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CAS No.: | 112965-21-6 |
---|---|
Name: | Calcipotriene |
Article Data: | 10 |
Molecular Structure: | |
Formula: | C27H40O3 |
Molecular Weight: | 412.613 |
Synonyms: | 9,10-Secochola-5,7,10(19),22-tetraene-1,3,24-triol,24-cyclopropyl-, (1a,3b,5Z,7E,22E,24S)- (9CI);Calciptriol;Daivonex;Dovonex;MC 903;PRI 2201;Psorcutan; |
EINECS: | 601-218-4 |
Density: | 1.12 g/cm3 |
Melting Point: | 166-168 ºC |
Boiling Point: | 582 ºC at 760 mmHg |
Flash Point: | 250.6 ºC |
Appearance: | white crystalline solid |
Hazard Symbols: | Xi |
Risk Codes: | 36/37/38 |
Safety: | 26 |
PSA: | 60.69000 |
LogP: | 5.09060 |
(1S,3R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'(S)-cyclopropyl-3'-hydroxyprop-1'(E)-enyl)-9,10-secopregna-5(Z),7(E),10(19)-triene
calcipotriene
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; | 87% |
With tetrabutyl ammonium fluoride In tetrahydrofuran at 60℃; for 0.833333h; | 73% |
With tetrabutyl ammonium fluoride In tetrahydrofuran at 40℃; for 2h; | |
With tetrabutyl ammonium fluoride In tetrahydrofuran at 60℃; | |
Stage #1: (1S,3R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'(S)-cyclopropyl-3'-hydroxyprop-1'(E)-enyl)-9,10-secopregna-5(Z),7(E),10(19)-triene With tetrabutyl ammonium fluoride In tetrahydrofuran at 60 - 65℃; for 2h; Stage #2: With water; sodium hydrogencarbonate In tetrahydrofuran; ethyl acetate for 0.25h; |
Cyclopropyl methyl ketone
calcipotriene
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1: 87 percent / bromine / methanol / 0.5 h / Ambient temperature 2: 84 percent 3: 86 percent / 2N sodium hydroxide / H2O; CH2Cl2 5: N-methylmorpholine N-oxide, selenium dioxide 6: imidazole / dimethylformamide 7: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H 8: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation 9: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C View Scheme | |
Multi-step reaction with 7 steps 1: 87 percent / bromine / methanol / 0.5 h / Ambient temperature 2: 84 percent 3: 86 percent / 2N sodium hydroxide / H2O; CH2Cl2 4: dimethylsulfoxide / 4 h / 105 °C 5: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H 6: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation 7: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C View Scheme |
2-bromo-1-cyclopropylethan-1-one
calcipotriene
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: 84 percent 2: 86 percent / 2N sodium hydroxide / H2O; CH2Cl2 4: N-methylmorpholine N-oxide, selenium dioxide 5: imidazole / dimethylformamide 6: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H 7: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation 8: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C View Scheme | |
Multi-step reaction with 6 steps 1: 84 percent 2: 86 percent / 2N sodium hydroxide / H2O; CH2Cl2 3: dimethylsulfoxide / 4 h / 105 °C 4: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H 5: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation 6: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C View Scheme |
1-cyclopropyl-2-(triphenyl-λ5-phosphanylidene)ethan-1-one
calcipotriene
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 2: N-methylmorpholine N-oxide, selenium dioxide 3: imidazole / dimethylformamide 4: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H 5: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation 6: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C View Scheme | |
Multi-step reaction with 4 steps 1: dimethylsulfoxide / 4 h / 105 °C 2: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H 3: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation 4: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C View Scheme |
3(R)-(tert-butyldimethylsilyloxy)-20(S)-formyl-9,10-secopregna-5(Z),7(E),10(19)-triene
calcipotriene
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 2: N-methylmorpholine N-oxide, selenium dioxide 3: imidazole / dimethylformamide 4: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H 5: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation 6: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C View Scheme |
(S)-3-[(1R,3aS,7aR)-7a-Methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-(4E)-ylidenemethyl]-2,2-dioxo-2,3,4,5,6,7-hexahydro-1H-2λ6-benzo[c]thiophen-5-ol
calcipotriene
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1: 42 percent / imidazole / dimethylformamide / 1.5 h / 20 °C 2: 1.) ozone 2.) PPh3 / 1.) CH2Cl2, MeOH, -60 deg C 2.) CH2Cl2, MeOH, -60 to 0 deg C 3: NaHCO3 / aq. ethanol / Heating 5: N-methylmorpholine N-oxide, selenium dioxide 6: imidazole / dimethylformamide 7: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H 8: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation 9: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C View Scheme | |
Multi-step reaction with 9 steps 1: 52 percent / imidazole / dimethylformamide / 1.5 h / 20 °C 2: 1.) ozone 2.) PPh3 / 1.) CH2Cl2, MeOH, -60 deg C 2.) CH2Cl2, MeOH, -60 to 0 deg C 3: NaHCO3 / aq. ethanol / Heating 5: N-methylmorpholine N-oxide, selenium dioxide 6: imidazole / dimethylformamide 7: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H 8: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation 9: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C View Scheme |
20(R),3(R)-(tert-butyldimethylsilyloxy)-20-(3'-cyclopropyl-3'-oxoprop-1'(E)-enyl)-9,10-secopregna-5(Z),7(E),10(19)-triene
calcipotriene
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: N-methylmorpholine N-oxide, selenium dioxide 2: imidazole / dimethylformamide 3: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H 4: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation 5: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C View Scheme |
calcipotriene
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: imidazole / dimethylformamide 2: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H 3: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation 4: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C View Scheme |
(2-cyclopropyl-2-oxoethyl) (triphenyl)phosphonium bromide
calcipotriene
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 86 percent / 2N sodium hydroxide / H2O; CH2Cl2 3: N-methylmorpholine N-oxide, selenium dioxide 4: imidazole / dimethylformamide 5: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H 6: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation 7: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C View Scheme | |
Multi-step reaction with 5 steps 1: 86 percent / 2N sodium hydroxide / H2O; CH2Cl2 2: dimethylsulfoxide / 4 h / 105 °C 3: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H 4: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation 5: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C View Scheme |
(7Z)-Vitamin D2
calcipotriene
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1: liq. SO2 / 0.5 h / Heating 2: 42 percent / imidazole / dimethylformamide / 1.5 h / 20 °C 3: 1.) ozone 2.) PPh3 / 1.) CH2Cl2, MeOH, -60 deg C 2.) CH2Cl2, MeOH, -60 to 0 deg C 4: NaHCO3 / aq. ethanol / Heating 6: N-methylmorpholine N-oxide, selenium dioxide 7: imidazole / dimethylformamide 8: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H 9: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation 10: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C View Scheme | |
Multi-step reaction with 10 steps 1: liq. SO2 / 0.5 h / Heating 2: 52 percent / imidazole / dimethylformamide / 1.5 h / 20 °C 3: 1.) ozone 2.) PPh3 / 1.) CH2Cl2, MeOH, -60 deg C 2.) CH2Cl2, MeOH, -60 to 0 deg C 4: NaHCO3 / aq. ethanol / Heating 6: N-methylmorpholine N-oxide, selenium dioxide 7: imidazole / dimethylformamide 8: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H 9: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation 10: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C View Scheme |
The Calcipotriene, with the CAS registry number 112965-21-6, is also known as (1S,3S,5Z)-5-[(2E)-2-[(1R,3aR,7aR)-1-[(E,2S)-5-Cyclopropyl-5-hydroxy-pent-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidene-cyclohexane-1,3-diol.It belongs to the product categories of Intermediates & Fine Chemicals;Pharmaceuticals;Isotope Labelled Compounds.This chemical's molecular formula is C27H40O3 and molecular weight is 412.61. What's more,Its systematic name is Calcipotriol.It is a topical dermatologic for the treatment of moderate plaque psoriasis. It is White Crystalline Solid.
Physical properties about Calcipotriene are:(1)ACD/LogP: 5.018; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.02; (4)ACD/LogD (pH 7.4): 5.02; (5)ACD/BCF (pH 5.5): 3834.42; (6)ACD/BCF (pH 7.4): 3834.42; (7)ACD/KOC (pH 5.5): 12788.11; (8)ACD/KOC (pH 7.4): 12788.11; (9)#H bond acceptors: 3; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 8; (12)Index of Refraction: 1.579; (13)Molar Refractivity: 122.172 cm3; (14)Molar Volume: 367.238 cm3; (15)Surface Tension: 48.1889991760254 dyne/cm; (16)Density: 1.124 g/cm3; (17)Flash Point: 250.613 °C; (18)Enthalpy of Vaporization: 99.905 kJ/mol; (19)Boiling Point: 581.963 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25°C.
Uses of Calcipotriene: It is an antipsoriatic. A vitamin D3 analogue with low calcemic activity.Vitamin D 3 analog that displays minimal effects on calcium homeostasis. Regulates cell differentiation and proliferation; exhibits antiproliferative activity against human HL-60, HL60/MX2, MCF-7, T47D, SCC-25 and mouse WEHI-3 cancer cell lines.
You can still convert the following datas into molecular structure:
(1)SMILES:O[C@@H]1CC(\C(=C)[C@@H](O)C1)=C\C=C2/CCC[C@]4([C@H]2CC[C@@H]4[C@@H](/C=C/[C@@H](O)C3CC3)C)C;
(2)Std. InChI:InChI=1S/C27H40O3/c1-17(6-13-25(29)20-8-9-20)23-11-12-24-19(5-4-14-27(23,24)3)7-10-21-15-22(28)16-26(30)18(21)2/h6-7,10,13,17,20,22-26,28-30H,2,4-5,8-9,11-12,14-16H2,1,3H3/b13-6+,19-7+,21-10-/t17-,22-,23-,24+,25-,26+,27-/m1/s1;
(3)Std. InChIKey:LWQQLNNNIPYSNX-UROSTWAQSA-N;
The toxicity data of Calcipotriene as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
dog | LD50 | skin | > 1500ug/kg (1.5mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) MUSCULOSKELETAL: OTHER CHANGES GASTROINTESTINAL: NAUSEA OR VOMITING | Journal of Toxicological Sciences. Vol. 21(Suppl, |
man | TDLo | skin | 11gm/kg/11W-I (11000mg/kg) | British Medical Journal. Vol. 306, Pg. 896, 1993. | |
rat | LD50 | skin | > 15mg/kg (15mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ATAXIA | Journal of Toxicological Sciences. Vol. 21(Suppl, |
rat | LD50 | subcutaneous | 2190ug/kg (2.19mg/kg) | GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Journal of Toxicological Sciences. Vol. 21(Suppl, |
women | TDLo | skin | 10gm/kg/6W-I (10000mg/kg) | British Medical Journal. Vol. 306, Pg. 896, 1993. |