[(2S,3R,4S,5R)-2-[(2S,3R,4S,5S)-3-acetyloxy-2-[[(3S,8R,9S,10R,13S,14S,16S,17S)-3,17-dihydroxy-10,13-dimethyl-17-[(2S)-6-methyl-3-oxoheptan-2-yl]-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-16-yl]oxy]-5-hydroxyoxan-4-yl]oxy-4-[2-[[4-(dimethylsulfamoyl)-2,1,3-benzoxadiazol-7-yl]-methylamino]acetyl]oxy-5-hydroxyoxan-3-yl] 4-methoxybenzoate | 1593111-61-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: [(2S,3R,4S,5R)-2-[(2S,3R,4S,5S)-3-acetyloxy-2-[[(3S,8R,9S,10R,13S,14S,16S,17S)-3,17-dihydroxy-10,13-dimethyl-17-[(2S)-6-methyl-3-oxoheptan-2-yl]-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-16-yl]oxy]-5-hydroxyoxan-4-yl]oxy-4-[2-[[4-(dimethylsulfamoyl)-2,1,3-benzoxadiazol-7-yl]-methylamino]acetyl]oxy-5-hydroxyoxan-3-yl] 4-methoxybenzoate
• CAS: 1593111-61-5
• 化学式: C₅₈H₈₀N₄O₁₉S
• 分子量: 1169.35
• InChiKey: RURWBATZJVQQIR-FXMGIAAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  82
• 可旋转键数：
  22
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  311
• 氢给体数：
  4
• 氢受体数：
  23

反应信息

• 作为产物：
  描述：

  N-[7-(N,N-二甲胺基)-4-苯并呋吖基]二甲氨乙酰基氯化铵 、 3β,16β,17α-trihydroxycholest-5-en-22-one 16-O-{O-[2-O-(4-methoxybenzoyl)-β-D-xylopyranosyl]-(1->3)-2-O-acetyl-β-L-arabinopyranoside} 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以17%的产率得到[(2S,3R,4S,5R)-2-[(2S,3R,4S,5S)-3-acetyloxy-2-[[(3S,8R,9S,10R,13S,14S,16S,17S)-3,17-dihydroxy-10,13-dimethyl-17-[(2S)-6-methyl-3-oxoheptan-2-yl]-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-16-yl]oxy]-5-hydroxyoxan-4-yl]oxy-4-[2-[[4-(dimethylsulfamoyl)-2,1,3-benzoxadiazol-7-yl]-methylamino]acetyl]oxy-5-hydroxyoxan-3-yl] 4-methoxybenzoate
  参考文献：
  名称：

  Fluorescent analog of OSW-1 and its cellular localization

  摘要：

  OSW-1 is a steroidal saponin, which has emerged as an attractive anticancer agent with highly cancer cell selective activity. A fluorescent analog was prepared from the natural product to analyze its cellular uptake and localization. We found that the fluorescent analog is rapidly internalized into cells and is primarily distributed in endoplasmic reticulum and Golgi apparatus. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.02.009

文献信息

• Synthesis of OSW-1 Derivatives by Site-Selective Acylation and Their Biological Evaluation
  作者：Kaori Sakurai、Tomoya Takeshita、Masato Hiraizumi、Rika Yamada

  DOI：10.1021/ol503044j

  日期：2014.12.19

  monoacylate an antitumor saponin OSW-1 was developed using an organotin reagent to rapidly access its derivatives that are useful as chemical probes. 4″-O-Acylated OSW-1 derivatives bearing a fluorophore, an alkyne tag, or biotin were prepared in good yields and were shown to maintain highly cytotoxic activity.

  使用有机锡试剂开发了一种位点选择性单酰基化抗肿瘤皂苷OSW-1的策略，以快速访问其用作化学探针的衍生物。制备具有良好收率的带有荧光团，炔烃标签或生物素的4” -O-酰化的OSW-1衍生物，并显示出其保持高度的细胞毒性活性。
• Development of Chemical Probes for Functional Analysis of Anticancer Saponin OSW‐1
  作者：Rina Komatsu、Kaori Sakurai

  DOI：10.1002/tcr.201900042

  日期：2019.12

  reviews recent progress in the development of OSW‐1 derived probes for exploring the mechanism of its action. The key to the probe development is a judicious choice of functionalization sites and a selective functionalization strategy. The types of probes include fluorescent probes for cellular imaging analysis and affinity probes for target identification analysis.

  近年来，在天然产物的目标识别研究中，基于化学探针的方法已被证明是有效的。OSW-1是一种天然的皂素类产品，对各种癌细胞具有高度有效的选择性细胞毒性。了解其作用机理对于开发具有潜在新型靶途径的抗癌药物很重要。此帐户回顾了OSW-1衍生探针在探索其作用机理方面的最新进展。探针开发的关键是明智选择功能化位点和选择性功能化策略。探针的类型包括用于细胞成像分析的荧光探针和用于靶标鉴定分析的亲和探针。