Heterocyclic Building Blocks-Pyridazine

Synthesis and characterization of some nitrogen containing heterocyclic derivatives via novel chalcones was written by Tupare, Shrikrishn D.. And the article was included in World Journal of Pharmaceutical Research in 2021.Electric Literature of C4H2Cl2N2 This article mentions the following:

A highly stable five-membered ring structures like 1, 3, 5-triphenyl 1H pyrazoles and its derivatives I [R = H, 2-NO₂, 4-NO₂] was prepared via novel chalcones II synthesized by aromatic ketone and aldehydes in alk. medium having heterocyclic moiety. These compounds were characterized using IR, ¹H-NMR and mass spectra and elemental anal. As per literature, they possess some potent biol. activities. Therefore, antibacterial and antifungal activities were screened for these derivatives most of the compounds were found to be the most active against bacterial and fungal human pathogens. In the experiment, the researchers used many compounds, for example, 3,6-Dichloropyridazine (cas: 141-30-0Electric Literature of C4H2Cl2N2).

3,6-Dichloropyridazine (cas: 141-30-0) belongs to pyridazine derivatives. The pyridazine structure is also found within the structure of several drugs such as cefozopran, cadralazine, minaprine, pipofezine, and hydralazine. 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.Electric Literature of C4H2Cl2N2

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Optimization of physicochemical properties for 4-anilinoquinazoline inhibitors of trypanosome proliferation was written by Woodring, Jennifer L.;Bachovchin, Kelly A.;Brady, Kimberly G.;Gallerstein, Mitchell F.;Erath, Jessey;Tanghe, Scott;Leed, Susan E.;Rodriguez, Ana;Mensa-Wilmot, Kojo;Sciotti, Richard J.;Pollastri, Michael P.. And the article was included in European Journal of Medicinal Chemistry in 2017.Related Products of 5469-70-5 This article mentions the following:

Human African trypanosomiasis (HAT) is a deadly disease in need of new chemotherapeutics that can cross into the central nervous system. The authors previously reported the discovery of (NEU-617), a small mol. with activity against T. brucei bloodstream proliferation. Further optimization of NEU-617 to improve the physicochem. properties (LogP, LLE, [1], and MPO score) [2] have led us to twelve sub-micromolar compounds, most importantly the headgroup variants I and II, and the linker variant III. Although these 3 compounds had reduced potency compared to NEU-617, they all had improved LogP, LLE and MPO scores. Cross-screening these analogs against other protozoan parasites uncovered IV with potent activity towards T. brucei, T. cruzi and L. major, while four others compounds showed activity towards P. falciparum D6. This reinforces the effectiveness of lead repurposing for the discovery of new protozoan disease therapeutics. In the experiment, the researchers used many compounds, for example, 3-Aminopyridazine (cas: 5469-70-5Related Products of 5469-70-5).

3-Aminopyridazine (cas: 5469-70-5) 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.Related Products of 5469-70-5

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

The effect of solvent on the synthesis of pyridazinones and some reactions of the new compounds was written by Sayed, Galal Hosni;Radwan, Azza;Hamed, Ashraf Ahmed;Boraie, Waleed El Sayed. And the article was included in Bulletin of the Chemical Society of Japan in 1993.Application of 2166-13-4 This article mentions the following:

The reaction of 4-aryl-4-oxo-2-(5-oxo-1,3-diphenyl-2-pyrazolin-4-yl)butanoic acids with hydrazine hydrate in ethanol afforded (oxopyrazolinyl)pyridazinones I (R = p-ClC₆H₄, p-tolyl); in 1-butanol pyrazolo[3,4-c]pyridazino[4,3-e]pyridazine derivative II was obtained, while in acetic acid the 6-aryl-3(2H)-pyridazinone was the product. A probable mechanism has been proposed. The behavior of I toward di-Me sulfate, di-Et sulfate, Et bromoacetate, p-anisaldehyde, phosphoryl chloride and phosphorus pentasulfide has been studied. In the experiment, the researchers used many compounds, for example, 6-(4-Chlorophenyl)pyridazin-3(2H)-one (cas: 2166-13-4Application of 2166-13-4).

6-(4-Chlorophenyl)pyridazin-3(2H)-one (cas: 2166-13-4) 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. 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.Application of 2166-13-4

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Discovery of VU6028418: A Highly Selective and Orally Bioavailable M₄ Muscarinic Acetylcholine Receptor Antagonist was written by Spock, Matthew;Carter, Trever R.;Bollinger, Katrina A.;Han, Changho;Baker, Logan A.;Rodriguez, Alice L.;Peng, Li;Dickerson, Jonathan W.;Qi, Aidong;Rook, Jerri M.;O’Neill, Jordan C.;Watson, Katherine J.;Chang, Sichen;Bridges, Thomas M.;Engers, Julie L.;Engers, Darren W.;Niswender, Colleen M.;Conn, P. Jeffrey;Lindsley, Craig W.;Bender, Aaron M.. And the article was included in ACS Medicinal Chemistry Letters in 2021.Quality Control of 3,6-Dichloropyridazine This article mentions the following:

Herein, we report the SAR leading to the discovery of VU6028418, a potent M₄ mAChR antagonist with high subtype-selectivity and attractive DMPK properties in vitro and in vivo across multiple species. VU6028418 was subsequently evaluated as a preclin. candidate for the treatment of dystonia and other movement disorders. During the characterization of VU6028418, a novel use of deuterium incorporation as a means to modulate CYP inhibition was also discovered. In the experiment, the researchers used many compounds, for example, 3,6-Dichloropyridazine (cas: 141-30-0Quality Control of 3,6-Dichloropyridazine).

3,6-Dichloropyridazine (cas: 141-30-0) belongs to pyridazine derivatives. The pyridazine structure is also found within the structure of several drugs such as cefozopran, cadralazine, minaprine, pipofezine, and hydralazine. 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.Quality Control of 3,6-Dichloropyridazine

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Production of 6-arylpyridazin-3-ones was written by Anonymous. And the article was included in Research Disclosure in 1990.Reference of 2166-13-4 This article mentions the following:

The cyclization of benzoylacrylic acid derivatives with NH₃ and hydrazine derivatives gave phenylpyridazinone derivatives I (R = H, Me, F, Cl, Br, OMe; R¹ = H, CH₂OH, Ph, CH(OH)Ph, CH(OH)CH₂OBu, CH₂CO₂H). In the experiment, the researchers used many compounds, for example, 6-(4-Chlorophenyl)pyridazin-3(2H)-one (cas: 2166-13-4Reference of 2166-13-4).

6-(4-Chlorophenyl)pyridazin-3(2H)-one (cas: 2166-13-4) 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. Pyridazine compounds have attracted interest in various fields like medicinal, industrial, and agricultural research as they are used for numerous biological activities and other applications.Reference of 2166-13-4

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Saturated heterocycles. Part 226. Copper(II) chloride as an efficient reagent for the dehydrogenation of pyridazinone derivatives was written by Csende, Ferenc;Szabo, Zoltan;Bernath, Gabor;Stajer, Geza. And the article was included in Synthesis in 1995.HPLC of Formula: 2166-13-4 This article mentions the following:

A new procedure is described for the preparation of the pyridazinones I [R = H, Me, F, Cl, Br; R¹ = H; R¹₂ = (CH₂)₄] from the corresponding 4,5-dihydropyridazinones under mild conditions with CuCl₂ in MeCN via halogenation and spontaneous HCl elimination. For the trans-phthalazinone I [R = Me; R¹₂ = (CH₂)₄], the HCl elimination is 5 times faster than for its cis isomer. In the experiment, the researchers used many compounds, for example, 6-(4-Chlorophenyl)pyridazin-3(2H)-one (cas: 2166-13-4HPLC of Formula: 2166-13-4).

6-(4-Chlorophenyl)pyridazin-3(2H)-one (cas: 2166-13-4) belongs to pyridazine derivatives. The pyridazine derivatives are mostly present in biologically active compounds and are also present with different pharmacophores. 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: 2166-13-4

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Pyridazine series. Absorption spectrum of pyridazine was written by Evans, Richard Castleman;Wiselogle, F. Y.. And the article was included in Journal of the American Chemical Society in 1945.COA of Formula: C5H6N2O This article mentions the following:

α-Oxoglutaric acid (380 g.) in 600 cc. hot H₂O, added to 230 g. tech. NaOH and 340 g. N₂H₄.H₂SO₄ in 1.5 l. H₂O, gives 50% of 1,4,5,6-tetrahydro-6-oxo-3-pyridazinecarboxylic acid (I), m. 195-6°; dehydrogenation of 284 g. of I in 1 l. boiling AcOH with 360 g. tech. Br (several drops per sec.) gives 65% of 1,6-dihydro-6-oxo-3-pyridazinecarboxylic acid (II), m. 257° (decomposition). Decarboxylation of I by melting gives 23% of 4,5-dihydro-3(2)-pyridazone, m. 41-3°; II gives 90% of 3(2)-pyridazone (III), b₁ 146-8°, m. 102°. III (30 g.), treated with 50 cc. POCl₃ and stirred 45 min. at 65-75°, gives 68% of 3-chloropyridazine (IV), which decomposes rapidly at 95°/1 mm.; solutions of IV in EtOH appear to be relatively stable at room temperature IV (24 g.) in 20 cc. concentrated NH₄OH and 50 cc. 95% EtOH and 0.75 g. Pd on Norite A, hydrogenated at room temperature and 45 lb. pressure for 15-30 min., give 5.2 g. pyridazine (V), b₁ 47-8°, b. 205-6°, d₂₀²⁰ 1.111, n_D³⁰ 1.5148. The ultraviolet absorption curves are given for V in hexane and H₂O and for its HCl salt in H₂O. III (15 g.) and 10 g. Me₂SO₄ in 50 cc. MeOH, treated with 8 g. NaOH and refluxed 1 hr., give 2 g. of the 2-Me derivative (VI), hygroscopic, m. 38-9°. IV (12 g.) and MeONa in MeOH give 6 g. of 3-methoxypyridazine (VII), b₅ 77-8°, n_D³⁰ 1.5086; 3-EtO analog, b_2-3 69-71°, m. 35-6°, n_D³⁰ 1.5000, 56% yield. VI is thermally stable but VII slowly decomposes at room temperature In the experiment, the researchers used many compounds, for example, 3-Methoxypyridazine (cas: 19064-65-4COA of Formula: C5H6N2O).

3-Methoxypyridazine (cas: 19064-65-4) 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.COA of Formula: C5H6N2O

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Electrochemical reduction of azaaromatics. V. Influence of fluorine substitution on the electron affinities was written by Van den Ham, D. M. W.;Harrison, G. F. S.;Spaans, A.;Van der Meer, D.. And the article was included in Recueil des Travaux Chimiques des Pays-Bas in 1975.Synthetic Route of C4H2F2N2 This article mentions the following:

The electrochem. reduction process of fluoro-substituted azaaromatics, e.g., 3,6-difluoropyridazine, is described by the pattern which is normally postulated for aryl halogenides, that is, fission of the C-halogen bond. However, the stability of the intermediate mononegative ions is generally higher than for the comparable fluoro-substituted arenes. As an example of this stability, the ERS spectrum of tetrafluoroquinoxaline is given. The half-wave reduction potentials of the first reduction wave are related to the electron affinities of the molecules. These electron affinities are correlated with those obtained by semi-empirical quantum chem. calculations In the experiment, the researchers used many compounds, for example, 3,6-Difluoropyridazine (cas: 33097-39-1Synthetic Route of C4H2F2N2).

3,6-Difluoropyridazine (cas: 33097-39-1) 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 and derivatives coordinate readily with transition metals to form complexes and catalysts with synthetic utility.Synthetic Route of C4H2F2N2

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Study on the synthetic condition of aryloxypyridazinoxy lactates – effect of halides in 3,6-dihalide pyridazines on nucleophilic substitution reaction was written by Hu, Fang-Zhong;Wang, Xiang;Ren, Kang-Tai;Yang, Hua-Zheng. And the article was included in Youji Huaxue in 2002.Related Products of 33097-39-1 This article mentions the following:

The synthetic condition of aryloxypyridazinoxy lactates was studied. Aryloxypyridazinoxy lactates can be obtained by two methods. The effect of halides in 3,6-dihalide pyridazines on nucleophilic substitution reaction was studied, too. Calculation of mol. mechanics and quantum chem. indicated that 3,6-difluoropyridazine had an advantage over other 3,6-dihalide pyridazines when it was treated with nucleophilic reagents and confirmed by the exptl. results. In the experiment, the researchers used many compounds, for example, 3,6-Difluoropyridazine (cas: 33097-39-1Related Products of 33097-39-1).

3,6-Difluoropyridazine (cas: 33097-39-1) 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. 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.Related Products of 33097-39-1

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Synthesis and herbicidal activity of 3-aryloxy-6-chloro(or fluoro)pyridazines was written by Wang, Zhanping;Hu, Fangzhong;Zou, Xiaomao;Yang, Xiufeng;Yang, Huazheng. And the article was included in Nongyaoxue Xuebao in 2004.HPLC of Formula: 33097-39-1 This article mentions the following:

3-Aryloxy-6-chloro(or fluoro)pyridazines I (X = Cl, F; R = Me, NO₂, Cl, CF₃, NH₂, Br, OMe, COOEt, etc.) were prepared from the condensation of various substituted phenols with starting material 3, 6-dichloropyridazine and its fluorinated derivative, 3, 6-difluoropyridazine in high yields. All compounds were characterized by ¹H NMR and elemental analyses, and some of the compounds were confirmed by IR. Preliminary bioassay indicates that some of the title compounds showed herbicidal activity to some extents against Brassica napus and Echinochloa crus-galli, for example, at 100 μg/mL, the inhibition of compounds I (X = Cl, R = 3-Me, 3-NO₂ and X = F, R = 3-Me) against E. crus-gall are 95.7%, 96.1% and 91.2% , resp. In the experiment, the researchers used many compounds, for example, 3,6-Difluoropyridazine (cas: 33097-39-1HPLC of Formula: 33097-39-1).

3,6-Difluoropyridazine (cas: 33097-39-1) belongs to pyridazine derivatives. The pyridazine derivatives are mostly present in biologically active compounds and are also present with different pharmacophores. Pyridazine and derivatives coordinate readily with transition metals to form complexes and catalysts with synthetic utility.HPLC of Formula: 33097-39-1

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem