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Naproxcinod

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Name

Naproxcinod

EINECS N/A
CAS No. 163133-43-5 Density 1.213 g/cm3
PSA 90.58000 LogP 4.00680
Solubility N/A Melting Point N/A
Formula C18H21NO6 Boiling Point 489.475 °C at 760 mmHg
Molecular Weight 347.368 Flash Point 193.208 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 163133-43-5 (4-(NITROOXY)BUTYL (2S)-2-(6-METHOXY-2-NAPHTHYL)PROPANOATE) Hazard Symbols N/A
Synonyms

2-Naphthaleneaceticacid, 6-methoxy-a-methyl-,4-(nitrooxy)butyl ester, (S)-;(S)-2-(6-Methoxy-2-naphthyl)propanoic acid4-nitrooxybutyl ester;Nitronaproxen;

Article Data 7

Naproxcinod Synthetic route

1395256-92-4

C21H18O4

22911-39-3

4-(nitrooxy)butan-1-ol

163133-43-5

naproxcinod

Conditions
ConditionsYield
With dmap In dichloromethane; 1,2-dichloro-ethane at 0℃;96.8%
1395256-94-6

C22H20O5

22911-39-3

4-(nitrooxy)butan-1-ol

163133-43-5

naproxcinod

Conditions
ConditionsYield
With dmap In dichloromethane; 1,2-dichloro-ethane at 0℃;92.8%
51091-84-0

(S)-naproxenoyl chloride

22911-39-3

4-(nitrooxy)butan-1-ol

163133-43-5

naproxcinod

Conditions
ConditionsYield
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%
22204-53-1

(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

22911-39-3

4-(nitrooxy)butan-1-ol

163133-43-5

naproxcinod

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 5℃; for 3h; Product distribution / selectivity;85%
1198786-35-4

4-bromo-butyl (S)-2-(6-methoxy-2-naphthyl)-propanoate

163133-43-5

naproxcinod

Conditions
ConditionsYield
With silver nitrate In tetrahydrofuran; acetonitrile at 50℃; for 4h;75%
3457-91-8

1,4-butanediol dinitrate

26159-34-2

Naprelan

163133-43-5

naproxcinod

Conditions
ConditionsYield
In dimethyl sulfoxide for 120h;75%
22204-53-1

(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

146563-40-8

4-(nitrooxy)butyl bromide

163133-43-5

naproxcinod

Conditions
ConditionsYield
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%
669692-75-5

4-(nitrooxy)butyl p-toluensulfonate

22204-53-1

(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

163133-43-5

naproxcinod

Conditions
ConditionsYield
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%

(S)-4-hydroxybutyl-2-(6-methoxynaphtalen-2-yl) propanoate

163133-43-5

naproxcinod

Conditions
ConditionsYield
With 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; tetraethylammonium nitrate In dichloromethane at -70 - 20℃; for 4h;65%
51091-84-0

(S)-naproxenoyl chloride

22911-39-3

4-(nitrooxy)butan-1-ol

A

1262962-53-7

2-(R)-(6-methoxy-2-naphthyl)-propanoic acid 4-nitroxybutyl ester

B

163133-43-5

naproxcinod

Conditions
ConditionsYield
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;

Naproxcinod Specification

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

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