(–)-5-hydroxy-2-(1'-hydoxyethyl)naphtho[2,3-b]furan-4,9-dione | 123297-90-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: (–)-5-hydroxy-2-(1'-hydoxyethyl)naphtho[2,3-b]furan-4,9-dione
• 英文别名: 5-hydroxy-2-[(1S)-1-hydroxyethyl]-naphtho[2,3-b]furan-4,9-dione；(S)-5-hydroxy-2-(1-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione；(-)-2-(1-hydroxyethyl)-5-hydroxynaphtho[2,3-b]furane-4,9-dione；(S)-2-(1-hydroxyethyl)-5-hydroxynaphtho[2,3-b]-furan-4,9-dione；(S)-2-(1-hydroxyethyl)-5-hydroxynaphtho[2,3-b]furan-4,9-dione；5-Hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione；5-hydroxy-2-[(1S)-1-hydroxyethyl]benzo[f][1]benzofuran-4,9-dione
• CAS: 123297-90-5
• 化学式: C₁₄H₁₀O₅
• 分子量: 258.23
• InChiKey: XJGFVZBTNKODFQ-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  87.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (–)-5-hydroxy-2-(1'-hydoxyethyl)naphtho[2,3-b]furan-4,9-dione 生成 (S)-NQ801 MTPA ester
  参考文献：
  名称：

  Preparation of optically active 2-(1-hydroxyethyl)-5-hydroxynaphtho[2,3-b]furan-4, 9-diones having anticancer activities

  摘要：

  本

  公开号：

  US20080300415A1
• 作为产物：
  描述：

  2-acetyl-5-hydroxynaphtho[2,3-b]furan-4,9-dione 在 甲酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以89%的产率得到(–)-5-hydroxy-2-(1'-hydoxyethyl)naphtho[2,3-b]furan-4,9-dione
  参考文献：
  名称：

  一种来自塔贝布氏菌的化学预防性萘醌的立体选择性合成和细胞毒性。

  摘要：

  通过利用Noyori还原作为关键步骤，从巴西传统药物Tabebuia avellanedae中选择性合成1种生物活性萘醌之一。与丝裂霉素相比，化合物1对几种人类肿瘤细胞系显示出有效的细胞毒性，而对某些人类正常细胞系显示出较低的细胞毒性。另一方面，其对映体对肿瘤细胞系的活性不如1。

  DOI：

  10.1016/j.bmcl.2007.10.005

文献信息

• Stereoselective synthesis and cytotoxicity of a cancer chemopreventive naphthoquinone from Tabebuia avellanedae
  作者：Mitsuaki Yamashita、Masafumi Kaneko、Akira Iida、Harukuni Tokuda、Katsumi Nishimura

  DOI：10.1016/j.bmcl.2007.10.005

  日期：2007.12

  Stereoselective synthesis of 1, one of biologically active naphthoquinones from a Brazilian traditional medicine Tabebuia avellanedae, was achieved by utilizing Noyori reduction as a key step. Compound 1 displayed potent cytotoxicity against several human tumor cell lines, whereas it showed lower cytotoxicity against some human normal cell lines compared with that of mitomycin. On the other hand, its

  通过利用Noyori还原作为关键步骤，从巴西传统药物Tabebuia avellanedae中选择性合成1种生物活性萘醌之一。与丝裂霉素相比，化合物1对几种人类肿瘤细胞系显示出有效的细胞毒性，而对某些人类正常细胞系显示出较低的细胞毒性。另一方面，其对映体对肿瘤细胞系的活性不如1。
• NOVEL PREPARATION OF ANTICANCER-ACTIVE TRICYCLIC COMPOUNDS VIA ALKYNE COUPLING REACTION
  申请人：IIDA Akira

  公开号：US20120077986A1

  公开（公告）日：2012-03-29

  The present invention is directed to provide a novel preparation of anticancer-active tricyclic compounds via alkyne coupling reaction. The present invention provides a process for preparing a compound of formula (Ia) or (Ib): wherein R 1 is optionally substituted C 1-6 alkyl, etc.; W is O, S or NR 2 ; R 2 is hydrogen atom, etc., which comprises Step (a) in which a compound of formula (II): wherein R 1 is the same as defined above, and a compound of formula (III) or (IV): wherein R 2 is the same as defined above; R 3 is hydrogen atom, etc.; X is halogen atom, etc., are reacted in the presence of a base, a copper catalyst and a palladium catalyst in an aprotic polar solvent.

  本发明旨在通过炔烃偶联反应提供一种新型抗癌活性三环化合物的制备方法。本发明提供了一种制备式(Ia)或(Ib)的化合物的方法：其中R1为可选择的取代的C1-6烷基等；W为O、S或NR2；R2为氢原子等；其中包括步骤(a)，其中式(II)的化合物：其中R1与上述定义相同，和式(III)或(IV)的化合物：其中R2与上述定义相同；R3为氢原子等；X为卤原子等，在无水极性溶剂中，在碱、铜催化剂和钯催化剂的存在下反应。
• Fujimoto, Yoshinori; Eguchi, Tadashi; Murasaki, Chikako, Journal of the Chemical Society. Perkin transactions I, 1991, # 10, p. 2323 - 2327
  作者：Fujimoto, Yoshinori、Eguchi, Tadashi、Murasaki, Chikako、Ohashi, Yuji、Kakinuma, Katsumi、et al.

  DOI：——

  日期：——
• Preparation of anticancer-active tricyclic compounds via alkyne coupling reaction
  申请人：Taheebo Japan Co., Ltd.

  公开号：EP2436669B1

  公开（公告）日：2016-01-13
• EFFICIENT PREPARATION OF NAPHTHOQUINONE ANTICANCER ACTIVE INGREDIENTS
  申请人：Iida Akira

  公开号：US20100215625A1

  公开（公告）日：2010-08-26

  One of the problems to be resolved by the present invention is to stably and sustainably produce active ingredients contained in Bignoniaceous plants of which a mass production is difficult in a conventional manner. The present invention relates to a method for efficiently preparing an anticancer active ingredient NQ 801 by a cell cultivation of Bignoniaceous plants under specific culture conditions. An ingredient-production system in the present invention has an anticancer activity.