97101-46-7Relevant academic research and scientific papers
Simplified captopril analogues as NDM-1 inhibitors
Li, Ningning,Xu, Yintong,Xia, Qiang,Bai, Cuigai,Wang, Taiyi,Wang, Lei,He, Dingdi,Xie, Nannan,Li, Lixin,Wang, Jing,Zhou, Hong-Gang,Xu, Feng,Yang, Cheng,Zhang, Quan,Yin, Zheng,Guo, Yu,Chen, Yue
supporting information, p. 386 - 389 (2014/01/17)
Captopril is a New Delhi metallo-β-lactamase-1 (NDM-1) inhibitor with an IC50 value of 7.9 μM. It is composed of two units: a 3-mercapto-2-methylpropanoyl fragment and a proline residue. In this study, we synthesized simple amide derivatives of 3-mercapto-2-methylpropanoic acid, and then tested them as NDM-1 inhibitors in order to identify the pharmacophore for NDM-1 inhibition. We found that the lead compound 22 had an IC50 value of 1.0 μM. Further structure simplification provided compounds 31 and 32, which had IC50 values of 15 and 10 μM, respectively. As compound 32 is a clinically used antidote for metal poisoning, it has great potential to be repurposed to treat bacterial infections.
Simplified captopril analogues as NDM-1 inhibitors
Li, Ningning,Xu, Yintong,Xia, Qiang,Bai, Cuigai,Wang, Taiyi,Wang, Lei,He, Dingdi,Xie, Nannan,Li, Lixin,Wang, Jing,Zhou, Hong-Gang,Xu, Feng,Yang, Cheng,Zhang, Quan,Yin, Zheng,Guo, Yu,Chen, Yue
supporting information, p. 386 - 389 (2015/08/26)
Captopril is a New Delhi metallo-β-lactamase-1 (NDM-1) inhibitor with an IC50 value of 7.9 μM. It is composed of two units: a 3-mercapto-2-methylpropanoyl fragment and a proline residue. In this study, we synthesized simple amide derivatives of 3-mercapto-2-methylpropanoic acid, and then tested them as NDM-1 inhibitors in order to identify the pharmacophore for NDM-1 inhibition. We found that the lead compound 22 had an IC50 value of 1.0 μM. Further structure simplification provided compounds 31 and 32, which had IC50 values of 15 and 10 μM, respectively. As compound 32 is a clinically used antidote for metal poisoning, it has great potential to be repurposed to treat bacterial infections.
Process Conditions for Production of D-β-Acetylthioisobutyric Acid from Methyl DL-β-Acetylthioisobutyrate with the Cells of Pseudomonas putida MR-2068
Sakimae, Akihiro,Ozaki, Eiji,Toyama, Hiroko,Ohsuga, Naoto,Numazawa, Ryozo,et al.
, p. 782 - 786 (2007/10/02)
The process conditions concerned with the production of D-β-acetylthioisobutyric acid were investigated.Methyl DL-β-acetylthioisobutyrate as an enzyme substrate was produced from methyl methacrylate in 96.6percent yield by allowing 1.0 mol of methyl methacrylate to react with 1.6 mol of thioacetic acid at 80 deg C for 6 h.Through the study of hydrolytic reaction of methyl DL-β-acetylthioisobutyrate with the cells of Pseudomonas putida MR-2068, it was found that D-β-acetylthioisobutyric acid having more than 98percent (e. e.) optical purity was obtained when the reaction was done below pH 7.5 and below 50 deg C.For example, 10percent (w/v) methyl DL-β-acetylthioisobutyrate in the reaction mixture was asymmetrically hydrolyzed by 0.2percent (w/v) cells at 45 deg C at pH 7.0 for 18 h to give DAT having 98.2percent (e. e.) optical purity in 49.7percent yield.To prevent the decomposition and racemization of D-β-acetylthioisobutyric acid in the purification process, the use of a thin-film distillation apparatus for a continuous distillation was proposed to be an effective purification method.
Chemical Racemization of Methyl L-β-Acetylthioisobutyrate
Sakimae, Akihiro,Kobayashi, Yoshimasa,Ohsuga, Naoto,Numazawa, Ryozo,Ohnishi, Hisao
, p. 17 - 19 (2007/10/02)
Methyl L-β-acetylthioisobutyrate was racemized with 1,8-diazabicyclo--undecene-7 as a catalyst.Methyl methacrylate and thioacetic acid were identified as the intermediates of the reaction.Thioacetic acid was relatively unstable and susceptible to decomposition during the racemization process.The addition of excess methyl methacrylate to the reaction mixture prevented a decrease of the racemate.The racemized ester was confirmed to be usable as a substrate for the enzymatic production of D-β-acetylthioisobutyric acid.
Screening of Microorganisms Producing D-β-Acetylthioisobutyric Acid from Methyl DL-β-Acetylthioisobutyrate
Sakimae, Akihiro,Hosoi, Akihiko,Kobayashi, Etsuko,Ohsuga, Naoto,Numazawa, Ryozo,et al.
, p. 1252 - 1256 (2007/10/02)
Microorganisms producing D-β-acetylthioisobutyric acid from methyl DL-β-acetylthioisobutyrate were screened from stock cultures.The D-β-acetylthioisobutyric acid-producing ability was found in 15 strains belonging to the genera Pseudomonas, Agrobacterium, Enterobacter, Cellulomonas, Rhodococcus, Brevibacterium, and Torulopsis.A strain of Pseudomonas fluorescens, IFO 3081, was selected as the best microorganism.The cells having activity (558 units/g of dry cells) could be easily prepared by cultivation at 25 deg C at pH 6.6 for 24 hr in a glucose-containing medium.The D-form of methyl DL-β-acetylthioisobutyrate was selectively hydrolyzed with the cells so that D-β-acetylthioisobutyric acid (97.2percent enantiomeric excess) was produced in a high yield.
Amide carbamates and amide oxime compounds
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, (2008/06/13)
Amide oxime compounds are useful intermediates in the preparation of pesticidally active amide carbamate compounds.
