Category: pyridazine

Mason, S. F. et al. published their research in Journal of the Chemical Society in 1959 | CAS: 19064-65-4

3-Methoxypyridazine (cas: 19064-65-4) 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 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-Methoxypyridazine

Electronic spectra of N-heteroaromatic systems. III. π → π transitions of the monocyclic hydroxyazines was written by Mason, S. F.. And the article was included in Journal of the Chemical Society in 1959.Recommanded Product: 3-Methoxypyridazine This article mentions the following:

The ultraviolet absorption spectra of the enolic, cationic, anionic, and zwitterionic forms of the monocyclic hydroxyazines have been measured in aqueous solution, and the spectra of the enols and zwitterions, fixed as the O- and the N-Me derivatives, resp., have been obtained in nonpolar solvents. The first absorption band in the spectra of the different charged forms of a given compound lies at wave lengths in the sequence, zwitterion > anion > cation > enol, and the spectrum of the zwitterion shifts considerably towards the red region on changing from aqueous to nonpolar solvents. The solvent effect is inconsistent with the valence-bond theory of the spectra, and a mol.-orbital theory is developed to account for the solvent shifts and the spectral differences between the compounds studied and their various charged forms. The electronic absorption spectra of the 4 forms and the oscillator strength of the π → π absorption band of longest wave length in the spectra of the enolic and zwitterionic forms are given for 2-hydroxy-, 2-methoxy-, 3-hydroxy-, 3-methoxy-, 4-hydroxy-, and 4-methoxypyridine, 1-methyl-2- and 1-methyl-4-pyridone, 3-hydroxypyridine 1-methochloride, 2-hydroxy- and 2-methoxypyrazine, 1-methyl-2-pyrazone, 3-hydroxy-, 3-methoxy-, 4-hydroxy-, and 4-methoxypyridazine, 2-hydroxy-, 2-methoxy-, 4-hydroxy-, 4-methoxy-, and 5-hydroxypyrimidine, 1- and 3-methyl-4-pyrimidone, in various solvents, at different pH values. In the experiment, the researchers used many compounds, for example, 3-Methoxypyridazine (cas: 19064-65-4Recommanded Product: 3-Methoxypyridazine).

3-Methoxypyridazine (cas: 19064-65-4) 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 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-Methoxypyridazine

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

 

Mason, S. F. et al. published their research in Journal of the Chemical Society in 1957 | CAS: 19064-65-4

3-Methoxypyridazine (cas: 19064-65-4) 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.Application of 19064-65-4

The tautomerism of N-heteroaromatic hydroxy compounds. I. Infrared spectra was written by Mason, S. F.. And the article was included in Journal of the Chemical Society in 1957.Application of 19064-65-4 This article mentions the following:

The IR spectra of 37 N-heterocyclic hydroxy compounds have been measured in the O-H, N-H, and double-bond stretching-vibration regions by use of a Perkin-Elmer model 12C spectrometer with a LiF or NaCl prism. The compounds were examined at concentrations of 10-2 to 10-3M in cells of 5 cm. (CCl4) or 1 cm. (CHCl3) thickness in the O-H and N-H regions, and 1 mm. in the double-bond region, and as solids included in pressed KBr disks. The compounds with a OH group α or γ to a ring-N atom absorb in the N-H and C:O stretching vibration regions both in the solid state and in CHCl3 solution, and so possess principally amide structures under these conditions. The remaining compounds have mainly enolic structures in solution, showing absorption due to a free or an intramolecularly H-bonded O-H group. The IR evidence for the zwitterionic structure of the latter group of compounds in the solid state is discussed. The compounds which tautomerize to an amide with a quasi ο-quinonoid structure show an N-H stretching vibration absorption in the range 3360-3420 cm.-1, while their quasi p-quinonoid isomers absorb in the range 3415-45 cm.-1, and their analogs with 5-membered rings in the range 3440-85 cm.-1 The position of the C:O band of such compounds depends upon the structural type and the number of N atoms in the ring carrying the potentially tautomeric OH group. For nuclei similarly substituted, the C:O band of the quasiο-quinonoid amides lies at a higher frequency than that of the quasi p-quinonoid isomers. The structures of some dihydroxy and polyaza compounds are elucidated by means of these correlations. In the experiment, the researchers used many compounds, for example, 3-Methoxypyridazine (cas: 19064-65-4Application of 19064-65-4).

3-Methoxypyridazine (cas: 19064-65-4) 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.Application of 19064-65-4

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

 

Wermuth, Camille Georges et al. published their research in Journal of Medicinal Chemistry in 1987 | CAS: 105537-97-1

5-Phenylpyridazin-3-amine (cas: 105537-97-1) 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.Quality Control of 5-Phenylpyridazin-3-amine

Synthesis and structure-activity relationships of a series of aminopyridazine derivatives of γ-aminobutyric acid acting as selective GABA-A antagonists was written by Wermuth, Camille Georges;Bourguignon, Jean Jacques;Schlewer, Gilbert;Gies, Jean Pierre;Schoenfelder, Angele;Melikian, Anita;Bouchet, Marie Jeanne;Chantreux, Dominique;Molimard, Jean Charles. And the article was included in Journal of Medicinal Chemistry in 1987.Quality Control of 5-Phenylpyridazin-3-amine The following contents are mentioned in the article:

Thirty-eight title compounds, e.g., I, were prepared by attaching various pyridazinic structures to GABA or GABA-like side chains. Thus, aminopyridazine II was treated with BrCH2CH2CO2Et, followed by K2CO3 and then HCl-AcOH to give I. Most of the compounds displaced [3H]GABA from rat brain membranes. All the active compounds antagonized the GABA-elicited enhancement of [3H]diazepam binding, strongly suggesting that all these compounds are GABA-A receptor antagonists. None of the compounds that displaced [3H]GABA from rat brain membranes interacted with other GABA recognition sites (GABA-B receptor, GABA uptake binding site, glutamate decarboxylase, GABA-transaminase). They did not interact with the Cl– ionophore associated with the GABA-A receptor and did not interact with the benzodiazepine, strychnine, and glutamate binding sites. Thus, these compounds appear to be specific GABA-A receptor antagonists. In terms of structure-activity, it is concluded that a GABA moiety bearing a pos. charge is necessary for optimal GABA-A receptor recognition. Addnl. binding sites are tolerated only if they are part of a charge-delocalized amidinic or guanidinic system. If this delocalization is achieved by linking a butyric acid moiety to the N(2) nitrogen of a 3-aminopyridazine, GABA-antagonistic character is produced. The highest potency (≃250 times bicuculline) was observed when an aromatic π system, bearing electron-donating substituents, was present on the 6-position of the pyridazine ring. This study involved multiple reactions and reactants, such as 5-Phenylpyridazin-3-amine (cas: 105537-97-1Quality Control of 5-Phenylpyridazin-3-amine).

5-Phenylpyridazin-3-amine (cas: 105537-97-1) 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.Quality Control of 5-Phenylpyridazin-3-amine

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

 

Chen, Zhao et al. published their research in Journal of Medicinal Chemistry in 2019 | CAS: 1439400-46-0

N-(6-Chloropyridazin-3-yl)-2-(3-(trifluoromethoxy)phenyl)acetamide (cas: 1439400-46-0) belongs to pyridazine derivatives. The pyridazine derivatives are mostly present in biologically active compounds and are also present with different pharmacophores. 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.Application In Synthesis of N-(6-Chloropyridazin-3-yl)-2-(3-(trifluoromethoxy)phenyl)acetamide

Novel 1,3,4-Selenadiazole-Containing Kidney-Type Glutaminase Inhibitors Showed Improved Cellular Uptake and Antitumor Activity was written by Chen, Zhao;Li, Di;Xu, Ning;Fang, Jinzhang;Yu, Yan;Hou, Wei;Ruan, Haoqiang;Zhu, Panpan;Ma, Renchao;Lu, Shiying;Cao, Danhui;Wu, Rui;Ni, Mowei;Zhang, Wei;Su, Weike;Ruan, Benfang Helen. And the article was included in Journal of Medicinal Chemistry in 2019.Application In Synthesis of N-(6-Chloropyridazin-3-yl)-2-(3-(trifluoromethoxy)phenyl)acetamide The following contents are mentioned in the article:

Kidney-type glutaminase [KGA/isoenzyme glutaminase C (GAC)] is becoming an important tumor metabolism target in cancer chemotherapy. Its allosteric inhibitor, CB839, showed early promise in cancer therapeutics but limited efficacy in in vivo cancer models. To improve the in vivo activity, the authors explored a bioisostere replacement of the sulfur atom in bis-2-(5-phenylacetamido-1,2,4-thiadiazol)ethyl sulfide and CB839 analogs with selenium using a novel synthesis of the selenadiazole moiety from carboxylic acids or nitriles. The resulting selenadiazole compounds showed enhanced KGA inhibition, more potent induction of reactive oxygen species, improved inhibition of cancer cells, and higher cellular and tumor accumulation than the corresponding sulfur-containing mols. However, both CB839 and its selenium analogs show incomplete inhibition of the tested cancer cells, and a partial reduction in tumor size was observed in both the glutamine-dependent HCT116 and aggressive H22 liver cancer xenograft models. Despite this, tumor tissue damage and prolonged survival were observed in animals treated with the selenium analog of CB839. This study involved multiple reactions and reactants, such as N-(6-Chloropyridazin-3-yl)-2-(3-(trifluoromethoxy)phenyl)acetamide (cas: 1439400-46-0Application In Synthesis of N-(6-Chloropyridazin-3-yl)-2-(3-(trifluoromethoxy)phenyl)acetamide).

N-(6-Chloropyridazin-3-yl)-2-(3-(trifluoromethoxy)phenyl)acetamide (cas: 1439400-46-0) belongs to pyridazine derivatives. The pyridazine derivatives are mostly present in biologically active compounds and are also present with different pharmacophores. 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.Application In Synthesis of N-(6-Chloropyridazin-3-yl)-2-(3-(trifluoromethoxy)phenyl)acetamide

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

 

Sitamze, Jean Marie et al. published their research in Journal of Organic Chemistry in 1992 | CAS: 105537-97-1

5-Phenylpyridazin-3-amine (cas: 105537-97-1) 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.Category: pyridazine

A general and convenient synthesis of 3-aminopyridazines was written by Sitamze, Jean Marie;Schmitt, Martine;Wermuth, Camille Georges. And the article was included in Journal of Organic Chemistry in 1992.Category: pyridazine The following contents are mentioned in the article:

Hydrogenolysis of 3-hydrazinopyridazines I (R = H, Ph, 4-MeOC6H4; R1 = H, Me, Pr, Ph; R2 = H, Me, Et, CHMe2, CH2Ph, CH2CH2Ph; R3 = NHNH2) by means of nickel-aluminum alloy in alk. medium yield the corresponding 3-aminopyridazines I (R3 = NH2) in approx. 80 % yield. This study involved multiple reactions and reactants, such as 5-Phenylpyridazin-3-amine (cas: 105537-97-1Category: pyridazine).

5-Phenylpyridazin-3-amine (cas: 105537-97-1) 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.Category: pyridazine

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

 

Haider, N. et al. published their research in Science of Synthesis in 2004 | CAS: 105537-97-1

5-Phenylpyridazin-3-amine (cas: 105537-97-1) belongs to pyridazine derivatives. Pyridazines are rare in nature, possibly reflecting the scarcity of naturally occurring hydrazines, common building blocks for the synthesis of these heterocycles. 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.Quality Control of 5-Phenylpyridazin-3-amine

Product class 8: pyridazines was written by Haider, N.;Holzer, W.. And the article was included in Science of Synthesis in 2004.Quality Control of 5-Phenylpyridazin-3-amine The following contents are mentioned in the article:

A review. Methods of preparing pyridazines are reviewed including cyclization, ring transformation, aromatization, and substituent modification. This study involved multiple reactions and reactants, such as 5-Phenylpyridazin-3-amine (cas: 105537-97-1Quality Control of 5-Phenylpyridazin-3-amine).

5-Phenylpyridazin-3-amine (cas: 105537-97-1) belongs to pyridazine derivatives. Pyridazines are rare in nature, possibly reflecting the scarcity of naturally occurring hydrazines, common building blocks for the synthesis of these heterocycles. 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.Quality Control of 5-Phenylpyridazin-3-amine

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

 

Heinisch, Gottfried’s team published research in Monatshefte fuer Chemie in 107 | CAS: 50901-42-3

Monatshefte fuer Chemie published new progress about 50901-42-3. 50901-42-3 belongs to pyridazine, auxiliary class Pyridazine,Aldehyde, name is Pyridazine-4-carbaldehyde, and the molecular formula is C5H4N2O, Safety of Pyridazine-4-carbaldehyde.

Heinisch, Gottfried published the artcileSyntheses and reactions of pyridazine derivatives, VI. 1,2-Dipyridazinylethene- and -ethane-1,2-diols from pyridazine carboxaldehydes, Safety of Pyridazine-4-carbaldehyde, the publication is Monatshefte fuer Chemie (1976), 107(3), 799-808, database is CAplus.

Treatment of pyridazine-4-carboxaldehyde with catalytic amounts of KCN gave pyridazine-4-carboxylic acid and two stereoisomeric diols I, II. Pyridazine-3-carboxaldehyde reacts with HCN to give III. HCN-elimination from III yields the enediol IV which is oxidized to pyridazine-3-carboxylic acid or its methyl ester.

Monatshefte fuer Chemie published new progress about 50901-42-3. 50901-42-3 belongs to pyridazine, auxiliary class Pyridazine,Aldehyde, name is Pyridazine-4-carbaldehyde, and the molecular formula is C5H4N2O, Safety of Pyridazine-4-carbaldehyde.

Referemce:
https://en.wikipedia.org/wiki/Pyridazine,
Pyridazine | C4H4N2 – PubChem

 

Heinisch, Gottfried’s team published research in Monatshefte fuer Chemie in 108 | CAS: 50901-42-3

Monatshefte fuer Chemie published new progress about 50901-42-3. 50901-42-3 belongs to pyridazine, auxiliary class Pyridazine,Aldehyde, name is Pyridazine-4-carbaldehyde, and the molecular formula is C5H4N2O, Formula: C5H4N2O.

Heinisch, Gottfried published the artcilePyridazines. 7. Preparation of pyridazine-3-carboxaldehyde: synthesis and reactivity studies, Formula: C5H4N2O, the publication is Monatshefte fuer Chemie (1977), 108(1), 213-24, database is CAplus.

MnO2-oxidation of 3-pyridazinemethanol gave 3-pyridazinecarboxaldehyde (I). Properties of I and its reactions with NH compounds and methylpiridazines were studied. Reaction of I with 3-methylpiridazine gave mainly products of aldol addition II and III. Elimination of H2O from II gave the alkene IV. Isolation of dipyridazinylethane V as main product of reaction of I with 4-methylpiperazine however shows, that thermally induced dismutation cannot be excluded also on pyridazinyl-3-carbinols.

Monatshefte fuer Chemie published new progress about 50901-42-3. 50901-42-3 belongs to pyridazine, auxiliary class Pyridazine,Aldehyde, name is Pyridazine-4-carbaldehyde, and the molecular formula is C5H4N2O, Formula: C5H4N2O.

Referemce:
https://en.wikipedia.org/wiki/Pyridazine,
Pyridazine | C4H4N2 – PubChem

 

Yamane, Daiki’s team published research in Chemical Science in 13 | CAS: 50901-42-3

Chemical Science published new progress about 50901-42-3. 50901-42-3 belongs to pyridazine, auxiliary class Pyridazine,Aldehyde, name is Pyridazine-4-carbaldehyde, and the molecular formula is C4H8Cl2S2, Recommanded Product: Pyridazine-4-carbaldehyde.

Yamane, Daiki published the artcileSelective covalent targeting of SARS-CoV-2 main protease by enantiopure chlorofluoroacetamide, Recommanded Product: Pyridazine-4-carbaldehyde, the publication is Chemical Science (2022), 13(10), 3027-3034, database is CAplus and MEDLINE.

An irreversible SARS-CoV-2 Mpro inhibitor possesseschlorofluoroacetamide (CFA) as a warhead for the covalent modification of Mpro. Ugi multicomponent reaction using chlorofluoroacetic acid enabled the rapid synthesis of dipeptidic CFA derivatives RC(O)N(C6H5R1)CH(R2)C(O)NHR3 (R = Ac, ethenyl, difluoroacetyl, furan-2-yl; R1 = i-Pr, t-Bu, 1-methylcyclohexyl, etc.; R2 = pyridin-3-yl, pyridazin-4-yl, pyridazin-3-yl, etc.; R3 = t-Bu, isoquinolin-7-yl, 2-(3-fluorophenyl)ethyl, etc.) that identified (SR)/(RR)/(RS)(SS)-2-chloro-2-fluoro-N-(2-[(3-fluorophenethyl)amino]-2-oxo-1-(pyrimidin-5-yl)ethyl)-N-[4-(pentafluoro-lmbda6-sulfaneyl)phenyl]acetamide as a potent inhibitor of SARS-CoV-2 Mpro. Among the four stereoisomers, (R)-2-chloro-2-fluoro-N-((R)-2-[(3-fluorophenethyl)amino]-2-oxo-1-(pyrimidin-5-yl)ethyl)-N-[4-(pentafluoro-lamda6-sulfaneyl)phenyl]acetamide exhibited a markedly higher inhibitory activity against Mpro than the other isomers. Reaction kinetics and computational docking studies suggest that the R configuration of the CFA warhead is crucial for the rapid covalent inhibition of Mpro. These findings highlight the prominent influence of the CFA chirality on the covalent modification of proteinous cysteines and provide the basis for improving the potency and selectivity of CFA-based covalent inhibitors.

Chemical Science published new progress about 50901-42-3. 50901-42-3 belongs to pyridazine, auxiliary class Pyridazine,Aldehyde, name is Pyridazine-4-carbaldehyde, and the molecular formula is C4H8Cl2S2, Recommanded Product: Pyridazine-4-carbaldehyde.

Referemce:
https://en.wikipedia.org/wiki/Pyridazine,
Pyridazine | C4H4N2 – PubChem

 

Mammoliti, Oscar’s team published research in Journal of Medicinal Chemistry in 64 | CAS: 1350543-95-1

Journal of Medicinal Chemistry published new progress about 1350543-95-1. 1350543-95-1 belongs to pyridazine, auxiliary class Pyridazine,Boronic acid and ester,Boronate Esters,Boronic Acids,Boronic acid and ester, name is 3-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridazine, and the molecular formula is C11H17BN2O2, Related Products of pyridazine.

Mammoliti, Oscar published the artcileDiscovery of the S1P2 Antagonist GLPG2938 (1-[2-Ethoxy-6-(trifluoromethyl)-4-pyridyl]-3-[[5-methyl-6-[1-methyl-3-(trifluoromethyl)pyrazol-4-yl]pyridazin-3-yl]methyl]urea), a Preclinical Candidate for the Treatment of Idiopathic Pulmonary Fibrosis, Related Products of pyridazine, the publication is Journal of Medicinal Chemistry (2021), 64(9), 6037-6058, database is CAplus and MEDLINE.

Mounting evidence from the literature suggests that blocking S1P2 receptor (S1PR2) signaling could be effective for the treatment of idiopathic pulmonary fibrosis (IPF). However, only a few antagonists have been so far disclosed. A chem. enablement strategy led to the discovery of a pyridine series with good antagonist activity. A pyridazine series with improved lipophilic efficiency and with no CYP inhibition liability was identified by scaffold hopping. Further optimization led to the discovery of 40 (GLPG2938)(I), a compound with exquisite potency on a phenotypic IL8 release assay, good pharmacokinetics, and good activity in a bleomycin-induced model of pulmonary fibrosis.

Journal of Medicinal Chemistry published new progress about 1350543-95-1. 1350543-95-1 belongs to pyridazine, auxiliary class Pyridazine,Boronic acid and ester,Boronate Esters,Boronic Acids,Boronic acid and ester, name is 3-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridazine, and the molecular formula is C11H17BN2O2, Related Products of pyridazine.

Referemce:
https://en.wikipedia.org/wiki/Pyridazine,
Pyridazine | C4H4N2 – PubChem