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| CAS No.: | 85-31-4 |
|---|---|
| Name: | 6-THIOGUANOSINE |
| Molecular Structure: | |
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| Formula: | C10H13 N5 O4 S |
| Molecular Weight: | 299.31 |
| Synonyms: | 6H-Purine-6-thione,2-amino-1,9-dihydro-9-b-D-ribofuranosyl- (8CI); 9H-Purine-6(1H)-thione, 2-amino-9-b-D-ribofuranosyl- (6CI,7CI);2-Amino-6-mercaptopurine ribonucleoside; 2-Amino-6-mercaptopurine riboside;2-Amino-9-(b-D-ribofuranosyl)purine-6-thiol;2-Amino-9-b-D-ribofuranosyl-9H-purine-6-thiol;2-Amino-9-b-D-ribofuranosylpurine-6-thione;6-Mercaptoguanine riboside; 6-Mercaptoguanosine; 6-Thioguanine ribonucleoside;6-Thioguanine riboside; 6-Thioguanosine; 9-b-D-Ribofuranosylthioguanine; NSC-29422; Thioguanosine |
| EINECS: | 201-597-2 |
| Density: | 2.18 g/cm3 |
| Melting Point: | 230-231°C |
| Boiling Point: | 756.9 °C at 760 mmHg |
| Flash Point: | 411.6 °C |
| Solubility: | Soluble in Ammonium Hydroxide and water |
| Appearance: | Yellow-Green Powder |
| Safety: | Poison by intraperitoneal route. When heated to decomposition it emits very toxic fumes of NOx and SOx. See also MERCAPTANS. |
| PSA: | 174.53000 |
| LogP: | -0.73620 |
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- 88010-92-8
O2',O3',O5'-tribenzoyl-6-thio-guanosine
- 85-31-4
6-thioguanosine
| Conditions | Yield |
|---|---|
| With sodium ethanolate |
| Conditions | Yield |
|---|---|
| With pyridine; sodium hydrogensulfide; trifluoroacetic anhydride 1) 40 min, ice-bath, 2) DMF, 24 h; Multistep reaction; |
- 66048-53-1
2',3',5'-tri-O-benzoylguanosine
- 85-31-4
6-thioguanosine
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: aqueous pyridine; P2S5 2: ethanolic sodium ethylate View Scheme |
- 70-34-8
2,4-Dinitrofluorobenzene
- 85-31-4
6-thioguanosine
- 74418-21-6
(2R,3R,4S,5R)-2-[2-Amino-6-(2,4-dinitro-phenylsulfanyl)-purin-9-yl]-5-hydroxymethyl-tetrahydro-furan-3,4-diol
| Conditions | Yield |
|---|---|
| With triethylamine | 80% |
| With triethylamine |
- 85-31-4
6-thioguanosine
- 123002-38-0
6-amino-1-β-D-ribofuranosylimidazo<4,5-c>pyridine-4-sulfenamide
| Conditions | Yield |
|---|---|
| With potassium hydroxide; chloroamine for 0.75h; from 0 deg C to RT; | 74% |
| With potassium hydroxide; chloroamine at 0℃; for 1.5h; | 73.7% |
- 15715-58-9
triethylamine carbonate
- 85-31-4
6-thioguanosine
| Conditions | Yield |
|---|---|
| Stage #1: 6-thioguanosine With trimethyl phosphite; trichlorophosphate at 0℃; for 48h; Stage #2: triethylamine carbonate In water | 68% |
| Conditions | Yield |
|---|---|
| In methanol; water at 86℃; for 3h; | 48% |
- 85-31-4
6-thioguanosine
| Conditions | Yield |
|---|---|
| With sodium hydroxide In water for 3h; pH=8; Reflux; | 15% |
| Conditions | Yield |
|---|---|
| With E. coli purine nucleoside phosphorylase Enzyme kinetics; Substitution; |
- 85-31-4
6-thioguanosine
- 623164-06-7
N2-phenoxyacetyl-S6-(2,4-dinitrophenyl)-6-thioguanosine
| Conditions | Yield |
|---|---|
| Multi-step reaction with 4 steps 1: 80 percent / triethylamine 2: NH3 / H2O View Scheme | |
| Multi-step reaction with 4 steps 1: Et3N 2: pyridine 3: pyridine 4: aq. NH3 View Scheme |
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Chemistry
Molecular Formula: C10H13N5O4S
Molar mass: 299.31 g/mol
EINECS: 201-597-2
Density: 2.18 g/cm3
Flash Point: 411.6 °C
Index of Refraction: 1.975
Boiling Point: 756.9 °C at 760 mmHg
Vapour Pressure: 4.44E-24 mmHg at 25°C
Melting point: 230-231°C
Appearance: Tan powder
Product categories of 6-Thioguanosine (85-31-4): Nucleotides and Nucleosides;Sulfur & Selenium Compounds;Bases & Related Reagents;Nucleotides
Structure of 6-Thioguanosine (85-31-4):
XLogP3-AA: -1.2
H-Bond Donor: 5
H-Bond Acceptor: 7
Systematic Name: 2-Amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-3H-purine-6-thione
SMILES: S=C3/N=C(/N)Nc1c3ncn1[C@@H]2O[C@@H]([C@@H](O)[C@H]2O)CO
InChI: InChI=1/C10H13N5O4S/c11-10-13-7-4(8(20)14-10)12-2-15(7)9-6(18)5(17)3(1-16)19-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,20)/t3-,5-,6-,9-/m1/s1
InChIKey: OTDJAMXESTUWLO-UUOKFMHZBV
Std. InChI: InChI=1S/C10H13N5O4S/c11-10-13-7-4(8(20)14-10)12-2-15(7)9-6(18)5(17)3(1-16)19-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,20)/t3-,5-,6-,9-/m1/s1
Std. InChIKey: OTDJAMXESTUWLO-UUOKFMHZSA-N
Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LD10 | unreported | 1700mg/kg (1700mg/kg) | Progress in Medical Chemistry. Vol. 7, Pg. 69, 1970. | |
| mouse | LD50 | intraperitoneal | 156mg/kg (156mg/kg) | National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986, | |
| rat | LD50 | intraperitoneal | 200mg/kg (200mg/kg) | Advances in Teratology. Vol. 3, Pg. 181, 1968. |
Safety Profile
Poison by intraperitoneal route. When heated to decomposition it emits very toxic fumes of NOx and SOx. See also MERCAPTANS.
Specification
6-Thioguanosine (85-31-4) also can be called 2-Amino-6-mercapto-9-b-D-ribofuranosylpurinee ; 6H-Purine-6-thione, 2-amino-1,9-dihydro-9-.beta.-D-ribofuranosyl- ; 2-Amino-9-(.beta.-D-ribofuranosyl)purine-6-thiol ; 9H-Purine-6-thiol, 2-amino-9-.beta.-D-ribofuranosyl- ; 2-Amino-6-mercapto-9-(.beta.-D-ribofuranosyl)purine ; and ; 6-Mercaptoguanosine .