152918-47-3

Basic information

• Product Name: 1-(6-Chloro-9H-purin-9-yl)-1-deoxy-N-methyl-2,3-O-isopropylidene-beta-D-ribofuranuronamide
• Synonyms: 1-(6-Chloro-9H-purin-9-yl)-1-deoxy-N-methyl-2,3-O-isopropylidene-beta-D-ribofuranuronamide;2',3'-O-isopropylidene-6-chloropurine-5'-N-MethyluronaMide;2',3'-isopropylidene-1-(6-chloro-9H-purin-9-yl)-1-deoxy-N-methyl-β-D-ribofuranosiduronamide
• CAS NO: 152918-47-3
• Molecular Formula: C₁₄H₁₆ClN₅O₄
• Molecular Weight: 353.76094
• Mol File: 152918-47-3.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Density: 1.74
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1-(6-Chloro-9H-purin-9-yl)-1-deoxy-N-methyl-2,3-O-isopropylidene-beta-D-ribofuranuronamide(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(6-Chloro-9H-purin-9-yl)-1-deoxy-N-methyl-2,3-O-isopropylidene-beta-D-ribofuranuronamide(152918-47-3)
• EPA Substance Registry System: 1-(6-Chloro-9H-purin-9-yl)-1-deoxy-N-methyl-2,3-O-isopropylidene-beta-D-ribofuranuronamide(152918-47-3)

Safety Data

• Hazardous Substances Data: 152918-47-3(Hazardous Substances Data)

Usage

Description

1-(6-Chloro-9H-purin-9-yl)-1-deoxy-N-methyl-2,3-O-isopropylidene-beta-D-ribofuranuronamide, commonly referred to as clade 9-CMP, is a complex chemical compound that features a purine base with a methyl group and a ribofuranuronamide moiety. It serves as a crucial intermediate in the synthesis of nucleoside analogs and their derivatives. 1-(6-Chloro-9H-purin-9-yl)-1-deoxy-N-methyl-2,3-O-isopropylidene-beta-D-ribofuranuronamide has garnered attention for its potential pharmaceutical applications, particularly in the realms of antiviral and anticancer drug development. Clade 9-CMP has shown biological activity in inhibiting viral replication and has demonstrated cytotoxic effects against cancer cells. Its distinctive structure and therapeutic potential render it a compelling subject for further exploration in medicinal chemistry.

Uses

Used in Pharmaceutical Industry:
1-(6-Chloro-9H-purin-9-yl)-1-deoxy-N-methyl-2,3-O-isopropylidene-beta-D-ribofuranuronamide is used as an intermediate in the synthesis of nucleoside analogs for its role in developing antiviral and anticancer drugs. Its ability to inhibit viral replication makes it a valuable component in the creation of new antiviral medications.
Used in Antiviral Applications:
In the field of virology, 1-(6-Chloro-9H-purin-9-yl)-1-deoxy-N-methyl-2,3-O-isopropylidene-beta-D-ribofuranuronamide is utilized as an antiviral agent due to its capacity to interfere with viral replication processes, thereby offering a potential treatment strategy for viral infections.
Used in Anticancer Applications:
Clade 9-CMP is employed as a cytotoxic agent in oncology, targeting and destroying cancer cells. Its potential to contribute to the development of anticancer drugs makes it a significant player in cancer research and treatment.
Used in Medicinal Chemistry Research:
1-(6-Chloro-9H-purin-9-yl)-1-deoxy-N-methyl-2,3-O-isopropylidene-beta-D-ribofuranuronamide is used as a subject of study in medicinal chemistry for its unique structure and the exploration of its therapeutic properties, paving the way for innovative drug discoveries.

Upstream product

• 39824-26-5 6-chloro-9-(2,3-O-isopropylidene-β-D-ribofuranosyl)-9H-purine 
• 2004-06-0 6-Chloropurine riboside 
• 120355-42-2 (3AS,4S,6R,6AR)-6-(6-chloro-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid 
• 74-89-5 methylamine 
• 28440-13-3 (3aS,4S,6R,6aR)-2,2-dimethyl-6-(6-oxo-1,6-dihydro-9H-purin-9-yl)tetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid 
• 104940-65-0 1'-deoxy-1'-(6-chloro-9H-purin-9-yl)2',3'-O-isopropylidene-β-D-ribofuranosyl chloride 
• 2140-11-6 2',3'-O-isopropylideneinosine 

Downstream Products

• 152918-48-4 IB-MECA acetonide 
• 152918-53-1 (3aS,4S,6R,6aR)-6-[6-(3-Acetylamino-benzylamino)-purin-9-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methylamide 
• 152918-27-9 (2S,3S,4R,5R)-5-[6-(4-Amino-3-iodo-benzylamino)-purin-9-yl]-3,4-dihydroxy-tetrahydro-furan-2-carboxylic acid methylamide 
• 152918-18-8 N⁶-(3-iodobenzyl)adenosine-5'-N-methyluronamide 
• 152918-26-8 [125I]-AB-MECA 
• 152918-20-2 Abamun 
• 152918-15-5 NNC 21-0242 
• 1054620-26-6 (3aS,4S,6R,6aR)-6-(6-{2-[1-(2,5-Dimethyl-benzyl)-1H-indol-3-yl]-ethylamino}-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methylamide 
• 1053645-63-8 (3aS,4S,6R,6aR)-6-(6-Benzylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methylamide 
• 1053726-11-6 (3aS,4S,6R,6aR)-6-[6-(4-Amino-3-iodo-benzylamino)-purin-9-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methylamide 
• 170966-20-8 (3aS,4S,6R,6aR)-6-[6-(3-Amino-benzylamino)-purin-9-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methylamide 

Relevant articles and documents

PROCESS FOR THE SYNTHESIS OF IB-MECA

The present disclosure provides a method for the synthesis of IB-MECA. More specifically, the present disclosure provides a simple and high yield method for Good Manufacturing Production (GMP) of IB-MECA. The method involves the reaction of 6-halopurine-9

N6-substituted N-alkyladenosine-5'-uronamides: bifunctional ligands having recognition groups for A1 and A2 adenosine receptors.

The coronary vasoactivity of N-ethyl-1'-deoxy-1'-(6-amino-9H-purin-9-yl)-beta-D-ribofuranuronamide (NECA, 1) is over 2 orders of magnitude greater than that of adenosine, and the vasoactivity of certain N6-substituted adenosines is as much as 1 order of m