2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl N,N-dimethyldithiocarbamate | 138528-05-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl N,N-dimethyldithiocarbamate
• 英文别名: OCT313-peracetate；[(2R,3S,4R,5R,6S)-5-acetamido-3,4-diacetyloxy-6-(dimethylcarbamothioylsulfanyl)oxan-2-yl]methyl acetate
• CAS: 138528-05-9
• 化学式: C₁₇H₂₆N₂O₈S₂
• 分子量: 450.534
• InChiKey: JGBZJISAJIXIMJ-QCODTGAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  178
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl N,N-dimethyldithiocarbamate 在 甲醇 、 sodium methylate 作用下， 反应 2.0h， 以59.7%的产率得到N,N-dimethyl 2-acetoamido-2-deoxy-β-D-glucopyranosyl dithiocarbamate
  参考文献：
  名称：

  Synthesis of new sugar derivatives and evaluation of their antibacterial activities against Mycobacterium tuberculosis

  摘要：

  A series of sugar derivatives (1-13) were synthesized and evaluated for antibacterial activity against Mycobacterium tuberculosis (MTB), especially multi-drug resistant (MDR) MTB, and the structure-activity relationships of these compounds were studied. The results showed that the compound OCT313 (2-acetamido-2deoxy-beta-D-glucopyranosyl N,N-dimethyldithiocarbamate) (4) exhibited significant in vitro bactericidal activity, and that the dithiocarbamate group at C-1 position of the glucopyranoside ring was requisite for the antibacterial activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.09.095
• 作为产物：
  描述：

  2-乙酰氨基-3,4,6-三-O-乙酰-2-脱氧-α-D-吡喃葡萄糖酰基氯 、 sodium dimethyldithiocarbamate 以 丙酮 为溶剂， 反应 0.25h， 以37.6%的产率得到2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl N,N-dimethyldithiocarbamate
  参考文献：
  名称：

  Synthesis of new sugar derivatives and evaluation of their antibacterial activities against Mycobacterium tuberculosis

  摘要：

  A series of sugar derivatives (1-13) were synthesized and evaluated for antibacterial activity against Mycobacterium tuberculosis (MTB), especially multi-drug resistant (MDR) MTB, and the structure-activity relationships of these compounds were studied. The results showed that the compound OCT313 (2-acetamido-2deoxy-beta-D-glucopyranosyl N,N-dimethyldithiocarbamate) (4) exhibited significant in vitro bactericidal activity, and that the dithiocarbamate group at C-1 position of the glucopyranoside ring was requisite for the antibacterial activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.09.095

文献信息

• Synthesis of new sugar derivatives and evaluation of their antibacterial activities against Mycobacterium tuberculosis
  作者：Yasuhiro Horita、Takemasa Takii、Taku Chiba、Ryuji Kuroishi、Yasuhiro Maeda、Yukihisa Kurono、Emi Inagaki、Kenji Nishimura、Yoshifumi Yamamoto、Chiyoji Abe、Masami Mori、Kikuo Onozaki

  DOI：10.1016/j.bmcl.2009.09.095

  日期：2009.11

  A series of sugar derivatives (1-13) were synthesized and evaluated for antibacterial activity against Mycobacterium tuberculosis (MTB), especially multi-drug resistant (MDR) MTB, and the structure-activity relationships of these compounds were studied. The results showed that the compound OCT313 (2-acetamido-2deoxy-beta-D-glucopyranosyl N,N-dimethyldithiocarbamate) (4) exhibited significant in vitro bactericidal activity, and that the dithiocarbamate group at C-1 position of the glucopyranoside ring was requisite for the antibacterial activity. (C) 2009 Elsevier Ltd. All rights reserved.