7-methyloxymethyloxy-4-trifluoromethylcoumarin | 277309-38-3

• 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-methyloxymethyloxy-4-trifluoromethylcoumarin
• 英文别名: 7-(methoxymethoxy)-4-(trifluoromethyl)chromen-2-one
• CAS: 277309-38-3
• 化学式: C₁₂H₉F₃O₄
• 分子量: 274.196
• InChiKey: SNADASFYCZMWBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 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：
  7

反应信息

• 作为产物：
  描述：

  7-羟基-4-三氟甲基香豆素 、 potassium carbonate 、 溴甲基甲基醚 、 乙酸乙酯 在 7-Methyloxymethyloxy-4-trifluorocoumarin 、 碳酸氢钠 、 乙醚 、 NaSO4 、 silica gel 作用下， 以 N,N-二甲基甲酰胺 、 乙醚 、 氯仿 、 正己烷 为溶剂， 反应 1.17h， 以Chromatography of the crude product on silica gel (gradient 0-5% MeOH in CHCl3) gave 11 mg of the purified 7-methyloxymethyloxy-4-trifluoromethylcoumarin (MOMFC) as a white solid的产率得到
  参考文献：
  名称：

  Optical molecular sensors for cytochrome P450 activity

  摘要：

  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，并提供使用该化合物筛选候选药物和通过这些方法识别的候选药物的方法。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：本文所定义的Q，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烷基，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（—OCR2H）p的组，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烷基，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p为1，R2为氢，Q为酚酸盐荧光团的醚形式。

  公开号：

  US06420130B1

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。
• Methods for detecting the interaction of compounds with cytochrome P450 using optical molecular sensors
  申请人：Invitrogen Corporation

  公开号：US07132252B2

  公开（公告）日：2006-11-07

  The invention provides methods of using an optical molecular probe or sensor to screen candidate drugs for their interaction with at least one cytochrome P450 enzyme. The optical molecular probe useful in the methods of the present 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 C1–C20 alkyl, unsaturated C1–C20 alkenyl, unsaturated C1–C20 alkynyl, substituted saturated C1–C20 alkyl, substituted unsaturated C1–C20 alkenyl, substituted unsaturated C1–C20 alkynyl, C1–C20 cycloalkyl, C1–C20 cycloalkenyl, substituted saturated C1–C20 cycloalkyl, substituted unsaturated C1–C20 cycloalkenyl, aryl, substituted aryl, heteroaryl and substituted heteroaryl; L is selected from the group of (—OCR2H)p—, wherein for each p, all R2 are separately selected from the group consisting of a hydrogen atom, saturated C1–C20 alkyl, unsaturated C1–C20 alkenyl, unsaturated C1–C20 alkynyl, substituted saturated C1–C20 alkyl, substituted unsaturated C1–C20 alkenyl, substituted unsaturated C1–C20 alkynyl, C1–C20 cycloalkyl, C1–C20 cycloalkenyl, substituted saturated C1–C20 cycloalkyl, substituted unsaturated C1–C20 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 hyrdoxylate, phenol or phenoxide form that are different from the optical properties that arise from its ether form. Most preferably, p is one, R2 is hydrogen, and Q is the ether form of a phenoxide fluorophore.

  本发明提供了使用光学分子探针或传感器筛选候选药物与至少一种细胞色素P450酶相互作用的方法。在本发明方法中有用的光学分子探针是具有通用结构Y-L-Q的化合物，其中Y选自以下组中的一种：Q，饱和C1-C20烷基，不饱和C1-C20烯基，不饱和C1-C20炔基，取代饱和C1-C20烷基，取代不饱和C1-C20烯基，取代不饱和C1-C20炔基，C1-C20环烷基，C1-C20环烯基，取代饱和C1-C20环烷基，取代不饱和C1-C20环烯基，芳香族，取代芳香族，杂环芳香族和取代杂环芳香族；L选自以下组中的一种：（—OCR2H）p—，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C1-C20烷基，不饱和C1-C20烯基，不饱和C1-C20炔基，取代饱和C1-C20烷基，取代不饱和C1-C20烯基，取代不饱和C1-C20炔基，C1-C20环烷基，C1-C20环烯基，取代饱和C1-C20环烷基，取代不饱和C1-C20环烯基，芳香族，取代芳香族，杂环芳香族和取代杂环芳香族，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，酚或酚盐形式中产生光学性质，其光学性质与其醚形式产生的光学性质不同。最好的情况是p为1，R2为氢，Q是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：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。
• US6143492A
  申请人：——

  公开号：US6143492A

  公开（公告）日：2000-11-07
• US6420130B1
  申请人：——

  公开号：US6420130B1

  公开（公告）日：2002-07-16