6H-Purin-6-one, 9-[[2-(acetyloxy)ethoxy]methyl]-2-amino-1, 9-dihydro-
Synonyms:9-(2-Acetoxyethoxymethyl)guanine;2-[(2-Amino-6-oxo-1, 6-dihydro-9H-purin-9-yl)methoxy]ethyl acetate;
- Melting Point:242-244°C (dec.)
- Boiling Point:565.4 °C at 760 mmHg
- Density:1.61 g/cm3
- Flash Point:295.7 °C
- Vapor Density:N/A
- Refractive Index:N/A
- Storage Temp.:Refrigerator
6H-Purin-6-one, 9-[[2-(acetyloxy)ethoxy]methyl]-2-amino-1, 9-dihydro- Safety information and MSDS
H341 Suspected of causing genetic defects
P201 Obtain special instructions before use.
P202 Do not handle until all safety precautions have been read and understood.
P280 Wear protective gloves/protective clothing/eye protection/face protection.
P308+P313 IF exposed or concerned: Get medical advice/ attention.
P405 Store locked up.
P501 Dispose of contents/container to ...
·Composition/information on ingredients:
|Chemical name||Common names and synonyms||CAS number||EC number||Concentration|
|Acyclovir Acetate||Acyclovir Acetate||102728-64-3||none||100%|
General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.
·Accidental release measures:
Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.
6H-Purin-6-one, 9-[[2-(acetyloxy)ethoxy]methyl]-2-amino-1, 9-dihydro- Relevant articlesAll total 22 Articles be found
Synthesis of acyclic nucleoside analogues based on 1,2,4-triazolo[1,5-a] pyrimidin-7-ones by one-step Vorbrüggen glycosylation
Khalymbadzha, Igor A.,Shestakova, Tatyana S.,Subbotina, Julia O.,Eltsov, Oleg S.,Musikhina, Alexandra A.,Rusinov, Vladimir L.,Chupakhin, Oleg N.,Karpenko, Inna L.,Jasko, Maxim V.,Kukhanova, Marina K.,Deev, Sergey L.
, p. 1298 - 1305 (2014/02/14)
New acyclovir analogues were obtained by reaction of 1,2,4-triazolo[1,5-a] pyrimidin-7-ones 4a-i with (2-acetoxyethoxy)methyl acetate 5 in the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) as catalyst (Vorbrüggen procedure). Coupling betwe
Novel water-soluble prodrugs of acyclovir cleavable by the dipeptidyl-peptidase IV (DPP IV/CD26) enzyme
Diez-Torrubia, Alberto,Cabrera, Silvia,De Castro, Sonia,García-Aparicio, Carlos,Mulder, Gwenn,De Meester, Ingrid,Camarasa, María-José,Balzarini, Jan,Velázquez, Sonsoles
, p. 456 - 468 (2013/11/19)
We herein report for the first time the successful use of the dipeptidyl peptidase IV (DPPIV/CD26) prodrug approach to guanine derivatives such as the antiviral acyclovir (ACV). The solution- and solid-phase synthesis of the tetrapeptide amide prodrug 3 and the tripeptide ester conjugate 4 of acyclovir are reported. The synthesis of the demanding tetrapeptide amide prodrug of ACV 3 was first established in solution and successfully transferred onto solid support by using Ellman's dihydropyran (DHP) resin. In contrast with the valyl ester prodrug (valacyclovir, VACV), the tetrapeptide amide prodrug 3 and the tripeptide ester conjugate 4 of ACV proved fully stable in PBS. Both prodrugs converted to VACV (for 4) or ACV (for 3) upon exposure to purified DPPIV/CD26 or human or bovine serum. Vildagliptin, a potent inhibitor of DPPIV/CD26 efficiently inhibited the DPPIV/CD26-catalysed hydrolysis reaction. Both amide and ester prodrugs of ACV showed pronounced anti-herpetic activity in cell culture and significantly improved the water solubility in comparison with the parent drug.
New potential prodrugs of aciclovir using calixarene as a lipophilic carrier: Synthesis and drug-release studies at the air-water interface
Sautrey, Guillaume,Clarot, Igor,Rogalska, Ewa,Regnouf-De-Vains, Jean-Bernard
, p. 2060 - 2069 (2013/02/25)
Two tetra-p-tert-butyl-calixarene species bearing one or two anti-HSV aciclovir units tethered via carbodiester linkages at the lower rim were synthesized as possible antiviral prodrugs. The amphiphilic properties of these derivatives were studied usin
New green synthesis and formulations of acyclovir prodrugs
De Regil-Hernandez, Ruben,Martinez-Lagos, Fernando,Rodriguez-Bayon, Amalia,Sinisterra, Jose-Vicente
experimental part, p. 1089 - 1093 (2011/10/03)
Different green synthesis of alkyl esters of acyclovir (acyclovir prodrugs) is described. Hexanoic, decanoic, dodecanoic and tetradecanoic acyclovir esters were synthesized reacting acyclovir and the respective acid anhydride in dimethyl sulfoxide (DMSO), in solvents from renewable sources and without solvent (T=30 °C). Yields in prodrugs after 10 min of reaction were >95% using DMSO as solvent. The purification methodology was very simple, shorter and greener than previously described. The biosolvent, N,N-dimethylamide of decanoic acid, let us to obtain >95% yield at 24 h. This oily biosolvent is not dermotoxic and the reaction crude can directly be used in topic formulations. Syntheses without solvent proceeded successfully for acyclovir esters. Indeed, dodecanoate and tetradecanoate yielding >98% conversion of reactants in 30 min. In spite of requiring mild temperature (65 °C), substrate molar ratios were lowered to 1 : 1, thus conducing to a more efficient use of raw materials. The synthetic procedures were scaled up to a 300 g batch (yield 98-99% isolated ester). These esters can be used as acyclovir prodrugs in topic formulations. The esters release from an oil/water micro-emulsion and a hydrogel formulation were tested with good results.
Chemoselective N-Deacetylation of Protected Nucleosides and Nucleotides Promoted by Schwartz's Reagent
Ferrari, Valentina,Serpi, Michaela,McGuigan, Christopher,Pertusati, Fabrizio
, p. 799 - 814 (2015/11/17)
Protection and deprotection strategies involving the N-acetyl group are widely utilized in nucleoside and nucleotide chemistry. Herein, we present a mild and selective N-deacetylation methodology, applicable to purine and pyrimidine nucleosides, by means of Schwartz's reagent, compatible with most of the common protecting groups used in nucleoside chemistry.
6H-Purin-6-one, 9-[[2-(acetyloxy)ethoxy]methyl]-2-amino-1, 9-dihydro- Synthetic route And Reaction conditions
Multi-step reaction with 2 steps
1: 81 percent / DMAP, Et3N / CH2Cl2 / 1 h / Ambient temperature
2: 2.2 percent Chromat. / hydrogen / Pd/CaCO3 / ethanol / 24 h / 70 °C
Acetic acid 2-(2-oxo-propoxy)-ethyl ester
2-acetoxyethyl acetoxymethyl ether
6H-Purin-6-one, 9-[[2-(acetyloxy)ethoxy]methyl]-2-amino-1, 9-dihydro- Raw materials
2-acetoxyethyl acetoxymethyl ether
6H-Purin-6-one, 9-[[2-(acetyloxy)ethoxy]methyl]-2-amino-1, 9-dihydro- Target Products
- Lab/Research institutionsTrading CompanyManufacturers
- Product LicenseEnterprise AuthenticationISOGMPFDAHALAL
- China (Mainland)(23)United States(3)China(Hongkong)(1)United Kingdom(1)India(1)Canada(1)
- 4-(diethyoxyphosphorylmethyl)benzoic acid methyl ester
- methyl 2-cyano-2-phenylacetate
- 2-methoxy-3-nitrobenzoic acid
- di-2-pyridyl sulfide
- europium(III) iodide
- (2S,3S)-2-(benzylamino)-3-methylpentanoic acid
- methyl 3-<4-(2,3-epoxypropoxy)phenyl>propionate
- N-tert-butyloxycarbonyl-D-proline benzylamide
- 2,4-dioxopentan-3-yl 4-methylbenzenesulfonate