(S)-1-((5E,8E)-5,8-bis(hydroxyimino)-1,4-dimethoxy-5,8-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 3-methylbut-2-enoate | 1622443-30-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-1-((5E,8E)-5,8-bis(hydroxyimino)-1,4-dimethoxy-5,8-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 3-methylbut-2-enoate
• CAS: 1622443-30-4
• 化学式: C₂₃H₂₈N₂O₆
• 分子量: 428.485
• InChiKey: RMKGHYFVGRQVJY-IMSPSDRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  109.94
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  (S)-4-methyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)pent-3-en-1-ol 在 吡啶 、 4-二甲氨基吡啶 、 ammonium cerium (IV) nitrate 、 盐酸羟胺 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 0.25h， 生成 (S)-1-((5E,8E)-5,8-bis(hydroxyimino)-1,4-dimethoxy-5,8-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 3-methylbut-2-enoate
  参考文献：
  名称：

  Synthesis and evaluation of novel alkannin and shikonin oxime derivatives as potent antitumor agents

  摘要：

  A set of forty alkannin and shikonin oxime derivatives were firstly designed and synthesized. Their cytotoxicities against three kinds of tumor cells and a normal cell line were tested and compared with alkannin and shikonin. The cell-based investigation demonstrated that some oxime derivatives were more or comparatively effective to the lead compounds, especially their selective and excellent antitumor activities towards K562 cells with no toxicity in normal cells. We may conclude that oximate modification to the mother nucleus of alkannin and shikonin is an available approach to acquire potent antitumor agents.

  DOI：

  10.1016/j.bmcl.2014.07.012

文献信息

• SHIKONIN, ALKANNIN, AND RACEMIC PARENT NUCLEUS CARBONYL OXIME DERIVATIVES AND APPLICATIONS THEREOF
  申请人：Shanghai Jiaotong University

  公开号：EP3002276A1

  公开（公告）日：2016-04-06

  The present invention discloses derivatives of shikonin, alkannin and a racemic mixture thereof with hydroxyl methylation and carbonyl oximation on the parent nucleus, and their application. The derivatives of shikonin with hydroxyl methylation and carbonyl oximation on the parent nucleus have structural formula (I) or (II); the derivatives of alkannin with hydroxyl methylation and carbonyl oximation on the parent nucleus have structural formula (III) or (IV); the derivatives of a racemic mixture of shikonin and alkannin with hydroxyl methylation and carbonyl oximation on the parent nucleus have structural formula (V) or (VI); wherein R1 is alkane, olefin, arene, or substituted arene comprising 1 to 6 carbon atoms; and R2 is alkane, olefin, arene, or substituted arene comprising 1 to 6 carbon atoms or is H. The oxime derivatives of shikonin, alkannin and a racemic mixture thereof in the present invention have novel structures; and in-vitro experiments show that said derivatives of the present invention have good growth inhibitory activity against tumor cells and thus can be used in tumor treatment.

  本发明公开了在母核上进行羟基甲基化和羰基氧化的志贺宁、烷宁及其外消旋混合物的衍生物及其应用。母核上羟基甲基化和羰基氧化的紫杉素衍生物的结构式为(I)或(II)；母核上羟基甲基化和羰基氧化的烷宁衍生物的结构式为(III)或(IV)；在母核上发生羟基甲基化和羰基氧化反应的紫杉素和烷宁的外消旋混合物的衍生物的结构式为(V)或(VI)；其中 R1 是包含 1 至 6 个碳原子的烷烃、烯烃、炔烃或取代的炔；R2 是包含 1 至 6 个碳原子的烷烃、烯烃、炔烃或取代的炔或 H。本发明中的志贺宁、烷宁及其外消旋混合物的肟衍生物具有新颖的结构；体外实验表明，本发明的上述衍生物对肿瘤细胞具有良好的生长抑制活性，因此可用于肿瘤治疗。
• Synthesis and evaluation of novel alkannin and shikonin oxime derivatives as potent antitumor agents
  作者：Rubing Wang、Xu Zhang、Hualong Song、Shanshan Zhou、Shaoshun Li

  DOI：10.1016/j.bmcl.2014.07.012

  日期：2014.9

  A set of forty alkannin and shikonin oxime derivatives were firstly designed and synthesized. Their cytotoxicities against three kinds of tumor cells and a normal cell line were tested and compared with alkannin and shikonin. The cell-based investigation demonstrated that some oxime derivatives were more or comparatively effective to the lead compounds, especially their selective and excellent antitumor activities towards K562 cells with no toxicity in normal cells. We may conclude that oximate modification to the mother nucleus of alkannin and shikonin is an available approach to acquire potent antitumor agents.