19690-23-4

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-6-iodopurine is used as a reagent for the synthesis of Lobucavir (L469360), an antiviral agent. 2-Amino-6-iodopurine plays a crucial role in the development of medications designed to combat viral infections, thereby contributing to the advancement of healthcare and treatment options for patients.

InChI:InChI=1/C5H4IN5/c6-3-2-4(9-1-8-2)11-5(7)10-3/h1H,(H3,7,8,9,10,11)

Upstream product

• 10310-21-1 2-Amino-6-chloropurin 
• 190962-00-6 6-chloro-2-formylaminopurine acetate 
• 7440-44-0 pyrographite 
• 10310-21-1 2-amino-6-chloropurine 

Downstream Products

• 128139-27-5 9-(4-acetoxy-3-acetoxymethylbutyl)-2-amino-6-iodopurine 
• 131266-22-3 7-(4-acetoxy-3-acetoxymethylbutyl)-2-amino-6-iodopurine 
• 132194-23-1 2-amino-6-iodo-9-(2,3-dideoxy-β-D-glycero-pentofuranosyl)-9H-purine 
• 1053636-56-8 9-((3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl)-6-iodo-9H-purin-2-ylamine 
• 2993-20-6 2-Amino-6-(trifluoromethyl)purine 

Relevant academic research and scientific papers

FragLites - Minimal, Halogenated Fragments Displaying Pharmacophore Doublets. An Efficient Approach to Druggability Assessment and Hit Generation

Identifying ligand binding sites on proteins is a critical step in target-based drug discovery. Current approaches to this require resource-intensive screening of large libraries of lead-like or fragment molecules. Here, we describe an efficient and effective experimental approach to mapping interaction sites using a set of halogenated compounds expressing paired hydrogen-bonding motifs, termed FragLites. The FragLites identify productive drug-like interactions, which are identified sensitively and unambiguously by X-ray crystallography, exploiting the anomalous scattering of the halogen substituent. This mapping of protein interaction surfaces provides an assessment of druggability and can identify efficient start points for the de novo design of hit molecules incorporating the interacting motifs. The approach is illustrated by mapping cyclin-dependent kinase 2, which successfully identifies orthosteric and allosteric sites. The hits were rapidly elaborated to develop efficient lead-like molecules. Hence, the approach provides a new method of identifying ligand sites, assessing tractability and discovering new leads.

Process for Preparing Entecavir and its Intermediates

A process of making entecavir comprising converting a compound of formula (M5) to entecavir, wherein the two PGs on the formula (M5) are taken together to form an optionally substituted six- or seven-member cyclic ring.

Synthesis of some biologically active halogenopurines

A series of some biologically active halogenopurines were synthesized from commercially available guanine (1). The reaction of guanine with acetic anhydride yielded 2,9-diacetylguanine (2-1) by acetylation reaction. Further treatment of 2-1 with POCl3 by PEG-2000 phase transfer catalysis furnished the important compound 3a, then 2-amino-6-halogenopurines (3b-d) were obtained through chlorine-exchange halogenations between KX and 3a by TPPB phase transfer catalyst. Further, 2-halogenopurines (2-2a-d, 4-2a-d, 5a-d) were efficiently prepared from 2-amino-6-substituted purines (1, 3a, 4-1) via a diazotization catalyzed by their corresponding CuX, and some new compounds 2-2a, 2-2c, 2-2d, 4-2c, 4-2d, 5b, 5c and 5d have been discovered. The structures of synthesized compounds were mainly established on the basis of their elemental analysis, 1H NMR, as well as their mass spectral data. All the title compounds were screened for their antifungal activities, and some of the compounds showed promising activity.

Synthesis of acyclic nucleoside derivatives

Methods and novel intermediates of the formula: wherein R6 and R7 are lower alkyl or benzyl or R6 and R7 taken together are —CH2CH2—, —CH2CH2CH2— or —CH2CH2CH2CH2CH2—, R8 is C1-C21 alkyl or a C2-C21 monounsaturated alkenyl, which may optionally be substituted with substitution substituents independently selected from the group consisting of hydroxy, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkanoyl, amino, halo, cyano, azido, oxo, mercapto and nitro, and R9 is an alcohol protecting group. The intermediates are useful for the preparation of acyclic nucleoside derivatives of the formula: where one of R1 and R2 is an amino acid acyl group and the other of R1 and R2 is a —C(O)C3-C21 saturated or monounsaturated, optionally substituted alkyl and R3 is OH or H; or a pharmaceutically acceptable salt thereof.

Process for preparing guanine-containing antiviral agents and purinyl salts useful in such process

A purine salt of the formula STR1 wherein Y1 is chloro, bromo, or iodo, and R1, R2, R3, and R4 are independently selected from alkyl and substituted alkyl is reacted with the compound of the formula to yield the purine of the formula STR2 wherein x is a leaving group, and Z1 is a protected form of the carbohydrate surrogate Z. Several routes are disclosed for converting this intermediate to the antiviral agent STR3

Process for producing 2-amino-6-iodopurine

The process for preparing 2-amino-6-iodopurine including the steps of suspending at least one chloropurine compound selected from 2-formylamino-6-chloropurine, 2-formylamino-6-chloropurine acetate and 2-amino-6-chloropurine in a solution comprising aqueous hydriodic acid and an alkyl ketone having 3 to 7 carbon atoms; and stirring the resulting suspension at 0° to 50° C. According to the process of the present invention, 2-amino-6-iodopurine can be simply, industrially, and advantageously prepared.

Purinyl salts useful for preparing guanine containing antiviral agents

A purine salt of the formula STR1 wherein Y1 is chloro, bromo, or iodo, and R1, R2, R3, and R4 are independently selected from alkyl and substituted alkyl.

Method for the treatment of protoza infections with 21 -deoxy-21 -fluoropurine nucleosides

A method for treating two specific protozoal infections, Trichomonas vaginalis and Giardia lamblia, comprising the administration to a mammal in need thereof one of the following purine nucleosides: 2,6-diamino-9-(2-deoxy-2-fluoro-β-D-ribofuranosyl)-9H-purine 2-amino-9-(2-deoxy-2-fluoro-β-D-ribofuranosyl)-9H-purine 2-amino-9-(2-deoxy-2-fluoro-β-D-ribofuranosyl)-6-methoxy-9H-purine.

2-formylamino-6-halogenopurine

The present invention is directed to a method for production of a 2-amino-6-halogenopurine, a novel synthesis intermediate therefor and a method for production of said synthesis intermediate. The desired 2-amino-6-halogenopurine is an intermediate for the production of compounds useful as antiviral agents, and by using the compound of the present invention as a starting material, the 2-amino-6-halogenopurine can be produced in high yield.