3-(((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methoxy)-7,8,9,10-tetrahydro-6H-benzo[c]chromen-6-one

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-(((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methoxy)-7,8,9,10-tetrahydro-6H-benzo[c]chromen-6-one
• 英文别名: 3-[[(1R,5S)-6,6-dimethyl-2-bicyclo[3.1.1]hept-2-enyl]methoxy]-7,8,9,10-tetrahydrobenzo[c]chromen-6-one
• 化学式: C₂₃H₂₆O₃
• 分子量: 350.458
• InChiKey: SPJGSLDQFWVYOR-YWZLYKJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (-)-桃金娘烯醇 在 三溴化磷 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 生成 3-(((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methoxy)-7,8,9,10-tetrahydro-6H-benzo[c]chromen-6-one
  参考文献：
  名称：

  Monoterpene-Containing Substituted Coumarins as Inhibitors of Respiratory Syncytial Virus (RSV) Replication

  摘要：

  呼吸道合胞病毒（RSV）是婴儿死亡的一个重要原因。然而，目前尚无疫苗和足够的药物用于治疗。我们首次展示，O-连接的香豆素-单萜共轭物是有效的RSV抑制剂。最有效的化合物对RSV的A型和B型两种血清型都具有活性。根据添加时间实验的结果，这些共轭物在病毒周期的早期阶段起作用。根据分子模拟数据，RSV F蛋白可能被视为一个可能的靶点。

  DOI：

  10.3390/molecules26247493

文献信息

• Anti-influenza activity of monoterpene-containing substituted coumarins
  作者：Tatyana M. Khomenko、Vladimir V. Zarubaev、Iana R. Orshanskaya、Renata A. Kadyrova、Victoria A. Sannikova、Dina V. Korchagina、Konstantin P. Volcho、Nariman F. Salakhutdinov

  DOI：10.1016/j.bmcl.2017.04.091

  日期：2017.7

  Compounds simultaneously carrying the monoterpene and coumarin moieties have been tested for cytotoxicity and inhibition of activity against influenza virus A/California/07/09 (H1N1)pdm09. The structure of substituents in the coumarin framework, as well as the structure and the absolute configuration of the monoterpenoid moiety, are shown to significantly influence the anti-influenza activity and cytotoxicity

  已经测试了同时带有单萜和香豆素部分的化合物的细胞毒性和对流感病毒A / California / 07/09（H1N1）pdm09的抑制活性。香豆素骨架中取代基的结构，以及单萜类结构部分的结构和绝对构型均显示出显着影响所研究化合物的抗流感活性和细胞毒性。具有双环pin烷骨架的化合物表现出最高的选择性指数（细胞毒性与有效剂量之间的比率）。（-）-myrtenol 15c的衍生物在这类化合物中，其具有有希望的活性，低细胞毒性和可合成的可及性，具有最大的潜力。当在病毒繁殖的早期添加到被感染的细胞培养物中时，它表现出最高的活性。
• Monoterpene-Containing Substituted Coumarins as Inhibitors of Respiratory Syncytial Virus (RSV) Replication
  作者：Tatyana M. Khomenko、Anna A. Shtro、Anastasia V. Galochkina、Yulia V. Nikolaeva、Galina D. Petukhova、Sophia S. Borisevich、Dina V. Korchagina、Konstantin P. Volcho、Nariman F. Salakhutdinov

  DOI：10.3390/molecules26247493

  日期：——

  Respiratory syncytial virus (RSV) is a critical cause of infant mortality. However, there are no vaccines and adequate drugs for its treatment. We showed, for the first time, that O-linked coumarin–monoterpene conjugates are effective RSV inhibitors. The most potent compounds are active against both RSV serotypes, A and B. According to the results of the time-of-addition experiment, the conjugates act at the early stages of virus cycle. Based on molecular modelling data, RSV F protein may be considered as a possible target.

  呼吸道合胞病毒（RSV）是婴儿死亡的一个重要原因。然而，目前尚无疫苗和足够的药物用于治疗。我们首次展示，O-连接的香豆素-单萜共轭物是有效的RSV抑制剂。最有效的化合物对RSV的A型和B型两种血清型都具有活性。根据添加时间实验的结果，这些共轭物在病毒周期的早期阶段起作用。根据分子模拟数据，RSV F蛋白可能被视为一个可能的靶点。
• New inhibitors of tyrosyl-DNA phosphodiesterase I (Tdp 1) combining 7-hydroxycoumarin and monoterpenoid moieties
  作者：Tatyana Khomenko、Alexandra Zakharenko、Tatyana Odarchenko、Homayon John Arabshahi、Victoriya Sannikova、Olga Zakharova、Dina Korchagina、Jóhannes Reynisson、Konstantin Volcho、Nariman Salakhutdinov、Olga Lavrik

  DOI：10.1016/j.bmc.2016.09.016

  日期：2016.11

  A number of derivatives of 7-hydroxycoumarins containing aromatic or monoterpene substituents at hydroxy-group were synthesized based on a hit compound from a virtual screen. The ability of these compounds to inhibit tyrosyl-DNA phosphodiesterase I (Tdp 1), important target for anti-cancer therapy, was studied for the first time. It was found that the 7-hydroxycoumarin derivatives with monoterpene pinene moiety are effective inhibitors of Tdp 1 with the most active derivative (+)-25c with IC50 value of 0.675 mu M. This compound has low cytotoxicity (CC50 >100 mu M) when tested against human cancer cells which is crucial for presupposed application in combination with clinically established anticancer drugs. The ability of the new compounds to enhance the cytotoxicity of camptothecin, an established topoisomerase 1 poison, was demonstrated. (C) 2016 Elsevier Ltd. All rights reserved.
• The Study of Hypoglycemic Activity of 7-Terpenylcoumarins
  作者：Sergey Kuranov、Mariya Marenina、Dmitriy Ivankin、Mikhail Blokhin、Sergey Borisov、Tatyana Khomenko、Olga Luzina、Mikhail Khvostov、Konstantin Volcho、Tatyana Tolstikova、Nariman Salakhutdinov

  DOI：10.3390/molecules27248663

  日期：——

  privileged scaffolds for obtaining pharmacological agents with hypoglycemic activity. Chemical modification of coumarins often leads to antidiabetic agents with greater efficacy. In the present work, twenty monoterpene-substituted 7-hydroxycoumarins were synthesized. A new approach using the Mitsunobu reaction was shown to be effective for the synthesis of target compounds. All of the synthesized compounds

  天然和合成香豆素通常被认为是获得具有降血糖活性的药物的特殊支架。香豆素的化学修饰通常会导致抗糖尿病药物具有更高的功效。在目前的工作中，合成了二十种单萜取代的 7-羟基香豆素。一种使用 Mitsunobu 反应的新方法被证明可有效合成目标化合物。所有合成的化合物都在口服葡萄糖耐量试验中进行了评估，其中两个含有香叶基和 (-)-月桂烯基取代基的化合物显示出体内降血糖作用。这些化合物的可能作用机制可能包括抑制 DPP IV，这在体外试验中得到证实。