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CAS No.: | 54-42-2 |
---|---|
Name: | (+)-5-Iodo-2'-deoxyuridine |
Article Data: | 27 |
Molecular Structure: | |
Formula: | C9H11IN2O5 |
Molecular Weight: | 354.101 |
Synonyms: | 1-(2-Deoxy-b-D-ribofuranosyl)-5-iodouracil;2'-Deoxy-5-iodouridine;5-Iodo-2'-deoxyuridine;5-Iodo-2'-desoxyuridine;5-Iododeoxyuridine;5-Iodouracil deoxyriboside;5IUDR;Allergan 211;Dendrid;Emanil;Herpe-Gel;Herpesil;Herpidu;Herplex;IDU;IDUR;IUDR;Idexur;Idoxene;Idoxuridin;Idoxuridine;Idu Oculos;Iducher;Idulea;Iduridin;Iododeoxyuridine;Joddeoxiuridin;Kerecid;NSC 39661;Ophthalmadine;SKF 14287;Stoxil;Stoxip;Synmiol;Virudox; |
EINECS: | 200-207-8 |
Density: | 2.148 g/cm3 |
Melting Point: | 194 °C(lit.) |
Solubility: | 1.6 g/L (20 ºC) |
Appearance: | crystalline solid |
Hazard Symbols: | T,Xn |
Risk Codes: | 45-46-61-40 |
Safety: | 53-45-36-22 |
PSA: | 104.55000 |
LogP: | -1.21810 |
Conditions | Yield |
---|---|
With iodine; silver nitrate In methanol at 40℃; for 3h; | 100% |
With iodine; silver nitrate In methanol at 40℃; for 3h; | 100% |
With sodium azide; Iodine monochloride In acetonitrile at 25℃; for 24h; Product distribution; Mechanism; other uracil nucleosides; other halogenation agents; var. temp. and time; | 96% |
Conditions | Yield |
---|---|
With sodium methylate In methanol for 1h; Ambient temperature; | 90% |
With methanol; sodium methylate at 20℃; for 1h; |
5-trimethylstannyl-2'-deoxyuridine
5-Iodo-2'-deoxyuridine
Conditions | Yield |
---|---|
With sodium hydroxide; dihydrogen peroxide; acetic acid; sodium iodide In chloroform for 0.00416667h; Irradiation; |
5-Iodo-2'-deoxyuridine
Conditions | Yield |
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With ammonia In methanol at 30℃; for 16h; |
Conditions | Yield |
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at 37℃; for 6h; alginate gel-entrapped cells of auxotrophic thymine-dependent strain of E. coli, ammonium acetate buffer pH 5.8; |
Conditions | Yield |
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With thymidine phosphorylase from Escherichia coli In phosphate buffer at 35℃; for 2h; pH=7.0; Title compound not separated from byproducts; | A 88 % Chromat. B n/a |
3',5'-di-O-acetyl-2'-deoxyuridine
5-Iodo-2'-deoxyuridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 93 percent / LiI, ceric ammonium nitrate (CAN) / acetonitrile / 1 h / 80 °C / other conditions and reagents investigated 2: 90 percent / 0.1 M NaOMe / methanol / 1 h / Ambient temperature View Scheme |
C5-chloromercuri-2'-deoxyuridine
1,3,4,6-tetrachloro-3α,6α-diphenyl glycoluril
5-Iodo-2'-deoxyuridine
Conditions | Yield |
---|---|
With sodium iodide In water |
Conditions | Yield |
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With thymidine phosphorylase from Escherichia coli (E.C. 2.4.2.4) immobilized on Sepabeads EC-EP In aq. phosphate buffer at 20℃; for 3h; pH=7.5; Reagent/catalyst; Enzymatic reaction; |
3',5'-di-O-acetyl-2'-deoxyuridine
A
5-Iodo-2'-deoxyuridine
E
2'-deoxy-4-thiouridine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: ammonium cerium (IV) nitrate; iodine / acetonitrile / 1 h / 80 °C 2: tetraphosphorus decasulfide / 1,4-dioxane / Reflux 3: sodium hydride / methanol / 0.17 h / 0 - 20 °C 4: aq. phosphate buffer; tert-butyl alcohol / Radiolysis View Scheme |
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The Uridine,2'-deoxy-5-iodo-, with the CAS registry number 54-42-2 and EINECS registry number 200-207-8, has the IUPAC name of 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidine-2,4-dione. It is a kind of crystalline solid which is sensitive to air and light, and it is always used as antiviral. The molecular formula of the chemical is C9H11IN2O5.
The physical properties of Uridine,2'-deoxy-5-iodo- are as followings: (1)ACD/LogP: -0.59; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1; (4)ACD/LogD (pH 7.4): -1; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 12; (8)ACD/KOC (pH 7.4): 6; (9)#H bond acceptors: 7; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 99.1 Å2; (13)Index of Refraction: 1.715; (14)Molar Refractivity: 64.752 cm3; (15)Molar Volume: 164.874 cm3; (16)Polarizability: 25.67×10-24cm3; (17)Surface Tension: 87.47 dyne/cm; (18)Density: 2.148 g/cm3.
Preparation: You can start with propiolic alcohol by oxidation and esterification, then it reacts with 2-amino-oxazoline nucleoside. By a series of acylation, bromination, catalytic hydrogenation and hydrolysis, you can get the product.
You should be cautious while dealing with this chemical. It may cause cancer and heritable genetic damage. Therefore, you had better take the following instructions: Do not breathe dust; Avoid exposure - obtain special instruction before use; In case of accident or if you feel unwell, seek medical advice immediately (show label where possible); Wear suitable protective clothing.
You can still convert the following datas into molecular structure:
(1)SMILES: I\C1=C\N(C(=O)NC1=O)C2C[C@H](O)[C@@H](CO)O2
(2)InChI: InChI=1/C9H11IN2O5/c10-4-2-12(9(16)11-8(4)15)7-1-5(14)6(3-13)17-7/h2,5-7,13-14H,1,3H2,(H,11,15,16)/t5-,6+,7?/m0/s1
(3)InChIKey: XQFRJNBWHJMXHO-GFCOJPQKBD
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 1gm/kg (1000mg/kg) | JNCI, Journal of the National Cancer Institute. Vol. 62, Pg. 911, 1979. | |
mouse | LD50 | oral | > 10gm/kg (10000mg/kg) | Drugs in Japan Vol. -, Pg. 153, 1995. | |
rat | LD50 | intraperitoneal | 4gm/kg (4000mg/kg) | Advances in Teratology. Vol. 3, Pg. 181, 1968. |