7-((3-methoxybenzyl)oxy)-2,3-dihydrocyclopenta[c]chromen-4(1H)-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 7-((3-methoxybenzyl)oxy)-2,3-dihydrocyclopenta[c]chromen-4(1H)-one
• 英文别名: 7-[(3-methoxybenzyl)oxy]-2,3-dihydrocyclopenta[c]chromen-4(1H)-one；7-[(3-methoxyphenyl)methoxy]-2,3-dihydro-1H-cyclopenta[c]chromen-4-one
• 化学式: C₂₀H₁₈O₄
• mdl: MFCD02184682
• 分子量: 322.361
• InChiKey: ROJAXROLRVQJKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  间甲氧基苯甲醇 在 三溴化磷 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 生成 7-((3-methoxybenzyl)oxy)-2,3-dihydrocyclopenta[c]chromen-4(1H)-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。
• 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.
• PHYTOESTROGENIC FORMULATIONS FOR ALLEVIATION OR PREVENTION OF MENOPAUSAL SYMPTOMS
  申请人：Brinton Roberta Diaz

  公开号：US20100113586A1

  公开（公告）日：2010-05-06

  Select phytoestrogen pharmaceutical compositions and methods of use for preventing or reducing one or more symptoms associated with pre menopause, menopause, and/or post menopause are described herein. These select phytoestrogen formulations are composed only of two or more plant-derived estrogenic molecules and/or their structural analogues and exhibit binding preference to ERβ over ERα and agonist activity in the brain. These ERβ-selective phytoestrogen formulations cross the blood-brain-barrier and promote estrogen-associated neurotrophism and neuroprotection mechanisms in the brain, without activating proliferative mechanisms in the reproductive tissues and are therefore devoid of other estrogen-associated problematic aspects. The formulations can be administered enterally, transdermally, transmucosally, intranasally or parenterally. The formulations preferably contain combinations of compounds, and can be formulated for daily, sustained, delayed or weekly/monthly administration. In a preferred embodiment, these are administered to women who are in menopause or post menopausal, most preferably early in menopausal.
• PHYTOESTROGENIC FORMULATIONS FOR ALLEVIATION OR PREVENTION OF HAIR LOSS
  申请人：Brinton Roberta Diaz

  公开号：US20110091435A1

  公开（公告）日：2011-04-21

  Select phytoestrogen pharmaceutical compositions and methods of use for preventing or reducing one or more symptoms associated with hair loss or prostate cancer/prostate hypertrophy are described herein. These select phytoestrogen formulations are preferably composed only of two or more plant-derived estrogenic molecules and/or their structural analogues and exhibit binding preference to ERβ over ERα and agonist activity in non-reproductive tissues including brain.
• PHYTOESTROGENIC FORMULATIONS FOR ALLEVIATION OR PREVENTION OF NEURODEGENERATIVE DISEASES
  申请人：Brinton Roberta Diaz

  公开号：US20120164122A1

  公开（公告）日：2012-06-28

  Select phytoestrogen pharmaceutical compositions and methods of use for promoting neurological heath and prevention of age-related neurodegeneration, such as AD, have been developed. These select phytoestrogen formulations are composed of a number of plant-derived estrogenic molecules and/or their structural analogues and exhibit binding preference to ERβ over ERα and agonist activity in the brain. These ERβ-selective phytoestrogen formulations cross the blood-brain-barrier and promote estrogen-associated neurotrophism and neuroprotections mechanisms in the brain, without activating proliferative mechanisms in the reproductive tissues and are therefore devoid of other estrogen-associated problematic aspects. These are administered enterally, transdermally, transmucosally, intranasally or parenterally, in a dosage effective to prevent or alleviate neuronal damage, effect neuronal regeneration or sustain viability, increase expression of anti-apoptotic proteins, and/or decrease indicators of Alzheimer's Disease.