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CAS No.: | 1404-64-4 |
---|---|
Name: | Sparsomycin |
Article Data: | 8 |
Molecular Structure: | |
Formula: | C13H19N3O5S2 |
Molecular Weight: | 361.443 |
Synonyms: | 2-Propenamide,N-[1-(hydroxymethyl)-2-[[(methylthio)methyl]sulfinyl]ethyl]-3-(1,2,3,4-tetrahydro-6-methyl-2,4-dioxo-5-pyrimidinyl)-,[R-[R*,S*-(E)]]-;5-Pyrimidineacrylamide,1,2,3,4-tetrahydro-N-[1-(hydroxymethyl)-2-[[(methylthio)methyl]sulfinyl]ethyl]-6-methyl-2,4-dioxo-,(E)-(1S)- (8CI);Sparsomycin (7CI);(+)-Sparsomycin;NSC 059729;NSC 59729;U19183; |
Density: | 1.466 g/cm3 |
Melting Point: | 208-209° (dec) |
Hazard Symbols: | T+ |
Risk Codes: | 28 |
Safety: | 28-36/37-45 |
Transport Information: | UN 2811 6.1/PG 2 |
PSA: | 176.63000 |
LogP: | 0.18770 |
O-(methoxymethyl)sparsomycin
sparsomycin
Conditions | Yield |
---|---|
With Dowex(R) 50W H(1+) form In methanol at 50℃; for 2h; | 74% |
With methanol; Dowex 50W at 50℃; | 73% |
With hydrogenchloride In methanol at 50℃; for 5h; | 65% |
Conditions | Yield |
---|---|
With Streptomyces sparsogenes var. sparsogenes at 32℃; for 240h; Mechanism; Streptomyces sparsogenes var. spartogenes; other labeled (2)H and (13)C educts; |
S-Oxo-S<(methylthio)methyl>-D-cysteinol
(E)-β-(2,4-Dioxo-6-methyl-1,2,3,4-tetrahydropyrimidin-5-yl)acrylic acid
sparsomycin
Conditions | Yield |
---|---|
With chloroformic acid ethyl ester; triethylamine 1.) THF/DMF, 0 deg C, 4 h; 2.) THF/DMF, room temp., 48 h; Yield given. Multistep reaction; |
(RS)-O-(methoxymethyl)-S-((methylthio)methyl)-D-cysteinol S-oxide
sparsomycin
Conditions | Yield |
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Multi-step reaction with 2 steps 1: 88 percent / dicyclohexyl carbodiimide; 1-hydroxy-7-azabenzotriazole / dimethylformamide / 12 h / 20 °C 2: 74 percent / Dowex(R) 50W H(1+) form / methanol / 2 h / 50 °C View Scheme | |
Multi-step reaction with 2 steps 1: 38 percent / 1,3-dicyclohexylcarbodiimide, 1-hydroxybenzo-7-azatriazole / tetrahydrofuran; dimethylformamide / Ambient temperature 2: 73 percent / Dowex 50W, MeOH / 50 °C View Scheme | |
Multi-step reaction with 2 steps 1: tetrahydrofuran; dimethylformamide / 36 h / Ambient temperature 2: 65 percent / 1 N HCl / methanol / 5 h / 50 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 77 percent / aq. NaOH / H2O / 40 h / 25 °C 2: 60 percent / ceric ammonium nitrate / H2O / 25 °C 3: 75 percent / dimethylsulfoxide / 50 h / 25 °C 4: 90 percent / 3 N aq. NaOH / methanol; dioxane / 24 h / 25 °C 5: 1.) triethylamine / 1.) DMF, THF, 0 deg C, 5 min, 2.) RT, 4 h 6: tetrahydrofuran; dimethylformamide / 36 h / Ambient temperature 7: 65 percent / 1 N HCl / methanol / 5 h / 50 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 60 percent / ceric ammonium nitrate / H2O / 25 °C 2: 75 percent / dimethylsulfoxide / 50 h / 25 °C 3: 90 percent / 3 N aq. NaOH / methanol; dioxane / 24 h / 25 °C 4: 1.) triethylamine / 1.) DMF, THF, 0 deg C, 5 min, 2.) RT, 4 h 5: tetrahydrofuran; dimethylformamide / 36 h / Ambient temperature 6: 65 percent / 1 N HCl / methanol / 5 h / 50 °C View Scheme | |
Multi-step reaction with 4 steps 1: 63 percent / K2S2O8, AgNO3 / H2O / 1.) 90-100 deg C; 2.) room temp. 16 h 2: 40 percent / dimethylformamide / 96 h / Ambient temperature 3: 90 percent / NaOH / methanol; dioxane; H2O / 16 h / 40 °C 4: 1.) Triethylamine, Ethyl chloroformate / 1.) THF/DMF, 0 deg C, 4 h; 2.) THF/DMF, room temp., 48 h View Scheme |
1,2,3,4-tetrahydro-6-methyl-2,4-dioxo-5-pyrimidinecarbaldehyde
sparsomycin
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 75 percent / dimethylsulfoxide / 50 h / 25 °C 2: 90 percent / 3 N aq. NaOH / methanol; dioxane / 24 h / 25 °C 3: 1.) triethylamine / 1.) DMF, THF, 0 deg C, 5 min, 2.) RT, 4 h 4: tetrahydrofuran; dimethylformamide / 36 h / Ambient temperature 5: 65 percent / 1 N HCl / methanol / 5 h / 50 °C View Scheme | |
Multi-step reaction with 3 steps 1: 40 percent / dimethylformamide / 96 h / Ambient temperature 2: 90 percent / NaOH / methanol; dioxane; H2O / 16 h / 40 °C 3: 1.) Triethylamine, Ethyl chloroformate / 1.) THF/DMF, 0 deg C, 4 h; 2.) THF/DMF, room temp., 48 h View Scheme |
sparsomycin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: tetrahydrofuran; dimethylformamide / 36 h / Ambient temperature 2: 65 percent / 1 N HCl / methanol / 5 h / 50 °C View Scheme |
(E)-β-(2,4-Dioxo-6-methyl-1,2,3,4-tetrahydropyrimidin-5-yl)acrylic acid
sparsomycin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.) triethylamine / 1.) DMF, THF, 0 deg C, 5 min, 2.) RT, 4 h 2: tetrahydrofuran; dimethylformamide / 36 h / Ambient temperature 3: 65 percent / 1 N HCl / methanol / 5 h / 50 °C View Scheme |
Ethyl (E)-3-(2,4-Dioxo-6-methyl-5-pyrimidinyl)acrylate
sparsomycin
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 90 percent / 3 N aq. NaOH / methanol; dioxane / 24 h / 25 °C 2: 1.) triethylamine / 1.) DMF, THF, 0 deg C, 5 min, 2.) RT, 4 h 3: tetrahydrofuran; dimethylformamide / 36 h / Ambient temperature 4: 65 percent / 1 N HCl / methanol / 5 h / 50 °C View Scheme | |
Multi-step reaction with 2 steps 1: 90 percent / NaOH / methanol; dioxane; H2O / 16 h / 40 °C 2: 1.) Triethylamine, Ethyl chloroformate / 1.) THF/DMF, 0 deg C, 4 h; 2.) THF/DMF, room temp., 48 h View Scheme |
The CAS registry number of Sparsomycin is 1404-64-4. In addition, the molecular formula is C13H19N3O5S2 and the molecular weight is 361.44. The IUPAC name is (E)-N-[(2S)-1-hydroxy-3-(methylsulfanylmethylsulfinyl)propan-2-yl]-3-(6-methyl-2,4-dioxo-1H-pyrimidin-5-yl)prop-2-enamide. What's more, it is a nucleotide analogue. Besides, it can be used as an anti-tumor drug and as a tool to study protein synthesis. But it is not usable as an antibiotic.
Physical properties about Sparsomycin are: (1)ACD/LogP: -1.92; (2)# of Rule of 5 Violations: 0; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 2.16; (6)ACD/KOC (pH 7.4): 1.96; (7)#H bond acceptors: 8; (8)#H bond donors: 4; (9)#Freely Rotating Bonds: 9; (10)Polar Surface Area: 131.74 Å2; (11)Index of Refraction: 1.656; (12)Molar Refractivity: 90.59 cm3; (13)Molar Volume: 246.4 cm3; (14)Polarizability: 35.91 ×10-24cm3; (15)Surface Tension: 76.7 dyne/cm; (16)Density: 1.466 g/cm3.
When you are using this chemical, please be cautious about it as the following:
This chemical is very toxic if swallowed. During using it, wear suitable protective clothing and gloves. If contact it with skin, wash it immediately with plenty of ... (to be specified by the manufacturer). And in case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.).
You can still convert the following datas into molecular structure:
(1)SMILES: O=C1N/C(=C(/C=C/C(=O)N[C@H](CS(=O)CSC)CO)C(=O)N1)C
(2)Std.InChI: InChI=1S/C13H19N3O5S2/c1-8-10(12(19)16-13(20)14-8)3-4-11(18)15-9(5-17)6-23(21)7-22-2/h3-4,9,17H,5-7H2,1-2H3,(H,15,18)(H2,14,16,19,20)/b4-3+/t9-,23?/m0/s1
(3)Std.InChIKey: XKLZIVIOZDNKEQ-RVUDUMFNSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
dog | LD50 | intravenous | 1mg/kg (1mg/kg) | "Compounds Available for Fundamental Research, Volume II-6, Antibiotics, A Program of Upjohn Company Research Laboratory." Vol. 2(6), Pg. -, 1971. | |
mouse | LD50 | intraperitoneal | 2400ug/kg (2.4mg/kg) | Cancer Chemotherapy Reports. Vol. 30, Pg. 9, 1963. | |
mouse | LD50 | intravenous | 4mg/kg (4mg/kg) | "Compounds Available for Fundamental Research, Volume II-6, Antibiotics, A Program of Upjohn Company Research Laboratory." Vol. 2(6), Pg. -, 1971. | |
mouse | LD50 | oral | 22mg/kg (22mg/kg) | "Compounds Available for Fundamental Research, Volume II-6, Antibiotics, A Program of Upjohn Company Research Laboratory." Vol. 2(6), Pg. -, 1971. |