2''-(S)-α-methylbutyrylalkannin | 52387-15-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2''-(S)-α-methylbutyrylalkannin
• 英文别名: (S)-alpha-Methylbutyryl alkannin；[(1S)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] (2S)-2-methylbutanoate
• CAS: 52387-15-2
• 化学式: C₂₁H₂₄O₆
• 分子量: 372.418
• InChiKey: ODQATBANLZCROD-SJCJKPOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 海关编码：
  2915900090

反应信息

• 作为产物：
  描述：

  (S)-(+)-2-甲基丁酸 、 紫草素 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 2''-(S)-α-methylbutyrylalkannin
  参考文献：
  名称：

  Antimicrobial Activities of Naphthazarins from Arnebia euchroma

  摘要：

  Bioassay-directed fractionation of extract of Arnebia euchroma led to the isolation of alkannin (1), shikonin (2), and their derivatives (3-8) as the active principles against methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant enterococci (VRE). The stereochemistry of alpha-methylbutyryl alkannin (8) is revealed for the first time, and the antimicrobial activity of 8 was compared with its corresponding diastereomer (9). The derivatives 3-9 showed stronger anti-MRSA activity [minimum inhibitory concentrations (MICs) ranged from 1.56 to 3.13 mug/mL] than alkannin or shikonin (MIC = 6.25 mug/mL). Anti-MRSA activity of derivatives was bactericidal with minimum bactericidal concentration (MBC)/ MIC less than or equal to 2. In a time-kill assay, the bactericidal activity against MRSA was achieved as rapidly as 2 h. The derivatives 3-9 were also active against vancomycin-resistant Enterococcus faecium (F935) and vancomycin-resistant Enterococcus faecalis (CKU-17) with MICs similar to those with MRSA. Aromatic ester derivatives were also synthesized for antimicrobial activity comparison. None of these compounds were active against Gram-negative bacteria tested. Their cytotoxicity was also evaluated on selected cancer cell lines, and they expressed their activity in the range 0.6-5.4 mug/mL (CD50). Our results indicate that the ester derivatives of alkannin are potential candidates of anti-MRSA and anti-VRE agents with antitumor activity.

  DOI：

  10.1021/np010599w

文献信息

• Antimicrobial Activities of Naphthazarins from <i>Arnebia </i><i>e</i><i>uchroma</i>
  作者：Chien-Chang Shen、Wan-Jr Syu、Shyh-Yuan Li、Chia-Hung Lin、Gum-Hee Lee、Chang-Ming Sun

  DOI：10.1021/np010599w

  日期：2002.12.1

  Bioassay-directed fractionation of extract of Arnebia euchroma led to the isolation of alkannin (1), shikonin (2), and their derivatives (3-8) as the active principles against methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant enterococci (VRE). The stereochemistry of alpha-methylbutyryl alkannin (8) is revealed for the first time, and the antimicrobial activity of 8 was compared with its corresponding diastereomer (9). The derivatives 3-9 showed stronger anti-MRSA activity [minimum inhibitory concentrations (MICs) ranged from 1.56 to 3.13 mug/mL] than alkannin or shikonin (MIC = 6.25 mug/mL). Anti-MRSA activity of derivatives was bactericidal with minimum bactericidal concentration (MBC)/ MIC less than or equal to 2. In a time-kill assay, the bactericidal activity against MRSA was achieved as rapidly as 2 h. The derivatives 3-9 were also active against vancomycin-resistant Enterococcus faecium (F935) and vancomycin-resistant Enterococcus faecalis (CKU-17) with MICs similar to those with MRSA. Aromatic ester derivatives were also synthesized for antimicrobial activity comparison. None of these compounds were active against Gram-negative bacteria tested. Their cytotoxicity was also evaluated on selected cancer cell lines, and they expressed their activity in the range 0.6-5.4 mug/mL (CD50). Our results indicate that the ester derivatives of alkannin are potential candidates of anti-MRSA and anti-VRE agents with antitumor activity.

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