爵床脂素 B | 17951-19-8

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基萘木脂素
• 中文名称: 爵床脂素 B
• 中文别名: 爵床脂素B
• 英文名称: justicidin B
• 英文别名: 9-benzo[1,3]dioxol-5-yl-6,7-dimethoxy-3H-naphtho[2,3-c]furan-1-one；9-(benzo[d][1,3]dioxol-5-yl)-6,7-dimethoxynaphtho[2,3-c]furan-1(3H)-one；6,7-dimethoxy-9-(1,3-benzodioxol-5-yl)naphtho[2,3-c]furan-1(3H)-one；3-Hydroxymethyl-6,7-dimethoxy-1-(3,4-methylendioxyphenyl)-<2>naphthoesaeure-lacton, Justicin B；4-(1,3-benzodioxol-5-yl)-6,7-dimethoxy-1H-benzo[f][2]benzofuran-3-one
• CAS: 17951-19-8
• 化学式: C₂₁H₁₆O₆
• 分子量: 364.354
• InChiKey: RTDRYYULUYRTAN-UHFFFAOYSA-N

物化性质

• 熔点：
  240°
• 沸点：
  601.9±55.0 °C(Predicted)
• 密度：
  1.376±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	Daurinol	79862-77-4	C20H14O6	350.328
  ——	6,7-Dimethoxy-1-(3,4-methylendioxyphenyl)-naphthalin-2,3-dicarbonsaeureanhydrid	96264-86-7	C21H14O7	378.338
  ——	6,7-dimethoxy-2,3-bis(methoxycarbonyl)-1-(3,4-methylenedioxyphenyl)naphthalene	95436-24-1	C23H20O8	424.407
  ——	6,7-dimethoxy-2-(methoxycarbonyl)-1-(3,4-methylenedioxyphenyl)naphthalene-3-carboxylic acid	225517-03-3	C22H18O8	410.38
  ——	6,7-dimethoxy-1-(benzo[1,3]dioxol-5-yl)naphthalene-2,3-dicarboxylic acid 2-ethyl ester	289622-34-0	C23H20O8	424.407
  ——	diethyl 6,7-dimethoxy-1-(benzo[1,3]dioxol-5-yl)naphthalene-2,3-dicarboxylate	289622-28-2	C25H24O8	452.461
  二叶草素	diphyllin	22055-22-7	C21H16O7	380.354
  ——	6,7-dimethoxy-1-(3,4-methylenedioxyphenyl)naphthalene-2,3-dimethanol	86431-57-4	C21H20O6	368.386
  ——	1,6,7-trimethoxy-9-(3,4-methylenedioxy)phenylnaphtho[2,3-c]furan	1453191-44-0	C22H20O6	380.397
  ——	3-(2,2-dimethylpropanoyloxymethyl)-1-(3,4-methylenedioxyphenyl)-6,7-dimethoxynaphthalene-2-ylmethanol	850785-61-4	C26H28O7	452.504
• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  二叶草素	diphyllin	22055-22-7	C21H16O7	380.354
  ——	6,7-dimethoxy-1-(3,4-methylenedioxyphenyl)naphthalene-2,3-dimethanol	86431-57-4	C21H20O6	368.386

反应信息

• 作为反应物：
  描述：

  爵床脂素 B 在 Tris-HCl buffer 、 还原型辅酶II(NADPH)四钠盐 作用下， 生成 二叶草素
  参考文献：
  名称：

  Justicidin B 7-hydroxylase, a cytochrome P450 monooxygenase from cell cultures of Linum perenne Himmelszelt involved in the biosynthesis of diphyllin

  摘要：

  Cell suspension cultures of Linum perenne L. Himmelszelt accumulate justicidin B as the main component together with glycosides of 7-hydroxyjusticidin B (diphyllin). A hypothetical biosynthetic pathway for these compounds is suggested. Justicidin B 7-hydroxylase (JusB7H) catalyzes the last step in the biosynthesis of diphyllin by introducing a hydroxyl group in position 7 of justicidin B. This enzyme was characterized from a microsomal fraction prepared from a Linum perenne Himmelszelt suspension culture for the first time. The hydroxylase activity was strongly inhibited by cytochrome c as well as other cytochrome P450 inhibitors like clotrimazole indicating the involvement of a cytochrome P450-dependent monooxygenase. JusB7H has a pH optimum of 7.4 and a temperature optimum of 26 degrees C. Justicidin B was the only substrate accepted by JusB7H with an apparent K-m of 3.9 +/- 1.3 mu M. NADPH is predominantly accepted as the electron donor, but NADH was a weak co-substrate. A synergistic effect of NADPH and NADH was not observed. The apparent K-m for NADPH is 102 +/- 10 mu M. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2007.10.025
• 作为产物：
  描述：

  二叶草素 在 4-二甲氨基吡啶 、 甲酸 、 palladium diacetate 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 爵床脂素 B
  参考文献：
  名称：

  Patentiflorin A Analogs as Antiviral Agents

  摘要：

  本公开涉及用作抗病毒药物的帕特尼氟林A类似物，例如抗HIV、抗冠状病毒、抗埃博拉病毒和抗流感病毒药物，以及它们的使用方法。

  公开号：

  US20210060042A1

文献信息

• Regiocontrolled Benzannulation of Diaryl(<i>gem</i>-dichlorocyclopropyl)methanols for the Synthesis of Unsymmetrically Substituted α-Arylnaphthalenes:  Application to Total Synthesis of Natural Lignan Lactones
  作者：Yoshinori Nishii、Taichi Yoshida、Hirofumi Asano、Kazunori Wakasugi、Jun-ichi Morita、Yoshifumi Aso、Eri Yoshida、Jiro Motoyoshiya、Hiromu Aoyama、Yoo Tanabe

  DOI：10.1021/jo047751u

  日期：2005.4.1

  synthesis of highly substituted α-arylnaphthalene analogues has been developed utilizing Lewis acid-promoted regiocontrolled benzannulation of aryl(aryl‘)-2,2-dichlorocyclopropylmethanols (aryl ≠ aryl‘; abbreviated as AACMs). Both AACM diastereomers were easily prepared via highly stereoselective addition (>95/5) of ArLi to gem-dichlorocyclopropropyl aryl‘ ketones. The choice of Lewis acids determined

  利用路易斯酸促进的芳基（芳基）-2，2-二氯环丙基甲醇（芳基≠芳基；缩写为AACMs）的路易斯酸区域控制的苯环已开发出高取代的α-芳基萘类似物的有效合成方法。两种AACM非对映异构体都可以通过将ArLi高​​度立体选择性地加成（> 95/5）到宝石-dichlorocyclopropropyl aryl'ketones上来制备。路易斯酸的选择决定了本苯并环的环化区域选择性。TiCl 4和SnCl 4使用螯合途径，而甲硅烷基三氟甲磺酸盐使用非螯合途径以40-91％的产率提供不对称取代的区域异构α-芳基萘，具有中等至出色的区域选择性（TiCl 4或SnCl 4 ; > 99 / 1-3 / 1，TBDMSOTf；> 1 / 99-1 / 4）。因此，通过选择反应顺序的顺序或合适的催化剂，可将α-芳基或α-芳基'部分（辅助芳基）引入α-芳基萘。证明了本方法在不对称取代的天然木脂素内酯，justicidin
• [EN] METHOD FOR PREPARATION OF JUSTICIDIN A DERIVATIVES OF ARYLNAPHTHALENE LIGNAN STRUCTURE<br/>[FR] PROCÉDÉ DE PRÉPARATION DE DÉRIVÉS DE JUSTICIDINE A DE STRUCTURE DE LIGNANE ARYLNAPHTHALÈNE
  申请人：KOREA INST SCI & TECH

  公开号：WO2014119892A1

  公开（公告）日：2014-08-07

  The present disclosure relates to a novel method for preparing an arylnaphthalene lignan compound. In synthesis of arylnaphthalene lignan compounds and derivatives according to the present disclosure, a naphthalene backbone may be constructed first and an aryl group may be introduced at the final stage. Through this, various kinds of derivatives that could not be prepared from the existing methods can be synthesized effectively. Further, the synthesis method according to the present disclosure is appropriate for large-scale production.

  本公开涉及一种制备芳基萘木脂素化合物的新方法。根据本公开的芳基萘木脂素化合物和衍生物的合成方法，首先可以构建萘骨架，然后在最后阶段引入芳基。通过这种方法，可以有效合成各种无法从现有方法中制备的衍生物。此外，根据本公开的合成方法适用于大规模生产。
• 아릴 나프탈렌 리그난 구조의 저스티시딘B 유도체 및 그의 제조방법
  申请人：KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY 한국과학기술연구원(319980077518) BRN ▼209-82-03522

  公开号：KR101492960B1

  公开（公告）日：2015-02-16

  본 발명은 아릴 나프탈렌 리그난 화합물의 신규한 제조방법에 관한 것이다.

  这项发明涉及新型芳香族萘烯化合物的制备方法。
• The efficient synthesis and biological evaluation of justicidin B
  作者：Taejung Kim、Young-Joo Kim、Kyu-Hyuk Jeong、Young-Tae Park、Hyukjoon Kwon、Pilju Choi、Ha-Neul Ju、Cheol Hee Yoon、Ji-Yool Kim、Jungyeob Ham

  DOI：10.1080/14786419.2021.1948843

  日期：2023.1.2

  Abstract A facile new synthetic method for the preparation of a Type-A 1-arylnaphthalene lactone skeleton was developed and used to synthesise justicidin B and several derivatives. Key synthesis steps included Hauser–Kraus annulation of a phthalide intermediate and Suzuki–Miyaura cross coupling between a triflated naphthalene lactone intermediate and various potassium organotrifluoroborates. With two

  摘要 开发了一种制备 A 型 1-芳基萘内酯骨架的简便新合成方法，并将其用于合成 justicidin B 和几种衍生物。关键的合成步骤包括苯酞中间体的 Hauser-Kraus 环化和三氟萘内酯中间体与各种有机三氟硼酸钾之间的 Suzuki-Miyaura 交叉偶联。除了两个例外，这些衍生物对脂多糖 (LPS) 诱导的小鼠巨噬细胞中一氧化氮 (NO) 的产生显示出显着的抑制作用。此外，包括 justicidin B 在内的几种化合物对六种人类肿瘤细胞系具有显着的细胞毒性。
• A new benzannulation reaction and its application in the multiple parallel synthesis of arylnaphthalene lignans
  作者：Stuart R Flanagan、David C Harrowven、Mark Bradley

  DOI：10.1016/s0040-4020(02)00616-6

  日期：2002.7

  described. The method is high yielding and provides a rapid entry to arylnaphthalenes. The lignan natural products justicidin B 1, retrojusticidin B 2, taiwanin C 3, justicidin E 4, chinensin 5 and retrochinensin 6 have all been synthesised in good overall yield using this protocol, demonstrating its potential in multiple parallel synthesis. The selective oxidation of diols 34–36 to the corresponding retrolactones

  描述了一种基于顺序霍纳-埃蒙斯和克莱森缩合反应的新型芳香环化反应。该方法产率高并且提供了芳基萘的快速进入方法。木质素天然产物正义肽B 1，逆转录酶B 2，台黄素C 3，正义肽E 4，chinensin 5和Retrochinensin 6均已使用该方案以良好的总收率合成，证明了其在多个平行合成中的潜力。同样值得注意的是，用锰酸钡（VI）将二醇34 – 36选择性氧化为相应的内酯。