New substituted 2-aminomethyl-2-oxo-2λ5-perhydro-[1,3,2]oxazaphospholo [3,4-a]pyridine: Design, synthesis and antimicrobial activity

Autor:	Rajasekhar Maram, Rasheed Syed, Subba Rao Devineni, Bhanu Kiran Rayalacheru, Madhava Golla, Chamarthi Naga Raju
Rok vydání:	2017
Předmět:	010405 organic chemistry Chemistry Organic Chemistry 010402 general chemistry Antimicrobial 01 natural sciences Biochemistry Combinatorial chemistry 0104 chemical sciences Inorganic Chemistry chemistry.chemical_compound Design synthesis Pyridine Organic chemistry
Zdroj:	Phosphorus, Sulfur, and Silicon and the Related Elements. 192:794-798
ISSN:	1563-5325 1042-6507
DOI:	10.1080/10426507.2016.1277528
Popis:	The synthesis of a new series of P-heterocyclic compounds, substituted 2-aminomethyl-2-oxo-2λ5-perhydro-[1,3,2]oxazaphospholo[3,4-a]pyridine derivatives 8(a-j), was accomplished. A key intermediate, 2-(chloromethyl)-2-oxo-2λ5-perhydro-[1,3,2]oxazaphospholo[3,4-a]pyridine (6) was primarily synthesized by the condensation of (±)-2-piperidinemethanol (4) and chloromethylphosphonic dichloride (5); subsequently, it was treated with various heterocyclic amines/benzylamines/aminoacid esters, 7(a-j) to obtain the desired products. The structures of the newly synthesized compounds were elucidated by 1H, 13C, and 31P NMR spectroscopy, mass spectra and elemental analyses. The biological potency of title products was investigated by screening in vitro antimicrobial activity. The bio-screening data revealed that most of the synthesized derivatives showed potent growth of inhibition against fungi while compared with bacteria. Particularly, compounds 8c and 8i against bacterial strains, and 8a and 8f against fungi exhibited promising activity.
Databáze:	OpenAIRE
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