7-乙氧基甲氧基-3-氰基香豆素 | 277309-36-1

• 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: 7-乙氧基甲氧基-3-氰基香豆素
• 英文名称: 7-Ethyloxymethyloxy-3-cyanocoumarin
• 英文别名: (7-ethoxy-methyloxy-3-cyanocoumarin) EOMCC；7-ethoxymethyloxy-3-cyanocoumarin；7-ethoxymethoxy-3-cyanocoumarin；Vivid EOMCC substrate；7-(ethoxymethoxy)-2-oxo-2H-chromene-3-carbonitrile；7-(ethoxymethoxy)-2-oxochromene-3-carbonitrile
• CAS: 277309-36-1
• 化学式: C₁₃H₁₁NO₄
• 分子量: 245.235
• InChiKey: GWVWVNOJPMPUEH-UHFFFAOYSA-N

物化性质

• 沸点：
  430.5±45.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  68.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-乙氧基甲氧基-3-氰基香豆素 在 cytochrome P₄₅₀ 1A₂ 、 还原型辅酶Ⅰ 作用下， 生成 3-氰基-7-羟基香豆素
  参考文献：
  名称：

  Simultaneous measurement of CYP1A2 activity, regioselectivity, and coupling: Implications for environmental sensitivity of enzyme–substrate binding

  摘要：

  The cytochrome P450 (CYP) reaction mechanism often yields a broad array of coupled and uncoupled products from a single substrate. While it is well known that reaction conditions can drastically affect the rate of P450 catalysis, their effects on regioselectivity and coupling are not well characterized. To investigate such effects, the CYP1A2 oxidation of 7-ethoxymethoxy-3-cyanocoumarin (EOMCC) was examined as a function of buffer type, buffer concentration, pH, and temperature. A high-throughput, optical method was developed to simultaneously measure the rate of substrate depletion, NADPH depletion, and generation of the O-dealkylated product. Increasing the phosphate buffer concentration and temperature increased both the NADPH and EOMCC depletion rates by 6-fold, whereas coupling was constant at 7.9% and the regioselectivity of O-dealkylation to other coupled pathways was constant at 21.7%. Varying the buffer type and pH increased NADPH depletion by 2.5-fold and EOMCC depletion by 3.5-fold; however, neither coupling nor regioselectivity was constant, with variations of 14.4% and 21.6%, respectively. Because the enzyme-substrate binding interaction is a primary determinant of both coupling and regioselectivity, it is reasonable to conclude that ionic strength, as varied by the buffer concentration, and temperature alter the rate without affecting binding while buffer type and pH alter both. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.abb.2010.10.002

文献信息

• OPTICAL MOLECULAR SENSORS FOR CYTOCHROME P450 ACTIVITY
  申请人：MAKINGS R. Lewis

  公开号：US20070072256A1

  公开（公告）日：2007-03-29

  The invention provides a compound, useful as an optical probe or sensor of the activity of at least one cytochrome P450 enzyme, and methods of using the compound to screen candidate drugs, and candidate drugs identified by these methods. The optical probe of the invention is a compound having the generic structure Y-L-Q, wherein Y is selected from the group consisting of Q as herein defined, saturated C 1 -C 20 alkyl, unsaturated C 1 -C 20 alkenyl, unsaturated C 1 -C 20 alkynyl, substituted saturated C 1 -C 20 alkyl, substituted unsaturated C 1 -C 20 alkenyl, substituted unsaturated C 1 -C 20 alkynyl, C 1 -C 20 cycloalkyl, C 1 -C 20 cycloalkenyl, substituted saturated C 1 -C 20 cycloalkyl, substituted unsaturated C 1 -C 20 cycloalkenyl, aryl, substituted aryl, heteroaryl and substituted heteroaryl; L is selected from the group of (—OCR 2 H) p —, wherein for each p, all R 2 are separately selected from the group consisting of a hydrogen atom, saturated C 1 -C 20 alkyl, unsaturated C 1 -C 20 alkenyl, unsaturated C 1 -C 20 alkynyl, substituted saturated C 1 -C 20 alkyl, substituted unsaturated C 1 -C 20 alkenyl, substituted unsaturated C 1 -C 20 alkynyl, C 1 -C 20 cycloalkyl, C 1 -C 20 cycloalkenyl, substituted saturated C 1 -C 20 cycloalkyl, substituted unsaturated C 1 -C 20 cycloalkenyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, and p is a positive integer no greater than twelve; and Q is a chemical moiety that gives rise to optical properties in its hydroxy or hydroxylate, phenol or phenoxide form that are different from the optical properties that arise from its ether form. Most preferably, p is one, R 2 is hydrogen, and Q is the ether form of a phenoxide fluorophore.

  本发明提供了一种化合物，可用作至少一种细胞色素P450酶活性的光学探针或传感器，并提供了使用该化合物筛选候选药物的方法以及使用这些方法鉴定出的候选药物。本发明的光学探针是一种具有通用结构Y-L-Q的化合物，其中Y选自以下组中的一种：Q如本文所定义的，饱和的C1-C20烷基，不饱和的C1-C20烯基，不饱和的C1-C20炔基，取代的饱和的C1-C20烷基，取代的不饱和的C1-C20烯基，取代的不饱和的C1-C20炔基，C1-C20环烷基，C1-C20环烯基，取代的饱和的C1-C20环烷基，取代的不饱和的C1-C20环烯基，芳基，取代的芳基，杂环芳基和取代的杂环芳基；L选自（—OCR2H）p—的组中，其中对于每个p，所有的R2分别选自以下组中的一种：氢原子，饱和的C1-C20烷基，不饱和的C1-C20烯基，不饱和的C1-C20炔基，取代的饱和的C1-C20烷基，取代的不饱和的C1-C20烯基，取代的不饱和的C1-C20炔基，C1-C20环烷基，C1-C20环烯基，取代的饱和的C1-C20环烷基，取代的不饱和的C1-C20环烯基，芳基，取代的芳基，杂环芳基，取代的杂环芳基，p为不大于12的正整数；Q是一种化学基团，在其羟基或羟基化物、酚或酚盐形式下产生的光学性质与其醚形式产生的光学性质不同。最好p为1，R2为氢，Q为酚盐荧光团的醚形式。
• Optical molecular sensors for cytochrome P450 activity
  申请人：Makings Lewis R.

  公开号：US20080125586A1

  公开（公告）日：2008-05-29

  The invention provides a compound, useful as an optical probe or sensor of the activity of at least one cytochrome P450 enzyme, and methods of using the compound to screen candidate drugs, and candidate drugs identified by these methods. The optical probe of the invention is a compound having the generic structure Y-L-Q, wherein Y is selected from the group consisting of Q as herein defined, saturated C 1 -C 20 alkyl, unsaturated C 1 -C 20 alkenyl, unsaturated C 1 -C 20 alkynyl, substituted saturated C 1 -C 20 alkyl, substituted unsaturated C 1 -C 20 alkenyl, substituted unsaturated C 1 -C 20 alkynyl, C 1 -C 20 cycloalkyl, C 1 -C 20 cycloalkenyl, substituted saturated C 1 -C 20 cycloalkyl, substituted unsaturated C 1 -C 20 cycloalkenyl, aryl, substituted aryl, heteroaryl and substituted heteroaryl; L is selected from the group of (—OCR 2 H) p —, wherein for each p, all R 2 are separately selected from the group consisting of a hydrogen atom, saturated C 1 -C 20 alkyl, unsaturated C 1 -C 20 alkenyl, unsaturated C 1 -C 20 alkynyl, substituted saturated C 1 -C 20 alkyl, substituted unsaturated C 1 -C 20 alkenyl, substituted unsaturated C 1 -C 20 alkynyl, C 1 -C 20 cycloalkyl, C 1 -C 20 cycloalkenyl, substituted saturated C 1 -C 20 cycloalkyl, substituted unsaturated C 1 -C 20 cycloalkenyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, and p is a positive integer no greater than twelve; and Q is a chemical moiety that gives rise to optical properties in its hydroxy or hydroxylate, phenol or phenoxide form that are different from the optical properties that arise from its ether form. Most preferably, p is one, R 2 is hydrogen, and Q is the ether form of a phenoxide fluorophore.

  该发明提供了一种化合物，可用作至少一种细胞色素P450酶活性的光学探针或传感器，并提供了使用该化合物筛选候选药物的方法，以及由这些方法鉴定的候选药物。该发明的光学探针是一种具有通用结构Y-L-Q的化合物，其中Y选自以下组：Q（如此处定义），饱和C1-C20烷基，不饱和C1-C20烯基，不饱和C1-C20炔基，取代的饱和C1-C20烷基，取代的不饱和C1-C20烯基，取代的不饱和C1-C20炔基，C1-C20环烷基，C1-C20环烯基，取代的饱和C1-C20环烷基，取代的不饱和C1-C20环烯基，芳基，取代的芳基，杂环芳基和取代的杂环芳基；L选自以下组：（—OCR2H）p—，其中对于每个p，所有R2分别选自以下组：氢原子，饱和C1-C20烷基，不饱和C1-C20烯基，不饱和C1-C20炔基，取代的饱和C1-C20烷基，取代的不饱和C1-C20烯基，取代的不饱和C1-C20炔基，C1-C20环烷基，C1-C20环烯基，取代的饱和C1-C20环烷基，取代的不饱和C1-C20环烯基，芳基，取代的芳基，杂环芳基，取代的杂环芳基，p为不大于12的正整数；Q是一种化学基团，在其羟基或羟基化物，酚或酚酸盐形式下产生不同于其醚形式的光学性质。最好的情况是，p为1，R2为氢，Q是酚酸盐荧光团的醚形式。
• SPIRO-OXINDOLE COMPOUNDS AND THEIR USE AS THERAPEUTIC AGENTS
  申请人：Chafeev Mikhail

  公开号：US20100099728A1

  公开（公告）日：2010-04-22

  This invention is directed to spiro-oxindole compounds, as stereoisomers, enantiomers, tautomers thereof or mixtures thereof; or pharmaceutically acceptable salts, solvates or prodrugs thereof, for the treatment and/or prevention of sodium channel-mediated diseases or conditions, such as pain.

  本发明涉及螺环-氧吲哚化合物，包括其立体异构体、对映异构体、互变异构体或其混合物；或其药学上可接受的盐、溶剂化合物或前药，用于治疗和/或预防钠通道介导的疾病或病症，例如疼痛。
• Optical Molecular Sensors for Cytochrome P450 Activity
  申请人：Makings Lewis R.

  公开号：US20100105095A1

  公开（公告）日：2010-04-29

  The invention provides a compound, useful as an optical probe or sensor of the activity of at least one cytochrome P450 enzyme, and methods of using the compound to screen candidate drugs, and candidate drugs identified by these methods. The optical probe of the invention is a compound having the generic structure Y-L-Q, wherein Y is selected from the group consisting of Q as herein defined, saturated C 1 -C 20 alkyl, unsaturated C 1 -C 20 alkenyl, unsaturated C 1 -C 20 alkynyl, substituted saturated C 1 -C 20 alkyl, substituted unsaturated C 1 -C 20 alkenyl, substituted unsaturated C 1 -C 20 alkynyl, C 1 -C 20 cycloalkyl, C 1 -C 20 cycloalkenyl, substituted saturated C 1 -C 20 cycloalkyl, substituted unsaturated C 1 -C 20 cycloalkenyl, aryl, substituted aryl, heteroaryl and substituted heteroaryl; L is selected from the group of (—OCR 2 H) p —, wherein for each p, all R 2 are separately selected from the group consisting of a hydrogen atom, saturated C 1 -C 20 alkyl, unsaturated C 1 -C 20 alkenyl, unsaturated C 1 -C 20 alkynyl, substituted saturated C 1 -C 20 alkyl, substituted unsaturated C 1 -C 20 alkenyl, substituted unsaturated C 1 -C 20 alkynyl, C 1 -C 20 cycloalkyl, C 1 -C 20 cycloalkenyl, substituted saturated C 1 -C 20 cycloalkyl, substituted unsaturated C 1 -C 20 cycloalkenyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, and p is a positive integer no greater than twelve; and Q is a chemical moiety that gives rise to optical properties in its hydroxy or hydroxylate, phenol or phenoxide form that are different from the optical properties that arise from its ether form. Most preferably, p is one, R 2 is hydrogen, and Q is the ether form of a phenoxide fluorophore.

  本发明提供了一种化合物，可用作至少一种细胞色素P450酶的光学探针或传感器，并提供了使用该化合物筛选候选药物的方法，以及通过这些方法鉴定的候选药物。本发明的光学探针是具有通用结构Y-L-Q的化合物，其中Y选自以下组：Q如本文所定义的，饱和的C1-C20烷基，不饱和的C1-C20烯基，不饱和的C1-C20炔基，取代的饱和的C1-C20烷基，取代的不饱和的C1-C20烯基，取代的不饱和的C1-C20炔基，C1-C20环烷基，C1-C20环烯基，取代的饱和的C1-C20环烷基，取代的不饱和的C1-C20环烯基，芳基，取代的芳基，杂环芳基和取代的杂环芳基；L选自以下组：（—OCR2H）p—，其中对于每个p，所有R2分别选自以下组：氢原子，饱和的C1-C20烷基，不饱和的C1-C20烯基，不饱和的C1-C20炔基，取代的饱和的C1-C20烷基，取代的不饱和的C1-C20烯基，取代的不饱和的C1-C20炔基，C1-C20环烷基，C1-C20环烯基，取代的饱和的C1-C20环烷基，取代的不饱和的C1-C20环烯基，芳基，取代的芳基，杂环芳基，取代的杂环芳基，p是不大于12的正整数；Q是一种化学基团，在其羟基或羟基酸盐，酚或酚盐形式下产生与其醚形式产生不同的光学性质。最好是，p为1，R2为氢，Q是酚盐荧光团的醚形式。
• SPIRO-OXINDOLE-DERIVATIVES AS SODIUM CHANNEL BLOCKERS
  申请人：Cadieux Jean-Jacques

  公开号：US20110269788A1

  公开（公告）日：2011-11-03

  This invention is directed to spiro-oxindole compounds of formulas (I), (II), (III), as stereoisomers, enantiomers, tautomers thereof or mixtures thereof; or pharmaceutically acceptable salts, solvates or prodrugs thereof, for the treatment and/or prevention of sodium channel-mediated diseases or conditions, such as pain.

  本发明涉及公式(I)、(II)、(III)的螺环-氧吲哚化合物，其为立体异构体、对映异构体、互变异构体或其混合物；或其药学上可接受的盐、溶剂合物或前药，用于治疗和/或预防钠通道介导的疾病或病症，如疼痛。