1011-46-7

Basic information

• Product Name: 4,5-DIHYDRO-6-PHENYL-3(2H)-PYRIDAZINONE
• Synonyms: 6-PHENYL-4,5-DIHYDRO-3(2H)-PYRIDAZINONE;6-PHENYL-4,5-DIHYDROPYRIDAZIN-3(2H)-ONE;4,5-DIHYDRO-6-PHENYL-3(2H)-PYRIDAZINONE;4,5-DIHYDRO-6-PHENYLPYRIDAZIN-3(2H)-ONE;TIMTEC-BB SBB003803;3(2H)-pyridazinone, 4,5-dihydro-6-phenyl-;3-phenyl-4,5-dihydro-1H-pyridazin-6-one;1,4,5,6-Tetrahydro-3-phenyl-6-pyridazinone
• CAS NO: 1011-46-7
• Molecular Formula: C₁₀H₁₀N₂O
• Molecular Weight: 174.2
• Product Categories: Heterocyclic Compounds;Building Blocks;Heterocyclic Building Blocks;Pyridazines
• Mol File: 1011-46-7.mol
• Article Data: 34

Chemical Properties

• Melting Point: 151-154 °C(lit.)
• Appearance: /
• Density: 1.21 g/cm³
• Refractive Index: 1.623
• PKA: 13.63±0.40(Predicted)
• CAS DataBase Reference: 4,5-DIHYDRO-6-PHENYL-3(2H)-PYRIDAZINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-DIHYDRO-6-PHENYL-3(2H)-PYRIDAZINONE(1011-46-7)
• EPA Substance Registry System: 4,5-DIHYDRO-6-PHENYL-3(2H)-PYRIDAZINONE(1011-46-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 1011-46-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Chemistry:
4,5-Dihydro-6-phenyl-3(2H)-pyridazinone is used as a key intermediate in the synthesis of various pharmaceutical compounds for its potential therapeutic properties.
Used in Research and Development:
In the field of research and development, 4,5-Dihydro-6-phenyl-3(2H)-pyridazinone is used as a chemical building block to explore its potential applications in drug discovery and development, given its unique structure and properties.
Used in Organic Chemistry:
4,5-Dihydro-6-phenyl-3(2H)-pyridazinone is utilized in organic chemistry as a reagent or starting material for the synthesis of more complex organic molecules, taking advantage of its reactive sites and heterocycle structure.
Used in Medicinal Chemistry:
In medicinal chemistry, 4,5-Dihydro-6-phenyl-3(2H)-pyridazinone is employed as a scaffold for the design and development of new drugs, leveraging its ability to interact with biological targets and modulate their activity.
Note: Since the provided materials do not specify different industries or application types, the uses listed are general and based on the compound's properties and potential applications in the field of chemistry and pharmaceuticals.

InChI:InChI=1/C10H10N2O/c13-10-7-6-9(11-12-10)8-4-2-1-3-5-8/h1-5H,6-7H2,(H,12,13)

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• 76617-80-6 6,6-Diphenylhexahydropyridazin-3-one 
• 76617-81-7 6-Phenyl-6-p-tolyl-tetrahydro-pyridazin-3-one 

Relevant articles and documents

Synthesis and antihypertensive activity of some novel pyridazinones

Four pyridazinones (2-5) were synthesized by the reaction of 3-benzoylpropionic acid with the corresponding hydrazines. These pyridazinones were further derivatized with appropriate aromatic aldehydes in the presence of piperidine to obtain the desired compounds (6-13). The chemical structures of the synthesized pyridazinones were elucidated on the basis of their spectral analysis (IR, 1H-NMR, and 13C-NMR). Molecular docking studies were carried out to identify the most active antihypertensive pyridazinone compound by using the crystal structure of human Angiotensin Converting Enzyme (ACE), the enzyme implicated in the pathogenesis of hypertension. The compound (6) was identified as the most active inhibitor of the Angiotensin Converting Enzyme (ACE). This compound was further assessed for its ACE inhibitory activity using Dojindo ACE Kit-WST test kit. The enzymatic ACE inhibitory activity revealed that the compound (6) had IC50 value of 5.78 μg/mL, wherein the standard drug Lisinopril had IC50 value of 0.85 μg/mL. It has been concluded that incorporation of free amino groups and free carboxylic acid groups in the structure of the synthesized pyridazinone (6-13) may provide more active and potent ACE inhibitors.

Synthesis of novel N-substitutedphenyl-6-oxo-3-phenylpyridazine derivatives as cyclooxygenase-2 inhibitors

Some novel non-ulcerogenic N-substitutedphenyl-6-oxo-3-phenylpyridazines as COX-2 inhibitors have been developed (Supplementary material Appendix 1). The novel aldehyde 3 was prepared by reacting 6-phenylpyridazin-3(2H)-one with 4-fluorobenzaldehyde. The aldehyde 3 was reacted with different hydrazines and thiazolidin-4-ones to obtain the novel N-substitutedphenyl-6-oxo-3-phenylpyridazine derivatives. These were assessed for their anti-inflammatory potential and gastric ulcerogenic effects. The molecular docking investigations were also undertaken. The spectroscopic data were coherent with the allocated structures of the compounds. The compounds 4a (IC50 = 17.45 nm; p 50 = 17.40 nm; p 50 = 16.76 nm; p 50 = 17.15 nm; p 50 = 17.79 nm; p .05). These findings were consistent with the molecular docking investigations of 4a, 4b, 5a, and 10. The in vivo anti-inflammatory profile of 4a, 4b, 5a, and 10 was also superior to celecoxib and indomethacin. The compounds 4b, 5a, and 10 revealed no gastric ulcerogenic effects, wherein the compound 4a produced almost negligible gastric ulcerogenic effects than celecoxib and indomethacin. The compounds 4a, 4b, 5a, and 10 have been postulated as promising non-ulcerogenic COX-2 inhibitors.

Solubility and thermodynamics of 6-phenyl-4,5-dihydropyridazin-3(2H)-one in various neat solvents at different temperatures

Pyridazinone derivatives have been investigated either pre-clinically or clinically in the treatment of various cardiovascular diseases. The main problems associated with these drugs are the poor aqueous solubility and toxicity. Therefore, in the current study, the solubility of pyridazinone derivative i.e. 6-phenyl-4,5-dihydropyridazin-3(2H)-one [coded as PDP-6] was determined in eleven different neat solvents at temperatures “T?=?293.2?K to 313.2?K” and “atmospheric pressure p?=?0.1?MPa”. Experimental mole fraction solubilities of PDP-6 were correlated well with van't Hoff and Apelblat models with mean percent deviation of ??1) followed by 2-(2-ethoxyethoxy) ethanol (Transcutol) (5.24?×?10??1), polyethylene glycol-400 [PEG-400] (8.47?×?10??2), ethyl acetate [EA] (1.45?×?10??2), ethylene glycol [EG] (1.09?×?10??2), propylene glycol [PG] (1.03?×?10??2), 2-butanol (7.78?×?10??3), 1-butanol (7.68?×?10??3), ethanol (6.96?×?10??3), isopropyl alcohol [IPA] (6.51?×?10??3) and water (1.61?×?10??6) and similar trend was also recorded at all five different temperatures investigated. “Apparent thermodynamic analysis” on mole fraction solubilities of PDP-6 indicated an endothermic dissolution of PDP-6 in all neat solvents studied. Based on these data, PDP-6 has been proposed as practically insoluble in water, sparingly soluble in ethanol, IPA, EG, PG, EA, 1-butanol and 2-butanol, soluble in PEG-400 and very soluble in DMSO and Transcutol.

An efficient synthesis of 4,5-dihydro-3(2H)-pyridazinone derivatives

Reaction of hydrazine with 5-(2-aryl-2-oxo-ethan-1-yl)-5-R Meldrum's acids 3 gives 4,6-disubstituted 4,5-dihydropyridazin-3(2H)-ones 4 at room temperature. The method is simple and the yield is good. The production of the starting material 3 also is discu

Synthesis of 1,2,4-triazolopyridazines, isoxazolofuropyridazines, and tetrazolopyridazines as antimicrobial agents

Through current and previous researches, it was found that the derivatives of pyridazine, isoxazole, tetrazole, quinazoline, hydrazinyl, and 1,2,4-triazole have many pharmacological activities. Thus, a series of novel furopyridazinones (7), isoxazolopyridazine (8), sub-benzylidene-furopyridazinones (9a-c), isoxazolofuropyridazines (10a-c), 3-chloro-(pyridin-4-ylmethylene)-dihydropyridazines (11), tetrazolopyridazines (12), pyridazinoquinazolinones (13), piperazinyl/morpholino-pyridazines (14a,b), hydrazinyl-pyridazines (15), and 1,2,4-triazolo-pyridazines (16a,b) in good yields (72%-90%) were synthesized from substituted ethyl 4-oxo-4-phenylbutanoate (2), 6-phenyl-4,5-dihydropyridazinone (3), and 6-phenyl-4-(pyridin-4-ylmethylene)-4,5-dihydropyridazinone (4) as beginning materials. All the chemical structures of the new compounds have been demonstrated by different spectroscopy analyses such as infrared, NMR, mass spectrum, and elemental analysis. Also, the activities of the newly prepared compounds were tested against many types of bacteria and fungi in vitro. Hence, 1,2,4-triazolopyridazines (16a,b), isoxazolofuropyridazines (10a-c), tetrazolopyridazines (12), Piperazinyl/morpholinyl-pyridazines (14a,b) displayed the most efficient antimicrobial activities compared with the cefotaxime sodium and nystatin as standard drugs.

Conversion of γ-bicyclic lactams to 4,5-dihydro-2H-pyridazin-3-ones

Bicyclic lactams are uniquely suited as precursors for the synthesis of chiral substituted 4,5-dihydro-2H-pyridazinones. This paper describes the development of a method for the direct conversion of unsubstituted and 4-substituted γ-bicyclic lactams to 4,5-dihydro-2H-pyridazin-3-ones and 2-phenyl-4,5-dihydro-2H-pyridazin-3-ones.

Brine Shrimp (Artemia salina) Lethality Bioassay of Some 2-(Alkyl/Aryl)-6-Phenyl-4,5-Dihydropyridazin-3(2H)-one Derivatives

A series of pyridazinone derivatives, 2-(alkyl/aryl)-6-phenyl-4,5-dihydropyridazin-3(2H)-ones (3a-h), was synthesized from 6-phenyl-4,5-dihydropyridazin-3(2H)-one (2). Compound 2 was synthesized from benzoylpropionic acid (1). The synthesized compounds were characterized on the basis of their spectral (infrared, proton nuclear magnetic resonance, carbon-13 nuclear magnetic resonance, and mass spectra) and elemental analytical data. The compounds 2 and 3a-h and potassium dichromate (as reference drug) were tested at the dose level of 10, 20, and 30 μg/mL. Compounds 3d and 3b exhibited potent brine shrimp lethality with LC50values of 4.023 μg and 4.20 μg. Other compounds 3g, 3f, 3c, 3h, 2, 3a, and 3e also showed significant cytotoxic activity with LC50values of 13.91, 12.58, 11.91, 11.76, 10.58, 9.76, and 7.46 μg, respectively. The present study supports that brine shrimp bioassay is a simple, reliable, and suitable method for estimation of bioactivity of synthesized compounds and provides support for their use in medicine.

Synthesis, anti-convulsant activity and molecular docking study of novel thiazole pyridazinone hybrid analogues

Pyridazinone analogues have been known to be potential candidates for anticonvulsant agents. We have identified several pyridazinone-based anticonvulsant agents. As a continuation to our previous research, a series of hybrid pyridazinone-thiazole connected through amide linkage were designed and synthesized. Among these, compound SP-5F demonstrated significant anticonvulsant activity with median effective dose of 24.38 mg/kg (MES) and 88.23 mg/kg (scPTz). Results of GABA estimation showed a marked increase in the GABA level when compared with control. Molecular docking studies at the active site of GABA receptor, further confirmed the GABA modulatory effects of SP-5F.

Design, Synthesis, and Pharmacological Screening of Pyridazinone Hybrids as Anticonvulsant Agents

A series of new hybrid benzimidazole containing pyridazinones derivatives were designed and synthesized in accordance with the pharmacophoric requirements essential for the anticonvulsant activity. The synthesized compounds were evaluated for anticonvulsant activity on mice by the gold standard maximal electroshock (MES) and subcutaneous pentylenetetrazole (scPTZ)-induced seizure models. Among the compounds tested, SS-4F showed significant anticonvulsant activity in both the screens with ED50 values of 25.10 and 85.33 mg/kg in the MES and scPTZ screens, respectively. Compound SS-4F emerged as safer and effective anticonvulsant due to its several-fold higher protective indices. Further, the gamma-aminobutyric acid (GABA) estimation result showed a marked increase in the GABA level (1.7-fold) as compared to the control, which was further confirmed by good binding properties with the GABAA receptor.

Efficient synthesis, anticonvulsant and muscle relaxant activities of new 2-((5-amino-1,3,4-thiadiazol-2-yl)methyl)-6-phenyl-4,5-dihydropyridazin-3(2H) -one derivatives

A series of 2-(2-(3-(4-chlorophenyl)-6-oxo-5,6-dihydropyridazin-1(4H)yl) acetyl)hydrazine carbothioamide and 2-((5-amino-1,3,4-thiadiazol-2-yl)methyl)-6- (4-chlorophenyl)-4,5-dihydropyridazin-3(2H)-one derivatives were synthesized, characterized, and evaluated for anticonvulsant activity and muscle relaxant activity. The synthesized compounds 5d (82.75 %) and 5e (85.44 %) showed promising anticonvulsant activity by protection against tonic hind limb extensor phase in maximal electroshock model (MES) at (50 mg/kg) compared to standard drug phenytoin and also compounds 5d (82.75 %), and 5e (85.44 %) showed significant anticonvulsant activity by protection against pentylenetetrazole- induced generalized convulsions in pentylenetetrazole model (PTZ) at (100 mg/kg) compared to standard drug diazepam. On the other hand, compound 5e showed significant muscle relaxant activity (84.57 %) by rotarod and traction test model comparing with diazepam as a standard drug.