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CAS No.: | 163133-43-5 |
---|---|
Name: | 4-(NITROOXY)BUTYL (2S)-2-(6-METHOXY-2-NAPHTHYL)PROPANOATE |
Article Data: | 7 |
Molecular Structure: | |
Formula: | C18H21NO6 |
Molecular Weight: | 347.368 |
Synonyms: | 2-Naphthaleneaceticacid, 6-methoxy-a-methyl-,4-(nitrooxy)butyl ester, (S)-;(S)-2-(6-Methoxy-2-naphthyl)propanoic acid4-nitrooxybutyl ester;Nitronaproxen; |
Density: | 1.213 g/cm3 |
Boiling Point: | 489.475 °C at 760 mmHg |
Flash Point: | 193.208 °C |
PSA: | 90.58000 |
LogP: | 4.00680 |
Conditions | Yield |
---|---|
With dmap In dichloromethane; 1,2-dichloro-ethane at 0℃; | 96.8% |
Conditions | Yield |
---|---|
With dmap In dichloromethane; 1,2-dichloro-ethane at 0℃; | 92.8% |
Conditions | Yield |
---|---|
With calcium aluminosilicate In dichloromethane at 0 - 20℃; for 10h; Product distribution / selectivity; | 90% |
With calcium carbonate In dichloromethane at 0 - 20℃; for 10h; Product distribution / selectivity; | 90% |
In dichloromethane at 40℃; for 8.33333h; Heating / reflux; | 88% |
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid
4-(nitrooxy)butan-1-ol
naproxcinod
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 5℃; for 3h; Product distribution / selectivity; | 85% |
4-bromo-butyl (S)-2-(6-methoxy-2-naphthyl)-propanoate
naproxcinod
Conditions | Yield |
---|---|
With silver nitrate In tetrahydrofuran; acetonitrile at 50℃; for 4h; | 75% |
Conditions | Yield |
---|---|
In dimethyl sulfoxide for 120h; | 75% |
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid
4-(nitrooxy)butyl bromide
naproxcinod
Conditions | Yield |
---|---|
Stage #1: (2S)-2-(6-methoxy(2-naphthyl))propanoic acid With potassium hydrogencarbonate In DMF (N,N-dimethyl-formamide) at 50 - 60℃; for 1.5h; Stage #2: 4-(nitrooxy)butyl bromide With potassium iodide In DMF (N,N-dimethyl-formamide) at 20℃; for 25h; | 73% |
4-(nitrooxy)butyl p-toluensulfonate
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid
naproxcinod
Conditions | Yield |
---|---|
Stage #1: (2S)-2-(6-methoxy(2-naphthyl))propanoic acid With potassium hydrogencarbonate In DMF (N,N-dimethyl-formamide) at 50 - 60℃; for 1.5h; Stage #2: 4-(nitrooxy)butyl p-toluensulfonate In DMF (N,N-dimethyl-formamide) at 20℃; for 25h; | 70% |
naproxcinod
Conditions | Yield |
---|---|
With 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; tetraethylammonium nitrate In dichloromethane at -70 - 20℃; for 4h; | 65% |
(S)-naproxenoyl chloride
4-(nitrooxy)butan-1-ol
A
2-(R)-(6-methoxy-2-naphthyl)-propanoic acid 4-nitroxybutyl ester
B
naproxcinod
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 10h; Product distribution / selectivity; | |
With 4-methyl-morpholine In dichloromethane at 0 - 20℃; for 10h; Product distribution / selectivity; |
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The Naproxcinod, with the CAS registry number 163133-43-5, is also known as (S)-2-(6-Methoxy-2-naphthyl)propanoic acid 4-nitrooxybutyl ester. It belongs to the classification codes of Cardiovascular Agents; Nitric Oxide Donors; Osteoarthritis. This chemical's molecular formula is C18H21NO6 and molecular weight is 347.36. What's more, both its IUPAC name and systematic name are the same which is called 4-Nitrooxybutyl (2S)-2-(6-methoxynaphthalen-2-yl)propanoate. Naproxcinod is a non-steroidal anti-inflammatory drug. It is a derivative of naproxen with a nitroxybutyl ester to allow it to also act as a nitric oxide donor. This second mechanism of action makes naproxcinod the first in a new class of drugs, the cyclooxygenase inhibiting nitric oxide donators, that are hoped to produce similar analgesic efficacy to traditional NSAIDs, but with less gastrointestinal and cardiovascular side effects.
Physical properties about Naproxcinod are: (1)ACD/LogP: 4.86; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4.86; (4)ACD/LogD (pH 7.4): 4.86; (5)ACD/BCF (pH 5.5): 2909.01; (6)ACD/BCF (pH 7.4): 2909.01; (7)ACD/KOC (pH 5.5): 10494.05; (8)ACD/KOC (pH 7.4): 10494.05; (9)#H bond acceptors: 7; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 10; (12)Polar Surface Area: 90.58 Å2; (13)Index of Refraction: 1.563; (14)Molar Refractivity: 93.033 cm3; (15)Molar Volume: 286.274 cm3; (16) Polarizability: 36.881×10-24cm3; (17)Surface Tension: 45.842 dyne/cm; (18)Density: 1.213 g/cm3; (19)Flash Point: 193.208 °C; (20)Enthalpy of Vaporization: 75.58 kJ/mol; (21)Boiling Point: 489.475 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.
You can still convert the following datas into molecular structure:
(1) SMILES: [O-][N+](=O)OCCCCOC(=O)[C@H](c1ccc2c(c1)ccc(OC)c2)C
(2) InChI: InChI=1S/C18H21NO6/c1-13(18(20)24-9-3-4-10-25-19(21)22)14-5-6-16-12-17(23-2)8-7-15(16)11-14/h5-8,11-13H,3-4,9-10H2,1-2H3/t13-/m0/s1
(3) InChIKey: AKFJWRDCWYYTIG-ZDUSSCGKSA-N