p-tolyl 4-O-acetyl-2-O-levulinyl-1-thio-α-L-rhamnopyranoside | 1242274-80-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-tolyl 4-O-acetyl-2-O-levulinyl-1-thio-α-L-rhamnopyranoside
• 英文别名: [(2S,3R,4R,5R,6S)-5-acetyloxy-4-hydroxy-6-methyl-2-(4-methylphenyl)sulfanyloxan-3-yl] 4-oxopentanoate
• CAS: 1242274-80-1
• 化学式: C₂₀H₂₆O₇S
• 分子量: 410.488
• InChiKey: YAIZTBDYMWMHNT-IZZXSCACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  124
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  p-tolyl 4-O-acetyl-2-O-levulinyl-1-thio-α-L-rhamnopyranoside 在 三氟甲磺酸三甲基硅酯 、 乙酸肼 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 2.5h， 生成 dodecyl 4-O-acetyl-α-L-rhamnopyranosyl-(1->3)-4-O-acetyl-α-L-rhamnopyranosyl-(1->3)-4-O-acetyl-α-L-rhamnopyranosyl-(1->4)-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis and antibacterial evaluation of a series of oligorhamnoside derivatives

  摘要：

  A series of novel oligorhamnoside derivatives (1-10) and naturally occurring cleistrioside-5 were synthesized and evaluated for their in vitro antibacterial activities. Among them, dirhamnoside derivative 7 and cleistrioside-5 displayed similar antibacterial profiles and exhibited moderate to good inhibitory activities on bacterial growth against a panel of Gram-positive bacteria (MICs <= 4-32 mu g/mL). The results revealed that these two compounds showed selectivity towards bacterial species strictly, without being affected by the antibiotic-resistant/susceptible properties of one species, which suggested that they might have the potential to avoid antibiotic cross-resistance. In addition, the preliminary SARs of this type of oligorhamnoside derivatives on the antibacterial activities were determined. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.07.028
• 作为产物：
  描述：

  p-tolyl 4-O-acetyl-3-O-(p-methoxybenzyl)-2-O-levulinoyl-1-thio-α-L-rhamnopyranoside 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 以76%的产率得到p-tolyl 4-O-acetyl-2-O-levulinyl-1-thio-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis and antibacterial evaluation of a series of oligorhamnoside derivatives

  摘要：

  A series of novel oligorhamnoside derivatives (1-10) and naturally occurring cleistrioside-5 were synthesized and evaluated for their in vitro antibacterial activities. Among them, dirhamnoside derivative 7 and cleistrioside-5 displayed similar antibacterial profiles and exhibited moderate to good inhibitory activities on bacterial growth against a panel of Gram-positive bacteria (MICs <= 4-32 mu g/mL). The results revealed that these two compounds showed selectivity towards bacterial species strictly, without being affected by the antibiotic-resistant/susceptible properties of one species, which suggested that they might have the potential to avoid antibiotic cross-resistance. In addition, the preliminary SARs of this type of oligorhamnoside derivatives on the antibacterial activities were determined. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.07.028

文献信息

• Synthesis and biological evaluation of cytotoxic activity of novel anthracene l-rhamnopyranosides
  作者：Gaopeng Song、Hongchun Liu、Wei Zhang、Meiyu Geng、Yingxia Li

  DOI：10.1016/j.bmc.2010.05.064

  日期：2010.7

  A series of anthracene L-rhamnopyranosides were designed and synthesized in a practical way and their cytotoxic activity was examined in vitro. Most compounds exhibited both potent cytotoxicity against several tumor cell lines and high DNA binding capacity. The preliminary results showed that subtle modifications of rhamnosyl moiety in anthracene rhamnosides with acetyl group had a selective toxicity for different tumor cells and the displacement of C-10 carbonyl group in emodin by acetylmethylene group was helpful to improve the inhibitory activity. Lipophilicity of the anthracene glycosides was not a crucial factor for cytotoxicity and most molecules with good cytotoxicity could inhibit the catalytic activity of Top2 alpha. (C) 2010 Elsevier Ltd. All rights reserved.