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CAS No.: | 63675-72-9 |
---|---|
Name: | Nisoldipine |
Article Data: | 10 |
Molecular Structure: | |
Formula: | C20H24N2O6 |
Molecular Weight: | 388.42 |
Synonyms: | 3,5-Pyridinedicarboxylicacid, 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-, methyl 2-methylpropyl ester(9CI);BAY-k 5552;Baymycard;Geomatrix 16E;Nisocor;Nisoldipin;Sular;Syscor;Zadipina; |
EINECS: | 264-407-7 |
Density: | 1.205 g/cm3 |
Melting Point: | 147-148 °C |
Boiling Point: | 503.3 °C at 760 mmHg |
Flash Point: | 258.2 °C |
Appearance: | light tan crystals |
Hazard Symbols: | Xn |
Risk Codes: | 20/21/22 |
Safety: | 36 |
PSA: | 110.45000 |
LogP: | 4.05380 |
2-(2-nitrobenzylidene)-acetoacetic acid-i-butyl ester
methyl 3-aminocrotonate
nisoldipine
Conditions | Yield |
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With dmap In cyclohexane at 75 - 85℃; for 26h; Heating / reflux; | 52.9% |
2'-nitrobenzylideneacetoacetic acid methyl ester
nisoldipine
Conditions | Yield |
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In 1,2-dimethoxyethane; toluene at 80 - 105℃; for 15 - 25h; |
2,3-dimethyl-2,3-diaminobutane
nisoldipine
Conditions | Yield |
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With n-butyllithium; ammonium chloride In tetrahydrofuran; methanol; hexane; dichloromethane | 1.4 g (30%) |
Conditions | Yield |
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Multi-step reaction with 2 steps 1: alumina / neat (no solvent) / 120 °C / Microwave irradiation; Green chemistry 2: 0.15 h / 90 °C / Microwave irradiation View Scheme |
2-(2-nitrobenzylidene)-acetoacetic acid-i-butyl ester
methyl 3-aminocrotonate
nisoldipine
Conditions | Yield |
---|---|
at 90℃; for 0.15h; Microwave irradiation; |
nisoldipine
Conditions | Yield |
---|---|
In acetonitrile Irradiation; | 95% |
at 25℃; for 720h; Decomposition; Photolysis; | |
With air In methanol Quantum yield; Further Variations:; Solvents; Reagents; Irradiation; |
nisoldipine
2,6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylic acid methyl 2-methylpropyl ester
Conditions | Yield |
---|---|
With lead(IV) acetate In dichloromethane; acetic acid at 20℃; for 1h; | 76% |
Stage #1: nisoldipine With hydrogenchloride In water Stage #2: In water at 20℃; for 5h; | 72.1% |
With nitric acid at 100℃; for 1h; | 63% |
nisoldipine
A
2,6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylic acid methyl 2-methylpropyl ester
Conditions | Yield |
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In ethanol for 144h; Irradiation; |
nisoldipine
Conditions | Yield |
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With α1-acid glycoprotein HPLC column resolution of racemate; | |
With Chiralpak IC In hexane; butan-1-ol Reagent/catalyst; Solvent; Resolution of racemate; | |
With isopropylamine In tetrahydrofuran; methanol; isopropyl alcohol at 35℃; under 103432 Torr; Resolution of racemate; Supercritical conditions; |
The IUPAC name of Nisoldipine is 3-O-methyl 5-O-(2-methylpropyl)2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate. With the CAS registry number 63675-72-9, it is also named as 1,4-Dihydro-2,6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylic acid methyl 2-methylpropyl ester. The product's categories are Active Pharmaceutical Ingredients; All Inhibitors; Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals; Calcium Channel. Besides, it is light tan crystals, which should be stored in sealed containers in a cool, dry place away from oxidizing agents. In addition, its molecular formula is C20H24N2O6 and molecular weight is 388.42.
The other characteristics of this product can be summarized as: (1)EINECS: 264-407-7; (2)ACD/LogP: 4.38; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): 4.38; (5)ACD/LogD (pH 7.4): 4.38; (6)ACD/BCF (pH 5.5): 1244.48; (7)ACD/BCF (pH 7.4): 1246.28; (8)ACD/KOC (pH 5.5): 5712.31; (9)ACD/KOC (pH 7.4): 5720.55; (10)#H bond acceptors: 8; (11)#H bond donors: 1; (12)#Freely Rotating Bonds: 8; (13)Index of Refraction: 1.544; (14)Molar Refractivity: 101.76 cm3; (15)Molar Volume: 322.1 cm3; (16)Surface Tension: 43.5 dyne/cm; (17)Density: 1.205 g/cm3; (18)Flash Point: 258.2 °C; (19)Melting Point: 147-148 °C; (20)Water Solubility: 24.6 mg/L at 25 °C; (21)Enthalpy of Vaporization: 77.25 kJ/mol; (22)Boiling Point: 503.3 °C at 760 mmHg; (23)Vapour Pressure: 2.95E-10 mmHg at 25 °C.
Preparation of Nisoldipine: frist, you can use o-Nitrobenzaldehyde to react with Isobutyl acetoacetate. And then use the resultant to react with Methyl 3-amino-2-butenoate by heating for 20 hours.
Uses of Nisoldipine: this chemical is a calcium channel blocker of the dihydropyridine class that acts as a potent arterial vasodilator and antihypertensive agent. It is also effective in patients with cardiac failure and angina. Similarly, it can be used to produce 2,6-Dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylic acid methyl 2-methylpropyl ester.
This reaction needs 20percent aq. HNO3 at temperature of 100 °C for 1 hour. The yield is 63 %.
People can use the following data to convert to the molecule structure.
(1)SMILES: O=C(OCC(C)C)\C1=C(\N/C(=C(/C(=O)OC)C1c2ccccc2[N+]([O-])=O)C)C
(2)InChI: InChI=1/C20H24N2O6/c1-11(2)10-28-20(24)17-13(4)21-12(3)16(19(23)27-5)18(17)14-8-6-7-9-15(14)22(25)26/h6-9,11,18,21H,10H2,1-5H3
(3)InChIKey: VKQFCGNPDRICFG-UHFFFAOYAI
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
dog | LD50 | intravenous | 2mg/kg (2mg/kg) | New Drugs Annual: Cardiovascular Drugs. Vol. 1, Pg. 243, 1983. | |
dog | LD50 | oral | 400mg/kg (400mg/kg) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 23, Pg. 682, 1992. | |
mouse | LD50 | intravenous | 360ug/kg (0.36mg/kg) | BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES SKIN AND APPENDAGES (SKIN): HAIR: OTHER | Kiso to Rinsho. Clinical Report. Vol. 22, Pg. 3285, 1988. |
mouse | LD50 | oral | 411mg/kg (411mg/kg) | BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) LUNGS, THORAX, OR RESPIRATION: CYANOSIS | Kiso to Rinsho. Clinical Report. Vol. 22, Pg. 3285, 1988. |
mouse | LD50 | subcutaneous | 384mg/kg (384mg/kg) | BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) SKIN AND APPENDAGES (SKIN): HAIR: OTHER | Kiso to Rinsho. Clinical Report. Vol. 22, Pg. 3285, 1988. |
rabbit | LD50 | intravenous | 2500ug/kg (2.5mg/kg) | New Drugs Annual: Cardiovascular Drugs. Vol. 1, Pg. 243, 1983. | |
rabbit | LD50 | oral | > 5gm/kg (5000mg/kg) | New Drugs Annual: Cardiovascular Drugs. Vol. 1, Pg. 243, 1983. | |
rat | LD50 | intravenous | 1120ug/kg (1.12mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Kiso to Rinsho. Clinical Report. Vol. 22, Pg. 3285, 1988. |
rat | LD50 | oral | 1257mg/kg (1257mg/kg) | BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) LUNGS, THORAX, OR RESPIRATION: CYANOSIS | Kiso to Rinsho. Clinical Report. Vol. 22, Pg. 3285, 1988. |
rat | LD50 | subcutaneous | 674mg/kg (674mg/kg) | BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) SKIN AND APPENDAGES (SKIN): HAIR: OTHER | Kiso to Rinsho. Clinical Report. Vol. 22, Pg. 3285, 1988. |