20375-65-9

Usage

Uses

Used in Organic Synthesis:
3-Chloro-6-phenylpyridazine is used as a key intermediate in the synthesis of 6-substituted phenyl-2-(3í-substituted phenylpyridazin-6í-yl)-2,3,4,5-tetrahydropyridazin-3-ones. These compounds have potential applications in various fields, such as pharmaceuticals and materials science, due to their unique chemical properties and structures.

InChI:InChI=1/C10H7ClN2/c11-10-7-6-9(12-13-10)8-4-2-1-3-5-8/h1-7H

Upstream product

• 141-30-0 3,6-dichlorpyridazine 
• 98-80-6 phenylboronic acid 
• 87769-64-0 4,5,-dihydro-6-phenyl-2-(phenylmethyl)-3(2H)-pyridazinone 
• 98-86-2 acetophenone 
• 603-33-8 triphenylbismuthane 
• 135034-10-5 3-chloro-6-iodopyridazine 
• 71-43-2 benzene 
• 2051-95-8 succinylbenzene 
• 108-86-1 bromobenzene 
• 2166-31-6 6-phenylpyridazin-3(2H)-one 
• 10025-87-3 trichlorophosphate 
• 1011-46-7 6-phenyl-2,3,4,5-tetrahydropyridazin-3-one 
• 90767-36-5 6-chloro-3-phenylpyridazine-1-oxide 
• 15150-84-2 3-phenylpyridazine 

Downstream Products

• 83506-38-1 6-phenyl-2-(3'-phenylpyridazin-6'-yl)-2,3,4,5-tetrahydropyridazin-3-one 
• 81819-98-9 10-(6-Phenyl-pyridazin-3-yl)-10H-phenothiazine 5-oxide 
• 73535-72-5 α-phenyl-α-(6-phenylpyridazin-3-yl)-acetonitrile 
• 81819-94-5 (4-Methyl-6-phenyl-pyridazin-3-yl)-(6-phenyl-pyridazin-3-yl)-amine 
• 66866-17-9 3,6-Diphenyl-s-triazolo<4,3-b>pyridazine 
• 81819-97-8 3-benzoylhydrazino-6-phenylpyridazine 
• 28657-39-8 3-chloro-4-methyl-6-phenylpyridazine 
• 76605-85-1 Diethyl-(2-phenyl-pyrrolo[1,2-b]pyridazin-7-yl)-amine 
• 65559-68-4 3-Methyl-6-phenyl-s-triazolo<4,3-b>pyridazine 
• 66549-54-0 3-ethyl-6-phenyl-[1,2,4]triazolo[4,3-b]pyridazine 
• 80602-17-1 dimethyloxosulfonium 6-phenyl-3-pyridazinylmethylide 
• 68321-52-8 3-phenyl-6-phenylethynyl-pyridazine 
• 81819-95-6 3-phenylhydrazino-6-phenylpyridazine 
• 55054-92-7 6-phenyl-[1,2,4]triazolo[4,3-b]pyridazine 

Relevant academic research and scientific papers

Structure-based discovery of receptor tyrosine kinase AXL degraders with excellent anti-tumor activity by selectively degrading AXL and inducing methuosis

The receptor tyrosine kinase (RTK) anexelekto (AXL) is mutated and/or overexpressed in various malignancies, and plays a central role in tumor development and acquired drug resistance. Although highly selective inhibitors have been developed in recent years, direct inhibition of AXL may block its ubiquitination, eventually leading to surface accumulation of the protein. Herein, we designed and synthesized a series of AXL degraders with high selectivity and without compensatory increase of AXL. In particular, compounds 20 and 22 showed significant AXL degradation capacity, which inhibited the proliferation and migration of cancer cells in vitro. In addition, these compounds induced the formation of cytoplasmic vacuoles and triggered methuosis, a new type of non-apoptotic cell death, by stimulating excessive production of macropinosomes. Vacuole formation was mediated via H-Ras activation, and was attenuated upon inhibition of its downstream regulatory factor Rac1. Furthermore, compound 20 inhibited the growth of tumor cell xenografts in vivo, and prolonged the survival of the tumor-bearing mice.

Pyridazine N-Oxides as Photoactivatable Surrogates for Reactive Oxygen Species

A method for the photoinduced evolution of atomic oxygen from pyridazine N-oxides was developed. This underexplored oxygen allotrope mediates arene C-H oxidation within complex, polyfunctional molecules. A water-soluble pyridazine N-oxide was also developed and shown to promote photoinduced DNA cleavage in aqueous solution. Taken together, these studies highlight the utility of pyridazine N-oxides as photoactivatable O(3P) precursors for applications in organic synthesis and chemical biology.

Development of pyridazine derivatives as potential EGFR inhibitors and apoptosis inducers: Design, synthesis, anticancer evaluation, and molecular modeling studies

Novel hybrids of pyridazine-pyrazoline were synthesized aiming to develop new antiproliferative candidates. All compounds were submitted to the National Cancer Institute (NCI), USA, and many were proved to have significant antiproliferative activity. In addition, in vitro studies of the epidermal growth factor receptor (EGFR) inhibition showed that compounds IXn, IXg, IXb and IXl exhibited excellent inhibitory effect (IC50 = 0.65, 0.75, 0.82 and 0.84 μM, respectively) compared to Erlotinib (IC50 = 0.95 μM). The mechanistic effectiveness in cell cycle progression, apoptotic induction and gene regulation were assessed for the promising compounds IXg and IXn due to their significant EGFR inhibition. Flow cytometeric analysis indicated that compounds IXg and IXn result in increased cell numbers in phase G2/M, suggesting cell cycle arrest in phase G2/M in UO-31cells. Furthermore, real time PCR assay illustrated that compounds IXg and IXn elevated Bax/Bcl2 ratio which confirmed the mechanistic pathway of them. Moreover, the apoptotic induction of UO-31 renal cancer cells was enhanced effectively through activation of caspase-3 by compounds IXg and IXn. On the other hand, molecular docking study was performed to investigate binding mode of interaction of compounds with EGFR-PK in the active site with the aim of rationalizing its promising inhibitory activity. Finally, based on the aforementioned findings, compounds IXg and IXn could be considered as effective apoptosis modulators and promising leads for future development of new anti-renal cancer agents.

Lewis Acid Directed Regioselective Metalations of Pyridazine

Mono- or bidentate boron Lewis acids trigger a regioselective magnesiation or zincation of pyridazine in position C3 (ortho product) or C4 (meta product). The regioselectivity of the metalation was rationalized with the help of calculated pKa values of both pyridazine and pyridazine/Lewis acid complexes.

Novel Triazolo Pyridazine Derivatives and Use Thereof

The present invention relates to a novel triazolo pyridazine derivative or a pharmaceutically acceptable salt thereof, to a pharmaceutical composition for inhibiting c-Met tyrosine kinase activity and a pharmaceutical composition for preventing or treating an abnormal proliferation disorder (hyperproliferative disorder) comprising same as an active ingredient, and to a method for preventing or treating an abnormal proliferation disorder (hyperproliferative disorder) comprising a step of administering a pharmaceutically effective amount of the pharmaceutical composition to a subject in need thereof. The present invention can advantageously be used as a therapeutic agent for various abnormal proliferation disorders such as cancer, psoriasis, rheumatoid arthritis and diabetic retinopathy which are associated with excessive cell proliferation and growth due to irregular kinase activity by effectively suppressing the activity of c-Met tyrosine kinase.

Synthesis, vasorelaxant activity and 2D-QSAR study of some novel pyridazine derivatives

Novel 3,6-disubstituted pyridazines were synthesized by facile method and screened for their vasorelaxant properties utilizing isolated thoracic rat aortic rings. Compounds 8a and 11a exerted potent vasorelaxant activity (IC50 = 198 and 177 μM, respectively) relative to doxazosin mesylate (used reference standard, IC50 = 226 μM), that, they may represent promising hits for treatment of cardiovascular disorders. The observed activity was validated by a statistically significant QSAR model (N = 32, n = 6, R2 = 0.811782, R2cvOO = 0.7153, R2cvMO = 0.7209, F = 17.9708, s2 = 9.65226 × 10-8) that was obtained employing CODESSA-Pro software.

Synthesis and cytotoxic activities of some pyrazoline derivatives bearing phenyl pyridazine core as new apoptosis inducers

The cyclization of chalcones 3a-3u with 3-hydrazinyl-6-phenylpyridazine 7 under basic condition led to the formation of new pyrazoline derivatives 8a-8u. All final compounds were characterized by spectral and elemental analyses. They were screened for their antiproliferative activities against A549 (lung), HepG-2 (liver), CaCo-2 (intestinal) and MCF-7 (breast) cancer cell lines. Some of the synthesized compounds exhibited promising antiproliferative activities especially compound 8k with IC50values of 8.33, 1.67 and 10?μM against HepG-2, MCF-7 and CaCo-2 cancer cell lines, respectively. Moreover, their antiproliferative activity was due to apoptosis rather than necrosis induction except compound 8h which exhibited equal apoptotic and necrotic properties. Compound 8k showed 5 fold increase in caspase-3 activity indicating that the apoptosis proceeds via caspase-3 activation.

Pd-catalyzed chemoselective cross-coupling reaction of triaryl- or triheteroarylbismuth compounds with 3,6-dihalopyridazines

The cross-coupling reactions of 3,6-dihalopyridazines with triaryl- or triheteroarylbismuth compounds were performed under palladium catalysis. The reaction was highly chemoselective, affording functionalized aryl- or heteroarylpyridazinyl chlorides in moderate to good yields. The cross-coupling reactions of 3,6-dihalopyridazines with triaryl- or triheteroarylbismuth compounds were performed under palladium catalysis. The reaction was highly chemoselective, affording functionalized aryl- or heteroarylpyridazinyl chlorides in moderate to good yields. Copyright

COMPOUNDS, COMPOSITIONS AND METHODS FOR TREATMENT OF ARTHRITIS

The invention relates to compounds, compositions, formulations and dosage forms comprising N-(Cyclopropylmethyl)-6-phenyl-4-(pyridin-4-yl)pyridazin-3- amine, or a pharmaceutically acceptable salt thereof, and methods for treating arthritis in a subject using such compounds, compositions, formulations and dosage forms.