4,4'-bis(pentafluorophenoxycarbonylmethoxy)diphenylmethane | 603956-14-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,4'-bis(pentafluorophenoxycarbonylmethoxy)diphenylmethane
• 英文别名: (2,3,4,5,6-Pentafluorophenyl) 2-[4-[[4-[2-oxo-2-(2,3,4,5,6-pentafluorophenoxy)ethoxy]phenyl]methyl]phenoxy]acetate
• CAS: 603956-14-5
• 化学式: C₂₉H₁₄F₁₀O₆
• 分子量: 648.411
• InChiKey: MUZDYTYMFWXJJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  45
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  4,4'-bis(pentafluorophenoxycarbonylmethoxy)diphenylmethane 在 ammonium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以98%的产率得到4,4'-bis(carbamoylmethoxy)diphenylmethane
  参考文献：
  名称：

  Design and Synthesis of a Novel Water-Soluble NMDA Receptor Antagonist with a 1,4,7,10-Tetraazacyclododecane Group

  摘要：

  多胺，尤其是精胺，作为开放通道阻滞剂抑制 N-甲基-<小>D-天冬氨酸 (NMDA) 受体。合成了两种具有1,4,7,10-四氮杂环十二烷环状多胺基团的水溶性NMDA受体拮抗剂ACCn (1)和TGCn (2)，并利用电压研究了两种化合物对NMDA受体的影响-非洲爪蟾卵母细胞中表达的重组 NMDA 受体的钳记录。这些化合物抑制电压钳位在-70 mV的卵母细胞中NR1/NR2A和NR1/NR2B受体亚型的宏观电流。 NR1/NR2A受体化合物的抑制作用比NR1/NR2B受体化合物更显着。 ACCn (1) 对两种 NMDA 受体的抑制作用比 TGCn (2) 更有效。

  DOI：

  10.1248/cpb.53.444
• 作为产物：
  描述：

  4,4'-二羟基二苯甲烷 在 氢氧化钾 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 50.0h， 生成 4,4'-bis(pentafluorophenoxycarbonylmethoxy)diphenylmethane
  参考文献：
  名称：

  Design and Synthesis of a Novel Water-Soluble NMDA Receptor Antagonist with a 1,4,7,10-Tetraazacyclododecane Group

  摘要：

  多胺，尤其是精胺，作为开放通道阻滞剂抑制 N-甲基-<小>D-天冬氨酸 (NMDA) 受体。合成了两种具有1,4,7,10-四氮杂环十二烷环状多胺基团的水溶性NMDA受体拮抗剂ACCn (1)和TGCn (2)，并利用电压研究了两种化合物对NMDA受体的影响-非洲爪蟾卵母细胞中表达的重组 NMDA 受体的钳记录。这些化合物抑制电压钳位在-70 mV的卵母细胞中NR1/NR2A和NR1/NR2B受体亚型的宏观电流。 NR1/NR2A受体化合物的抑制作用比NR1/NR2B受体化合物更显着。 ACCn (1) 对两种 NMDA 受体的抑制作用比 TGCn (2) 更有效。

  DOI：

  10.1248/cpb.53.444

文献信息

• Measurement of Inclusion Complex Formation between Cyclophane and Biological Relevant Amino Acids Using Electrospray Ionization, Cold-Spray Ionization and Fast Atom Bombardment Mass Spectrometry
  作者：Koichi Metori、Yoshihisa Sei、Yumiko Kimura、Tomoyuki Ozawa、Kentaro Yamaguchi、Muneharu Miyake

  DOI：10.1248/cpb.53.1029

  日期：——

  The investigation of the host–guest complex formations between cyclophane (TGDMAP) (1) as a host and L-acidic amino acids such as L-glutamic acid (Glu) and L-aspartic acid (Asp) as guests was carried out using fast atom bombardment (FAB), electrospray ionization (ESI) and cold-spray ionization (CSI) mass spectrometry (MS). The stability constant (Ks) values obtained by the three different MS methods almost agreed. However, the complex ion peaks of a novel cyclophane (CPCn) (2) with Glu and Asp were not observed in FAB-MS. Then, these host–guest complex formations by use of CSI-MS and ESI-MS was examined, as the results, these complex ion peaks were observed clearly and the measurement values by the two MS methods are mostly in agreement. It was concluded that ESI-MS and CSI-MS are available for the determination of Ks value as well as FAB-MS.

  采用快速原子轰击（FAB）、电喷雾电离（ESI）和冷喷雾电离（CSI）质谱法研究了以环烷（TGDMAP）（1）为宿主，以L酸性氨基酸（如L-谷氨酸（Glu）和L-天冬氨酸（Asp））为客体形成的宿主-客体复合物。三种不同质谱方法得到的稳定常数（Ks）值基本一致。但是，在 FAB-MS 中没有观察到新型环烷（CPCn）（2）与 Glu 和 Asp 的络合离子峰。然后，利用 CSI-MS 和 ESI-MS 对这些主-客复合物的形成进行了检测，结果发现这些复合物离子峰被清晰地观察到，而且两种 MS 方法的测量值基本一致。由此得出结论，ESI-MS 和 CSI-MS 与 FAB-MS 一样，都可用于测定 Ks 值。
• Synthesis of a Novel Water-Soluble Cleft-Type Cyclophane as an N-Methyl-D-aspartate Receptor Antagonist
  作者：Takashi Masuko、Tadashi Kusama、Rie Namiki、Koichi Metori、Yasuo Kizawa、Muneharu Miyake

  DOI：10.1248/cpb.57.95

  日期：——

  NMDA receptors was then studied using voltage-clamp recordings of recombinant NMDA receptors expressed in Xenopus oocytes. ACPCm (1) and ACPCn (2) inhibited macroscopic currents in the NR1/NR2A, NR1/NR2B, NR1/NR2C and NR1/NR2D receptor subtypes in oocytes voltage-clamped at -70 mV. The IC50 values of ACPCm (1) and ACPCn (2) for NR1/NR2A and NR1/NR2B receptors were 1.06 microM and, 0.92 microM and 1

  新型水溶性N-甲基-D-天冬氨酸（NMDA）受体拮抗剂4,4'-双（[2- [N-（1,4,8,11-四氮杂环十四烷-1-基）乙酰基] -N-苯乙基]氨基乙氧基）二苯甲烷八盐酸盐（1，ACPCm）和4,4'-双（[2- [N-（1,4,7,10-四氮杂环十二烷-1-基）乙酰基] -N-苯乙基]氨基乙氧基）二苯甲烷合成八盐酸盐（2，ACPCn），然后使用爪蟾卵母细胞中表达的重组NMDA受体的电压钳记录研究这些studied裂型环烷对NMDA受体的作用。ACPCm（1）和ACPCn（2）抑制了电压钳制在-70 mV的卵母细胞NR1 / NR2A，NR1 / NR2B，NR1 / NR2C和NR1 / NR2D受体亚型中的宏观电流。NR1 / NR2A和NR1 / NR2B受体的ACPCm（1）和ACPCn（2）的IC50值分别为1.06 microM，0.92 microM，1.47 microM和1
• Synthesis of Two Novel Water-soluble Cleft-Type Cyclophanes Effective as N-Methyl-D-aspartate Receptor Antagonist
  作者：Muneharu Miyake、Takashi Masuko、Yuta Nemoto、Tadashi Kusama、Koichi Metori、Yasuo Kizawa

  DOI：10.3987/com-09-11722

  日期：——

  Novel cleft-type cyclophanes, 4,4'-bis[N-5-dimethylaminoaphthalene-sulfonylaminoethyl)-N-(1,4,7,10-tetraazacyclododecane-1-ylacetyl)-2-aminoethoxy]diphenylmethane octahydrochloride (1a, DNCn) and 4,4'-bis[N-(p-toluene-sulfonylaminoethyl)-N-(1,4,7,10-tetraazacyclododencane-1-ylacetyl-2-aminoethody]diphenylmethane octahydrochloride (1b, TsDCN) having an effective role as N-methyl-D-aspartate (NMDA) receptor antagonist were synthesized. Neuroprotective effects of cleft-type cyclophanes, DNCn (1a) and TsDCn (1b) against cell damage caused by NMDA were measured in cultured rat hippocampal neurons. DNCn (1a) and TsDCn (1b) reduced the neurotoxicity and acted as open channel blocker for NMDA receptor.
• Design and Synthesis of a Novel Water-Soluble NMDA Receptor Antagonist with a 1,4,7,10-Tetraazacyclododecane Group
  作者：Takashi Masuko、Koichi Metori、Yasuo Kizawa、Tadashi Kusama、Muneharu Miyake

  DOI：10.1248/cpb.53.444

  日期：——

  Polyamines, especially spermine, inhibit N-methyl-D-aspartate (NMDA) receptors as open channel blockers. Two types of water-soluble NMDA receptor antagonist, ACCn (1) and TGCn (2), with a 1,4,7,10-tetraazacyclododecane cyclic polyamine group, were synthesized and the effects of both compounds on NMDA receptors were studied using voltage-clamp recordings of recombinant NMDA receptors expressed in Xenopus oocytes. These compounds inhibited macroscopic currents in both NR1/NR2A and NR1/NR2B receptor subtypes in oocytes voltage-clamped at −70 mV. Inhibition by the compounds of NR1/NR2A receptors were more prominent than that of NR1/NR2B receptors. The inhibitory effects of ACCn (1) on both NMDA receptors were more potent than those of TGCn (2).

  多胺，尤其是精胺，作为开放通道阻滞剂抑制 N-甲基-<小>D-天冬氨酸 (NMDA) 受体。合成了两种具有1,4,7,10-四氮杂环十二烷环状多胺基团的水溶性NMDA受体拮抗剂ACCn (1)和TGCn (2)，并利用电压研究了两种化合物对NMDA受体的影响-非洲爪蟾卵母细胞中表达的重组 NMDA 受体的钳记录。这些化合物抑制电压钳位在-70 mV的卵母细胞中NR1/NR2A和NR1/NR2B受体亚型的宏观电流。 NR1/NR2A受体化合物的抑制作用比NR1/NR2B受体化合物更显着。 ACCn (1) 对两种 NMDA 受体的抑制作用比 TGCn (2) 更有效。