172529-94-1

Basic information

• Product Name: 1,3-Propanediol, 2-[2-(2-amino-6-chloro-9H-purin-9-yl)ethyl]-
• Synonyms: 1,3-Propanediol, 2-[2-(2-amino-6-chloro-9H-purin-9-yl)ethyl]-;FaMciclovir iMpurity 1
• CAS NO: 172529-94-1
• Molecular Formula: C₁₀H₁₄ClN₅O₂
• Molecular Weight: 272
• Mol File: 172529-94-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,3-Propanediol, 2-[2-(2-amino-6-chloro-9H-purin-9-yl)ethyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Propanediol, 2-[2-(2-amino-6-chloro-9H-purin-9-yl)ethyl]-(172529-94-1)
• EPA Substance Registry System: 1,3-Propanediol, 2-[2-(2-amino-6-chloro-9H-purin-9-yl)ethyl]-(172529-94-1)

Safety Data

• Hazardous Substances Data: 172529-94-1(Hazardous Substances Data)

Usage

Uses

6-Chloro Didesacetyl Famciclovir is a prodrug of Penciclovir (P221500); an antiviral.

Upstream product

• 122497-17-0 2-[2-(2-Amino-6-chloro-purin-9-yl)-ethyl]-2-ethoxycarbonyl-malonic acid diethyl ester 
• 71170-82-6 triethyl 3-bromopropane-1,1,1-tricarboxylate 
• 10310-21-1 2-Amino-6-chloropurin 
• 97845-72-2 2-[(acetyloxy)methyl]-4-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)butyl acetate 
• 39809-25-1 Penciclovir 
• 177838-59-4 2-amino-6-chloro-9-(ethyl 2-carboethoxybutanoate-4-yl)purine 
• 333335-54-9 benzoic acid 5-(2-amino-6-chloro-purin-9-yl)-tetrahydro-furan-3-ylmethyl ester 
• 333335-49-2 2-acetoxy-4-benzoyloxymethylterahydrofuran 
• 333335-47-0 benzoic acid 5-ethoxy-tetrahydro-furan-3-ylmethyl ester 
• 333335-48-1 benzoic acid 5-hydroxy-tetrahydro-furan-3-ylmethyl ester 
• 333335-46-9 (5-ethoxy-tetrahydro-furan-3-yl)-methanol 
• 21339-47-9 diethyl 2-(2,2-diethoxyethyl)malonate 
• 55387-85-4 3-hydroxymethyl-4-hydroxybutanal diethyl acetal 
• 97845-60-8 9-<4-acetoxy-3-(acetoxymethyl)butyl>-2-amino-6-chloro-9H-purine 

Downstream Products

• 104227-86-3 6-deoxypenciclovir 
• 39809-25-1 Penciclovir 
• 104227-87-4 9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine 
• 97845-60-8 9-<4-acetoxy-3-(acetoxymethyl)butyl>-2-amino-6-chloro-9H-purine 

Relevant articles and documents

Virtual Screening of Acyclovir Derivatives as Potential Antiviral Agents: Design, Synthesis, and Biological Evaluation of New Acyclic Nucleoside ProTides

Following our findings on the anti-human immunodeficiency virus (HIV) activity of acyclovir (ACV) phosphate prodrugs, we herein report the ProTide approach applied to a series of acyclic nucleosides aimed at the identification of novel and selective antiv

The new convenient synthesis of fluorinated Penciclovir analogues 9-(4-fluoro-3-hydroxymethylbutyl) guanine (FHBG) and 2-amino-6-fluoro-9-(4-hydroxy-3-hydroxymethylbutyl) purine (6-Fluoropenciclovir)

9-(4-Hydroxy-3-hydroxymethylbutyl) guanine (Penciclovir) is a potent and selective inhibitor of members of the herpes virus family. A new convenient synthesis of fluorinated Penciclovir analogues 9-(4-fluoro-3-hydroxymethylbutyl) guanine (FHBG) and 2-amin

The synthesis of a new probe for PET imaging reporter gene HSV1-tk: 2-Amino-6-[18F] fluoro-9- (4-hydroxy-3-hydroxymethylbutyl) purine (6-[18F]fluoropenciclovir)

The one step radiosynthesis of 2-amino-6- [18F]fluoro-9-(4- hydroxy-3-hydroxymethyl-butyl) purine (6-[18F]fluoropenciclovir) 6 is reported. Radiolabeled product 6-[18F]fluoropenciclovir 6 was prepared by radiofluorination of compound 4 with [18F]KF and isolated by a silica Sep-Pak cartridge. The radiochemical yield of compound 6 was 45-55% decay corrected (d.c.) in six runs with radiochemical purity >98% and the radiosynthesis time was 35-42 min from end of bombardment (EOB). Copyright

Preparation method of penciclovir

The invention discloses a preparation method of penciclovir. An existing synthetic route mainly has the following defects that the N-7 site by-products need to be removed through column chromatography, a large amount of three wastes are generated, and the yield of N-9 site products is not high. According to the technical scheme adopted by the invention, the preparation method comprises the following steps: carrying out alkylation on 2-amino-6-chloropurine and triethyl bromopropane under an alkaline condition to introduce an N-9 site side chain, carrying out decarboxylation and transesterification in a methanol solution of sodium methoxide to generate the 2-amino-6-chloro-9-(3,3-dimethoxycarbonyl-1-propyl)purine; then reducing the 2-amino-6-chloro-9-(3,3-dimethoxycarbonyl-1-propyl)purine togenerate 2-amino-6-chloro-9-(3-hydroxymethyl-4-hydroxy-1-butyl)purine with sodium borohydride; and finally, directly hydrolyzing under acidic conditions to obtain penciclovir. According to the method, the target product is obtained by directly hydrolyzing the reduction product, ester group protection and deprotection are not needed, and the method has the advantages of few reaction steps, good product quality, simplicity and convenience in operation, suitability for industrial production and the like.

Preparation of famciclovir and other purine derivatives

Purine derivatives, substituted at the 9-position, are prepared from a chloro substituted purine starting material, first making an alkyl substitution at the 9-position, then forming the desired esterified side chain, reducing this and hydrogenating the resultant diol prior to addition of alkyl carbonyl groups.

Regioselective alkylation of guanines using 2-acetoxytetrahydrofurans

Reaction of silylated guanine derivatives with 2-acetoxy-4-benzoyloxymethyltetrahydrofuran in DMF or NMP resulted in selective N-9 alkylation. This was used as the basis for a regioselective synthesis of the anti-viral agents famciclovir and penciclovir.

A direct approach to the synthesis of famciclovir and penciclovir

Reaction of 2-amino-6-chloropurine with triethyl 3-bromopropane-1,1,1- tricarboxylate followed by decarbethoxylation/transsesterification of the unpurified product was the key sequence in sythesising both the anti- herpesvirus agent penciclovir and its form famciclovir in three isolated steps.