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CAS No.: | 53164-05-9 |
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Name: | Acemetacin |
Article Data: | 14 |
Molecular Structure: | |
Formula: | C21H18ClNO6 |
Molecular Weight: | 415.83 |
Synonyms: | 1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-aceticacid carboxymethyl ester;1-(p-Chlorobenzoyl)-5-methoxy-2-methylindole-3-aceticacid carboxymethyl ester;2-[2-[1-[(4-Chlorophenyl)carbonyl]-5-methoxy-2-methylindol-3-yl]acetyloxy]aceticacid;Acemet;Acemethacin;Acemix;Emflex;K 708;Rantudil;Rheumibis;Rheutrop;Solart;TV 1322;TVX 1322; |
EINECS: | 258-403-4 |
Density: | 1.36 g/cm3 |
Melting Point: | 151.5 °C |
Boiling Point: | 565.5 °C at 760 mmHg |
Flash Point: | 295.8 °C |
Appearance: | Light yellow solid |
Hazard Symbols: | T+ |
Risk Codes: | 26/27/28 |
Safety: | 22-25-36/37/39-45 |
Transport Information: | UN 2811 |
PSA: | 94.83000 |
LogP: | 3.47050 |
acemetacin tert-butyl ester
acemetacin
Conditions | Yield |
---|---|
With hydrogenchloride; acetic anhydride In acetic acid at 80℃; for 5h; Large scale; | 99.45% |
With trifluoroacetic acid In dichloromethane at 20℃; for 48h; | 80% |
2-{1-[(4-chlorophenyl)carbonyl]-5-methoxy-2-methyl-1H-indol-3-yl}acetic acid tert-butyl ester
acetic acid
acemetacin
Conditions | Yield |
---|---|
With hydrogenchloride; aluminum (III) chloride at 60℃; for 5h; Reagent/catalyst; Temperature; Large scale; | 98.8% |
<1-(4-Chlorbenzoyl)-5-methoxy-2-methylindol-3-acetoxy>essigsaeurebenzylester
acemetacin
Conditions | Yield |
---|---|
With aluminum (III) chloride In dichloromethane; N,N-dimethyl-formamide at 80℃; for 24h; Temperature; | 97.8% |
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; under 760.051 Torr; for 20h; | 95% |
With hydrogen; palladium on activated charcoal In ethyl acetate at 40℃; for 1h; | 93% |
acemetacin tert-butyl ester
A
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
B
acemetacin
Conditions | Yield |
---|---|
With iodine; aluminium In acetonitrile at 20℃; for 6h; chemoselective reaction; | A 30% B 66% |
4-methoxyphenylhydrazine hydrochloride
acemetacin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 80 percent / acetic acid / 1.) 42 h, 28 deg C, 2.) 5 h, 50 deg C 2: 78 percent / various solvent(s) / 3 h / 190 - 195 °C 3: 93 percent / H2 / 5 percent Pd/C / ethyl acetate / 1 h / 40 °C View Scheme |
(5-Methoxy-2-methylindol-3-acetoxy)essigsaeurebenzylester
acemetacin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 78 percent / various solvent(s) / 3 h / 190 - 195 °C 2: 93 percent / H2 / 5 percent Pd/C / ethyl acetate / 1 h / 40 °C View Scheme |
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
acemetacin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) K2CO3 / 1.) DMF, 45 min, 50 deg C, 2.) 3 h, 50 deg C 2: 93 percent / H2 / 5 percent Pd/C / ethyl acetate / 1 h / 40 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 1.) K2CO3 / 1.) DMF, 70 min, 40 deg C, 2.) 4 h, 50 deg C 2: 80 percent / acetic acid / 1.) 42 h, 28 deg C, 2.) 5 h, 50 deg C 3: 78 percent / various solvent(s) / 3 h / 190 - 195 °C 4: 93 percent / H2 / 5 percent Pd/C / ethyl acetate / 1 h / 40 °C View Scheme |
Laevulinoyloxyessigsaeurebenzylester
acemetacin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 80 percent / acetic acid / 1.) 42 h, 28 deg C, 2.) 5 h, 50 deg C 2: 78 percent / various solvent(s) / 3 h / 190 - 195 °C 3: 93 percent / H2 / 5 percent Pd/C / ethyl acetate / 1 h / 40 °C View Scheme |
acemetacin
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 68 percent / conc. HCl / H2O / 2 h / 20 °C 2: 80 percent / acetic acid / 1.) 42 h, 28 deg C, 2.) 5 h, 50 deg C 3: 78 percent / various solvent(s) / 3 h / 190 - 195 °C 4: 93 percent / H2 / 5 percent Pd/C / ethyl acetate / 1 h / 40 °C View Scheme |
Acemetacin is a non-steroidal anti-inflammatory drug, used for the treatment of osteoarthritis, rheumatoid arthritis, lower back pain, and relieving post-operative pain.
Acemetacin, a glycolic acid ester of indometacin, acts as a prodrug; in the body, it is metabolized to indometacin, which then acts as an inhibitor of cyclooxygenase, producing the anti-inflammatory effects.