41933-33-9

Usage

Uses

Used in Pharmaceutical Industry:
2-Benzyl-4,5-dichloro-2,3-dihydropyridazin-3-one is used as an antipsychotic agent for its potential to treat psychiatric disorders by modulating the central nervous system. Its specific mechanism of action and efficacy in managing symptoms are under investigation.
Used in Oncology:
In the field of oncology, 2-Benzyl-4,5-dichloro-2,3-dihydropyridazin-3-one is utilized as a photosensitizer in photodynamic therapy. It is being studied for its ability to absorb light and generate reactive oxygen species, which can cause cell death in cancerous tissues upon exposure to light, offering a targeted approach to cancer treatment.
Used in Medicinal Chemistry Research:
2-Benzyl-4,5-dichloro-2,3-dihydropyridazin-3-one serves as a subject of research in medicinal chemistry for the development of novel therapeutic agents. Its unique structure and potential biological activities make it a valuable compound for exploring new drug candidates and understanding their mechanisms of action.

InChI:InChI=1/C11H8Cl2N2O/c12-9-6-14-15(11(16)10(9)13)7-8-4-2-1-3-5-8/h1-6H,7H2

Upstream product

• 932-22-9 4,5-dichloro-2H-pyridazin-3-one 
• 100-39-0 benzyl bromide 
• 87-56-9 mucochloric acid 
• 1073-62-7 N-benzylhydrazine hydrochloride 
• 100-44-7 benzyl chloride 

Downstream Products

• 69152-64-3 2-benzyl-4-chloro-5-morpholin-4-yl-2H-pyridazin-3-one 
• 41933-15-7 2-benzyl-4-chloro-5-(1-methylhydrazino)-3(2H)-pyridazinone 
• 40890-47-9 2-benzyl-4-chloro-5-methoxy-2H-pyridazin-3-one 
• 825633-93-0 2-benzyl-5-iodo-2,3-dihydropyridazin-3-one 
• 59026-56-1 2-benzyl-5-benzylidene-hydrazino-4-chloro-3(2H)-pyridazinone 
• 59026-45-8 5-benzyl-1-methyl-3-phenyl-1H-pyrazolo<3,4-d>pyridazin-4(5H)-one 
• 59026-51-6 2-Benzyl-4-chloro-5-{N-methyl-N'-[1-phenyl-meth-(E)-ylidene]-hydrazino}-2H-pyridazin-3-one 
• 96017-21-9 2-Benzyl-4-chloro-5-{N'-[1-(2-methoxy-phenyl)-meth-(E)-ylidene]-hydrazino}-2H-pyridazin-3-one 
• 96017-41-3 1,5-Dibenzyl-3-(2-methoxy-phenyl)-1,5-dihydro-pyrazolo[3,4-d]pyridazin-4-one 
• 96017-31-1 2-Benzyl-5-{N-benzyl-N'-[1-(2-methoxy-phenyl)-meth-(E)-ylidene]-hydrazino}-4-chloro-2H-pyridazin-3-one 
• 77541-65-2 2-benzyl-5-chloro-4-methoxypyridazin-3(2H)-one 
• 1027344-36-0 ethyl 2-(2'-benzyl-4'-chloro-3'-oxopyridazin-5'-yl)-2-(4''-nitrophenyl)propanoate 
• 182943-69-7 4-chloro-5-fluoro-2-benzyl-3(2H)-pyridazinone 

Relevant academic research and scientific papers

Design, synthesis, and bioactivities of novel pyridazinone derivatives containing 2-phenylthiazole or oxazole skeletons

A series of novel pyridazinone derivatives were designed and synthesized by replacing 4-(tert-butyl)phenyl moiety of pyridaben with 2-phenylthiazole or oxazole fragments via activity substructure connecting approach. The structures of all target compounds were characterized through NMR, MS, and elemental analysis. Bioassay results exhibit that most compounds showed potent bioactivities against Aphis fabae, Tetranychus urticae, Erysiphe graminis, and/or Puccinia polysora. Among the newly synthesized compounds, 2-(tert-butyl)-4-chloro-5-(((2-phenylthiazol-4-yl)methyl)thio)pyridazin-3(2H)-one (12b) displays remarkable insecticidal activity against A fabae. Its LC50 value (2.73 mg/L) is better than that of pyridaben (5.46 mg/L), although inferior to that of imidacloprid (0.51 mg/L). In addition to its extraordinary insecticidal activity, compound 12b also exerts 96.9% fungicidal activities against P polysora at 500 mg/L in vivo, significantly superior to that of pyridaben (50.0%), while slightly lower than that of tebuconazole (100%). This article discusses the synthesis, bioassay results, and structure-activity relationship of this series of novel pyridazinone derivatives.

Synthesis and evaluation of nevirapine analogs to study the metabolic activation of nevirapine

Nevirapine (NVP) is widely used as a non-nucleoside reverse transcriptase inhibitor of HIV-1, however, it is associated with severe skin and liver injury. The mechanisms of these adverse reactions are not yet clear, but the metabolic activation of NVP is thought to be related to the injury process. Until now, several metabolic activation pathways of NVP have been reported. In this study, in order to identify the reactive metabolite of NVP mainly responsible for CYP inhibition and liver injury, we synthesized five NVP analogs designed to avoid the proposed bioactivation pathway and evaluated their metabolic stabilities, CYP3A4 time-dependent inhibitory activities, and cytotoxicity. As a result, only a pyrimidine analog of NVP, which could avoid the formation of a reactive epoxide intermediate, did not inhibit CYP3A4. Outside of this compound, the other synthesized compounds, which could avoid the generation of a reactive quinone-methide intermediate, inhibited CYP3A4 equal to or stronger than NVP. The pyrimidine analog of NVP did not induce cytotoxicity in HepG2 and transchromosomic HepG2 cells, expressing major four CYP enzymes and CYP oxidoreductase. These results indicated that the epoxide intermediate of NVP might play an important role in NVP-induced liver injury.

One-Pot Highly Regioselective Synthesis of Indole-Fused Pyridazino[4,5- b ][1,4]benzoxazepin-4(3 H)-ones by a Smiles Rearrangement

A simple and convenient synthesis of indole-fused pyridazino[4,5- b ][1,4]benzoxazepin-4(3 H)-ones is described. A range of 2-(1 H -indol-2-yl)phenols and 4,5-dichloropyridazin-3-ones are compatible with this reaction. A Smiles rearrangement is proposed as a key step in the highly regioselective construction of the products. The easy availability of the starting materials makes this an appealing method in organic synthesis.

NOVEL NITROGEN-CONTAINING AROMATIC HETEROCYCLIC COMPOUND

A compound represented by general formula [1] wherein X represents N or the like, Y represents CH or the like; RA represents a cycloalkyl group which may be substituted or the like, R1 represents an alkyl group or the like, R2 represents an alkyl group which may be substituted or the like, R3 represents a hydrogen atom or an alkyl group, or a pharmaceutically acceptable salt thereof has an inhibitory activity on aldosterone synthetase, and is useful as a prophylactic and/or therapeutic agent for various diseases or symptoms associated with aldosterone.

Discovery of a new series of potent prostacyclin receptor agonists with in vivo activity in rat

The design and synthesis of two closely related series of prostacyclin receptor agonist compounds that showed excellent human IP receptor potency and efficacy is described. Compounds from this series showed in vivo activity after SC dosing in the monocrotaline model of PAH in rat.

IMIDAZO[1,2-a]PYRIDINES AND IMIDAZO[1,2-b]PYRIDAZINES AS MARK INHIBITORS

The invention encompasses imidazo[1,2-a]pyridine and imidazo[1,2-b]pyridazine derivatives which selectively inhibit microtubule affinity regulating kinase (MARK) and are therefore useful for the treatment or prevention of Alzheimer's disease. Pharmaceutical compositions and methods of use are also included.

PYRIDAZINONES AND FURAN-CONTAINING COMPOUNDS

The present invention is directed to pyridazinone compounds of formula (I) and furan compounds of formula (II), pharmaceutical compositions of compounds of formula (I) and (II), kits containing these compounds, methods of syntheses, and a method of treatment of a proliferative disease in a subject by administration of a therapeutically effective amount of a compound of formulae (I) or (II). Both classes of compounds were identified through screening of a collection of small molecule libraries.

CASPASE INHIBITORS BASED ON PYRIDAZINONE SCAFFOLD

The present invention relates to a pyridazinone derivative which can be used as a caspase inhibitor, process for the preparation thereof, and pharmaceutical composition for inhibiting caspase comprising the same.

Azabicyclic heterocycles as cannabinoid receptor modulators

The present application describes compounds according to Formula I, pharmaceutical compositions comprising at least one compound according to Formula I and optionally one or more additional therapeutic agents and methods of treatment using the compounds according to Formula I both alone and in combination with one or more additional therapeutic agents. The compounds have the general Formula I and Formula II: including all prodrugs, pharmaceutically acceptable salts and stereoisomers, R1, R2, R3 and R4 are described herein.

Azabicyclic heterocycles as cannabinoid receptor modulators

The present application describes compounds according to Formula I, pharmaceutical compositions comprising at least one compound according to Formula I and optionally one or more additional therapeutic agents and methods of treatment using the compounds according to Formula I both alone and in combination with one or more additional therapeutic agents. The compounds have the general Formula I: including all prodrugs, pharmaceutically acceptable salts and stereoisomers, R1, R2, R3, R6, R7, m and n are described herein.