1079-73-8

Basic information

• Product Name: 2,3,4,5-TETRAHYDRO-6(4-CHLOROPHENYL)-3(2H)-PYRIDAZINONE
• Synonyms: TIMTEC-BB SBB003462;2,3,4,5-TETRAHYDRO-6(4-CHLOROPHENYL)-3(2H)-PYRIDAZINONE;6-(4-CHLOROPHENYL)-4,5-DIHYDRO-3(2H)-PYRIDAZINONE;6-(4-CHLOROPHENYL)-4,5-DIHYDROPYRIDAZIN-3(2H)-ONE;3-(4-chlorophenyl)-4,5-dihydro-1H-pyridazin-6-one
• CAS NO: 1079-73-8
• Molecular Formula: C₁₀H₉ClN₂O
• Molecular Weight: 208.64
• Mol File: 1079-73-8.mol
• Article Data: 20

Chemical Properties

• Melting Point: 178 °C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.36g/cm³
• Refractive Index: 1.641
• PKA: 13.52±0.40(Predicted)
• CAS DataBase Reference: 2,3,4,5-TETRAHYDRO-6(4-CHLOROPHENYL)-3(2H)-PYRIDAZINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,5-TETRAHYDRO-6(4-CHLOROPHENYL)-3(2H)-PYRIDAZINONE(1079-73-8)
• EPA Substance Registry System: 2,3,4,5-TETRAHYDRO-6(4-CHLOROPHENYL)-3(2H)-PYRIDAZINONE(1079-73-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26
• Hazardous Substances Data: 1079-73-8(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 75, p. 1117, 1953 DOI: 10.1021/ja01101a032

InChI:InChI=1/C10H9ClN2O/c11-8-3-1-7(2-4-8)9-5-6-10(14)13-12-9/h1-4H,5-6H2,(H,13,14)

Upstream product

• 18338-90-4 5-(4-chlorophenyl)-2(3H)-furanone 
• 62903-14-4 4-(3-chlorophenyl)-4-oxobutyric acid 
• 108-90-7 chlorobenzene 
• 7148-01-8 methyl 4-(4-chlorophenyl)-4-oxobutanoate 
• 3984-34-7 4-(4-chlorophenyl)-4-oxobutanoic acid 

Downstream Products

• 142027-67-6 6-(4-chlorophenyl)-2-(4'-chloro-2'-butynyl)-4,5-dihydropyridazinone 
• 2166-13-4 6-(p-chlorophenyl)-3(2H)-pyridazinone 
• 58059-29-3 6-(p-chlorophenyl)-3-chloropyridazine 
• 1229037-51-7 6-(4-chlorophenyl)-2-(1H-indol-1-ylmethyl)-4,5-dihydropyridazin-3(2H)-one 
• 1229037-50-6 6-(4-chlorohenyl)-2-(1,2-dihydro-10H-phenothiazin-10-ylmethyl)-4,5-dihydropyridazin-3(2H)-one 
• 1427435-49-1 7-(4-chlorophenyl)-3,4,8,9-tetrahydro-2H-pyridazino[1,6-a][1,3,5]triazin-2-imine 
• 1427435-50-4 C₁₂H₁₁ClN₄O 
• 1427435-51-5 7-(4-chlorophenyl)-3,4,8,9-tetrahydro-2H-pyridazino[1,6-a][1,3,5]triazin-2-thione 
• 66122-52-9 6-(4-chloro-phenyl)-2-hydroxymethyl-4,5-dihydro-2H-pyridazin-3-one 
• 127941-47-3 ethyl 2-[3-(4-chlorophenyl)-6-oxo-4,5-dihydropyridazin-1-yl]acetate 
• 70751-11-0 ethyl 2-(3-(4-chlorophenyl)-6-oxopyridazin-1(6H)-yl)acetate 
• 70751-13-2 2-[6-(4-chlorophenyl)-3-oxo-2H-pyridazin-2-yl]acetohydrazide 

Relevant articles and documents

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.