Synthesis of novel 1H-pyrrolizine-5-carboxamides and their antimicrobial properties.
A variety of N-aryl-7-cyano-2,3-dihydro-1H-pyrrolizine-5-carboxamides 6, 8-11 were synthesized through the reaction of the 2-amino derivatives 3 with acid chlorides, aromatic and aliphatic aldehydes. In addition, 3 could directly obtained through the reaction of 2-pyrrolidinylidenepropanedinitrile (1) with chloroacetanilides 2a,b. However, reaction of 1 with-chloropropionanilide 2c gave the open-chain compound 5. The antimicrobial properties of the newly prepared compounds were screened against a variety of Gram positive, Gram-negative bacteria and yeast. Some of the prepared compounds (8a, 8c and 9a) show moderate activity against the tested Gram-positive bacteria (Staphylococcus aureus and/or Coagulase negative Staphylococcus). In addition, other compounds (6a, 9d and 9e) exhibit slight (weak) activity against Coagulase negative Staphylococcus.
Barsoum
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Pharmaceutical Chemistry Department, Faculty of Pharmacy, Cairo University, Cairo, Egypt.
Nawar
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D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects*; D005658:Fungi / Q000187:drug effects*; D007202:Indicators and Reagents; D008826:Microbial Sensitivity Tests; D011763:Pyrrolizidine Alkaloids / Q000138:chemical synthesis* / Q000494:pharmacology*; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D007202:Indicators and Reagents; D011763:Pyrrolizidine Alkaloids