5-羟基香豆素 | 6093-67-0

• 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
• 中文名称: 5-羟基香豆素
• 英文名称: 5-hydroxycoumarin
• 英文别名: 5-Hydroxy-cumarin；2H-1-Benzopyran-2-one, 5-hydroxy-；5-hydroxychromen-2-one
• CAS: 6093-67-0
• 化学式: C₉H₆O₃
• mdl: MFCD18450684
• 分子量: 162.145
• InChiKey: CDHSCTCRBLLCBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2932209090

反应信息

• 作为反应物：
  描述：

  5-羟基香豆素 在 甲醇 、 氢氧化钾 、 sodium methylate 、 sodium sulfite 作用下， 生成 3-(2-羟基-6-甲氧基苯基)-丙烯酸
  参考文献：
  名称：

  [与香豆素的光学研究。二。一羟基香豆素及其衍生物的紫外线吸收]

  摘要：

  DOI：

  10.1002/ardp.19572900809
• 作为产物：
  描述：

  2-羟基-6-甲氧基苯甲醛 在 aluminum (III) chloride 、 sodium hydrogensulfite 、 溶剂黄146 、 苯胺 作用下， 以 水 、 苯 为溶剂， 反应 12.0h， 生成 5-羟基香豆素
  参考文献：
  名称：

  Synthesis and SAR studies of mono O-prenylated coumarins as potent 15-lipoxygenase inhibitors

  摘要：

  All of the mono isopentenyloxy, -geranyloxy and -farnesyloxy derivatives of coumarin were synthesized and their inhibitory potency against soybean 15-lipoxygenase (SLO) and human 15-lipoxygenase-1 (HLO-1) were determined. Amongst the synthetic analogs, 5-farnesyloxycoumarin showed the most potent inhibitory activity against SLO (IC50 = 0.8 mu M) while 6-farnesyloxycoumarin was the strongest HLO-1 inhibitor (IC50 = 1.3 mu M). The IC50 variations of the farnesyl derivatives for HLO-1 (1.3 to similar to 75 mu M) were much higher than that observed for SLO (0.8-5.8 mu M). SAR studies showed that hydrogen bonding, CH/pi, anion-pi and S-O=C interactions with Fe-III-OH, Leu408, Glu357 and Met419 were the distinct intermolecular interactions which can lead to important role of the coumarin substitution site in HLO-1 inhibitory potency, respectively. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.09.006

文献信息

• Design, Synthesis, and Biological Evaluation of Coumarin Derivatives Tethered to an Edrophonium-like Fragment as Highly Potent and Selective Dual Binding Site Acetylcholinesterase Inhibitors
  作者：Leonardo Pisani、Marco Catto、Ilenia Giangreco、Francesco Leonetti、Orazio Nicolotti、Angela Stefanachi、Saverio Cellamare、Angelo Carotti

  DOI：10.1002/cmdc.201000210

  日期：2010.9.3

  N‐trialkylbenzaminium moieties were synthesized and evaluated as acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitors. The highest AChE inhibitory potency in the 3‐hydroxy‐N,N‐dimethylanilino series was observed with a 6,7‐dimethoxy‐3‐substituted coumarin derivative, which, along with an outstanding affinity (IC50=0.236 nM) exhibits excellent AChE/BChE selectivity (SI>300 000). Most of the synthesized

  合成了一系列通过适当的间隔基连接到3-羟基-N ， N-二甲基苯胺基或3-羟基-N ， N ， N-三烷基苯甲min部分的取代香豆素，并将其评估为乙酰胆碱酯酶（AChE）和丁酰胆碱酯酶（BChE）抑制剂。用6,7-二甲氧基-3-取代的香豆素衍生物观察到3-羟基N ， N-二甲基苯胺基系列中最高的AChE抑制力，并具有出色的亲和力（IC 50 = 0.236 n M）。 AChE / BChE选择性（SI> 300 000）。大部分合成的3-羟基N ， N， Ñ -trialkylbenzaminium盐显示在亚纳摩尔以优异的乙酰胆碱酯酶/的BChE选择性沿着皮摩尔范围一种AChE亲和力（SI值高达138 333）。对接和分子动力学模拟的结合使用使我们能够阐明观察到的结构亲和力和结构选择性关系，检测两种可能的替代结合模式，并评估AChE外围中π-π堆积相互作用的关键作用结合位点。
• [EN] C-TERMINAL HSP90 INHIBITORS<br/>[FR] INHIBITEURS DE HSP90 C-TERMINAUX
  申请人：UNIV KANSAS

  公开号：WO2013119985A1

  公开（公告）日：2013-08-15

  Hsp90 C-terminal inhibitors and pharmaceutical compositions containing such compounds are provided. The compounds of the disclosure are useful for the treatment and/or prevention of neurodegenerative disorders such as diabetic peripheral neuropathy.

  Hsp90 C端抑制剂及含有此类化合物的药物组合物。本发明公开的化合物可用于治疗和/或预防神经退行性疾病，如糖尿病周围神经病变。
• [EN] HYDANTOIN DERIVATIVES USEFUL AS KV3 INHIBITORS<br/>[FR] DÉRIVÉS D'HYDANTOÏNE UTILES EN TANT QU'INHIBITEURS DE KV3
  申请人：AUTIFONY THERAPEUTICS LTD

  公开号：WO2012076877A1

  公开（公告）日：2012-06-14

  The invention provides compounds of formula (I): Said compounds being inhibitors of Kv3 channels and of use in the prophylaxis or treatment of related disorders.

  该发明提供了化合物的公式(I)：所述化合物是Kv3通道的抑制剂，可用于预防或治疗相关疾病。
• Intramolecular Conjugate Addition of α,β-Unsaturated Lactones Having an Alkanenitrile Side Chain: Stereocontrolled Construction of Carbocycles with Quaternary Carbon Atoms
  作者：Fumihiko Yoshimura、Keiji Tanino、Makoto Torizuka、Genki Mori

  DOI：10.1055/s-0031-1290074

  日期：2012.1

  Title Intramolecular Conjugate Addition of α,β-Unsaturated Lactones Having an Alkanenitrile Side Chain: Stereocontrolled Construction of Carbocycles with Quaternary Carbon Atoms Author(s) Yoshimura, Fumihiko; Torizuka, Makoto; Mori, Genki; Tanino, Keiji Citation Synlett, 2012(2), 251-254 https://doi.org/10.1055/s-0031-1290074 Issue Date 2012-01 Doc URL http://hdl.handle.net/2115/51017 Rights © 2012

  标题 具有链烷腈侧链的 α,β-不饱和内酯的分子内共轭加成：具有四元碳原子的碳环的立体控制结构 鸟冢诚；森，元气；Tanino, Keiji Citation Synlett, 2012(2), 251-254 https://doi.org/10.1055/s-0031-1290074 发行日期 2012-01 Doc URL http://hdl.handle.net/2115/51017 权利© 2012 Georg Thieme Verlag 类型文章（作者版）文件信息 Syn2012-2_251-254.pdf
• [EN] 2-SUBSTITUTED-5-HYDROXY-4H-CHROMEN-4-ONES AS NOVEL LIGANDS FOR THE SEROTONIN RECEPTOR 2B (5-HT2B)<br/>[FR] 5-HYDROXY-4 H-CHROMÈNE-4-ONES SUBSTITUÉS EN 2 COMME NOUVEAUX LIGANDS POUR LE RÉCEPTEUR DE LA SÉROTONINE 2B (5-HT2B)
  申请人：UNIV VIRGINIA COMMONWEALTH

  公开号：WO2015116460A1

  公开（公告）日：2015-08-06

  A family of compounds which function as selective ligands for the serotonin receptor 2B (5-HT2B) is identified. Some of the compounds are synthetic non-natural ligands which have a relatively strong interaction with 5-HT2B compared to naturally occurring compounds (some of which are identified for the first time herein as ligands for 5-HT2B). Because the compounds, both naturally occurring and synthetically produced, function as ligands for 5-HT2B they will have application in, for example, the treatment and/or prevention of nervous system disorders such as Alzheimer's disease.

  已鉴定出一类化合物家族，其作为选择性血清素受体2B（5-HT2B）的配体。其中一些化合物是合成的非天然配体，与天然存在的化合物相比，它们与5-HT2B有相对较强的相互作用（其中一些在此处首次被确认为5-HT2B的配体）。由于这些化合物，无论是天然存在的还是合成的，都作为5-HT2B的配体，它们将在治疗和/或预防神经系统疾病如阿尔茨海默病等方面发挥作用。

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