5454-50-2

Basic information

• Product Name: 1-phenyl-2-(5H-purin-6-ylsulfanyl)ethanone
• CAS NO: 5454-50-2
• Molecular Formula: C₁₃H₁₀N₄OS
• Molecular Weight: 270.3097
• Mol File: 5454-50-2.mol

Chemical Properties

• Boiling Point: 451.5°C at 760 mmHg
• Flash Point: 226.9°C
• Density: 1.44g/cm³
• Vapor Pressure: 2.42E-08mmHg at 25°C
• Refractive Index: 1.743
• CAS DataBase Reference: 1-phenyl-2-(5H-purin-6-ylsulfanyl)ethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-phenyl-2-(5H-purin-6-ylsulfanyl)ethanone(5454-50-2)
• EPA Substance Registry System: 1-phenyl-2-(5H-purin-6-ylsulfanyl)ethanone(5454-50-2)

Safety Data

• Hazardous Substances Data: 5454-50-2(Hazardous Substances Data)

Usage

Sulfanyl derivative of a purine compound

5H-purin-6-ylsulfanyl (indicates the presence of a sulfur atom in the purine compound)

Phenyl group attached at position 1

indicates the presence of a six-membered aromatic ring with a single carbon atom attached to the first carbon of the ethanone molecule)

5H-purin-6-ylsulfanyl group attached at position 2

indicates the presence of a purine compound with a sulfur atom attached to the sixth carbon of the ethanone molecule)

Building block in organic synthesis and medicinal chemistry

(used as a starting material or intermediate in the synthesis of more complex molecules)

Used in the development of pharmaceuticals and bioactive compounds

(indicates the potential use of the compound in the creation of drugs and other biologically active substances)

Exhibits various biological activities

(capable of interacting with biological systems and producing various effects)

Structural resemblance to purine and its derivatives

(has a similar structure to purine and its related compounds, which may contribute to its biological activity)

Upstream product

• 98-86-2 acetophenone 
• 50-44-2 6-mercaptopurine 
• 70-11-1 α-bromoacetophenone 
• 157930-09-1 6-Mercaptopurine 
• 532-27-4 1-chloroacetophenone 

Downstream Products

• 1253797-55-5 7-phenyl[1,4]thiazino[4,3,2-gh]purine 
• 106609-74-9 1-Phenyl-2-(9H-purin-6-ylsulfanyl)-ethanol 
• 276873-26-8 1-(4-methoxy-phenyl)-5-(9H-purin-6-ylsulfanyl)-pentan-1-one 
• 276873-36-0 9-methyl-6-(ω-p-methylbenzoylbutylthio)purine 
• 276873-25-7 5-(9H-purin-6-ylsulfanyl)-1-p-tolyl-pentan-1-one 
• 875-31-0 9-methylhypoxanthine 
• 68-94-0 hypoxanthine 
• 50-44-2 6-mercaptopurine 
• 119011-46-0 9-methyl-6-(phenacylthio)purine 

Relevant articles and documents

Design, Synthesis, and Anticancer Activity of Novel Fused Purine Analogues

6-Mercaptopurine has been utilized for the synthesis of various fused purine analogues through different chemical reactions to yield [1,4]thiazino[4,3,2-gh]purines 2, 3, 10a,b, 14, (8-oxo-[1,4]thiazino[4,3,2-gh]purin-7(8H)-ylidene) acetate 4, [1,4]thiazepino[4,3,2-gh]purine 6, thiazolo[3,4,5-gh]purine 7, imidazo[1,5,4-gh]purin-5-amine 8, 5-methylimidazo[1,5,4-gh]purine 9, [1,2,4]triazino[4,3-i]purines 16, 18, 21, [1,2,4]triazino[4,5,6-gh]purine 20, 5-methyl-2-(7H-purin-6-yl)-1H-pyrazol-3(2H)-one 22, [1,2,4]triazolo[4,3-i]purine 23, [1,2,5]triazepino[5,4,3-gh]purine 24, and ethyl 6-(2-(ethoxycarbonyl)hydrazinyl)-9H-purine-9-carboxylate 26. Seventeen of the newly synthesized compounds were selected by the NCI, Maryland, USA, and were tested for their anticancer activity in an initial single high dose in the full NCI 60 cell line panel among which [1,4]thiazino[4,3,2-gh]purine-7,8-dione 2, 7-benzyl-[1,4]thiazino[4,3,2-gh]purine 10b, and 3-(2,4-dimethoxyphenyl)-7H-[1,2,4]triazolo[4,3-i]purine 23 were found to possess very potent anticancer activity against most of the cancer cell lines.

Some cyclization reactions of 6-mercaptopurine with expected biological activity

The reaction of 6-mercaptopurine 1 with aromatic ketones 2a-h using the acidified acetic acid method afforded the S-acetyl derivatives 3a-h in good yields. While, the cyclized product 4i was obtained directly upon reaction of 1 with 9-acetyl anthracene. Compounds 3a-h were cyclized directly to the corresponding 1,4-thiazino[2,3,4-bc]purine derivatives (4a-h). In the same manner the reaction of 1 with aliphatic, aromatic, alicyclic ketones, α-tetralone and 1-methyl-4-piperidone gave compounds 6, 7, 8, 9a,b, 11 and 12. The cyclized compounds 10a,b were obtained by cyclization of 9a,b. The synthesized compounds were screened for their in vitro antitumor activity at National Cancer Institute.

SYNTHESIS AND SOME PROPERTIES OF 6-β-OXOALKYL(ARALKYL, HETARALKYL, CYCLOALKYL)THIOPURINES

The reaction of 6-purinethione with α-haloketones has given a series of new 6-β-oxoalkyl(aralkyl, hetaralkyl, cycloalkyl)thiopurines.Their alkylation in position 9 and acid hydrolysis to hypoxanthine and its 9-alkyl derivatives has been studied.The hydrolysis of the acetals of 6-formylmethylthiopurine and the oxidation of 6-(2,3-dihydroxypropyl)thiopurine leads to 6-formylmethylthiopurine, which shows a ring-chain tautomerism and exists in the form of 7-hydroxy-7,8-dihydrothiazolopurine.

On the Tautomerism of 2-Phenacyl-4-pyrimidinones and Related Compounds

3-Methyl-2-phenacyl-4-pyrimidinones 1, 2 have been synthesized using the sulfide contraction.According to the NMR data, the compounds 1, 2 exist exclusively as the benzoylmethylene tautomers a both in solution and in the solid state.AM1 calculations of the parent system are in agreement with the experimental observations.The study of the tautomeric equilibrium by this semiempirical method has been extended to other cases of enaminoketone/enolimine tautomerism. - Key Words: Pyrimidinones / Tautomerism / AM1 calculations