N-octyl-2-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-1-sulfonyl-β-D-glucopyranosyl)acetamide | 1058156-35-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-octyl-2-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-1-sulfonyl-β-D-glucopyranosyl)acetamide
• 英文别名: [(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2R,3R,4S,5R,6S)-4,5-diacetyloxy-2-(acetyloxymethyl)-6-[2-(octylamino)-2-oxoethyl]sulfonyloxan-3-yl]oxyoxan-2-yl]methyl acetate
• CAS: 1058156-35-6
• 化学式: C₃₆H₅₅NO₂₀S
• 分子量: 853.893
• InChiKey: GDKFZXQGGLGEAO-CTVZUSKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  58
• 可旋转键数：
  28
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  283
• 氢给体数：
  1
• 氢受体数：
  20

反应信息

• 作为产物：
  描述：

  [(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2R,3R,4S,5R,6S)-4,5-diacetyloxy-2-(acetyloxymethyl)-6-[2-(octylamino)-2-oxoethyl]sulfanyloxan-3-yl]oxyoxan-2-yl]methyl acetate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以94%的产率得到N-octyl-2-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-1-sulfonyl-β-D-glucopyranosyl)acetamide
  参考文献：
  名称：

  Synthesis and evaluation of antitubercular activity of glycosyl thio- and sulfonyl acetamide derivatives

  摘要：

  A series of glycosyl thioacetamide and glycosyl sulfonyl acetamide derivatives have been prepared following a convenient reaction protocol and evaluated for their antitubercular activity against Mycobacterium tuberculosis H(37)Rv. Amongst 32 compounds evaluated 3 compounds were effective in inhibiting mycobacterial growth at MIC of 6.25 mu g/mL, 6 compounds at MIC of 3.125 mu g/mL and 1 compound at MIC of 1.56 mu g/mL. All active compounds were found nontoxic in Vero cell lines and mice bone marrow macrophages. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.06.004

文献信息

• Synthesis and evaluation of antitubercular activity of glycosyl thio- and sulfonyl acetamide derivatives
  作者：Samir Ghosh、Pallavi Tiwari、Shashi Pandey、Anup Kumar Misra、Vinita Chaturvedi、Anil Gaikwad、Shalini Bhatnagar、Sudhir Sinha

  DOI：10.1016/j.bmcl.2008.06.004

  日期：2008.7

  A series of glycosyl thioacetamide and glycosyl sulfonyl acetamide derivatives have been prepared following a convenient reaction protocol and evaluated for their antitubercular activity against Mycobacterium tuberculosis H(37)Rv. Amongst 32 compounds evaluated 3 compounds were effective in inhibiting mycobacterial growth at MIC of 6.25 mu g/mL, 6 compounds at MIC of 3.125 mu g/mL and 1 compound at MIC of 1.56 mu g/mL. All active compounds were found nontoxic in Vero cell lines and mice bone marrow macrophages. (c) 2008 Elsevier Ltd. All rights reserved.