A new class of potential anti-tuberculosis agents: Synthesis and preliminary evaluation of novel acrylic acid ethyl ester derivatives.
Novel acrylic acid ethyl ester derivatives were synthesized and evaluated as potential agents against Mycobacterium species. A versatile and efficient copper-catalyzed coupling process was developed and used to prepare a library of substituted acrylic acid ethyl ester analogs. Minimum inhibitory concentration assays indicated that two of these compounds 3 and 4 have greater in vitro activity against Mycobacterium smegmatis than rifampin, one of the current, first-line anti-mycobacterial chemotherapeutic agents. Moreover, members of this new class of compounds appear to exhibit a specific anti-mycobacterial effect and do not inhibit the growth of the other Gram-positive or Gram-negative species tested.
Department of Chemistry and Biochemistry, University of Wisconsin-Milwaukee, Milwaukee, WI 53211, USA.
M Shahjahan
MS
Kabir
Ojas A
OA
Namjoshi
Ranjit
R
Verma
Rebecca
R
Polanowski
Sarah M
SM
Krueger
David
D
Sherman
Marc A
MA
Rott
William R
WR
Schwan
Aaron
A
Monte
James M
JM
Cook
D000179:Acrylates / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D000995:Antitubercular Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D052160:Benzothiazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D008826:Microbial Sensitivity Tests; D009161:Mycobacterium / Q000187:drug effects; D013440:Sulfides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
C552750:3-(4-tert-butyl-phenylsulfanyl)acrylic acid ethyl ester; C552751:3-(benzothiazol-2-ylsulfanyl)acrylic acid ethyl ester; D000179:Acrylates; D000995:Antitubercular Agents; D052160:Benzothiazoles; D013440:Sulfides; C040833:ethyl acrylate; D003300:Copper