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CAS No. : | 60084-10-8 | MDL No. : | MFCD00866494 |
Formula : | C9H12N2O5S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FVRDYQYEVDDKCR-DBRKOABJSA-N |
M.W : | 260.27 | Pubchem ID : | 457954 |
Synonyms : |
Riboxamide;NSC 286193;TCAR.
|
Num. heavy atoms : | 17 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.56 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 6.0 |
Num. H-bond donors : | 4.0 |
Molar Refractivity : | 56.86 |
TPSA : | 154.14 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -9.12 cm/s |
Log Po/w (iLOGP) : | 1.14 |
Log Po/w (XLOGP3) : | -1.73 |
Log Po/w (WLOGP) : | -1.93 |
Log Po/w (MLOGP) : | -2.68 |
Log Po/w (SILICOS-IT) : | -0.27 |
Consensus Log Po/w : | -1.09 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 1.0 |
Egan : | 1.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.38 |
Solubility : | 108.0 mg/ml ; 0.414 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.99 |
Solubility : | 26.5 mg/ml ; 0.102 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | 0.51 |
Solubility : | 833.0 mg/ml ; 3.2 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 4.12 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
The residue was dissolved in hot ethanol and than, while stirring, 2-propanol was added. 103.2 g of compound 6, mp 142-144 C. were obtained and later an additional 3 g of compound 6, mp. 139-140 C. The two crops of solid were combined (106.2 g, 0.4 mol) and dissolved in boiling ethanol. The mixture was refrigerated (5 C.) for 2 hours and then filtered. The precipitate was washed with ethanol and dried. 89.3 g (0.34 mol) of the compound 6 was obtained, mp 144-146 C., i.e. 80.5%. The filtrate was evaporated to turbidity and the mixture vigorously stirred and cooled. The solid was collected by filtration, washed with ethanol and dried. 4.5 g (0.017 mol) of compound 6 was obtained, mp 142-144 C., i.e. 4.1%. The total yield of tiazofurin 6 was 93.4 g (0.357 mol) i.e. 84.6%. | ||
1.6 g (74%) | EXAMPLE 1 2-beta-D-Ribofuranosylthiazole-4-Carboxamide, COMPOUND 1 Ethyl 2-(2,3,5-tri-o-benzoyl-beta-D-ribofuranosyl)thiazole-4-carboxamide was utilized as prepared in Srivastova et. al, J. Med. Chem, 1977, Volume 20, No. 2, 256, herein incorporated by reference. A concentrated solution of ethyl 2-(2,3,5-tri-O-benzyl-beta-D-ribofuranosyl)thiazole-4-carboxamide (5.0 g, 8.31 mmol) in methanol (15 ml) was stirred with methanolic ammonia (saturated at 0 C., 100 ml) in a pressure bottle at room temperature for 2 days. The solvent was evaporated and the residue was chromatographed through a column (2.5*35 cm) of silica gel (100 g) packed in ethyl acetate. Elution of the column with a solvent system (ethyl acetate-1-propanolwater, 4:1:2; v/v; top layer) removed the fast-moving methyl benzoate and benzamide. The slower moving, major, UV and sugar-positive fractions were collected and the solvent was evaporated in vacuo. The residue (syrup), thus obtained, was readily crystallized from ethanol-ethyl acetate to provide 1.6 g (74%) of pure product, compound 1: mp 144-145 C.; [alpha] 25 p-14.3 (c 1, DMF); UV lambdamax pH1 237 nm (8640); UV lambdamaxpH11 238 nm (8100); 1 H-NMR(Me2 SO-d6) delta 7.5-7.8 [S(br), 2, CONH2 ]1 H-NMR (Me2 SO-d6 -D2 O) delta 4.99 (d, 1, J=5 Hz, H1'), 8.25 (s, 1, H5). Anal. (C9 H12 N2 O5 S) C, H, N, S. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
560 mg (47%) | With pyridine; trichlorophosphate; In water; acetonitrile; | EXAMPLE 3 2-(5-O-Phosphoryl-beta-D-Ribofuranosyl)thiazole-4 Carboxamide (2-beta-D-Ribofuranosylthiazole-4-Carboxamide 5'-Phosphate), COMPOUND 3 Water (151 mg, 8.4 mmol) was added carefully to a solution (maintained at 0 C. with stirring) of freshly distilled phosphoryl chloride (2.0 g, 13.2 mmol), pyridine (1.21 g, 14.4 mmol) and acetonitrile (2.3 g, 56.7 mmol). 2-beta-D-Ribofuranosylthiazole-4-carboxamide, compound 1, (dried over P2 O5 and powdered, 800 mg, 3.0 mmol) was added to the solution and the reaction mixture was stirred continuously for 4 hrs at 0 C. The reaction mixture was poured into ice water (ca. 50 ml) and the pH was adjusted to 2.0 with 2N sodium hydroxide. The solution was applied to a column of activated charcoal (20 g), and the column was washed thoroughly with water until the elude was salt-free. The column was eluted with a solution ethanol-water-concentrated ammonium hydroxide (10:10:1) and the fractions (25 ml each) were collected. The fractions containing pure (tlc, silica gel, acetonitrile-0.1N ammonium chloride (7:3)) nucleotide, compound 3, were collected and evaporated to dryness under vacuum. The anhydrous residue was dissolved in water and passed through a column of dowex 50W-X8 (20-50 mesh, H+ form, 15 ml). The column was washed with water and the fraction containing the nucleotide was collected. The solution was concentrated to a small volume (5 ml) and passed through a column of Dowex 50W-X8 (20-50 mesh, Na+ form, 15 ml). The column was washed with water. The nucleotide containing fraction was lyophilized. The residue was triturated with ethanol, collected by filtration and dried (P2 O5), to provide 560 mg (47%) of compound 3 as monosodium dihydrate in the crystalline form. Anal. calcd. for C9 H12 N2 O8 PSNa.2H2 O: C, 27.13; H, 4.04; N, 7.04; P, 7.78; S, 8.05. Found: C, 27.42; H, 3.87; N, 7.07; P, 8.03; S, 8.41. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.085 g (16%) | With ammonium formate; silver nitrate; In pyridine; water; formamide; | Method b. TRMP (1b) (0.27 g, 0.72 mmol) was dissolved in formamide (5 mL) and added to a solution of 2c (0.7 g, 1.43 mmol) in pyridine (50 mL). The resulting solution was concentrated in vacuo and dissolved in 6 mL of dry pyridine. Silver nitrate (0.91 g, 5.36 mmol) was added and the mixture stirred for 36 hr. After the addition of water (70 mL), H2 S was bubbled into the reaction mixture and the black precipitate formed removed by filtration. The filtrate was lyophilized and the resulting syrupy liquid was diluted with 5 mL of water and applied to a column of Bio-Rad AG1-X2 (HCO2 form, 100-200 mesh, 1.5*5 cm) and eluted with water (50 ml) followed by 2 M ammonium formate (50 ml). The ammonium formate fraction was lyophilized several times, redissolved in water and precipitated with ethanol. The precipitate that formed was saved and the filtrate concentrated and treated again with ethanol. The combined precipitates (0.325 g) were chromatographed on a Hamilton HA-X4 column as in Method a. to afford 0.08 g of TAD which eluted as a single peak. An extra 5 mg of TAD was obtained from a third precipitation of the mother solution bringing the total yield to 0.085 g (16%). Analysis: Calculated for C19 H29 N8 O14 P2 S.2.5H2 O (monoammonium salt): C, 31.14; H, 4.51; N, 15.30; P, 8.47; S, 4.37. Found: C, 31.16; H, 4.63; N, 15.67; P, 8.53; S, 4.14. |