Category: pyridazine

Salisbury, R. G.’s team published research in Journal of Heterocyclic Chemistry in 1967 | CAS: 5788-60-3

3-Chloro-6-propoxypyridazine(cas: 5788-60-3) belongs to pyridazine derivatives.The pyridazine derivatives are mostly present in biologically active compounds and are also present with different pharmacophores. Pyridazines are also important because of their utility in synthetic organic chemistry and in physical organic chemistry.There are reports available for the synthesis of pyridazine and their derivatives by using 2-oxoaldehyes.HPLC of Formula: 5788-60-3

《Diazine systems. I. Infrared spectra of 3,6-disubstituted pyridazines》 was published in Journal of Heterocyclic Chemistry in 1967. These research results belong to Salisbury, R. G.; Ryan, D. P.; Mason, James W.. HPLC of Formula: 5788-60-3 The article mentions the following:

The ir spectra of 26 3-halo-6-alkoxypyridazines (I) was given. Three bands at 1600-1540, 1325-1295, and 1065-935 cm.-1, found in all spectra gave evidence for the presence of the pyridazine nucleus. The bands at 1450-1400 cm.-1 were subject to many interfering factors. The H in-plane and out-of-plane deformation bands at 1150-1100 and 860-830 cm.-1 were useful in determining the substitution pattern. In the part of experimental materials, we found many familiar compounds, such as 3-Chloro-6-propoxypyridazine(cas: 5788-60-3HPLC of Formula: 5788-60-3)

3-Chloro-6-propoxypyridazine(cas: 5788-60-3) belongs to pyridazine derivatives.The pyridazine derivatives are mostly present in biologically active compounds and are also present with different pharmacophores. Pyridazines are also important because of their utility in synthetic organic chemistry and in physical organic chemistry.There are reports available for the synthesis of pyridazine and their derivatives by using 2-oxoaldehyes.HPLC of Formula: 5788-60-3

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

 

Al-Awadi, Nouria’s team published research in Journal of the Chemical Society in 1986 | CAS: 62567-44-6

3-Ethoxypyridazine(cas: 62567-44-6) belongs to pyridazine derivatives.The pyridazine derivatives are mostly present in biologically active compounds and are also present with different pharmacophores. Pyridazines are also important because of their utility in synthetic organic chemistry and in physical organic chemistry.There are reports available for the synthesis of pyridazine and their derivatives by using 2-oxoaldehyes.Formula: C6H8N2O

The author of 《The mechanism of thermal eliminations. Part 19. Relative rates of pyrolysis of 2-ethoxypyrazine, 3-ethoxypyridazine, 2- and 4-ethoxypyrimidine, 3-chloro-6-ethoxypyridazine, and 2-chloro-4-ethoxypyrimidine: the effect of the aza ‘substituent’ and π-bond order on the elimination rate》 were Al-Awadi, Nouria; Taylor, Roger. And the article was published in Journal of the Chemical Society in 1986. Formula: C6H8N2O The author mentioned the following in the article:

The kinetics were examined of the 1st-order thermal decomposition of the title compounds into C2H4 and the corresponding aza-substituted pyridines at 650-713 K. The electronic effects of the aza substituent are small; a more important factor appears to be the C-N π-bond order, which accounts for the high reactivity of the pyridazines. The substituent effects of the Cl and aza groups are explicable in terms of the balance between electron withdrawal from the C-O bond, producing activation, and from the N in the cyclic transition state, producing deactivation. The most important reaction step is cleavage of the C-O bond. The statistically corrected rate (per ring N atom) of 2-ethoxypyrimidine is unexpectedly low. This may reflect difficulty in achieving the coplanar transition state in which the lone pairs in the s-orbitals of O and N not involved in the elimination are brought into close proximity. The experimental process involved the reaction of 3-Ethoxypyridazine(cas: 62567-44-6Formula: C6H8N2O)

3-Ethoxypyridazine(cas: 62567-44-6) belongs to pyridazine derivatives.The pyridazine derivatives are mostly present in biologically active compounds and are also present with different pharmacophores. Pyridazines are also important because of their utility in synthetic organic chemistry and in physical organic chemistry.There are reports available for the synthesis of pyridazine and their derivatives by using 2-oxoaldehyes.Formula: C6H8N2O

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

 

Bambury, Ronald E.’s team published research in Journal of Medicinal Chemistry in 1984 | CAS: 1445-56-3

3-Chloropyridazine-4-carbonitrile(cas: 1445-56-3) belongs to pyridazine derivatives.The pyridazine derivatives are mostly present in biologically active compounds and are also present with different pharmacophores. Pyridazines are also important because of their utility in synthetic organic chemistry and in physical organic chemistry.There are reports available for the synthesis of pyridazine and their derivatives by using 2-oxoaldehyes.Formula: C5H2ClN3

The author of 《Mesoionic pyridazine ribonucleosides. A novel biologically active nucleoside metabolite》 were Bambury, Ronald E.; Feeley, Daniel T.; Lawton, Gerald C.; Weaver, John M.; Wemple, James. And the article was published in Journal of Medicinal Chemistry in 1984. Formula: C5H2ClN3 The author mentioned the following in the article:

Ribofuranosylpyridazinium I was prepared from 4-cyano-3(2H)-pyridazinone (II) by using a low-temperature, kinetically controlled, silyl Hilbert-Johnson reaction followed by deblocking of the resulting triacetate derivative with NaHCO3 in MeOH. I is a urine metabolite of II in mice. I possesses Gram-neg. antibacterial activity in vivo against a systemic Escherichia coli infection in mice with an ED50 of 25-50 mg/kg. A series of 4-substituted 3-oxidopyridazinium ribonucleosides were synthesized as analogs of I. 4-Chloro-3-oxido-1-β-D-ribofuranoylpyridazinium was several times more active than I against E. coli in vitro although it showed no in vivo activity.3-Chloropyridazine-4-carbonitrile(cas: 1445-56-3Formula: C5H2ClN3) was used in this study.

3-Chloropyridazine-4-carbonitrile(cas: 1445-56-3) belongs to pyridazine derivatives.The pyridazine derivatives are mostly present in biologically active compounds and are also present with different pharmacophores. Pyridazines are also important because of their utility in synthetic organic chemistry and in physical organic chemistry.There are reports available for the synthesis of pyridazine and their derivatives by using 2-oxoaldehyes.Formula: C5H2ClN3

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

 

Li, Xin’s team published research in Journal of the American Chemical Society in 2019 | CAS: 53085-52-2

6-Chloro-3-methyl-[1,2,4]triazolo[4,3-b]pyridazin-8-amine(cas: 53085-52-2) belongs to anime. The reaction of alkyl halides, R―X, where X is a halogen, or analogous reagents with ammonia (or amines) is useful with certain compounds. Not all alkyl halides are effective reagents; the reaction is sluggish with secondary alkyl groups and fails with tertiary ones. Its usefulness is largely confined to primary alkyl halides (those having two hydrogen atoms on the reacting site).Name: 6-Chloro-3-methyl-[1,2,4]triazolo[4,3-b]pyridazin-8-amine

Li, Xin; Wu, Yizhe; Tian, Gaofei; Jiang, Yixiang; Liu, Zheng; Meng, Xianbin; Bao, Xiucong; Feng, Ling; Sun, Hongyan; Deng, Haiteng; Li, Xiang David published an article in Journal of the American Chemical Society. The title of the article was 《Chemical Proteomic Profiling of Bromodomains Enables the Wide-Spectrum Evaluation of Bromodomain Inhibitors in Living Cells》.Name: 6-Chloro-3-methyl-[1,2,4]triazolo[4,3-b]pyridazin-8-amine The author mentioned the following in the article:

Bromodomains, epigenetic “”readers”” of lysine acetylation marks, exist in different nuclear proteins with diverse biol. functions in chromatin biol. Malfunctions of bromodomains are associated with the pathogenesis of human diseases, such as cancer. Bromodomains have therefore emerged as therapeutic targets for drug discovery. Given the high structural similarity of bromodomains, a critical step in the development of bromodomain inhibitors is the evaluation of their selectivity to avoid off-target effects. While numerous bromodomain inhibitors have been identified, new methods to evaluate the inhibitor selectivity toward endogenous bromodomains in living cells remain needed. Here we report the development of a photoaffinity probe, photo-bromosporine (photo-BS), that enables the wide-spectrum profiling of bromodomain inhibitors in living cells. Photo-BS allowed light-induced crosslinking of recombinant bromodomains and endogenous bromodomain-containing proteins (BCPs) both in vitro and in living cells. The photo-BS-induced labeling of the bromodomains was selectively competed by the corresponding bromodomain inhibitors. Proteomics anal. revealed that photo-BS captured 28 out of the 42 known BCPs from the living cells. Assessment of the two bromodomain inhibitors, bromosporine and GSK6853, resulted in the identification of known as well as previously uncharacterized bromodomain targets. Collectively, we established a chem. proteomics platform to comprehensively evaluate bromodomain inhibitors in terms of their selectivity against endogenous BCPs in living cells. The experimental part of the paper was very detailed, including the reaction process of 6-Chloro-3-methyl-[1,2,4]triazolo[4,3-b]pyridazin-8-amine(cas: 53085-52-2Name: 6-Chloro-3-methyl-[1,2,4]triazolo[4,3-b]pyridazin-8-amine)

6-Chloro-3-methyl-[1,2,4]triazolo[4,3-b]pyridazin-8-amine(cas: 53085-52-2) belongs to anime. The reaction of alkyl halides, R―X, where X is a halogen, or analogous reagents with ammonia (or amines) is useful with certain compounds. Not all alkyl halides are effective reagents; the reaction is sluggish with secondary alkyl groups and fails with tertiary ones. Its usefulness is largely confined to primary alkyl halides (those having two hydrogen atoms on the reacting site).Name: 6-Chloro-3-methyl-[1,2,4]triazolo[4,3-b]pyridazin-8-amine

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

 

Gumus, Selcuk’s team published research in Turkish Journal of Chemistry in 2011 | 20744-39-2

Turkish Journal of Chemistry published new progress about Aromaticity. 20744-39-2 belongs to class pyridazine, and the molecular formula is C4H5N3, Reference of 20744-39-2.

Gumus, Selcuk published the artcile< A computational study on substituted diazabenzenes>, Reference of 20744-39-2, the main research area is aromaticity diazabenzene substituent effect.

The results of computational calculations on the aromaticity of the monosubstituted diazabenzenes (pyridazine, pyrimidine, and pyrazine) are reported herein. The aromaticity of the parent heterocycle was enhanced by substitution of strong electron-withdrawing groups. The effects of the position of the substituent on the aromaticity and the stability of the system were also studied by studying all possible derivatives of the systems.

Turkish Journal of Chemistry published new progress about Aromaticity. 20744-39-2 belongs to class pyridazine, and the molecular formula is C4H5N3, Reference of 20744-39-2.

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

 

Ren, Huiyu’s team published research in Journal of Medicinal Chemistry in 2020-12-10 | 20744-39-2

Journal of Medicinal Chemistry published new progress about Antitumor agents. 20744-39-2 belongs to class pyridazine, and the molecular formula is C4H5N3, Computed Properties of 20744-39-2.

Ren, Huiyu; Bakas, Nicole A.; Vamos, Mitchell; Chaikuad, Apirat; Limpert, Allison S.; Wimer, Carina D.; Brun, Sonja N.; Lambert, Lester J.; Tautz, Lutz; Celeridad, Maria; Sheffler, Douglas J.; Knapp, Stefan; Shaw, Reuben J.; Cosford, Nicholas D. P. published the artcile< Design, Synthesis, and Characterization of an Orally Active Dual-Specific ULK1/2 Autophagy Inhibitor that Synergizes with the PARP Inhibitor Olaparib for the Treatment of Triple-Negative Breast Cancer>, Computed Properties of 20744-39-2, the main research area is pyrimidine synthesis anticancer ULK1 ULK2 PARP breast cancer autophagy.

Inhibition of autophagy, the major cellular recycling pathway in mammalian cells, is a promising strategy for the treatment of triple-neg. breast cancer (TNBC). We previously reported SBI-0206965, a small mol. inhibitor of unc-51-like autophagy activating kinase 1 (ULK1), which is a key regulator of autophagy initiation. Herein, we describe the design, synthesis, and characterization of new dual inhibitors of ULK1 and ULK2 (ULK1/2). One inhibitor, SBP-7455 (compound 26), displayed improved binding affinity for ULK1/2 compared with SBI-0206965, potently inhibited ULK1/2 enzymic activity in vitro and in cells, reduced the viability of TNBC cells and had oral bioavailability in mice. SBP-7455 inhibited starvation-induced autophagic flux in TNBC cells that were dependent on autophagy for survival and displayed synergistic cytotoxicity with the poly (ADP-ribose) polymerase (PARP) inhibitor olaparib against TNBC cells. These data suggest that combining ULK1/2 and PARP inhibition may have clin. utility for the treatment of TNBC.

Journal of Medicinal Chemistry published new progress about Antitumor agents. 20744-39-2 belongs to class pyridazine, and the molecular formula is C4H5N3, Computed Properties of 20744-39-2.

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

 

Ding, Xiao’s team published research in Bioorganic & Medicinal Chemistry Letters in 2019-01-15 | 20744-39-2

Bioorganic & Medicinal Chemistry Letters published new progress about Central nervous system. 20744-39-2 belongs to class pyridazine, and the molecular formula is C4H5N3, Formula: C4H5N3.

Ding, Xiao; Stasi, Luigi Piero; Dai, Xuedong; Long, Kai; Peng, Cheng; Zhao, Baowei; Wang, Hailong; Sun, Changhui; Hu, Huan; Wan, Zehong; Jandu, Karamjit S.; Philps, Oliver J.; Chen, Yan; Wang, Lizhen; Liu, Qian; Edge, Colin; Li, Yi; Dong, Kelly; Guan, Xiaoming; Tattersall, F. David; Reith, Alastair D.; Ren, Feng published the artcile< 5-Substituted-N-pyridazinylbenzamides as potent and selective LRRK2 inhibitors: Improved brain unbound fraction enables efficacy>, Formula: C4H5N3, the main research area is CNS penetration LRRK2 Parkinson’s disease PFI unbound fraction; CNS penetration; LRRK2; PFI; Parkinson’s disease; Unbound fraction.

We describe the discovery and optimization of 5-substituted-N-pyridazinylbenzamide derivatives as potent and selective LRRK2 inhibitors. Extensive SAR studies led to the identification of compounds 18 and 23, which demonstrated good in vitro pharmacokinetic profile and excellent selectivity over 140 other kinases. Both compounds demonstrated high unbound fractions in both blood and brain. Compound 18, 2-(benzyloxy)-5-morpholino-N-(pyridazin-4-yl)benzamide [2305380-32-7], proved to be brain penetrant, and the high unbound fraction of compound 18 in brain enabled its in vivo efficacy in CNS, wherein a significant inhibition of LRRK2 Ser935 phosphorylation was observed in rat brain following i.v. infusion at 5 mg/kg/h.

Bioorganic & Medicinal Chemistry Letters published new progress about Central nervous system. 20744-39-2 belongs to class pyridazine, and the molecular formula is C4H5N3, Formula: C4H5N3.

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

 

Zhang, Hai-xiang’s team published research in Yingyong Huagong in 2013-08-28 | 20744-39-2

Yingyong Huagong published new progress about 20744-39-2. 20744-39-2 belongs to class pyridazine, and the molecular formula is C4H5N3, Category: pyridazine.

Zhang, Hai-xiang; Hong, Dong-feng; Chen, Cheng-liang published the artcile< Synthesis of 4-aminopyridazine>, Category: pyridazine, the main research area is dichloro amino pyridazine amino synthesis yield.

The starting material 3,6-dichloropyridazine reacted with chlorine to produce 3,4,6-trichloropyridazine, then followed with methanol and ammonia to synthesize 3,6-dichloro-4-aminopyridazine, which via catalytic dechlorination reaction achieved object compound 4-amino pyridazine and gave a 48.2% overall molar yield. Its structure was analyzed and characterized through m.p. testing, 1H NMR and mass spectrometry.

Yingyong Huagong published new progress about 20744-39-2. 20744-39-2 belongs to class pyridazine, and the molecular formula is C4H5N3, Category: pyridazine.

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

 

Garcia-Carceles, Javier’s team published research in Journal of Medicinal Chemistry in 2017-12-14 | 20744-39-2

Journal of Medicinal Chemistry published new progress about 5-HT2C receptors Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 20744-39-2 belongs to class pyridazine, and the molecular formula is C4H5N3, Product Details of C4H5N3.

Garcia-Carceles, Javier; Decara, Juan M.; Vazquez-Villa, Henar; Rodriguez, Ramon; Codesido, Eva; Cruces, Jacobo; Brea, Jose; Loza, Maria I.; Alen, Francisco; Botta, Joaquin; McCormick, Peter J.; Ballesteros, Juan A.; Benhamu, Bellinda; Rodriguez de Fonseca, Fernando; Lopez-Rodriguez, Maria L. published the artcile< A Positive Allosteric Modulator of the Serotonin 5-HT2C Receptor for Obesity>, Product Details of C4H5N3, the main research area is anorectic serotonin receptor modulator preparation obesity benzylindolyl methylpyridinamine.

The 5-HT2CR agonist lorcaserin, clin. approved for the treatment of obesity, causes important side effects mainly related to subtype selectivity. In the search for 5-HT2CR allosteric modulators as safer antiobesity drugs, a chem. library from Vivia Biotech was screened using ExviTech platform. Structural modifications of identified hit VA240 in synthesized analogs 6-41 afforded compound 11 (N-[(1-benzyl-1H-indol-3-yl)methyl]pyridin-3-amine, VA012), which exhibited dose-dependent enhancement of serotonin efficacy, no significant off-target activities, and low binding competition with serotonin or other orthosteric ligands. PAM 11 was very active in feeding inhibition in rodents, an effect that was not related to the activation of 5-HT2AR. A combination of 11 with the SSRI sertraline increased the anorectic effect. Subchronic administration of 11 reduced food intake and body weight gain without causing CNS-related malaise. The behavior of compound 11 identified in this work supports the interest of a serotonin 5-HT2CR PAM as a promising therapeutic approach for obesity.

Journal of Medicinal Chemistry published new progress about 5-HT2C receptors Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 20744-39-2 belongs to class pyridazine, and the molecular formula is C4H5N3, Product Details of C4H5N3.

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

 

Chen, Ying-Chu’s team published research in Bioconjugate Chemistry in 2020-03-18 | 20744-39-2

Bioconjugate Chemistry published new progress about Anilines Role: CMB (Combinatorial Study), RCT (Reactant), RACT (Reactant or Reagent). 20744-39-2 belongs to class pyridazine, and the molecular formula is C4H5N3, Related Products of 20744-39-2.

Chen, Ying-Chu; Faver, John C.; Ku, Angela F.; Miklossy, Gabriella; Riehle, Kevin; Bohren, Kurt M.; Ucisik, Melek N.; Matzuk, Martin M.; Yu, Zhifeng; Simmons, Nicholas published the artcile< C-N Coupling of DNA-Conjugated (Hetero)aryl Bromides and Chlorides for DNA-Encoded Chemical Library Synthesis>, Related Products of 20744-39-2, the main research area is DNA encoded heteroaryl amide library synthesis.

DNA-encoded chem. library (DECL) screens are a rapid and economical tool to identify chem. starting points for drug discovery. As a robust transformation for drug discovery, palladium-catalyzed C-N coupling is a valuable synthetic method for the construction of DECL chem. matter; however, currently disclosed methods have only been demonstrated on DNA-attached (hetero)aromatic iodide and bromide electrophiles. We developed conditions utilizing an N-heterocyclic carbene-palladium catalyst that extends this reaction to the coupling of DNA-conjugated (hetero)aromatic chlorides with (hetero)aromatic and select aliphatic amine nucleophiles. In addition, we evaluated steric and electronic effects within this catalyst series, carried out a large substrate scope study on two representative (hetero)aryl bromides, and applied this newly developed method within the construction of a 63 million-membered DECL.

Bioconjugate Chemistry published new progress about Anilines Role: CMB (Combinatorial Study), RCT (Reactant), RACT (Reactant or Reagent). 20744-39-2 belongs to class pyridazine, and the molecular formula is C4H5N3, Related Products of 20744-39-2.

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem