2846-96-0

Basic information

• Product Name: 6-morpholinopurine
• Synonyms: 6-morpholinopurine;6-Morpholino-1H-purine;6-Morpholino-9H-purine;6-(4-Morpholinyl)-1H-purine;4-(7H-purin-6-yl)morpholine;4-(1H-Purin-6-yl)Morpholine;6-(Morpholin-4-yl)-9H-purine
• CAS NO: 2846-96-0
• Molecular Formula: C₉H₁₁N₅O
• Molecular Weight: 205.21654
• EINECS: 220-645-3
• Mol File: 2846-96-0.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 527.1°Cat760mmHg
• Flash Point: 272.6°C
• Appearance: /
• Density: 1.416g/cm³
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 6-morpholinopurine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-morpholinopurine(2846-96-0)
• EPA Substance Registry System: 6-morpholinopurine(2846-96-0)

Safety Data

• Hazardous Substances Data: 2846-96-0(Hazardous Substances Data)

Usage

General Description

6-morpholinopurine is a chemical compound that belongs to the purine group, consisting of a six-membered morpholine ring fused to the purine base. It is also known as 6-methylaminopurine and is a derivative of adenine. 6-morpholinopurine is an important intermediate in the synthesis of various pharmaceuticals, especially antiviral and anticancer drugs. It acts as a potent inhibitor of cGMP-specific phosphodiesterase, which makes it a potential therapeutic agent for pulmonary hypertension and other cardiovascular diseases. It also has potential applications in the field of agriculture, as it has been shown to promote plant growth and increase resistance to abiotic stress. Overall, 6-morpholinopurine is a versatile compound with various potential pharmaceutical and agricultural applications.

InChI:InChI=1/C9H11N5O/c1-3-15-4-2-14(1)9-7-8(11-5-10-7)12-6-13-9/h5-6H,1-4H2,(H,10,11,12,13)

Upstream product

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• 4010-79-1 2,8-dichloro-6-morpholin-4-yl-7⁽⁹⁾H-purine 
• 110-91-8 morpholine 
• 50-66-8 6-(methylthio)-1H-purine 
• 2562-52-9 2,6,8-trichloro-7H-purine 
• 50-44-2 6H-purine-6-thione 
• 68-94-0 1,7-dihydro-6H-purin-6-one 
• 5451-40-1 2,6-dichloro-7H-purine 
• 68-94-0 hypoxanthine 
• 87-42-3 6-chloropurine 
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• 87-42-3 6-chloro-7H-purine 

Relevant articles and documents

6-Morpholino- and 6-amino-9-sulfonylpurine derivatives. Synthesis, computational analysis, and biological activity

The synthesis of novel 6-chloro/morpholino/amino/-9-sulfonylpurine derivatives was accomplished in two ways, either (i) involving the condensation reaction of 6-chloropurine with commercially available arylsulfonyl chlorides in acetone and the presence of aqueous KOH at 0 °C, followed by the substitution of C6-chlorine with morpholine, or (ii) employing a reversed synthetic approach where 6-morpholinopurine and commercially available adenine bases were reacted with the corresponding alkyl, 2-arylethene and arylsulfonyl chlorides giving the N9 sulfonylated products, the latter particularly used where prior nonselective sulfonylation was observed. In both approaches, the sulfonylation reaction occurred regioselectively at the purine N9 position lacking any concurrent N7 derivatives, except in the case of a smaller methyl substituent on SO2 and the free amino group at C6 of the purine ring. The tautomeric features of initial N9 unsubstituted purines, as well as stability trends among the prepared N-9-sulfonylpurine derivates, were investigated using DFT calculations with an important conclusion that electron-donating C6 substituents are beneficial for the synthesis as they both promote the predominance of the desired N9 tautomers and help to assure the stability of the final products. The newly synthesized 6-morpholino and 6-amino-9-sulfonylpurine derivatives showed antiproliferative activity on human carcinoma, lymphoma, and leukemia cells. Among the tested compounds, 6-morpholino 17 and 6-amino 22 derivatives, with trans-β-styrenesulfonyl group attached at the N9 position of purine, proved to be the most effective antiproliferative agents, causing accumulation of leukemia cells in subG0 cell cycle phase.

Room-Temperature Amination of Chloroheteroarenes in Water by a Recyclable Copper(II)-Phosphaadamantanium Sulfonate System

Buchwald-Hartwig amination of chloroheteroarenes has been a challenging synthetic process, with very few protocols promoting this important transformation at ambient temperature. The current report discusses about an efficient copper-based catalytic system (Cu/PTABS) for the amination of chloroheteroarenes at ambient temperature in water as the sole reaction solvent, a combination that is first to be reported. A wide variety of chloroheteroarenes could be coupled efficiently with primary and secondary amines as well as selected amino acid esters under mild reaction conditions. Catalytic efficiency of the developed protocol also promotes late-stage functionalization of active pharmaceutical ingredients (APIs) such as antibiotics (floxacins) and anticancer drugs. The catalytic system also performs efficiently at a very low concentration of 0.0001 mol % (TON = 980,000) and can be recycled 12 times without any appreciable loss in activity. Theoretical calculations reveal that the π-acceptor ability of the ligand PTABS is the main reason for the appreciably high reactivity of the catalytic system. Preliminary characterization of the catalytic species in the reaction was carried out using UV-VIS and ESR spectroscopy, providing evidence for the Cu(II) oxidation state.

1-methylpurine-4-methyleneandrostane-triazole derivative, synthesis method and application thereof

The invention belongs to the technical field of medicinal chemistry, and relates to a 1- methylpurine-4- methyleneandrostane-triazole derivative with anticancer activity. The compound has the generalformula as shown in the specification. The derivative of the invention is prepared by using a 6-chloropurine compound as a raw material and through nucleophilic reaction, halogenation, azidation, cycloaddition and a Claisen-Schmidt condensation reaction. The preparation method is simple and the conditions are mild. These compounds have obvious inhibitory effects on cell lines such as gastric cancer and prostate cancer, can be used for preparing antitumor drugs, and provide a lead compound structure for further research on anticancer drugs.