C33H45NO4S
cyclopamine
Conditions | Yield |
---|---|
Stage #1: C33H45NO4S With naphthalene; sodium In 1,2-dimethoxyethane at -78℃; for 3h; Inert atmosphere; Stage #2: With water; sodium hydrogencarbonate In 1,2-dimethoxyethane at -78 - 20℃; Inert atmosphere; | 91% |
Conditions | Yield |
---|---|
With potassium hydroxide; hydrazine hydrate Heating; 1.) triethylene glycol, 120 deg C, 1 h, 2.) triethylene glycol, 200 deg C, 3 h; | 51% |
With sodium; hydrazine In diethylene glycol Heating; |
Conditions | Yield |
---|---|
With water at 37℃; pH=7; aq. phosphate buffer; Inert atmosphere; |
Conditions | Yield |
---|---|
With b-glucuronidase from E. Coli at 37℃; for 2h; pH=7; aq. phosphate buffer; Enzymatic reaction; |
cyclopamine
Conditions | Yield |
---|---|
With water; 2-amino-2-hydroxymethyl-1,3-propanediol In ethanol; dimethyl sulfoxide at 37℃; for 22h; pH=7.2; pH-value; Reagent/catalyst; Solvent; Temperature; Enzymatic reaction; |
cyclopamine
Conditions | Yield |
---|---|
With aluminum isopropoxide; butanone for 6.5h; Oppenauer oxidation; Reflux; | 99% |
With aluminum isopropoxide; butanone for 6.5h; Oppenauer oxidation; Reflux; Inert atmosphere; | 85% |
With cyclohexanone; aluminum isopropoxide In toluene for 2h; Heating / reflux; | 70% |
With cyclohexanone; aluminum isopropoxide In toluene for 2h; Heating / reflux; | 70% |
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In toluene; acetonitrile for 2.5h; Heating; | 94% |
With sodium hydrogencarbonate In toluene; acetonitrile for 2.5h; Reflux; | 94% |
Conditions | Yield |
---|---|
With dmap; triethylamine In 1-Propyl acetate at 20℃; for 4h; Inert atmosphere; Large scale; | 91.8% |
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 6h; | 85% |
Conditions | Yield |
---|---|
With pyridine In N,N-dimethyl-formamide at 20℃; for 20h; | 85% |
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; | 85% |
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
cyclopamine
Fmoc-cyclopamine
Conditions | Yield |
---|---|
In dichloromethane at 23℃; for 64h; Inert atmosphere; | 81% |
In dichloromethane at 20℃; |
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 6h; | 80% |
cyclopamine
(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-[2-nitro-4-(4-nitro-phenoxycarbonyloxymethyl)-phenoxy]-tetrahydro-pyran-2-carboxylic acid methyl ester
C48H62N2O16
Conditions | Yield |
---|---|
With pyridine In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere; | 76% |
Conditions | Yield |
---|---|
Stage #1: C9H14O5 With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 0.5h; Stage #2: cyclopamine With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h; | 76% |
2-(2,2,2-trifluoroacetamido)acetic acid succinimidyl ester
cyclopamine
N-(N'-trifluoroacetylglycyl)cyclopamine
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 1h; | 60% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 15℃; for 16h; | 56.33% |
With triethylamine In dichloromethane at 20℃; for 0.166667h; | 51% |
Conditions | Yield |
---|---|
With pyridine |
Conditions | Yield |
---|---|
With pyridine at 60℃; for 18h; | 80 % Spectr. |
cyclopamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 80 percent Spectr. / pyridine / 18 h / 60 °C 2: 1,3-dicyclohexylcarbodiimide / CHCl3 / 16 h / 20 °C View Scheme |
Conditions | Yield |
---|---|
With potassium carbonate In dimethyl sulfoxide at 70℃; for 36h; |
Conditions | Yield |
---|---|
With triethylamine In methanol; dichloromethane at 0℃; for 3.5h; | |
With triethylamine In methanol; dichloromethane for 3.5h; Cooling with ice; |
Conditions | Yield |
---|---|
With dmap; triethylamine In pyridine at 40℃; for 2h; Product distribution / selectivity; | |
With dmap; triethylamine In methanol; ethyl acetate at 40℃; for 18h; Product distribution / selectivity; |
cyclopamine
1-benzyloxycarbonyloxy-1H-benzotriazole
bis-CBz-cyclopamine
Conditions | Yield |
---|---|
With dmap; triethylamine In pyridine at 40℃; for 2h; | |
With pyridine; dmap; triethylamine at 40℃; for 2h; |
Conditions | Yield |
---|---|
In methanol |
cyclopamine
C32H52N2O5
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: aluminum isopropoxide; butanone / 6.5 h / Reflux 2: palladium 10% on activated carbon; hydrogen / pyridine / 4 h 3: ethanol; water / 1 h 4: sodium cyanoborohydride; acetic acid / methanol; 1,1-dichloroethane / 1.5 h 5: acetic acid / methanol / 40 °C View Scheme |
cyclopamine
C34H56N2O5
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: aluminum isopropoxide; butanone / 6.5 h / Reflux 2: palladium 10% on activated carbon; hydrogen / pyridine / 4 h 3: ethanol; water / 1 h 4: sodium cyanoborohydride; acetic acid / methanol; 1,1-dichloroethane / 1.5 h 5: acetic acid / methanol / 40 °C View Scheme |
cyclopamine
C33H54N2O6
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: aluminum isopropoxide; butanone / 6.5 h / Reflux 2: palladium 10% on activated carbon; hydrogen / pyridine / 4 h 3: ethanol; water / 1 h 4: sodium cyanoborohydride; acetic acid / methanol; 1,1-dichloroethane / 1.5 h 5: acetic acid / methanol / 40 °C View Scheme |
cyclopamine
C33H54N2O6
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: aluminum isopropoxide; butanone / 6.5 h / Reflux 2: palladium 10% on activated carbon; hydrogen / pyridine / 4 h 3: ethanol; water / 1 h 4: sodium cyanoborohydride; acetic acid / methanol; 1,1-dichloroethane / 1.5 h 5: acetic acid / methanol / 40 °C View Scheme |
cyclopamine
C33H54N2O6
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: aluminum isopropoxide; butanone / 6.5 h / Reflux 2: palladium 10% on activated carbon; hydrogen / pyridine / 4 h 3: ethanol; water / 1 h 4: sodium cyanoborohydride; acetic acid / methanol; 1,1-dichloroethane / 1.5 h 5: acetic acid / methanol / 40 °C View Scheme |
cyclopamine
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: aluminum isopropoxide; butanone / 6.5 h / Reflux 2: palladium 10% on activated carbon; hydrogen / pyridine / 4 h 3: ethanol; water / 1 h 4: sodium cyanoborohydride; acetic acid / methanol; 1,1-dichloroethane / 1.5 h 5: acetic acid / methanol / 40 °C View Scheme |
The Cyclopamine is an organic compound with the formula C27H41NO2. The IUPAC name of this chemical is (3S,3'R,3'aS,6'S,6aS,6bS,7'aR,9R,11aS,11bR)-3',6',10,11b-tetramethylspiro[2,3,4,6,6a,6b,7,8,11,11a-decahydro-1H-benzo[a]fluorene-9,2'-3a,4,5,6,7,7a-hexahydro-3H-furo[3,2-b]pyridine]-3-ol. With the CAS registry number 4449-51-8, it is also named as 11-Deoxojervine. The product's categories are Intermediates & Fine Chemicals; Pharmaceuticals; Steroids; Lipid Signaling. Besides, it is a white crystalline solid, which should be stored in a dark dry and well-ventilated place.
The Cyclopamine can prevent the fetal brain from dividing into two lobes (holoprosencephaly) and cause the development of a single eye (cyclopia). It does so by suppressing the hedgehog gene (Hh). Cyclopamine is useful in studying the role of Hh in normal development, and as a potential treatment for certain cancers in which Hh is overexpressed.
Physical properties about Cyclopamine are: (1)ACD/LogP: 6.10; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 3.005; (4)ACD/LogD (pH 7.4): 3.263; (5)ACD/BCF (pH 5.5): 20.45; (6)ACD/BCF (pH 7.4): 37.05; (7)ACD/KOC (pH 5.5): 39.815; (8)ACD/KOC (pH 7.4): 72.134; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 41.49 Å2; (13)Index of Refraction: 1.583; (14)Molar Refractivity: 120.716 cm3; (15)Molar Volume: 360.973 cm3; (16)Polarizability: 47.856×10-24cm3; (17)Surface Tension: 46.114 dyne/cm; (18)Density: 1.14 g/cm3; (19)Flash Point: 286.91 °C; (20)Enthalpy of Vaporization: 95.514 kJ/mol; (21)Boiling Point: 550.794 °C at 760 mmHg.
You can still convert the following datas into molecular structure:
(1)SMILES: C[C@H]1C[C@@H]2[C@H]([C@H]([C@]3(O2)CC[C@H]4[C@@H]5CC=C6C[C@H](CC[C@@]6([C@H]5CC4=C3C)C)O)C)NC1
(2)InChI: InChI=1/C27H41NO2/c1-15-11-24-25(28-14-15)17(3)27(30-24)10-8-20-21-6-5-18-12-19(29)7-9-26(18,4)23(21)13-22(20)16(27)2/h5,15,17,19-21,23-25,28-29H,6-14H2,1-4H3/t15-,17+,19-,20-,21-,23-,24+,25-,26-,27-/m0/s1
(3)InChIKey: QASFUMOKHFSJGL-LAFRSMQTBZ
(4)Std. InChI: InChI=1S/C27H41NO2/c1-15-11-24-25(28-14-15)17(3)27(30-24)10-8-20-21-6-5-18-12-19(29)7-9-26(18,4)23(21)13-22(20)16(27)2/h5,15,17,19-21,23-25,28-29H,6-14H2,1-4H3/t15-,17+,19-,20-,21-,23-,24+,25-,26-,27-/m0/s1
(5)Std. InChIKey: QASFUMOKHFSJGL-LAFRSMQTSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
hamster | LDLo | oral | 170mg/kg (170mg/kg) | Proceedings of the Society for Experimental Biology and Medicine. Vol. 149, Pg. 302, 1975. | |
mouse | LDLo | oral | 180mg/kg (180mg/kg) | Proceedings of the Society for Experimental Biology and Medicine. Vol. 149, Pg. 302, 1975. |
About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia
Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog
©2008 LookChem.com,License: ICP
NO.:Zhejiang16009103
complaints:service@lookchem.com Desktop View