期刊
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
卷 20, 期 12, 页码 3692-3697出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2010.04.087
关键词
Antithyroid drugs; Charge-transfer complexes; Iodine; Sulfur compounds; Thiols
资金
- Department of Science and Technology (DST), New Delhi, India
- University Grants Commission (UGC)
Hydrolysis of beta-lactam antibiotics by beta-lactamases (e. g., metallo-beta-lactamase, m beta l) is one of the major bacterial defense systems. These enzymes can catalyze the hydrolysis of a variety of antibiotics including the latest generation of cephalosporins, cephamycins and imipenem. It is shown in this paper that the thiol/thione moieties eliminated from certain cephalosporins by m beta l-mediated hydrolysis readily react with molecular iodine to produce ionic compounds having S-I bonds. While the reaction of MTT with iodine produced the corresponding disulfide, MDT and DMETT produced the charge-transfer complexes MDT-I(2) and DMETT-I(2), respectively. Addition of two equivalents of I(2) to MDT produced a novel cationic complex having an almost linear S-I(+)-S moiety and I(5)(-) counter anion. However, this reaction appears to be highly solvent dependent. When the reaction of MDT with I2 was carried out in water, the reaction produced a monocation having I(5)(-), indicating the reactivity of MDT toward I2 is very similar to that of the most commonly used antithyroid drug methimazole (MMI). In contrast to MMI, MDT and DMETT, the triazine-based compound MTDT acts as a weak donor toward iodine. (C) 2010 Elsevier Ltd. All rights reserved.
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