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Sparsomycin
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Name

Sparsomycin

 EINECS N/A
CAS No. 1404-64-4 Density 1.466 g/cm3
PSA 176.63000 LogP 0.18770
Solubility N/A Melting Point 208-209° (dec)
Formula C13H19N3O5S2 Boiling Point N/A
Molecular Weight 361.443 Flash Point N/A
Transport Information UN 2811 6.1/PG 2 Appearance N/A
Safety 28-36/37-45 Risk Codes 28
Molecular Structure Molecular Structure of 1404-64-4 (Sparsomycin) Hazard Symbols VeryT+
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;

Article Data 8

Sparsomycin Synthetic route

95407-15-1

O-(methoxymethyl)sparsomycin

1404-64-4

sparsomycin

Conditions
ConditionsYield
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%
52-90-4

L-Cysteine

73-22-3

L-Tryptophan

1404-64-4

sparsomycin

Conditions
ConditionsYield
With Streptomyces sparsogenes var. sparsogenes at 32℃; for 240h; Mechanism; Streptomyces sparsogenes var. spartogenes; other labeled (2)H and (13)C educts;
77826-38-1

S-Oxo-S<(methylthio)methyl>-D-cysteinol

28277-67-0

(E)-β-(2,4-Dioxo-6-methyl-1,2,3,4-tetrahydropyrimidin-5-yl)acrylic acid

1404-64-4

sparsomycin

Conditions
ConditionsYield
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;
95407-13-9

(RS)-O-(methoxymethyl)-S-((methylthio)methyl)-D-cysteinol S-oxide

1404-64-4

sparsomycin

Conditions
ConditionsYield
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
626-48-2

6-Methyluracil

ZnCl2

ZnCl2

1404-64-4

sparsomycin

Conditions
ConditionsYield
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
147-61-5

5-hydroxymethyl-6-methyluracil

1404-64-4

sparsomycin

Conditions
ConditionsYield
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
24048-74-6

1,2,3,4-tetrahydro-6-methyl-2,4-dioxo-5-pyrimidinecarbaldehyde

1404-64-4

sparsomycin

Conditions
ConditionsYield
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

C11H12N2O6

1404-64-4

sparsomycin

Conditions
ConditionsYield
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
28277-67-0

(E)-β-(2,4-Dioxo-6-methyl-1,2,3,4-tetrahydropyrimidin-5-yl)acrylic acid

1404-64-4

sparsomycin

Conditions
ConditionsYield
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
28277-68-1

Ethyl (E)-3-(2,4-Dioxo-6-methyl-5-pyrimidinyl)acrylate

1404-64-4

sparsomycin

Conditions
ConditionsYield
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

Sparsomycin History

The compound was discovered in 1962 and the structure was determined in 1970; a first total synthesis was reported in 1981.

Sparsomycin Specification

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.

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