyridazine (cas: 5469-70-5) belongs to pyridazine derivatives. The pyridazine derivatives are mostly present in biologically active compounds and are also present with different pharmacophores. Pyridazine is bioavailable (especially in the CNS) and can reduce toxicity. Pyridazine is a component of several drug molecules, and the pyridazine pharmacophore has contributed to a variety of pharmacologically active compounds.Recommanded Product: 3-Aminopyridazine

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Ultrasonicated synthesis of N-benzyl-2,3-substituted morpholines, via the Mitsunobu diol cyclisation was written by Reddy, B. Jayachandra;Reddy, M. C. Somasekhara. And the article was included in E-Journal of Chemistry in 2010.Name: 3-Aminopyridazine This article mentions the following:

A facile five-step synthesis of N-benzyl-2,3-substituted morpholines was performed. The key steps were microwave-assisted Friedel-Crafts acylation and diol cyclization carried out via an ultra sonication of Mitsunobu reaction using diethylazodicarboxylate, TPP in THF for 1 h. The morpholine products were generated as diastereomers which was separated by the column chromatog. in yields. The structure of compounds was characterized by the spectral data. In the experiment, the researchers used many compounds, for example, 3-Aminopyridazine (cas: 5469-70-5Name: 3-Aminopyridazine).

3-Aminopyridazine (cas: 5469-70-5) belongs to pyridazine derivatives. Pyridazine-based compounds continued to be a great source of biologically active compounds as evidenced by the number of publications which emerged in 2021. Specifically, the pyridazine moiety is an important structural feature of various pharmacologically important compounds with activities like antimicrobial, analgesic, anti-inflammatory, antiplatelet, anticancer, antisecretory, antiulcer, antidepressant, cardiotonic, vasodilator, antiarrhythmic, and hypocholesterolaemic.Name: 3-Aminopyridazine

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Manual and automated Cu-mediated radiosynthesis of the PARP inhibitor [¹⁸F]olaparib was written by Guibbal, Florian;Isenegger, Patrick G.;Wilson, Thomas C.;Pacelli, Anna;Mahaut, Damien;Sap, Jeroen B. I.;Taylor, Nicholas J.;Verhoog, Stefan;Preshlock, Sean;Hueting, Rebekka;Cornelissen, Bart;Gouverneur, Veronique. And the article was included in Nature Protocols in 2020.Category: pyridazine This article mentions the following:

Abstract: PET is a diagnostic nuclear imaging modality that relies on automated protocols to prepare agents labeled with a positron-emitting radionuclide (e.g., ¹⁸F). In recent years, new reactions have appeared for the ¹⁸F-labeling of agents that are difficult to access by applying traditional radiochem., for example those requiring ¹⁸F incorporation into unactivated (hetero)arenes. However, automation of these new methods for translation to the clinic has progressed slowly because extensive modification of manual protocols is typically required when implementing novel ¹⁸F-labeling methodologies within automated modules. Here, we describe the workflow that led to the automated radiosynthesis of the poly(ADP-ribose) polymerase (PARP) inhibitor [¹⁸F]olaparib. First, we established a robust manual protocol to prepare [¹⁸F]olaparib from the protected N-[2-(trimethylsilyl)ethoxy]methyl (SEM) arylboronate ester precursor in a 17% ± 5% (n = 15; synthesis time, 135 min) non-decay-corrected (NDC) activity yield, with molar activity (A_m) up to 34.6 GBq/μmol. Automation of the process, consisting of copper-mediated ¹⁸F-fluorodeboronation followed by deprotection, was achieved on an Eckert & Ziegler Modular-Lab radiosynthesis platform, affording [¹⁸F]olaparib in a 6% ± 5% (n = 3; synthesis time, 120 min) NDC activity yield with A_m up to 319 GBq/μmol. In the experiment, the researchers used many compounds, for example, Imidazo[1,2-b]pyridazine (cas: 766-55-2Category: pyridazine).

Imidazo[1,2-b]pyridazine (cas: 766-55-2) belongs to pyridazine derivatives. The pyridazine derivatives are mostly present in biologically active compounds and are also present with different pharmacophores. Specifically, the pyridazine moiety is an important structural feature of various pharmacologically important compounds with activities like antimicrobial, analgesic, anti-inflammatory, antiplatelet, anticancer, antisecretory, antiulcer, antidepressant, cardiotonic, vasodilator, antiarrhythmic, and hypocholesterolaemic.Category: pyridazine

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Unprotected Amino Acids as Stable Radical Precursors for Heterocycle C-H Functionalization was written by Mai, Duy N.;Baxter, Ryan D.. And the article was included in Organic Letters in 2016.Recommanded Product: 141-30-0 This article mentions the following:

An efficient and general method for the C-H alkylation of heteroarenes using unprotected amino acids as stable alkyl radical precursors is reported. This one-pot procedure is performed open to air under aqueous conditions and is effective for several natural and unnatural amino acids. Heterocycles of varying structure are suitably functionalized, and reactivity trends reflect the nucleophilic character of the radical species generated. In the experiment, the researchers used many compounds, for example, 3,6-Dichloropyridazine (cas: 141-30-0Recommanded Product: 141-30-0).

3,6-Dichloropyridazine (cas: 141-30-0) belongs to pyridazine derivatives. Pyridazine-based compounds continued to be a great source of biologically active compounds as evidenced by the number of publications which emerged in 2021. Pyridazine can act as a hydrogen bond acceptor to improve the physicochemical properties of drug molecules by increasing their water solubility, and has a high affinity for complexing with targets due to its dipole moment.Recommanded Product: 141-30-0

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Cu-Catalyzed Aerobic Oxidative Cyclization of Guanidylpyridines and Derivatives was written by Bartels, Bjorn;Bolas, Conor Gordon;Cueni, Philipp;Fantasia, Serena;Gaeng, Nicolas;Trita, Andrada Stefania. And the article was included in Journal of Organic Chemistry in 2015.Synthetic Route of C4H5N3 This article mentions the following:

A new method for the straightforward synthesis of 2-amino-[1,2,4]triazolo[1,5-a]pyridines and derivatives is presented. The target products are synthesized in high yields from guanidylpyridines and analogs via copper-catalyzed N-N coupling. The present methodol. shows a wide scope, tolerating not only different substituents on the pyridine ring but also different heterocylic rings such as pyrazines, pyrimidines, and pyridazines. In the experiment, the researchers used many compounds, for example, 3-Aminopyridazine (cas: 5469-70-5Synthetic Route of C4H5N3).

3-Aminopyridazine (cas: 5469-70-5) belongs to pyridazine derivatives. Pyridazines is a six-membered nitrogen-containing significant heterocycle. It has received considerable interest because of its useful applications as natural products, pharmaceuticals, and various bioactive molecules. Specifically, the pyridazine moiety is an important structural feature of various pharmacologically important compounds with activities like antimicrobial, analgesic, anti-inflammatory, antiplatelet, anticancer, antisecretory, antiulcer, antidepressant, cardiotonic, vasodilator, antiarrhythmic, and hypocholesterolaemic.Synthetic Route of C4H5N3

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem