52854-12-3

Basic information

• Product Name: N-(5H-purin-6-yl)octanamide
• CAS NO: 52854-12-3
• Molecular Formula: C₁₃H₁₉N₅O
• Molecular Weight: 261.3229
• Mol File: 52854-12-3.mol
• Article Data: 2

Chemical Properties

• Density: 1.27g/cm³
• Refractive Index: 1.634
• CAS DataBase Reference: N-(5H-purin-6-yl)octanamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(5H-purin-6-yl)octanamide(52854-12-3)
• EPA Substance Registry System: N-(5H-purin-6-yl)octanamide(52854-12-3)

Safety Data

• Hazardous Substances Data: 52854-12-3(Hazardous Substances Data)

Upstream product

• 14464-30-3 2,5-dioxopyrrolidin-1-yl octanoate 
• 66224-66-6 adenine 
• 124-07-2 Octanoic acid 

Downstream Products

• 491837-17-3 S,S'-bis(2-nitrophenylsulfanyl)-3',5'-dithio-2'-deoxy-β-4-N-n-octanoyladenosine 
• 491837-18-4 S,S'-bis(2-nitrophenylsulfanyl)-3',5'-dithio-2'-deoxy-α-4-N-n-octanoyladenosine 
• 1394848-48-6 C₄₁H₄₄N₆O₆ 
• 1394848-47-5 N6-n-octanoyl-3',5'-di-O-benzyl-2'-deoxy-2'-C-α-phthalimidomethyladenosine 
• 66323-44-2 9-(3-azido-2,3-dideoxy-β-D-erythro-pentofuranosyl)adenine 
• 124288-88-6 (2S,5S)-5-Azido-6-[(2R,3R,4R,5R)-3,4-diacetoxy-5-(6-octanoylamino-purin-9-yl)-tetrahydro-furan-2-yl]-2-(toluene-4-sulfonylamino)-hexanoic acid tert-butyl ester 

Relevant articles and documents

Isolation and synthesis of N-acyladenine and adenosine alkaloids from a southern Australian marine sponge, Phoriospongia sp.

Chemical fractionation of the southern Australian marine sponge Phoriospongia sp. (CMB-03107) yielded phorioadenine A (1) as a nematocidal agent and the first reported example of a 6-N-acyladenine natural product. The structure of 1 was confirmed by spectroscopic analysis and the chemical synthesis of racemic (1a) and enantiomeric (1b) analogues. HPLC-ESIMS analysis of the crude sponge extract with comparisons to the synthetic 6-N-acyladenosine 2a provided evidence that the biosynthetically related adenosine, phorioadenosine A (2), was present as a trace co-metabolite. The rare starfish metabolite asterubine (3) was also isolated as a co-metabolite, and its structure confirmed by spectroscopic analysis and chemical synthesis. Biological investigations confirmed that natural products 1-3 and synthetic analogues 1a-e and 2a were not cytotoxic to multiple mammalian cancer cell lines, or Gram-positive or -negative bacteria. Nematocidal activity (inhibition of larval development of Haemonchus contortus) detected in the Phoriospongia sp. extract was attributed to 1 (LD9931 μg/mL), with preliminary structure-activity relationship investigations confirming the importance of the N-acyl side chain.