3-hydroxy-4-aza-8-oxaheptacyclo[9.4.1.0(2,10).0(3,14).0(4,9).0(9,13).0(12,15)]hexadecane | 1082459-07-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-hydroxy-4-aza-8-oxaheptacyclo[9.4.1.0(2,10).0(3,14).0(4,9).0(9,13).0(12,15)]hexadecane
• 英文别名: 15-Oxa-11-azaheptacyclo[7.6.1.01,11.02,5.03,10.04,8.06,16]hexadecan-10-ol
• CAS: 1082459-07-1
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: LYKRXSOAZPJOIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-hydroxy-4-aza-8-oxaheptacyclo[9.4.1.0(2,10).0(3,14).0(4,9).0(9,13).0(12,15)]hexadecane 、 N-甲基蒽 在 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 96.0h， 以36%的产率得到4-aza-8-oxa-heptacyclo[9.4.1.0(2,10).0(3,14).0(4,9).0(9,13).0(12,15)]hexadecan-3-yl 2-(methylamino)benzoate
  参考文献：
  名称：

  用于抑制一氧化氮合酶（NOS）的荧光多环配体。

  摘要：

  近年来，已显示出多环化合物在神经退行性疾病（例如帕金森氏症和阿尔茨海默氏病）的对症治疗和拟议治疗中具有重要的药理作用。这些结构还显示出当前使用中药物的药代动力学和药效学性质的修饰和改善。一氧化氮（NO）是分子信使，涉及哺乳动物的许多生理过程。它是由L-精氨酸中的一氧化氮合酶（NOS）合成的，过量生产可能导致许多神经系统疾病。这项研究的目的是合成一系列新颖的吲唑，吲哚和其他与多环结构缀合的荧光衍生物，以便在NOS分析中进行评估。NOS是目标系统，其中荧光技术和荧光标记的NOS抑制剂可用于检测酶-配体相互作用的生物物理特性，从而促进新型神经退行性抑制剂的开发。这可能会导致对神经保护机制有更深入的了解，并可能治愈/治疗神经退行性疾病。一系列结合多环结构的化合物，例如3-羟基-4-氮杂-8-氧杂七环[9.4.1.0。（2,10）0.（3,14）0.（4,9）0.（9,13 ）0（12,15）] t

  DOI：

  10.1016/j.bmc.2008.08.049
• 作为产物：
  描述：

  五环[5.4.0.02,6.03,10.05,9]十一烷-8,11-二酮 以 四氢呋喃 、 苯 为溶剂， 生成 3-hydroxy-4-aza-8-oxaheptacyclo[9.4.1.0(2,10).0(3,14).0(4,9).0(9,13).0(12,15)]hexadecane
  参考文献：
  名称：

  Synthesis, evaluation and application of polycyclic fluorescent analogues as N-methyl-d-aspartate receptor and voltage gated calcium channel ligands

  摘要：

  A series of polycyclic fluorescent ligands were synthesised and evaluated in murine striatal synaptoneurosomes for N-methyl-D-aspartate receptor (NMDAR) mediated calcium flux inhibition and inhibition of calcium influx through voltage gated calcium channels (VGCC). Amantadine (a) and N-(1-adamantyl)-1,3-propanediamine (c) substituted with 1-cyanoisoindole (3), indazole (5), dinitrobenzene (7, 8), dansyl (9, 10) and coumarin (11) moieties showed moderate to high inhibition of the NMDAR. A high degree of VGCC inhibition was observed for the cyanoisoindole compounds (3,4) the dansyl compounds (9,10) and the coumarin compound (12). Fluorophores conjugated to hydroxy-4-aza-8-oxoheptacyclotetradecane (13, 14) did not exhibit any significant VGCC inhibition, but the indazole conjugate (14) showed promising NMDAR activity. Dose response curves were calculated for selected NMDAR inhibitors (8-11) and N-[3-(1-adamantylamino)propyl]-5-dimethylaminonaphthalene-1-sulfonamide (10) exhibited the highest activity of the novel compounds. Compound 10 was further used as a fluorescent NMDAR ligand in a fluorescent competition assay utilizing MK-801, NGP1-01 and amantadine as known NMDAR inhibitors to demonstrate the possible applications of the novel fluorescent compounds. These small molecule fluorescent ligands can be considered as possible pharmacological tools in assay development and/or other investigations in the study of neurodegeneration. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.08.008

文献信息

• Synthesis, evaluation and application of polycyclic fluorescent analogues as N-methyl-d-aspartate receptor and voltage gated calcium channel ligands
  作者：Jacques Joubert、Sandra van Dyk、Ivan R. Green、Sarel F. Malan

  DOI：10.1016/j.ejmech.2011.08.008

  日期：2011.10

  A series of polycyclic fluorescent ligands were synthesised and evaluated in murine striatal synaptoneurosomes for N-methyl-D-aspartate receptor (NMDAR) mediated calcium flux inhibition and inhibition of calcium influx through voltage gated calcium channels (VGCC). Amantadine (a) and N-(1-adamantyl)-1,3-propanediamine (c) substituted with 1-cyanoisoindole (3), indazole (5), dinitrobenzene (7, 8), dansyl (9, 10) and coumarin (11) moieties showed moderate to high inhibition of the NMDAR. A high degree of VGCC inhibition was observed for the cyanoisoindole compounds (3,4) the dansyl compounds (9,10) and the coumarin compound (12). Fluorophores conjugated to hydroxy-4-aza-8-oxoheptacyclotetradecane (13, 14) did not exhibit any significant VGCC inhibition, but the indazole conjugate (14) showed promising NMDAR activity. Dose response curves were calculated for selected NMDAR inhibitors (8-11) and N-[3-(1-adamantylamino)propyl]-5-dimethylaminonaphthalene-1-sulfonamide (10) exhibited the highest activity of the novel compounds. Compound 10 was further used as a fluorescent NMDAR ligand in a fluorescent competition assay utilizing MK-801, NGP1-01 and amantadine as known NMDAR inhibitors to demonstrate the possible applications of the novel fluorescent compounds. These small molecule fluorescent ligands can be considered as possible pharmacological tools in assay development and/or other investigations in the study of neurodegeneration. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Fluorescent polycyclic ligands for nitric oxide synthase (NOS) inhibition
  作者：Jacques Joubert、Sandra van Dyk、Sarel F. Malan

  DOI：10.1016/j.bmc.2008.08.049

  日期：2008.10

  pharmacodynamic properties of drugs in current use. Nitric oxide (NO) is a molecular messenger involved in a number of physiological processes in mammals. It is synthesised by nitric oxide synthase (NOS) from L-arginine and its overproduction could lead to a number of neurological disorders. The aim of this study was to synthesise a series of novel indazole, indole and other fluorescent derivatives conjugated

  近年来，已显示出多环化合物在神经退行性疾病（例如帕金森氏症和阿尔茨海默氏病）的对症治疗和拟议治疗中具有重要的药理作用。这些结构还显示出当前使用中药物的药代动力学和药效学性质的修饰和改善。一氧化氮（NO）是分子信使，涉及哺乳动物的许多生理过程。它是由L-精氨酸中的一氧化氮合酶（NOS）合成的，过量生产可能导致许多神经系统疾病。这项研究的目的是合成一系列新颖的吲唑，吲哚和其他与多环结构缀合的荧光衍生物，以便在NOS分析中进行评估。NOS是目标系统，其中荧光技术和荧光标记的NOS抑制剂可用于检测酶-配体相互作用的生物物理特性，从而促进新型神经退行性抑制剂的开发。这可能会导致对神经保护机制有更深入的了解，并可能治愈/治疗神经退行性疾病。一系列结合多环结构的化合物，例如3-羟基-4-氮杂-8-氧杂七环[9.4.1.0。（2,10）0.（3,14）0.（4,9）0.（9,13 ）0（12,15）] t