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

General Description

4,5-Dihydro-6-phenyl-3(2H)-pyridazinone is a chemical compound that belongs to the class of organic compounds known as phenylpyridazines, a subclass of pyridazines. Pyridazines are compounds containing a pyridazine ring, which is a six-membered aromatic heterocycle made up of two nitrogen atoms and four carbon atoms. It is also known as 4,5-dihydro-6-Phenyl-3(2H)-pyridazinone and it comes with the molecular formula C10H10N2O. This chemical is mostly utilized in the field of organic chemistry, like pharmaceutical chemistry to synthesize new drugs, for example, sedatives, antihypertensives or anti-inflammatory drugs. As far as we know, It is not commercially available as a commodity chemical and thus, is used primarily for experimental and research purposes.

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)

Upstream product

• 2051-95-8 succinylbenzene 
• 88730-07-8 1-amino-5-phenylpyrrolidin-2-one 
• 307526-15-4 β-benzoylpropionic acid hydrazone 
• 66549-13-1 6-(2-chlorophenyl)-4,5-dihydropyridazin-3(2H)-one 
• 1444833-11-7 C₁₀H₈Cl₂N₂O 
• 139050-32-1 6-(2-bromophenyl)-4,5-dihydropyridazin-3(2H)-one 
• 71-43-2 benzene 
• 51800-35-2 4-hydroxy-4-phenylbutyric acid hydrazide 
• 1008-76-0 4,5-dihydro-5-phenyl-2(3H)-furanone 
• 161970-71-4 (3S,7aS)-3,7a-Diphenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one 
• 88670-16-0 (3S,7aS)-3-isopropyl-7a-phenyl-5-oxo-2,3,5,6,7,7a-hexahydropyrrolo<2,1-b>oxazole 
• 25333-24-8 3-benzoylpropionic acid methyl ester 
• 135578-08-4 2,2-dimethyl-5-phenacyl-1,3-dioxane-4,6-dione 
• 77903-44-7 t-2-Phenyl-c-2-(trimethylsiloxy)-r-1-cyclopropancarbonsaeure-methylester 

Downstream Products

• 94331-20-1 4-benzo[1,3]dioxol-5-ylmethylene-6-phenyl-4,5-dihydro-2H-pyridazin-3-one 
• 21841-86-1 2-(2-Hydroxyethyl)-6-phenyl-4,5-dihydro-3-pyridazone 
• 126775-19-7 mercuri-bis{6-phenyl-4,5-dihydro-pyridazin-3(2H)-one-4-yl} 
• 1456921-49-5 6-phenyl-2-[2-(pyridin-2-ylamino)ethyl]-4,5-dihydropyridazin-3(2H)-one 
• 127806-52-4 2-Carbethoxymethyl-4-phenyl-1,2,5,6-tetrahydro-1-oxo-pyridazine 
• 83506-38-1 6-phenyl-2-(3'-phenylpyridazin-6'-yl)-2,3,4,5-tetrahydropyridazin-3-one 
• 87769-64-0 4,5,-dihydro-6-phenyl-2-(phenylmethyl)-3(2H)-pyridazinone 

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.

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.

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.

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.

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.