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  • A new class of potential anti-tuberculosis agents: Synthesis and preliminary evaluation of novel acrylic acid ethyl ester derivatives.

A new class of potential anti-tuberculosis agents: Synthesis and preliminary evaluation of novel acrylic acid ethyl ester derivatives.

Bioorganic & medicinal chemistry (2010-06-12)
M Shahjahan Kabir, Ojas A Namjoshi, Ranjit Verma, Rebecca Polanowski, Sarah M Krueger, David Sherman, Marc A Rott, William R Schwan, Aaron Monte, James M Cook
ABSTRACT

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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Ethyl acrylate, SAJ first grade, ≥99.0%
Supelco
Ethyl acrylate, analytical standard
Sigma-Aldrich
Ethyl acrylate, contains 10-20 ppm MEHQ as inhibitor, 99%
Sigma-Aldrich
Rifampicin, ≥95% (HPLC), powder or crystals
Sigma-Aldrich
Rifampicin, suitable for plant cell culture, BioReagent, ≥95% (HPLC), powder or crystals
Sigma-Aldrich
Ethyl acrylate, ≥99.5%, stabilized
Supelco
Isoniazid, analytical standard, ≥99% (TLC)