100960-20-1

Basic information

• Product Name: 2-CHLORO-N,N-DIMETHYL-9H-PURIN-6-AMINE
• Synonyms: 2-CHLORO-N,N-DIMETHYL-9H-PURIN-6-AMINE;9H-Purin-6-amine, 2-chloro-N,N-dimethyl-
• CAS NO: 100960-20-1
• Molecular Formula: C₇H₈ClN₅
• Molecular Weight: 197.62
• Mol File: 100960-20-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 404.8 °C at 760 mmHg
• Flash Point: 198.6 °C
• Appearance: /
• Density: 1.502 g/cm³
• Vapor Pressure: 9.16E-07mmHg at 25°C
• Refractive Index: 1.721
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-CHLORO-N,N-DIMETHYL-9H-PURIN-6-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-N,N-DIMETHYL-9H-PURIN-6-AMINE(100960-20-1)
• EPA Substance Registry System: 2-CHLORO-N,N-DIMETHYL-9H-PURIN-6-AMINE(100960-20-1)

Safety Data

• Hazardous Substances Data: 100960-20-1(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 80, p. 404, 1958 DOI: 10.1021/ja01535a040

InChI:InChI=1/C7H8ClN5/c1-13(2)6-4-5(10-3-9-4)11-7(8)12-6/h3H,1-2H3,(H,9,10,11,12)

Upstream product

• 124-40-3 dimethyl amine 
• 5451-40-1 2,6 dichloropurine 
• 10310-21-1 2-Amino-6-chloropurin 
• 73-40-5 2-amino-1,9-dihydro-6H-purin-6-one 
• 149948-30-1 N-(6-chloro-9H-purin-2-yl)formamide 
• 506-59-2 N,N-dimethylammonium chloride 

Relevant articles and documents

Design, synthesis and evaluation of 4-aminoquinoline-purine hybrids as potential antiplasmodial agents

A novel series of 4-aminoquinoline-purine hybrids were synthesized and assessed for their antiplasmodial activity against CQ-sensitive and CQ-resistant strains of P. falciparum. It was envisaged that linking of the 4-aminoquinoline pharmacophore (targeting heme-detoxification pathway of malarial parasite) with the purine functionality (targeting plasmodial HG(X)PRT enzyme) will produce a hybrid antiplasmodial agent with increased potency. The synthesized hybrids displayed good antiplasmodial activities against both the sensitive and resistant strains of P. falciparum with up to six-fold better activity (compound 10i, IC50: 0.08?μM) compared to the reference drug CQ (IC50: 0.5?μM) against the resistant strain. The synthesized compounds were also checked for their cytotoxicity towards mammalian cells and with the exception of two compounds out of the twenty synthesized hybrids, all others were non-cytotoxic up to 11.86?μM concentration. Mechanistic heme-binding studies were performed to identify the mechanism of action of the synthesized molecules and good binding interactions were observed. Computational docking studies showed that the most active hybrids dock well within the binding site of HGPRT protein. In silico ADME predictions of the most active hybrids showed that these compounds possess good pharmacokinetic behavior.

Anticonvulsive substituted-9-benzyl-9H-purines

The invention relates to novel 9H-purine derivatives, especially to the novel substituted 9-benzyl-9H-purines of the general formula STR1 in which Ph is a phenyl radical substituted by halogen, R1 is hydrogen or a free amino group or an amino group that is substituted aliphatically, cycloaliphatically, cycloaliphatically-aliphatically and/or by acyl, and R2 is halogen, lower alkoxy, lower alkyl, a free amino group, or an amino group that is substituted aliphatically, cycloaliphatically, cycloaliphatically-aliphatically and/or by acyl, with the proviso that R2 is other than halogen when Ph is 2-fluorophenyl or 2,5- or 2,6-difluorophenyl and R1 is a radical of the formula --N(R11)(R12) (Ia) in which either R11 is hydrogen, methyl or ethyl and R12 is hydrogen, methyl, hydroxymethyl, ethyl, n-propyl, isopropyl, cyclopropyl, cyclopenthyl or cyclopropylmethyl, or R11 is hydrogen and R12 is methoxymethyl, and with the further proviso that R2 is other than chlorine when Ph is 3-chlorophenyl, 4-chlorophenyl or 3,4-dichlorophenyl and R1 is N,N-dimethylamino, and to the novel compounds of formula I in which Ph is 2-fluorophenyl or 2,6-difluorophenyl, R1 is N-methylamino or N,N-dimethylamino and R2 is chlorine, and to the salts thereof in each case. These compounds and the salts thereof can be used as pharmaceutical active ingredients and can be manufactured in a manner known per se.