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Basic Information
CAS No.: 156897-06-2
Name: Licofelone
Article Data: 10
Molecular Structure:
Molecular Structure of 156897-06-2 (Licofelone)
Formula: C23H22ClNO2
Molecular Weight: 379.886
Synonyms: ML 3000;[2,2-Dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl]aceticacid;
EINECS: 694-581-3
Density: 1.23 g/cm3
Melting Point: 162-163 °C
Boiling Point: 539.7 °C at 760 mmHg
Flash Point: 280.2 °C
Appearance: Yellowish solid
PSA: 42.23000
LogP: 5.68490
Synthetic route
156897-35-7

ethyl 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)acetate

156897-06-2

licofelone

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water at 80℃;77%
With sodium hydroxide In ethanol at 80℃; for 0.25h;77%
With sodium hydroxide In ethanol for 0.166667h; Heating;75.5%
Stage #1: ethyl 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)acetate With sodium hydroxide; water In ethanol for 0.5h; Heating / reflux;
Stage #2: With hydrogenchloride In ethanol; water Product distribution / selectivity;
64%
With aq. alkaline hydroxide at 60 - 70℃; for 1h;
1061179-20-1

methyl 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine-5-yl)acetate

156897-06-2

licofelone

Conditions
ConditionsYield
Stage #1: methyl 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine-5-yl)acetate With sodium hydroxide; water In ethanol for 0.5h; Heating / reflux;
Stage #2: With hydrogenchloride In ethanol; water Product distribution / selectivity;
71%
With aq. alkaline hydroxide at 60 - 70℃; for 1h;
262426-70-0

[6-(4-chlorophenyl)-2,3-dihydro-2,2-dimethyl-7-phenyl-1H-pyrrolizin-5-yl]acetic acid tert-butyl ester

156897-06-2

licofelone

Conditions
ConditionsYield
Stage #1: [6-(4-chlorophenyl)-2,3-dihydro-2,2-dimethyl-7-phenyl-1H-pyrrolizin-5-yl]acetic acid tert-butyl ester With sodium hydroxide; water In ethanol for 8h; Heating / reflux;
Stage #2: With hydrogenchloride In ethanol; water Product distribution / selectivity;
60%
With aq. alkaline hydroxide at 60 - 70℃; for 10h;

C23H20ClNO3

156897-06-2

licofelone

Conditions
ConditionsYield
With hydrazine hydrate; potassium hydroxide In ethylene diglycol at 85 - 145℃; for 7h; Wolff-Kishner reduction;55%
With hydrazine hydrate; potassium hydroxide In diethylene glycol at 85 - 145℃; for 7h; Wolff-Kishner reduction;55%
With hydrazine hydrate; potassium hydroxide In diethylene glycol at 50 - 145℃; Wolff-Kishner reduction;55.6%
1061179-22-3

2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine-5-yl)acetamide

156897-06-2

licofelone

Conditions
ConditionsYield
Stage #1: 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine-5-yl)acetamide With sulfuric acid; water In methanol for 4h; Heating / reflux;
Stage #2: With sodium hydroxide; water In methanol for 4h; Heating / reflux;
Stage #3: With hydrogenchloride In methanol; water Product distribution / selectivity;
50%
3355-31-5

1-chloro-3-phenyl-2-propyne

(1,2-dimethyl-3-zirconacyclopent-1-ene)(C5H5)2

(1,2-dimethyl-3-zirconacyclopent-1-ene)(C5H5)2

156897-06-2

licofelone

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 90 percent / aq. NaOH, NaI, n-Bu4NI / toluene / 24 h / 50 °C
2: 1.) Et3N, 2.) NaBH(OAc)3 / 1) CH2Cl2, rt, 15 min; 2) CH2Cl2, rt, 12 h
3: 68 percent / pivalic acid / 5 h / 150 °C
4: 77 percent / EtONa / ethanol / 15 h / Ambient temperature
5: 1.) NaH / 1) THF, rt, 1 h; 2) THF, rt, 12 h
6: 92 percent / Pd(PPh3)4, Na2CO3 / tetrahydrofuran; H2O / 1) rt, 1 h; 2) reflux, 1 h
7: 1.) p-toluenesulfonhydrazide, p-TsOH*H2O, 2.) NaBH3CN / 1) EtOH, reflux, 7 h; 2) EtOH, reflux, 4 h
8: 77 percent / aq. NaOH / ethanol / 0.25 h / 80 °C
View Scheme
197963-29-4

2,2-dimethyl-5-phenylpent-4-ynal

156897-06-2

licofelone

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 1.) Et3N, 2.) NaBH(OAc)3 / 1) CH2Cl2, rt, 15 min; 2) CH2Cl2, rt, 12 h
2: 68 percent / pivalic acid / 5 h / 150 °C
3: 77 percent / EtONa / ethanol / 15 h / Ambient temperature
4: 1.) NaH / 1) THF, rt, 1 h; 2) THF, rt, 12 h
5: 92 percent / Pd(PPh3)4, Na2CO3 / tetrahydrofuran; H2O / 1) rt, 1 h; 2) reflux, 1 h
6: 1.) p-toluenesulfonhydrazide, p-TsOH*H2O, 2.) NaBH3CN / 1) EtOH, reflux, 7 h; 2) EtOH, reflux, 4 h
7: 77 percent / aq. NaOH / ethanol / 0.25 h / 80 °C
View Scheme
Multi-step reaction with 7 steps
1: 80 percent / NaBH(OAc)3, Et3N / CH2Cl2 / Ambient temperature
2: 68 percent / t-BuCO2H / 150 °C
3: 77 percent / EtONa / ethanol / Ambient temperature
4: 80 percent / NaH / tetrahydrofuran / Ambient temperature
5: 92 percent / Pd(PPh3)4, Na2CO3 / H2O; tetrahydrofuran / Heating
6: 1.) p-toluenesulfonyl hydrazide, p-TsOH, 2.) NaBH3CN / 1.) EtOH, reflux, 2.) EtOH, reflux
7: 77 percent / NaOH / ethanol; H2O / 80 °C
View Scheme
197963-31-8

2,2-dimethyl-7-phenyl-2,3,5,6-tetrahydro-1H-pyrrolizin-6-one

156897-06-2

licofelone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 77 percent / EtONa / ethanol / 15 h / Ambient temperature
2: 1.) NaH / 1) THF, rt, 1 h; 2) THF, rt, 12 h
3: 92 percent / Pd(PPh3)4, Na2CO3 / tetrahydrofuran; H2O / 1) rt, 1 h; 2) reflux, 1 h
4: 1.) p-toluenesulfonhydrazide, p-TsOH*H2O, 2.) NaBH3CN / 1) EtOH, reflux, 7 h; 2) EtOH, reflux, 4 h
5: 77 percent / aq. NaOH / ethanol / 0.25 h / 80 °C
View Scheme
Multi-step reaction with 5 steps
1: 77 percent / EtONa / ethanol / Ambient temperature
2: 80 percent / NaH / tetrahydrofuran / Ambient temperature
3: 92 percent / Pd(PPh3)4, Na2CO3 / H2O; tetrahydrofuran / Heating
4: 1.) p-toluenesulfonyl hydrazide, p-TsOH, 2.) NaBH3CN / 1.) EtOH, reflux, 2.) EtOH, reflux
5: 77 percent / NaOH / ethanol; H2O / 80 °C
View Scheme
197963-30-7

methyl N-(2,2-dimethyl-5-phenylpent-4-ynyl)glycinate

156897-06-2

licofelone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 68 percent / pivalic acid / 5 h / 150 °C
2: 77 percent / EtONa / ethanol / 15 h / Ambient temperature
3: 1.) NaH / 1) THF, rt, 1 h; 2) THF, rt, 12 h
4: 92 percent / Pd(PPh3)4, Na2CO3 / tetrahydrofuran; H2O / 1) rt, 1 h; 2) reflux, 1 h
5: 1.) p-toluenesulfonhydrazide, p-TsOH*H2O, 2.) NaBH3CN / 1) EtOH, reflux, 7 h; 2) EtOH, reflux, 4 h
6: 77 percent / aq. NaOH / ethanol / 0.25 h / 80 °C
View Scheme
Multi-step reaction with 6 steps
1: 68 percent / t-BuCO2H / 150 °C
2: 77 percent / EtONa / ethanol / Ambient temperature
3: 80 percent / NaH / tetrahydrofuran / Ambient temperature
4: 92 percent / Pd(PPh3)4, Na2CO3 / H2O; tetrahydrofuran / Heating
5: 1.) p-toluenesulfonyl hydrazide, p-TsOH, 2.) NaBH3CN / 1.) EtOH, reflux, 2.) EtOH, reflux
6: 77 percent / NaOH / ethanol; H2O / 80 °C
View Scheme
197963-32-9

ethyl 2-(2,2-dimethyl-6-hydroxy-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)-2-oxoacetate

156897-06-2

licofelone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.) NaH / 1) THF, rt, 1 h; 2) THF, rt, 12 h
2: 92 percent / Pd(PPh3)4, Na2CO3 / tetrahydrofuran; H2O / 1) rt, 1 h; 2) reflux, 1 h
3: 1.) p-toluenesulfonhydrazide, p-TsOH*H2O, 2.) NaBH3CN / 1) EtOH, reflux, 7 h; 2) EtOH, reflux, 4 h
4: 77 percent / aq. NaOH / ethanol / 0.25 h / 80 °C
View Scheme
Multi-step reaction with 4 steps
1: 80 percent / NaH / tetrahydrofuran / Ambient temperature
2: 92 percent / Pd(PPh3)4, Na2CO3 / H2O; tetrahydrofuran / Heating
3: 1.) p-toluenesulfonyl hydrazide, p-TsOH, 2.) NaBH3CN / 1.) EtOH, reflux, 2.) EtOH, reflux
4: 77 percent / NaOH / ethanol; H2O / 80 °C
View Scheme
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Specification

The Licofelone is an organic compound with the formula C23H22ClNO2. The systematic name of this chemical is [6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl]acetic acid. With the CAS registry number 156897-06-2, it is also named as (2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine-5-yl)acetic acid. The product's categories are Intermediates & Fine Chemicals; Pharmaceuticals. Besides, it is a dual COX/LOX inhibitor being considered as a treatment for osteoarthritis. Licofelone is both an analgesic and an anti-inflammatory. Inhibition of 5-LOX may reduce the gastrointestinal toxicity associated with other non-steroidal anti-inflammatory drugs, which only inhibit COX (cyclooxygenase).

Physical properties about Licofelone are: (1)ACD/LogP: 6.73; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.66; (4)ACD/LogD (pH 7.4): 3.86; (5)ACD/BCF (pH 5.5): 6567.38; (6)ACD/BCF (pH 7.4): 103.76; (7)ACD/KOC (pH 5.5): 9340.49; (8)ACD/KOC (pH 7.4): 147.58; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 31.23 Å2; (13)Index of Refraction: 1.626; (14)Molar Refractivity: 108.77 cm3; (15)Molar Volume: 306.9 cm3; (16)Polarizability: 43.12×10-24cm3; (17)Surface Tension: 45.5 dyne/cm; (18)Density: 1.23 g/cm3; (19)Flash Point: 280.2 °C; (20)Enthalpy of Vaporization: 86.01 kJ/mol; (21)Boiling Point: 539.7 °C at 760 mmHg; (22)Vapour Pressure: 1.76E-12 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: Clc4ccc(c1c(n3c(c1c2ccccc2)CC(C)(C3)C)CC(=O)O)cc4
(2)InChI: InChI=1/C23H22ClNO2/c1-23(2)13-19-22(15-6-4-3-5-7-15)21(16-8-10-17(24)11-9-16)18(12-20(26)27)25(19)14-23/h3-11H,12-14H2,1-2H3,(H,26,27)
(3)InChIKey: UAWXGRJVZSAUSZ-UHFFFAOYAP
(4)Std. InChI: InChI=1S/C23H22ClNO2/c1-23(2)13-19-22(15-6-4-3-5-7-15)21(16-8-10-17(24)11-9-16)18(12-20(26)27)25(19)14-23/h3-11H,12-14H2,1-2H3,(H,26,27)
(5)Std. InChIKey: UAWXGRJVZSAUSZ-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD oral > 300mg/kg (300mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 45, Pg. 159, 1995.