IUPAC Name: 6-[4-(3,4-Dimethoxybenzoyl)piperazin-1-yl]-3,4-dihydro-1H-quinolin-2-one
Synonyms of 3,4-Dihydro-6-(4-(3,4-dimethoxybenzoyl)-1-piperazinyl)-2(1h)-quinolinone (CAS NO.81840-15-5) : 2(1H)-Quinolinone, 6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-3,4-dihydro- ; 3,4-Dihydro-6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-2(1H)-quinolinone ; 6-[4-(3,4-Dimethoxybenzoyl)-1-piperazinyl]-3,4-dihydro-2(1H)-quinolinone ; 6-[4-(3,4-Dimethoxybenzoyl)piperazin-1-yl]-3,4-dihydroquinolin-2(1H)-one
CAS NO: 81840-15-5
Molecular Formula :C22H25N3O4
Molecular Weight :395.4516
Molecular Structure :
Index of Refraction: 1.601
Surface Tension: 50.1 dyne/cm
Density: 1.246 g/cm3
Flash Point: 364 °C
Enthalpy of Vaporization: 99.56 kJ/mol
Boiling Point: 678.3 °C at 760 mmHg
Vapour Pressure: 2.96E-18 mmHg at 25°C
Melting point :289 - 293 °C (decomposition).
Solubility% (25°C): Acetic acid 18.68, 14.19 ,Chloroform, benzyl alcohol 5.913, N-methyl -2 -PvP 3.407, 2.509 ,Dimethyl sulfoxide, sulfolane 1.229, 1.179 ,Dimethylformamide, dioxane ring 0.1653, 0.1151, Methanol, acetone, 0.06389, 0.04005 Ethanol, water .002086. pKa 2.86.
3,4-Dihydro-6-(4-(3,4-dimethoxybenzoyl)-1-piperazinyl)-2(1h)-quinolinone (CAS NO.81840-15-5) is a cardiotonic agent. A mixed phosphodiesterase inhibitor and ion-channel modifier that has modest, dose-dependent, positive inotropic activity, but minimal negative chronotropic activity. 3,4-Dihydro-6-(4-(3,4-dimethoxybenzoyl)-1-piperazinyl)-2(1h)-quinolinone (CAS NO.81840-15-5) improves ventricular performance most in patients with the worst degree of heart failure.
Raw materials :1,4-Diazacyclohexane-->Formamide-->4-Methylanisole-->1,2,3,4-Tetrahydroquinolin-2-one
With 6 - Amino -3,4 - dihydro -2 (1H) - quinolinone as raw material. The 6 - Amino -3,4 - dihydro -2 (1H) - quinolinone (21.1g, 0.13mo1) and Double (Iraq-bromoethyl) amine hydrobromide (40.5g, 0.13mo1) dissolved in 150ml ethanol, reflux with mixing 8h. Cooling, adding Sodium carbonate (13.8g, 0.13mo1), and then reflux with mixining 8h. Cool to room temperature, filtered, collect precipitation, ethanol wash, ethanol - water, recrystallization,obtaining colorless needle-like crystals 26.4g 3,4-Dihydro-6-(4-(3,4-dimethoxybenzoyl)-1-piperazinyl)-2(1h)-quinolinone (CAS NO.81840-15-5) , the yield was 64%.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
dog | LD50 | intravenous | 63300ug/kg (63.3mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: CYANOSIS GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 18, Pg. 922, 1987. |
dog | LD50 | oral | > 3gm/kg (3000mg/kg) | LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES LIVER: OTHER CHANGES KIDNEY, URETER, AND BLADDER: OTHER CHANGES | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 18, Pg. 922, 1987. |
mouse | LD50 | intraperitoneal | > 1200mg/kg (1200mg/kg) | LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES LIVER: OTHER CHANGES KIDNEY, URETER, AND BLADDER: OTHER CHANGES | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 18, Pg. 922, 1987. |
mouse | LD50 | intravenous | 56300ug/kg (56.3mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS LUNGS, THORAX, OR RESPIRATION: CYANOSIS | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 18, Pg. 922, 1987. |
mouse | LD50 | oral | > 7594mg/kg (7594mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) SKIN AND APPENDAGES (SKIN): HAIR: OTHER | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 18, Pg. 922, 1987. |
mouse | LD50 | subcutaneous | > 1200mg/kg (1200mg/kg) | LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES KIDNEY, URETER, AND BLADDER: OTHER CHANGES LIVER: OTHER CHANGES | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 18, Pg. 922, 1987. |
rabbit | LD50 | oral | > 3gm/kg (3000mg/kg) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 18, Pg. 922, 1987. | |
rat | LD50 | intraperitoneal | > 1200mg/kg (1200mg/kg) | LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES LIVER: OTHER CHANGES KIDNEY, URETER, AND BLADDER: OTHER CHANGES | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 18, Pg. 922, 1987. |
rat | LD50 | intravenous | 79300ug/kg (79.3mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: CYANOSIS GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 18, Pg. 922, 1987. |
rat | LD50 | oral | > 7594mg/kg (7594mg/kg) | LIVER: OTHER CHANGES KIDNEY, URETER, AND BLADDER: OTHER CHANGES | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 18, Pg. 922, 1987. |
rat | LD50 | subcutaneous | > 3gm/kg (3000mg/kg) | LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES LIVER: OTHER CHANGES KIDNEY, URETER, AND BLADDER: OTHER CHANGES | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 18, Pg. 922, 1987. |
women | TDLo | oral | 16800ug/kg/14 (16.8mg/kg) | BLOOD: AGRANULOCYTOSIS | American Journal of Hematology. Vol. 44, Pg. 217, 1993. |
Poison by intravenous route. An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx.
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