3-(bromomethyl)-6,7-dimethoxycoumarin | 133932-21-5

• 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: 3-(bromomethyl)-6,7-dimethoxycoumarin
• 英文别名: 3-(bromomethyl)-6,7-dimethoxy-2H-chromen-2-one；3-(bromomethyl)-6,7-dimethoxychromen-2-one
• CAS: 133932-21-5
• 化学式: C₁₂H₁₁BrO₄
• 分子量: 299.121
• InChiKey: FXUOEDMPHNZWHM-UHFFFAOYSA-N

物化性质

• 熔点：
  182-184 °C
• 沸点：
  417.1±45.0 °C(Predicted)
• 密度：
  1.515±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• 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

• 作为反应物：
  描述：

  3-(bromomethyl)-6,7-dimethoxycoumarin 、 甲胺 在 potassium carbonate 、 盐酸 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 以92%的产率得到6,7-dimethoxy-3-[(methylamino)methyl]-2H-chromen-2-one hydrochloride
  参考文献：
  名称：

  寻找针对阿尔茨海默氏症的多靶点神经治疗药物：通过装饰2H-Chromen-2-one结构基序来发现有效的AChE-MAO B抑制剂。

  摘要：

  对开发针对神经退行性综合症，尤其是阿尔茨海默氏病（AD）的真正的疾病缓解药物的需求，使研究转向可靠的药物发现策略，以揭示具有比单靶标药物更高的治疗功效的临床候选药物。通过遵循多目标方法，我们设计和合成了新型的双乙酰胆碱酯酶（AChE）-单胺氧化酶B（MAO-B）抑制剂，通过装饰2H-chromen-2-one骨架。在位置3带有炔丙基胺部分的化合物在体外对MAO-B表现出最高的抑制活性。在该系列中，衍生物3h成为最有趣的命中化合物，是中度AChE抑制剂（IC50 = 8.99 µM）和有效且选择性的MAO-B抑制剂（IC50 = 2.8 nM）。对人类神经母细胞瘤SH-SY5Y细胞系的初步研究表明，它具有较低的细胞毒性，并揭示了在两种线粒体毒素（寡霉素-A和鱼藤酮）促进的氧化应激条件下，低剂量（0.1 µM）下有希望的神经保护作用。在基于Madin-Darby犬肾（MDCK）II-MDR1细

  DOI：

  10.3390/molecules21030362
• 作为产物：
  描述：

  3,4-二甲氧基苯酚 在 N-溴代丁二酰亚胺(NBS) 、 磷酸 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 3.5h， 生成 3-(bromomethyl)-6,7-dimethoxycoumarin
  参考文献：
  名称：

  Fluorescent markers for hypoxic cells: a study of nitroaromatic compounds, with fluorescent heterocyclic side chains, that undergo bioreductive binding

  摘要：

  Several novel compounds having both a 2-nitroimidazole nucleus and a fluorescent ring system in their molecular structure were prepared and evaluated as potential fluorescent probes for hypoxia. Bioreduction of nitroimidazoles, which is inhibited by oxygen, is known to lead to binding of bioreductive metabolites to cellular macromolecules and this provides a mechanism for binding the fluorescent moiety to hypoxic cells. These compounds can incorporate a wide range of fluorophors and can therefore be designed to suit the laser-line wavelengths available for excitation of fluorescence in the flow cytometer. Several nitroimidazoles with naphthalimide side chains were rapidly taken up into cells and became concentrated in the cells, thus reducing their concentration in the extracellular medium. This suggests a potential microscopic bioavailability problem with probes of this type when used in vivo as they would become progressively depleted in the extracellular fluid as they diffused from blood vessels, through layers of packed cells in tumors, to the hypoxic cells where they could undergo hypoxia-specific metabolism. Synthesis of nitroimidazoles with coumarin fluorophors led to several potentially useful probes for hypoxia; substituents on the coumarin fluorophor had a marked effect on the cellular fluorescence of these compounds.

  DOI：

  10.1021/jm00111a049

文献信息

• Analogs of terpene trilactones from Ginkgo biloba and related compounds and uses thereof
  申请人：——

  公开号：US20030225052A1

  公开（公告）日：2003-12-04

  The subject invention provides compounds having the structure: 1 wherein R 1 is H, OH, a photoactivatable moiety, a fluorescent moiety, or a radioactive moiety; R 2 is H, OH, a photoactivatable moiety, a fluorescent-moiety, or a radioactive moiety; R 3 is H or OH; R 4 is H, OH, a photoactivatable moiety, a fluorescent moiety, or a radioactive moiety; and wherein at least one of R 1 , R 2 , R 3 , or R 4 is a photoactivatable moiety, a fluorescent moiety, or a radioactive moiety, or an optically pure enantiomer of the compound or wherein R1 is H or OH; R2 is H, OH, halogen, unsubstituted or substituted, straight or branched (C 1 -C 5 ) alkyl group, (C 2 -C 5 ) alkenyl, or a (C 2 -C 5 ) alkynyl, (C 1 -C 5 ) alkoxy, (C 2 -C 5 ) alkenyloxy, or (C 2 -C 5 ) alkynyloxy, —N3, —COR5, —CONR5R6, —CO2R5, —OCOR5, —NH(OH), —NR5R6, —NHCOR5, —N(OH)COR5, —CH2OR5, —OCH2CO2R5, —CH2SR5, —CH2NR5R6, —SR5, —OSR5, or —NR5SO2R6, where R5 and R6 are each independently hydrogen, substituted or unsubstituted (C 1 -C 5 ) alkyl, (C 2 -C 5 ) alkenyl, or (C 2 -C 5 ) alkynyl, or a cycloalkyl or aryl group having 3 to 10 carbon atoms; R3 is H or OH; R4 is H, (C1-C10) alkyl, (C1-C10) alkenyl, (C1-C10) alkynyl, -A-Ar, -A-Z-Ar, —SO 2 —Ar, or -A-NR 5 , or —R 7 , where A, Z and Ar are as defined herein, and the use of the compounds for detecting or identifying a receptor which binds the compounds of the invention or for treating a PAF associated condition in a subject.

  本发明主题提供具有以下结构的化合物：1其中R1为H、OH、光活化基团、荧光基团或放射性基团；R2为H、OH、光活化基团、荧光基团或放射性基团；R3为H或OH；R4为H、OH、光活化基团、荧光基团或放射性基团；并且其中至少一个R1、R2、R3或R4为光活化基团、荧光基团或放射性基团，或该化合物的一个光学纯对映体，或者其中R1为H或OH；R2为H、OH、卤素、未取代或取代的直链或支链（C1-C5）烷基、（C2-C5）烯基、或（C2-C5）炔基、（C1-C5）烷氧基、（C2-C5）烯氧基、或（C2-C5）炔氧基、—N3、—COR5、—CONR5R6、—CO2R5、—OCOR5、—NH(OH)、—NR5R6、—NHCOR5、—N(OH)COR5、—CH2OR5、—OCH2CO2R5、—CH2SR5、—CH2NR5R6、—SR5、—OSR5、或—NR5SO2R6，其中R5和R6各自独立地为氢、取代或未取代的（C1-C5）烷基、（C2-C5）烯基、或（C2-C5）炔基，或具有3至10个碳原子的环烷基或芳基；R3为H或OH；R4为H、（C1-C10）烷基、（C1-C10）烯基、（C1-C10）炔基、-A-Ar、-A-Z-Ar、—SO2—Ar、或-A-NR5，或—R7，其中A、Z和Ar如本文所定义，以及这些化合物用于检测或鉴定与本发明化合物结合的受体，或在受试者中治疗与PAF相关的病症的用途。
• Analogs of terpene trilactones from ginkgo biloba for bioorganic and imaging studies
  申请人：The Trustees of Columbia University

  公开号：US20030194370A1

  公开（公告）日：2003-10-16

  A compound having the structure: 1 wherein R 1 is H, OH, a photoactivatable moiety, a fluorescent moiety, or a radioactive moiety; wherein R 2 is H, OH, a photoactivatable moiety, a fluorescent moiety, or a radioactive moiety; wherein R 3 is H or OH; wherein R 4 is H, OH, a photoactivatable moiety, a fluorescent moiety, or a radioactive moiety; and wherein at least one of R 1 , R 2 , R 31 or R 4 is a photoactivatable moiety, a fluorescent moiety, or a radioactive moiety. Optically pure enantiomers and salts of the compound are also described. Also, the synthesis of the compound, and uses of the compound, such as in a method for detecting the localization of, or identifying, receptors, enzymes or other targets, whether in a cell or in a subject.

  一种具有以下结构的化合物：1其中，R1为H、OH、光致活性基团、荧光基团或放射性基团；R2为H、OH、光致活性基团、荧光基团或放射性基团；R3为H或OH；R4为H、OH、光致活性基团、荧光基团或放射性基团；且R1、R2、R3或R4中至少有一个为光致活性基团、荧光基团或放射性基团。该化合物的光学纯对映体和盐也被描述。此外，还描述了该化合物的合成方法以及该化合物的用途，例如用于检测细胞或主体中的受体、酶或其他靶点的定位或识别的方法。
• Analogs of terpene trilactones from ginkgo biloba and related compounds and uses thereof
  申请人：Stromgaard Kristian

  公开号：US20070098632A1

  公开（公告）日：2007-05-03

  The subject invention provides compounds having the structure: wherein R 1 is H, OH, a photoactivatable moiety, a fluorescent moiety, or a radioactive moiety; R 2 is H, OH, a photoactivatable moiety, a fluorescent moiety, or a radioactive moiety; R 3 is H or OH; R 4 is H, OH, a photoactivatable moiety, a fluorescent moiety, or a radioactive moiety; and wherein at least one of R 1 , R 2 , R 3 , or R 4 is a photoactivatable moiety, a fluorescent moiety, or a radioactive moiety, or an optically pure enantiomer of the compound or wherein R1 is H or OH; R2 is H, OH, halogen, unsubstituted or substituted, straight or branched (C 1 -C 5 ) alkyl group, (C 2 -C 5 ) alkenyl, or a (C 2 -C 5 ) alkynyl, (C 1 -C 5 ) alkoxy, (C 2 -C 5 ) alkenyloxy, or (C 2 -C 5 ) alkynyloxy, —N3, —COR5, —CONR5R6, —CO2R5, —OCOR5, —NH(OH), —NR5R6, —NHCOR5, —N(OH)COR5, —CH2OR5, —OCH2CO2R5, —CH2SR5, —CH2NR5R6, —SR5, —OSR5, or —NR5SO2R6, where R5 and R6 are each independently hydrogen, substituted or unsubstituted (C 1 -C 5 ) alkyl, (C 2 -C 5 ) alkenyl, or (C 2 -C 5 ) alkynyl, or a cycloalkyl or aryl group having 3 to 10 carbon atoms; R3 is H or OH; R4 is H, (C1-C10) alkyl, (C1-C10) alkenyl, (C1-C10) alkynyl, -A-Ar, -A-Z-Ar, —SO 2 —Ar, or -A-NR 5 , or —R 7 , where A, Z and Ar are as defined herein, and the use of the compounds for detecting or identifying a receptor which binds the compounds of the invention or for treating a PAF associated condition in a subject.

  该发明涉及具有以下结构的化合物：其中R1为H，OH，光活性基团，荧光基团或放射性基团；R2为H，OH，光活性基团，荧光基团或放射性基团；R3为H或OH；R4为H，OH，光活性基团，荧光基团或放射性基团；且其中至少一个R1，R2，R3或R4为光活性基团，荧光基团或放射性基团，或该化合物的光学纯对映体，或其中R1为H或OH；R2为H，OH，卤素，未取代或取代，直链或支链（C1-C5）烷基，（C2-C5）烯基或（C2-C5）炔基，（C1-C5）烷氧基，（C2-C5）烯氧基或（C2-C5）炔氧基，-N3，-COR5，-CONR5R6，-CO2R5，-OCOR5，-NH（OH），-NR5R6，-NHCOR5，-N（OH）COR5，-CH2OR5，-OCH2CO2R5，-CH2SR5，-CH2NR5R6，-SR5，-OSR5或-NR5SO2R6，其中R5和R6各自独立地为氢，取代或未取代的（C1-C5）烷基，（C2-C5）烯基或（C2-C5）炔基，或具有3至10个碳原子的环烷基或芳基；R3为H或OH；R4为H，（C1-C10）烷基，（C1-C10）烯基，（C1-C10）炔基，-A-Ar，-A-Z-Ar，-SO2-Ar或-A-NR5，或-R7，其中A，Z和Ar如本文所定义，并且使用这些化合物用于检测或识别结合该发明化合物的受体或用于治疗与PAF相关的疾病。
• HODGKISS, RICHARD J.;JONES, GARETH W.;LONG, ANTHONY;MIDDLETON, RICHARD W.+, J. MED. CHEM., 34,(1991) N, C. 2268-2274
  作者：HODGKISS, RICHARD J.、JONES, GARETH W.、LONG, ANTHONY、MIDDLETON, RICHARD W.+

  DOI：——

  日期：——
• Ginkgolide Compounds, Compositions, And Extracts, And Uses Thereof
  申请人：Vitolo Ottavio V.

  公开号：US20090156668A1

  公开（公告）日：2009-06-18

  The present invention relates to Ginkgolide derivatives, compositions and extracts comprising one or more Ginkgolides and/or derivatives thereof and methods of use of the compositions to treat neurological disorders and as imaging agents.