5-azacytidine
Conditions | Yield |
---|---|
With triethylamine In methanol at 25 - 30℃; for 2h; Product distribution / selectivity; Inert atmosphere; | 99.13% |
5-azacytidine
Conditions | Yield |
---|---|
With ammonia In methanol for 2h; | 89.2% |
With sodium methylate In methanol for 2h; Inert atmosphere; | 74.4% |
2,3,5-tri-O-acetyl-β-D-ribofuranose-4-amino-1,3,5-triazine
5-azacytidine
Conditions | Yield |
---|---|
With sodium methylate In methanol for 2h; Inert atmosphere; | 80.2% |
With methanol; sodium methylate at 20 - 25℃; for 1.58333h; Product distribution / selectivity; | 75% |
With sodium methylate In methanol for 3h; Solvent; | 38.8% |
4-amino-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one
5-azacytidine
Conditions | Yield |
---|---|
With sodium methylate In methanol for 2h; Inert atmosphere; | 75.9% |
With ammonia In methanol at 0 - 20℃; for 7h; | 60% |
2',3',5'-tri-O-acetylcytidine
5-azacytidine
Conditions | Yield |
---|---|
With N-butylamine In methanol at 65℃; for 1h; | 75.3% |
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose
2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine
5-azacytidine
Conditions | Yield |
---|---|
Stage #1: 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose; 2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine; trifluorormethanesulfonic acid In acetonitrile at 55℃; for 12.5h; Industry scale; Stage #2: With methanol; sodium methylate In dimethyl sulfoxide; acetonitrile at 22 - 23℃; for 3.75h; | 71% |
1,2,3,5-tetraacetylribose
5-azacytidine
Conditions | Yield |
---|---|
Stage #1: 5-azacytosine With chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane In acetonitrile for 20h; Heating / reflux; Stage #2: 1,2,3,5-tetraacetylribose With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 20℃; for 20h; Stage #3: With sodium methylate; sodium hydrogencarbonate more than 3 stages; | 41.3% |
Stage #1: 5-azacytosine With chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane In acetonitrile for 20h; Heating / reflux; Stage #2: 1,2,3,5-tetraacetylribose With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 20℃; for 20h; Stage #3: With sodium methylate; sodium hydrogencarbonate more than 3 stages; |
N-(Formylamidino)-N'-β-D-ribofuranosylharnstoff
5-azacytidine
Conditions | Yield |
---|---|
at 37℃; Rate constant; pH 9.5; other temperature, pH; decomposition of 5-aza-2'-deoxycytidine and 5-azacytidine on alkali and neutral solutions, HPLC study; |
5-azacytidine
Conditions | Yield |
---|---|
With sodium methylate In methanol |
2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine
1,2,3,5-tetraacetylribose
5-azacytidine
Conditions | Yield |
---|---|
Stage #1: 2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine; 1,2,3,5-tetraacetylribose With tin(IV) chloride In 1,2-dichloro-ethane at 5 - 20℃; for 2.25h; Stage #2: With water; sodium hydrogencarbonate In 1,2-dichloro-ethane at 15 - 20℃; for 0.5h; Product distribution / selectivity; |
5-azacytosine
1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose
5-azacytidine
Conditions | Yield |
---|---|
Stage #1: 5-azacytosine With N,O-Bis(trimethylsilyl)trifluoroacetamide In dichloromethane for 1.5h; Reflux; Stage #2: 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose; trimethylsilyl trifluoromethanesulfonate In dichloromethane for 2.16667h; Reflux; Stage #3: With methanol; sodium methylate at 50℃; for 1h; | |
Stage #1: 5-azacytosine With N,O-Bis(trimethylsilyl)trifluoroacetamide In dichloromethane for 1.5h; Reflux; Stage #2: 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose In dichloromethane for 2h; Reflux; Stage #3: With methanol; sodium methylate at 50℃; for 1h; Product distribution / selectivity; |
Conditions | Yield |
---|---|
Stage #1: 5-azacytosine With N,O-Bis(trimethylsilyl)trifluoroacetamide In dichloromethane for 1.5h; Reflux; Stage #2: 1,2,3,5-tetra-O-acetyl-D-ribofuranose; trimethylsilyl trifluoromethanesulfonate In dichloromethane for 2.16667h; Reflux; Stage #3: With methanol; sodium methylate at 50℃; for 1h; Product distribution / selectivity; | |
Stage #1: 5-azacytosine With N,O-Bis(trimethylsilyl)trifluoroacetamide In dichloromethane for 1.5h; Reflux; Stage #2: 1,2,3,5-tetra-O-acetyl-D-ribofuranose With trimethylsilyl trifluoromethanesulfonate In dichloromethane for 2h; Reflux; Stage #3: With methanol; sodium methylate at 50℃; for 1h; Product distribution / selectivity; |
5-azacytidine
Conditions | Yield |
---|---|
With methanol; sodium methylate at 20℃; for 12h; | 10.3 g |
5-azacytidine
Conditions | Yield |
---|---|
With methanol; sodium methylate In dichloromethane at 20℃; for 12h; | 8 g |
Conditions | Yield |
---|---|
In methanol; water for 0.333333h; | 99% |
Conditions | Yield |
---|---|
In methanol; water for 0.333333h; | 99% |
5-azacytidine
Conditions | Yield |
---|---|
With zinc(II) chloride In methanol; water for 0.333333h; | 98% |
5-azacytidine
4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5,6-dihydro-1,3,5-triazin-2(1H)-one
Conditions | Yield |
---|---|
With sodium tetrahydroborate In water at 20℃; for 1.5h; | 97% |
5-azacytidine
Conditions | Yield |
---|---|
With hydrogenchloride In methanol; isopropyl alcohol at 25 - 30℃; for 4h; Product distribution / selectivity; Inert atmosphere; | 93.29% |
Conditions | Yield |
---|---|
In acetone for 24h; Inert atmosphere; | 90% |
5-azacytidine
Conditions | Yield |
---|---|
With sulfuric acid In methanol at 25 - 30℃; for 2.5h; Product distribution / selectivity; Inert atmosphere; | 87.7% |
5-azacytidine
5-azacytidine mono-hydrobromide
Conditions | Yield |
---|---|
With hydrogen bromide In methanol; acetic acid at 25 - 30℃; for 12.5h; Product distribution / selectivity; Inert atmosphere; | 67% |
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 15h; Cooling with ice; | 67% |
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 1h; Cooling with ice; | 64% |
In pyridine Yield given; |
4,4'-dimethoxytrityl chloride
5-azacytidine
5'-O-(4,4'-dimethoxytrityl)-5-azacytidine
Conditions | Yield |
---|---|
With pyridine | 59% |
In pyridine | 2.89 g (59%) |
Conditions | Yield |
---|---|
In methanol at 25 - 30℃; for 2h; Product distribution / selectivity; Inert atmosphere; | 52.7% |
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 15 - 30℃; for 2h; Cooling with ice; | 48% |
elaidoyl chloride
5-azacytidine
5-azacytidine 5'-elaidic acid ester
Conditions | Yield |
---|---|
Stage #1: 5-azacytidine With hydrogenchloride In diethyl ether; ISOPROPYLAMIDE at 20℃; Stage #2: elaidoyl chloride In ISOPROPYLAMIDE at 20 - 30℃; Stage #3: With water; sodium hydrogencarbonate In ethyl acetate | 43% |
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 17h; Cooling with ice; | 23% |
5-azacytidine
Conditions | Yield |
---|---|
Stage #1: 5-azacytidine With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h; Inert atmosphere; Stage #2: 2-(1-bromo-1-methylethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere; regioselective reaction; | 18% |
Conditions | Yield |
---|---|
With pyridine at 0℃; for 0.1h; | 16% |
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 15 - 30℃; for 1h; Cooling with ice; | 14% |
Conditions | Yield |
---|---|
Stage #1: 5-azacytidine With triethyl phosphate; trichlorophosphate at 0℃; for 0.1h; Stage #2: benzyl alcohol With pyridine at 0℃; for 1h; | 13% |
tert-butyldimethylsilyl chloride
5-azacytidine
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 3h; Cooling with ice; | 12% |
Conditions | Yield |
---|---|
In water Heating; |
1. Introduction of 5-Azacytidine
5-Azacytidine is one kind of white-to-off-white crystalline solid. Its IUPAC Name is 4-Amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one. Its Classification Code is Antimetabolites; Antimetabolites, antineoplastic; Antineoplastic; Antineoplastic Agents; Drug / Therapeutic Agent; Enzyme inhibitors; Human Data; Mutation data; Noxae; Reproductive Effect; Skin / Eye Irritant; Tumor data. It belongs to API intermediates;Antitumors for Research and Experimental Use;Biochemistry;Chemical Reagents for Pharmacology Research;Nucleosides and their analogs;Nucleosides, Nucleotides & Related Reagents;Bases & Related Reagents;Nucleotides;Carbohydrates & Derivatives.
5-Azacytidine is sensitive to oxidation. 5-Azacytidine is unstable in solution. 5-Azacytidine undergoes hydrolysis in aqueous buffers. 5-Azacytidine is incompatible with strong oxidizers.
It is Slightly water soluble. Unstable in solution.
2. Properties of 5-Azacytidine
Physical properties about 5-Azacytidine are:
(1)Index of Refraction: 1.823; (2)Molar Refractivity: 51.08 cm3; (3)Molar Volume: 117 cm3; (4)Surface Tension: 106.7 dyne/cm; (5)Density: 2.08 g/cm3; (6)Flash Point: 277 °C; (7)Enthalpy of Vaporization: 93.24 kJ/mol; (8)Boiling Point: 534.5 °C at 760 mmHg; (9)Melting Point: 226-232 °C (dec.)(lit.); (10)alpha: 40 °(C=1, H2O 22 °C); (11)storage temperature: 2-8 °C; (12)Water Solubility: 0.5-1.0 g/100 mL at 21 °C; (13)Vapour Pressure of Azacitidine: 1.18E-13 mmHg at 25 °C.
3. Structure Descriptors of 5-Azacytidine
(1)InChI=1S/C8H12N4O5/c9-7-10-2-12(8(16)11-7)6-5(15)4(14)3(1-13)17-6/h2-6,13-15H,1H2,(H2,9,11,16)/t3-,4-,5-,6-/m1/s1;
(2)InChIKey=NMUSYJAQQFHJEW-KVTDHHQDSA-N; (3)Smiles:n1([C@@H]2O[C@H](CO)[C@H]([C@H]2O)O)c(nc(N)nc1)=O
(3)Smiles: n1([C@@H]2O[C@H](CO)[C@H]([C@H]2O)O)c(nc(N)nc1)=O
4. Toxicity of 5-Azacytidine
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
bird - wild | LD50 | oral | 100mg/kg (100mg/kg) | Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983. | |
dog | LD50 | intravenous | 7200ug/kg (7.2mg/kg) | BLOOD: OTHER CHANGES | Advances in Pharmacology and Chemotherapy. Vol. 14, Pg. 285, 1977. |
mouse | LD50 | intraperitoneal | 68mg/kg (68mg/kg) | Experientia. Vol. 22, Pg. 53, 1966. | |
mouse | LD50 | intravenous | 229mg/kg (229mg/kg) | BEHAVIORAL: ATAXIA GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | National Technical Information Service. Vol. PB84-211432, |
mouse | LD50 | oral | 572mg/kg (572mg/kg) | Toxicology and Applied Pharmacology. Vol. 19, Pg. 382, 1971. | |
quail | LD50 | oral | > 100mg/kg (100mg/kg) | Ecotoxicology and Environmental Safety. Vol. 6, Pg. 149, 1982. | |
women | TDLo | intravenous | 500ug/kg (.5mg/kg) | GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" GASTROINTESTINAL: NAUSEA OR VOMITING | Cancer Chemotherapy Reports, Part 1. Vol. 56, Pg. 413, 1972. |
women | TDLo | intravenous | 6mg/kg/10D-I (6mg/kg) | BLOOD: LEUKOPENIA BLOOD: AGRANULOCYTOSIS | Cancer Chemotherapy Reports, Part 1. Vol. 56, Pg. 413, 1972. |
Physical Property | Value | Units | Temp (deg C) | Source |
---|---|---|---|---|
Melting Point | 229 | deg C | EXP | |
log P (octanol-water) | -3.830 | (none) | EST | |
Water Solubility | 8.90E+04 | mg/L | 25 | EST |
Vapor Pressure | 4.10E-12 | mm Hg | 25 | EST |
Henry's Law Constant | 3.80E-21 | atm-m3/mole | 25 | EST |
Atmospheric OH Rate Constant | 9.72E-11 | cm3/molecule-sec | 25 | EST |
6. Safety Information of 5-Azacytidine
Confirmed carcinogen with experimental carcinogenic, neoplastigenic, tumorigenic data. Poison by ingestion, intravenous, and intraperitoneal routes. Human systemic effects by intravenous route: nausea, vomiting and diarrhea, reduction in white cell count (luekopenia and agranulocytosis). An experimental teratogen. Other experimental reproductive effects. Human mutation data reported. A skin irritant. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes: T
Risk Statements: 45-46-22
R45:May cause cancer.
R46:May cause heritable genetic damage.
R22:Harmful if swallowed.
Safety Statements: 53-22-36/37/39-45
S53:Avoid exposure - obtain special instructions before use.
S22:Do not breathe dust.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
WGK Germany: 3
RTECS of Azacitidine (CAS NO.320-67-2): XZ3017500
7. Uses of 5-Azacytidine
Azacitidine is mainly used in the treatment of myelodysplastic syndrome (MDS). It can also be used in vitro to remove methyl groups from DNA. 5-Azacytidine is a potent growth inhibitor and cytotoxic agent. It acts as a demethylating agent by inhibiting DNA methyltransferase. 5-azacytidine has been in the public eye for quite a while now, and it's been widely known as a powerful demethylating agent in clinical trials.
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