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CAS No.: | 73963-72-1 |
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Name: | Cilostazol |
Article Data: | 18 |
Cas Database | |
Molecular Structure: | |
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Formula: | C20H27N5O2 |
Molecular Weight: | 369.467 |
Synonyms: | 6-[4-(1-cyclohexyltetrazol-5-yl)butoxy]-3,4-dihydro-1H-quinolin-2-one;Pletal;OPC 13013;Cilostazol (JAN/USAN);2(1H)-Quinolinone,6-[4-(1-cyclohexyl-1Htetrazol- 5-yl)butoxy]-3,4-dihydro-;Pletal (TN);Cilostazole;Cilostal; |
EINECS: | 689-122-9 |
Density: | 1.34 g/cm3 |
Melting Point: | 159-160 °C |
Boiling Point: | 664.7 °C at 760 mmHg |
Flash Point: | 355.8 °C |
Solubility: | DMSO: 18 mg/mL, soluble |
Appearance: | off-white solid |
Hazard Symbols: |
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PSA: | 81.93000 |
LogP: | 3.60270 |
cilostazol bisulfate
6-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy]-3,4-dihydrocarbostyril
Conditions | Yield |
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With sodium hydroxide In chloroform; water Product distribution / selectivity; | 98.7% |
cilostazol oxalate
6-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy]-3,4-dihydrocarbostyril
Conditions | Yield |
---|---|
With sodium hydroxide In chloroform; water Product distribution / selectivity; | 97.9% |
cilostazol malate
6-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy]-3,4-dihydrocarbostyril
Conditions | Yield |
---|---|
With sodium hydroxide In chloroform; water Product distribution / selectivity; | 97.8% |
6-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy]-3,4-dihydrocarbostyril
Conditions | Yield |
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With tetrakis(triphenylphosphine) palladium(0); N-ethyl-N,N-diisopropylamine In acetonitrile for 10h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; Reflux; | 96% |
3,4-dihydro-6-hydroxy-2(1H)-quinolinone
1-cyclohexyl-5-(4-chlorobutyl)-1,2,3,4-tetrazole
6-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy]-3,4-dihydrocarbostyril
Conditions | Yield |
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With potassium carbonate; sodium hydroxide; sodium sulfite In ethanol for 8h; Reflux; | 92.5% |
With potassium carbonate; sodium hydroxide; sodium sulfite In water at 92℃; for 6h; Solvent; Reagent/catalyst; Temperature; | 91.5% |
With potassium hydroxide In ethanol at 80℃; for 12h; Solvent; Reagent/catalyst; Temperature; Inert atmosphere; Sealed tube; | 90% |
3,4-dihydro-6-hydroxy-2(1H)-quinolinone
1-cyclohexyl-5-(4-chlorobutyl)-1,2,3,4-tetrazole
A
6-[4-(1-cyclohexyl-1H-tetrazol-5-yl)-butoxy]-1-[4-(1-cyclohexyl-1H-tetrazol-5-yl)-butyl]-3,4-dihydro-1H-quinolin-2-one
B
6-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy]-3,4-dihydrocarbostyril
C
OPC 13015
Conditions | Yield |
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With 1,8-diazabicyclo[5.4.0]undec-7-ene In ethanol at 75 - 80℃; | A n/a B 89% C n/a |
6-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy]-3,4-dihydrocarbostyril
Conditions | Yield |
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With bis(triphenylphosphine)nickel(II) chloride; N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 25℃; for 8h; Inert atmosphere; | 88% |
6-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy]-3,4-dihydrocarbostyril
Conditions | Yield |
---|---|
With bis(triphenylphosphine)nickel(II) chloride; N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 25℃; for 8h; Inert atmosphere; | 85% |
1-cyclohexyl-5-(4-chlorobutyl)-1,2,3,4-tetrazole
6-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy]-3,4-dihydrocarbostyril
Conditions | Yield |
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Stage #1: 3,4-dihydro-6-hydroxy-2(1H)-quinolinone With 1,8-diazabicyclo[5.4.0]undec-7-ene In ethanol for 6.5h; Heating / reflux; Molecular sieve; Stage #2: 1-cyclohexyl-5-(4-chlorobutyl)-1,2,3,4-tetrazole In ethanol for 6.5h; Product distribution / selectivity; Heating / reflux; | 40.2% |
Multi-step reaction with 4 steps 1: sodium hydroxide / butan-1-ol / 8 h / Reflux 2: iron; ammonium chloride; acetic acid / methanol; water / 5 h / 45 °C / Reflux 3: triethylamine / dichloromethane / 3 h / 0 °C 4: N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium(0) / acetonitrile / 10 h / Inert atmosphere; Reflux View Scheme |
4-methoxy-aniline
6-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy]-3,4-dihydrocarbostyril
Conditions | Yield |
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Multi-step reaction with 3 steps 1: potassium carbonate / acetone / 0.5 h 2: aluminum (III) chloride / N,N-dimethyl acetamide / 2 h / 150 °C 3: potassium hydroxide / ethanol / 12 h / 80 °C / Inert atmosphere; Sealed tube View Scheme |
1. Introduction of Cilostazol
Cilostazol is one kind of white crystalline powder or off-white solid. The IUPAC Name of it is 6-[4-(1-cyclohexyltetrazol-5-yl)butoxy]-3,4-dihydro-1H-quinolin-2-one. The Solubility of it is DMSO: 18 mg/mL, soluble. Besides, it belongs to Intermediates & Fine Chemicals;Isotope Labeled Compounds;Pharmaceuticals.
Its Classification Code is Anti-Asthmatic Agents; Antithrombotic; Autonomic Agents; Bronchodilator Agents; Cardiovascular Agents; Central Nervous System Agents; Drug / Therapeutic Agent; Enzyme Inhibitors; Fibrin Modulating Agents; Fibrinolytic Agents; Hematologic Agents; Human Data; Inhibitor [platelet]; Neuroprotective Agents; Peripheral Nervous System Agents; Phosphodiesterase 3 Inhibitors; Phosphodiesterase Inhibitors; Platelet Aggregation Inhibitors; Protective Agents; Reproductive Effect; Respiratory System Agents; Vasodilator; Vasodilator Agents.
2. Properties of Cilostazol
Physical properties about Cilostazol are:
(1)Empirical Formula: C20H27N5O2; (2)H bond acceptors: 7; (3)H bond donors: 1; (4)Freely Rotating Bonds: 7; (5)Polar Surface Area: 73.14 Å2; (6)Index of Refraction: 1.675; (7)Molar Refractivity: 102.93 cm3; (8)Molar Volume: 273.7 cm3; (9)Surface Tension: 54.9 dyne/cm; (10)Density: 1.34 g/cm3; (11)Flash Point: 355.8 °C; (12)Enthalpy of Vaporization: 97.74 kJ/mol; (13)Boiling Point: 664.7 °C at 760 mmHg; (14)Vapour Pressure: 1.56E-17 mmHg at 25°C; (15)Melting point: 159-160°C.
3. Structure Descriptors of Cilostazol
(1)InChI: InChI=1/C20H27N5O2/c26-20-12-9-15-14-17(10-11-18(15)21-20)27-13-5-4-8-19-22-23-24-25(19)16-6-2-1-3-7-16/h10-11,14,16H,1-9,12-13H2,(H,21,26)
(2)Smiles: n1(c(nnn1)CCCCOc1cc2c(NC(=O)CC2)cc1)C1CCCCC1
(3)InChIKey: InChIKey=RRGUKTPIGVIEKM-UHFFFAOYSA-N
4. Toxicity of Cilostazol
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
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dog | LD50 | oral | > 2gm/kg (2000mg/kg) | Drugs in Japan Vol. -, Pg. 504, 1990. | |
man | TDLo | oral | 1248ug/kg (1.248mg/kg) | BEHAVIORAL: HEADACHE | Arzneimittel-Forschung. Drug Research. Vol. 35, Pg. 1173, 1985. |
mouse | LD50 | intramuscular | > 1gm/kg (1000mg/kg) | Drugs in Japan Vol. -, Pg. 504, 1990. | |
mouse | LD50 | intraperitoneal | > 2gm/kg (2000mg/kg) | Drugs in Japan Vol. -, Pg. 504, 1990. | |
mouse | LD50 | oral | > 5gm/kg (5000mg/kg) | Drugs in Japan Vol. -, Pg. 504, 1990. | |
rat | LD50 | intramuscular | > 1gm/kg (1000mg/kg) | Drugs in Japan Vol. -, Pg. 504, 1990. | |
rat | LD50 | intraperitoneal | > 2gm/kg (2000mg/kg) | Drugs in Japan Vol. -, Pg. 504, 1990. | |
rat | LD50 | oral | > 5gm/kg (5000mg/kg) | Drugs in Japan Vol. -, Pg. 504, 1990. |