15-methoxy-N-nonyl-Lat B | 1201325-45-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: 15-methoxy-N-nonyl-Lat B
• 英文别名: 15-Methoxy N-nonyl Latrunculin B；(4R)-4-[(1R,4Z,8Z,10S,13R,15R)-15-methoxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,8-dien-15-yl]-3-nonyl-1,3-thiazolidin-2-one
• CAS: 1201325-45-2
• 化学式: C₃₀H₄₉NO₅S
• 分子量: 535.789
• InChiKey: LZEJTUOARKJMOM-ZZQMKPEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  90.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  6,7-(Z)-15-OMe-Latrunculin B 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以55%的产率得到15-methoxy-N-nonyl-Lat B
  参考文献：
  名称：

  Semisynthetic latrunculin B analogs: Studies of actin docking support a proposed mechanism for latrunculin bioactivity

  摘要：

  Latrunculins are unique macrolides containing a thiazolidinone moiety. Latrunculins A, B and T and 16-epi-latrunculin B were isolated from the Red Sea sponge Negombata magnifica. N-Alkylated, O-methylated analogs of latrunculin B were synthesized and biological evaluation was performed for antifungal and antiprotozoal activity. The natural latrunculins showed significant bioactivity, while the semisynthetic analogs did not. Docking studies of these analogs into the X-ray crystal structure of G-actin showed that, in comparison with latrunculins A and B, N-alkylated latrunculins did not dock satisfactorily. This suggests that the analogs do not fit well into the active site of G-actin due to steric clashes and provides an explanation for the absence of bioactivity. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2009.09.012

文献信息

• Semisynthetic latrunculin B analogs: Studies of actin docking support a proposed mechanism for latrunculin bioactivity
  作者：Sucheta Kudrimoti、Safwat A. Ahmed、Pankaj R. Daga、Amir E. Wahba、Sherief I. Khalifa、Robert J. Doerksen、Mark T. Hamann

  DOI：10.1016/j.bmc.2009.09.012

  日期：2009.11

  Latrunculins are unique macrolides containing a thiazolidinone moiety. Latrunculins A, B and T and 16-epi-latrunculin B were isolated from the Red Sea sponge Negombata magnifica. N-Alkylated, O-methylated analogs of latrunculin B were synthesized and biological evaluation was performed for antifungal and antiprotozoal activity. The natural latrunculins showed significant bioactivity, while the semisynthetic analogs did not. Docking studies of these analogs into the X-ray crystal structure of G-actin showed that, in comparison with latrunculins A and B, N-alkylated latrunculins did not dock satisfactorily. This suggests that the analogs do not fit well into the active site of G-actin due to steric clashes and provides an explanation for the absence of bioactivity. Published by Elsevier Ltd.