Synthesis and antimicrobial evaluation of l-phenylalanine-derived C5-substituted rhodanine and chalcone derivatives containing thiobarbituric acid or 2-thioxo-4-thiazolidinone

The Synthesis and Anti-Bacterial Activities of N-carboxymethyl Rhodanines

“…Based on these results, Jin et al [46] synthesized several chalcone analogues bearing an N-carboxymethyl rhodanine (9a-q) and tested their antibacterial activities against several different strains of bacteria ( Figure 7). These particular compounds exhibited significant levels of antibacterial activity with MIC values in the range of 2-16 µg/mL.…”

“…With this in mind, Jin et al [46] designed and synthesized a series of chalcone derivatives containing non-substituted rhodanine (7a-e) and evaluated their antimicrobial activities against several different strains of bacteria ( Figure 7). Some of the compounds in this series were found to be inactive against the bacteria evaluated in this study at 64 µg/mL.…”

Synthesis and biological evaluation of (E)-1-(substituted)-3-phenylprop-2-en-1-ones bearing rhodanines as potent anti-microbial agents

“…An aqueous solution of sodium chloroacetate (30.3 mmol) was added to the mixture and stirring was continued at 23 C for 3 h. Then, the reaction mixture was acidified with dilute HCl until pH 1.0 and refluxed overnight. The reaction mixture was neutralized with saturated NaHCO 3 solution.…”

“…Their anti-bacterial tests in vitro showed that these compounds all exhibited good inhibitory activity against the Gram-positive microorganisms especially for the multi-drug-resistant clinical isolates such as MRSA and quinolone-resistant S. aureus (QRSA). Especially in the series of I, compound 6q (A moiety was a naphthalene nucleus) showed the strongest activity with a minimum inhibitory concentration (MIC) value of 2 mg/mL against the multi-drugresistant clinical isolates 23 . In the present work, as a part of our ongoing research, a new series of rhodanine derivatives (4a-i) were designed using 6q as the lead compound, in which the modification of 6q was focused on reserving the naphthalene nucleus, substituting the acetic acid group on the three-position of the rhodanine with different amino acid side chains (including Dor L-phenylalanine, D-or L-tyrosine, D-or L-valine, D-or Lleucine and L-isoleucine) as shown in Figure 2.…”

“…In our previous study, we designed and synthesized three series of rhodanine derivatives bearing chalcone (Figure 1, I), 4-(2-oxo-2-phenylethoxy)benzene (Figure 1, II) and 5-aryloxy pyrazole moieties ( Figure 1, III), respectively [16][17][18][19][20][21][22][23] . Their anti-bacterial tests in vitro showed that these compounds all exhibited good inhibitory activity against the Gram-positive microorganisms especially for the multi-drug-resistant clinical isolates such as MRSA and quinolone-resistant S. aureus (QRSA).…”