p-tolyl 4-O-acetyl-3-O-(p-methoxybenzyl)-2-O-levulinoyl-1-thio-α-L-rhamnopyranoside | 943221-78-1

• 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-3-O-(p-methoxybenzyl)-2-O-levulinoyl-1-thio-α-L-rhamnopyranoside
• 英文别名: p-tolyl 4-O-acetyl-2-O-levulinyl-3-O-p-methoxybenzyl-1-thio-α-L-rhamnopyranoside；[(2S,3R,4R,5S,6S)-5-acetyloxy-4-[(4-methoxyphenyl)methoxy]-6-methyl-2-(4-methylphenyl)sulfanyloxan-3-yl] 4-oxopentanoate
• CAS: 943221-78-1
• 化学式: C₂₈H₃₄O₈S
• 分子量: 530.639
• InChiKey: UZQPPPNFRBPWCU-YSNGLDQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  p-tolyl 4-O-acetyl-3-O-(p-methoxybenzyl)-2-O-levulinoyl-1-thio-α-L-rhamnopyranoside 在 N-碘代丁二酰亚胺 、 4 Angstroem MS 、 silver trifluoromethanesulfonate 、 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， 反应 12.0h， 生成 dodecanyl 4-O-acetyl-2,3-O-isopropylidene-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-acetyl-α-L-rhamnopyranosyl-(1->3)-4-O-acetyl-2-O-levulinoyl-α-L-rhamnopyranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside
  参考文献：
  名称：

  分离自油菜（Cleistopholis patens）和油酸油菜（Cleistopholis glauca）的部分部分乙酰化的十二烷酰基四十二烷衍生物cleistetroside-2的全合成。

  摘要：

  首次实现了部分乙酰化的十二烷基四鼠李糖苷衍生物cleistetroside-2的总合成，该衍生物是从Cleistopholis patens和Cleistopholis glauca中分离出来的，并且对革兰氏阳性细菌显示出显着的体外抗菌活性。

  DOI：

  10.1016/j.carres.2007.03.014
• 作为产物：
  描述：

  p-tolyl 4-O-acetyl-2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside 在 4-二甲氨基吡啶 、 水 、 二正丁基氧化锡 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 43.5h， 生成 p-tolyl 4-O-acetyl-3-O-(p-methoxybenzyl)-2-O-levulinoyl-1-thio-α-L-rhamnopyranoside
  参考文献：
  名称：

  分离自油菜（Cleistopholis patens）和油酸油菜（Cleistopholis glauca）的部分部分乙酰化的十二烷酰基四十二烷衍生物cleistetroside-2的全合成。

  摘要：

  首次实现了部分乙酰化的十二烷基四鼠李糖苷衍生物cleistetroside-2的总合成，该衍生物是从Cleistopholis patens和Cleistopholis glauca中分离出来的，并且对革兰氏阳性细菌显示出显着的体外抗菌活性。

  DOI：

  10.1016/j.carres.2007.03.014

文献信息

• Synthesis and antibacterial evaluation of a series of oligorhamnoside derivatives
  作者：Ning Ding、Zaihong Zhang、Wei Zhang、Yuexing Chun、Peng Wang、Huimin Qi、Shan Wang、Yingxia Li

  DOI：10.1016/j.carres.2011.07.028

  日期：2011.10

  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.
• 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.