Synthesis and bio-activity of alkyl/aryl [2-(1,2,4,5-tetrahydro-3-sulfanylene/selenylene naphtha[1,8][1,5,3]diazaphosphocin- 3-yl)methyl amino acid esters]

✍ Scribed by S. Subba Reddy; V. K. Rao; A. U. Ravi Sankar; C. N. Raju

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2010
• Tongue: English
• Weight: 101 KB
• Volume: 47
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.195

✦ Synopsis

Abstract

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Synthesis of alkyl/aryl [2‐(1,2,4,5‐tetrahydro‐3‐sulfanylene/selenylene naphtha[1,8‐f,g][1,5,3]diazaphosphocin‐3‐yl) methyl amino acid esters] (6, 7, 8, 9, 10, 11, 12, 13, 14, 15) was accomplished in three steps. 1, 8‐diamino naphthalene (2) was reacted with tris (bromomethyl) phosphine (1) in the presence of triethylamine in dry tetrahydrofuran (THF) under N~2~ atmosphere to form a P~III~ intermediate (3). It was converted to the corresponding sulfide (4) and selenide (5) by reacting with sulfur and selenium, respectively. The intermediates 4 and 5 were further reacted with amino acid esters to obtain the title compounds (6, 7, 8, 9, 10, 11, 12, 13, 14, 15). The structures of the title compounds were established by elemental analysis and spectral data (IR, ^1^H, ^13^C, ^31^P NMR, and FAB mass). The antimicrobial activity of these compounds was evaluated and they exhibited significant activity. J. Heterocyclic Chem., (2010).