Heterocyclic Building Blocks-Pyridazine

Studies on diazepines. XIII. Photochemical behavior of pyrazine, pyrimidine, and pyridazine N-imides was written by Tsuchiya, Takashi;Kurita, Jyoji;Takayama, Kazuko. And the article was included in Chemical & Pharmaceutical Bulletin in 1980.Formula: C5H6N2O This article mentions the following:

Photolysis of various diazine N-ethoxycarbonylimides, I (R = H, Me; R¹, R² = H, Me, Ph), II, and III (R³ = R⁴ = H, Me; R³ = MeO, R⁴ = H) prepared from the corresponding diazines, gave the pyrazole derivatives, e.g. IV from pyrazine and pyridmidine N-imides, and the pyrrole derivatives from pyridazine N-imides. These photolyses may proceed by rearrangement to diaziridine intermediates, followed by ring expansion to the corresponding 1,2,5-, 1,2,4-, or 1,2,3-triazepines, which then undergo isomerization to the triazabicyclo[3.2.0]heptadienes, followed by elimination. In the experiment, the researchers used many compounds, for example, 3-Methoxypyridazine (cas: 19064-65-4Formula: C5H6N2O).

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

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Steric and electronic effects on the ¹H hyperpolarization of substituted pyridazines by signal amplification by reversible exchange was written by Rayner, Peter j.;Burns, Michael j.;Fear, Elizabeth j.;Duckett, Simon b.. And the article was included in Magnetic Resonance in Chemistry in 2021.Electric Literature of C5H6N2O This article mentions the following:

Utility of the pyridazine motif is growing in popularity as pharmaceutical and agrochem. agents. The detection and structural characterization of such materials is therefore imperative for the successful development of new products. Signal amplification by reversible exchange (SABRE) offers a route to dramatically improve the sensitivity of magnetic resonance methods, and we apply it here to the rapid and cost-effective hyperpolarization of substituted pyridazines. The 33 substrates investigated cover a range of steric and electronic properties and their capacity to perform highly effective SABRE is assessed. We find the method to be tolerant to a broad range of electron donating and withdrawing groups; however, good sensitivity is evident when steric bulk is added to the 3- and 6-positions of the pyridazine ring. We optimize the method by reference to a disubstituted ester that yields signal gains of >9000-fold at 9.4 T (>28% spin polarization). In the experiment, the researchers used many compounds, for example, 3-Methoxypyridazine (cas: 19064-65-4Electric Literature of C5H6N2O).

3-Methoxypyridazine (cas: 19064-65-4) belongs to pyridazine derivatives. The pyridazine structure is also found within the structure of several drugs such as cefozopran, cadralazine, minaprine, pipofezine, and hydralazine. 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.Electric Literature of C5H6N2O

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Discovery of imidazopyridine derivatives as novel c-Met kinase inhibitors: Synthesis, SAR study, and biological activity was written by Yang, Yifei;Zhang, Yuan;Yang, Ling Yun;Zhao, Leilei;Si, Lianghui;Zhang, Huibin;Liu, Qingsong;Zhou, Jinpei. And the article was included in Bioorganic Chemistry in 2017.Related Products of 33050-32-7 This article mentions the following:

Receptor tyrosine kinase c-Met acts as an alternative angiogenic pathway in the process and contents of cancers. A series of imidazopyridine derivatives were designed and synthesized according to the established docking studies as possible c-Met inhibitors. Most of these imidazopyridine derivatives displayed nanomolar potency against c-Met in both biochem. enzymic screens and cellular pharmacol. studies. Especially, compound 7 g exhibited the most inhibitory activity against c-Met with IC₅₀ of 53.4 nM and 253 nM in enzymic and cellular level, resp. Following that, the compound 7 g was docked into the protein of c-Met and the structure-activity relationship was analyzed in detail. These findings indicated that the novel imidazopyridine derivative compound 7 g was a potential c-Met inhibitor deserving further investigation for cancer treatment. In the experiment, the researchers used many compounds, for example, 6-Chloro-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (cas: 33050-32-7Related Products of 33050-32-7).

6-Chloro-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (cas: 33050-32-7) 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.Related Products of 33050-32-7

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Pyridazines. XXI. Reaction of 1-methylpyridazinium salts with potassium cyanide was written by Kaneko, Chisato;Tsuchiya, Takashi;Igeta, Hiroshi. And the article was included in Chemical & Pharmaceutical Bulletin in 1973.Related Products of 19064-65-4 This article mentions the following:

The reaction of pyridazinium sulfates, prepared from the corresponding pyridazines and Me2SO4, with KCN was studied. The pyridazines (I, R = H, Me, MeO; R1 = R2 = H) gave dimers II and III and the pyridazinone IV. 3-Phenylpyridazines (I, R = Ph; R1 = R2 = H, Me) gave the 4-pyridazinenitriles (V) as the main product. Other pyridazines (e.g., I, R = R2 = H, R1 = Me; R = R2 = Me, R1 = H; R = MeO, R1 = H, R2 = Me) gave various cyano- and dicyanopyridazines. The mechanism of their formation were discussed. In the experiment, the researchers used many compounds, for example, 3-Methoxypyridazine (cas: 19064-65-4Related Products of 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 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.Related Products of 19064-65-4

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Synthesis of pyridazine derivatives. VIII. Imidazo[1,2-b]pyridazines and some tricyclic aza analogs was written by Stanovnik, B.;Tisler, Miha. And the article was included in Tetrahedron in 1967.Reference of 13493-79-3 This article mentions the following:

6-Substituted and 3,6-disubstituted imidazo[1,2-b]pyridazines were prepared Some of these derivatives were used for convenient syntheses of a new azaheterocycle, imidazo[1,2-b]-s-triazolo-[3,4-f]pyridazine (I) and its derivatives Another new heterocyclic system, imidazo [1,2-b]tetrazolo[5,1-f]pyridazine (II) was also prepared 40 references. In the experiment, the researchers used many compounds, for example, 6-Chloroimidazo[1,2-b]pyridazine hydrochloride (cas: 13493-79-3Reference of 13493-79-3).

6-Chloroimidazo[1,2-b]pyridazine hydrochloride (cas: 13493-79-3) 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.Reference of 13493-79-3

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Synthesis and herbicidal evaluation of 3-N-substituted amino-6-benzyloxypyridazine derivatives was written by Zhang, Min;Hu, Fang-Zhong;Zhao, Ting;Yang, Liu-Qing;Yang, Hua-Zheng. And the article was included in Journal of Heterocyclic Chemistry in 2014.Reference of 33097-39-1 This article mentions the following:

A variety of 3-amino-6-benzyloxypyridazine derivatives I (R¹ = 2-OMe, 3,5-Me₂, 4-NO₂, etc.; R² = NMe₂, piperidin-1-yl, morpholin-4-yl) were designed and synthesized in satisfactory yields. The compound I (R¹ = 4-NO₂; R² = piperidin-1-yl) was further determined by X-ray diffraction crystallog. The synthesized compounds herbicidal activities were evaluated against barnyard grass and rape. Most of the compounds I displayed moderate herbicidal activities against the dicotyledonous plant Brassica campestris L. The most active compounds in the laboratory were also evaluated in the greenhouse. In the experiment, the researchers used many compounds, for example, 3,6-Difluoropyridazine (cas: 33097-39-1Reference 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. 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.Reference of 33097-39-1

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Acids of the pyridazine series. I. New preparations of 3-chloro-6-pyridazinyloxyacetic acid and some of its derivatives was written by Rosseels, G.. And the article was included in Bulletin des Societes Chimiques Belges in 1964.Recommanded Product: 3-Methoxypyridazine This article mentions the following:

Treatment of dimethylaminoethylamine with chloroacetyl chloride in EtOAc at 0° led to the hydrochloride of R₂NCH₂CH₂NHCOCH₂Cl (I, R = Me), m. 121°, in 50% yield. Similarly, the hydrochloride of N,N-diethylaminoethyl-2-chloroacetamide (I, R = Et), m. 77° was prepared in 50% yield from diethylaminoethylamine. Treatment of 3,6-dichloropyridazine with glycolic acid in alk. solution afforded 65% 3-chloro-6-pyridazinyloxyacetic acid (II, R = H), m. 145°, 278 mμ (log ε 3.27). Reaction of 3-chloropyridazin-6-one with chloroacetic acid in KOH solution gave 85% 3-chloro-6-oxo-1-pyridazinylacetic acid (III, R = OH), m. 220°, k 300 mμ (log ε 3.47). Et diazoacetate reacts with 3-chloropyridazin-6-one in C₆H₆ in the presence of Cu powder to give a mixture of Et 3-chloro-6-pyridazinyloxyacetate (II, R = Et), b_0.2 120-4°, m. 67° (60%), and Et 3-chloro-6-oxo-1-pyridazinylacetate (III, R = OEt), b_0.2 131-5°, m. 78° (6.7%). The major product (II, R = Et) was identified by the similarity of its ultraviolet and infrared spectra to those of II (R = H) to which it was converted by alk. hydrolysis. Esterification of II (R = H) with EtOH and H₂SO₄ gave II (R = Et) which was identical with the product from the diazoacetate reaction. Et glycolate reacted with 3,6-dichloropyridazine to give II (R = Et) directly in 60% yield. The minor product (III, R = OEt) was similarly identified by its spectra and hydrolysis to 3-chloro-6-oxo-1-pyridazinylacetic acid (III, R = OH) which was reesterified to give III (R = OEt), which was independently prepared by the action of Et chloroacetate on 3-chloropyridazin-6-one. Attempts to chlorinate 3-oxo-6-pyridazinylacetic acid with POCla led only to 3-chloropyridazin-6-one, m. 140°. Treatment with POCl₃ of 3-hydroxy-6-oxo-1-pyridazinylacetic acid gave 3,6-dichloropyridazine. Reaction of II (R = H) with 2-chloro-1-dimethylaminoethane (IV) in iso-PrOH led, in 60% yield, to dimethylaminoethyl 3-chloro-6-pyridazinyloxyacetate (II, R = CH₂CH₂NMe₂) hydrochloride, m. 120°, X 275 mμ (log ε 3.240). Similarly, II (R = H) was converted to the hydrochloride of II (R = CH₂CH₂NEt₂), m. 118°, in 50% yield, by reaction with 2-chloro-1-diethylaminoethane (V). Treatment of III (R = OH) with IV or V led to the hydrochloride of III (R = CH₂CH₂NMe₂), m. 120°, in 60% yield or the hydrochloride of III (R = CH₂CH₂NEt₂), m. 118°, in 58% yield, resp. Reaction of IV with 3-oxo-6-pyridazinyloxyacetic acid and working up with tartaric acid led to the tartrate of dimethylaminoethyl 3-oxo-6pyridazinyloxyacetate, m. 314° (decomposition), in 50% yield. Similarly, the tartrate of dimethylaminoethyl 3-hydroxy-6-oxo-1-pyridazinylacetate, m. 310° (decomposition), was prepared in 51% yield from 3-hydroxy-6-oxo-1-pyridazinylacetic acid and IV and working up with tartaric acid. The hydrochloride of the β-dimethylaminoethylamide of 3-chloro-6-oxo-1-pyridazinylacetic acid (III, R = NHCH₂CH₂NMe₂.HCl), m. 263°, was prepared in 50% yield from I (R = Me) and 3-chloropyridazin-6-one. Similarly, III (R = NHCH₂CH₂NEt₂.HCl), m. 258°, was prepared in 50% yield from I (R = Et) and 3-chloropyridazin-6-one. 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. 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.Recommanded Product: 3-Methoxypyridazine

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Photochemistry. VI. Photo-induced methylation of pyridazines was written by Tsuchiya, Takashi;Arai, Heihachiro;Igeta, Hiroshi. And the article was included in Chemical & Pharmaceutical Bulletin in 1972.Recommanded Product: 19064-65-4 This article mentions the following:

Irradiation of pyridazine (I, R = R1 = H) (MeOH containing 5% HCl) gave II (R = R1 = H) and III (R = R1 = H). I (R = H, R1 = Me) gave II (R = H, R1 = Me; R = Me, R1 = H) and III (R = H, R1 = Me). I (R = MeO, R1 = H) gave II (R = H, R1 = MeO; R = Me, R1 = MeO). I (R = R1 = Me) gave II (R = R1 = Me) and III (R = R1 = Me). I (R = Me, R1 = MeO) gave only II (R = Me, R1 = MeO). I (R = Me, R1 = Cl; R = R1 = Cl; R = Cl, R1 = Ph, gave the 5-methylated and 4,5-dimethylated compounds resp. I (R = Cl, R1 = H) (IV) did not give monomethylation, but gave III (R = Cl, R1 = H) (1-2%), due to decomposition of IV. In the experiment, the researchers used many compounds, for example, 3-Methoxypyridazine (cas: 19064-65-4Recommanded Product: 19064-65-4).

3-Methoxypyridazine (cas: 19064-65-4) belongs to pyridazine derivatives. Pyridazine and phthalazine have quite different spectroscopic properties compared with their isomers, pyrazine and quinoxaline. In the past decade, X-ray data were reported with regard to the characterization and structural elucidation of a number of pyridazine-metal complexes, including pyridazine ligands with zinc, nickel, copper, cadmium and ruthenium.Recommanded Product: 19064-65-4

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Ring-closing metathesis for the synthesis of heteroaromatics: evaluating routes to pyridines and pyridazines was written by Donohoe, Timothy J.;Bower, John F.;Basutto, Jose A.;Fishlock, Lisa P.;Procopiou, Panayiotis A.;Callens, Cedric K. A.. And the article was included in Tetrahedron in 2009.Application In Synthesis of 3-Methoxypyridazine This article mentions the following:

Ring-closing olefin metathesis (RCM) has been applied to the efficient synthesis of densely and diversely substituted pyridine and pyridazine frameworks. Routes to suitable metathesis precursors have been investigated and the scope of the metathesis step has been probed. The metathesis products function as precursors to the target heteroaromatic structures via elimination of a suitable leaving group, which also facilitates earlier steps by serving as a protecting group at nitrogen. Further functionalization of the metathesis products is possible both prior to and after aromatization. The net result is a powerful strategy for the de novo synthesis of highly substituted heteroaromatic scaffolds. In the experiment, the researchers used many compounds, for example, 3-Methoxypyridazine (cas: 19064-65-4Application In Synthesis of 3-Methoxypyridazine).

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

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Discovery of Reldesemtiv, a Fast Skeletal Muscle Troponin Activator for the Treatment of Impaired Muscle Function was written by Collibee, Scott E.;Bergnes, Gustave;Chuang, Chihyuan;Ashcraft, Luke;Gardina, Jeffrey;Garard, Marc;Jamison, Chris R.;Lu, Kevin;Lu, Pu-Ping;Muci, Alexander;Romero, Antonio;Valkevich, Ellen;Wang, Wenyue;Warrington, Jeffrey;Yao, Bing;Durham, Nickie;Hartman, James;Marquez, Anna;Hinken, Aaron;Schaletzky, Julia;Xu, Donghong;Hwee, Darren T.;Morgans, David;Malik, Fady I.;Morgan, Bradley P.. And the article was included in Journal of Medicinal Chemistry in 2021.HPLC of Formula: 33097-39-1 This article mentions the following:

Herein, the discovery of reldesemtiv I, a second-generation fast skeletal muscle troponin activator (FSTA) that increases force production at submaximal stimulation frequencies, is reported. Property-based optimization of high throughput screening hit, 4-(4-fluorobenzyl)-5-(phenethylamino)-1,2,4-thiadiazole, led to compounds with improved free exposure and in vivo muscle activation potency compared to the first-generation FSTA, tirasemtiv. The compound I demonstrated increased muscle force generation in a phase 1 clin. trial and is currently being evaluated in clin. trials for the treatment of amyotrophic lateral sclerosis. 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. 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. In the past decade, X-ray data were reported with regard to the characterization and structural elucidation of a number of pyridazine-metal complexes, including pyridazine ligands with zinc, nickel, copper, cadmium and ruthenium.HPLC of Formula: 33097-39-1

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem