2-(12-hydroxydodecyl)isoindoline-1,3-dione | 207453-53-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-(12-hydroxydodecyl)isoindoline-1,3-dione
• 英文别名: N-(12-hydroxydodecyl)phthalimide；2-(12-hydroxydodecyl)isoindole-1,3-dione
• CAS: 207453-53-0
• 化学式: C₂₀H₂₉NO₃
• 分子量: 331.455
• InChiKey: AZSATGGUIIEDIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  24
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(12-hydroxydodecyl)isoindoline-1,3-dione 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 2.5h， 以55%的产率得到12-氨基-1-十二烷醇
  参考文献：
  名称：

  发现用于LuxAB细菌生物发光的新底物

  摘要：

  在本文中，已成功设计并合成了四种具有长半衰期的新型底物，用于luxAB细菌生物发光。经过体外和体内生物学评估后，这些分子可以利用已知的细菌荧光素酶发出明显的生物发光，从而为开发细菌生物发光系统提供了一种新的有前途的方法。

  DOI：

  10.1111/cbdd.12747
• 作为产物：
  描述：

  12-溴-1-十二烷醇 、 potassium phtalimide 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以89%的产率得到2-(12-hydroxydodecyl)isoindoline-1,3-dione
  参考文献：
  名称：

  Enzymatic synthesis of β-mannosyl phosphates on solid support

  摘要：

  将合成的磷酸多酚 1 的双功能类似物 4a、b 和 14 附着在固体支持物上，结果表明它们是 Dol-P-Man 合成酶的底物。

  DOI：

  10.1039/b206451k

文献信息

• Synthesis, Cytotoxicity, and Insight into the Mode of Action of Re(CO)3 Thymidine Complexes
  作者：Mark D. Bartholomä、Anthony R. Vortherms、Shawn Hillier、Birgit Ploier、John Joyal、John Babich、Robert P. Doyle、Jon Zubieta

  DOI：10.1002/cmdc.201000196

  日期：2010.9.3

  and C5 with spacers of various lengths. The corresponding organometallic thymidine complexes were fully characterized by IR and NMR spectroscopy and mass spectrometry. Their cytotoxicity was assessed against the A549 lung carcinoma cell line. Toxicity is dependent on the site and mode of conjugation as well as on the nature and the length of the tether. Moderate toxicity was observed for conjugates carrying

  核苷类似物被广泛用于癌症和病毒性疾病的治疗。迄今为止，几乎没有研究过有机or（I）配合物的抗增殖特性。在这里，我们介绍胸苷和尿苷的Re I（CO）3核心配合物的合成，表征和体外评估。用于绑定Re I（CO）3作为核心，在位置C5'，C2'，N3和C5处引入具有不同长度间隔基的三齿二聚二烯丙基胺金属螯合物。相应的有机金属胸苷配合物通过IR和NMR光谱法和质谱法充分表征。评估了它们对A549肺癌细胞系的细胞毒性。毒性取决于结合的部位和方式，以及系链的性质和长度。观察到用于承载铼部分在位置C5'或N3缀合物中等毒性（IC 50 = 124-160μ中号）。对于在C2'或C5处修饰的复合物，未观察到毒性。在C5'处带有十二碳烯间隔基的配合物53具有显着的毒性，并且比顺铂更有效，IC 50为50的6.0μ值中号。据我们所知，这是[M（CO）3 ] + 1-核苷结合物的抗增殖特性的首次报道。在使用A5
• Synthesis, cytotoxicity and cellular uptake studies of N3 functionalized Re(CO)3 thymidine complexes
  作者：Mark D. Bartholomä、Anthony R. Vortherms、Shawn Hillier、John Joyal、John Babich、Robert P. Doyle、Jon Zubieta

  DOI：10.1039/c0dt01452d

  日期：——

  Nucleoside-derived drugs play an important role in the treatment of cancer. Here, we present the synthesis and characterization of an intriguing series of N3 conjugated Re(CO)3 thymidine complexes. The complexes were characterized by NMR spectroscopy and mass spectrometry and their cytotoxicity was assessed against A549 cells. A similar dependence on the spacer length and the toxicity has been found for N3 functionalized complexes as recently reported for their C5′ counterparts. A remarkable cytotoxic complex 22, carrying a dodecylene spacer at position N3 with a bis-quinoline metal chelate moiety, with an IC50 value of 3.4 ± 1.6 μM, has been identified. Addition of a 100-fold excess of thymidine did not statistically reduce the observed cytotoxicity of all complexes. Cellular uptake studies of complex 22 have been performed by fluorescent microscopy, showing that compound 22 was clearly internalized into A549 cells. Temperature dependent uptake studies, blocking experiments with thymidine, and endosomal co-localization suggest that uptake of 22 occurs via passive diffusion and endocytosis.

  核苷类药物在癌症治疗中发挥着重要作用。在此，我们介绍了一系列有趣的 N3 共轭 Re(CO)3 胸苷复合物的合成和表征。我们通过核磁共振光谱和质谱对这些复合物进行了表征，并评估了它们对 A549 细胞的细胞毒性。研究发现，N3 功能化复合物的毒性与间隔长度的关系与最近报道的 C5′ 复合物类似。我们发现了一种具有显著细胞毒性的复合物 22，它在 N3 位带有十二烷基间隔物和双喹啉金属螯合物，IC50 值为 3.4 ± 1.6 μM。加入过量 100 倍的胸腺嘧啶并没有在统计学上降低所有复合物的细胞毒性。通过荧光显微镜对复合物 22 进行了细胞摄取研究，结果表明复合物 22 能明显内化到 A549 细胞中。温度依赖性摄取研究、胸腺嘧啶阻断实验以及内体共定位表明，22 的摄取是通过被动扩散和内吞作用进行的。
• [EN] PROTECTED LINKER COMPOUNDS<br/>[FR] COMPOSÉS LIEURS PROTÉGÉS
  申请人：RESEACHEM GMBH

  公开号：WO2013091120A1

  公开（公告）日：2013-06-27

  The invention features protected linker compounds which comprise at one terminus a protected amino group and at another other terminus a phosphorous activating group, such as a phosphoramidite group. These protected linker compounds are introduced chemically at the 5'-end of oligonucleotides for the purpose of preparing 5'-amino modified oligonucleotides. After deprotection, the thereby introduced amino group then allows further modification (e.g. attachment of dyes) or immobilization (on surfaces or beads) of the oligonucleotide. Specifically, the presented amino protecting group is designed to provide such protected linker compounds in a solid form, which facilitates efficient purification by precipitation or crystallization and aliquoting for distribution and storage.

  该发明涉及一种保护链连接物，其在一个端部具有保护的氨基基团，在另一个端部具有磷酸化活性基团，例如磷酰胺基基团。这些保护链连接物在化学上被引入到寡核苷酸的5'-端，以制备5'-氨基修饰的寡核苷酸。去保护后，引入的氨基基团允许进一步修饰（例如附着染料）或固定（在表面或珠子上）寡核苷酸。具体而言，所提供的氨基保护基团旨在以固体形式提供这些保护链连接物，从而通过沉淀或结晶实现高效纯化和分配存储。
• Pyridinecarboxamide derivatives
  申请人：Nisshin Flour Milling Co., Ltd.

  公开号：US06046201A1

  公开（公告）日：2000-04-04

  N-(12-Nitroxydodecyl)-6-(4-ethyl or isopropyl-1-piperazinyl)pyridine-3-carboxamide or physiologically acceptable salts thereof. The said compounds have excellent inhibiting activity of cerebral edema, especially ischemic cerebral edema, and inhibiting activity of delayed neuronal death (an inhibiting activity of Ca-influx in neuronal cells). Cerebral edema is a pathologic condition accompanying cerebrovascular disorders, especially the acute stage cerebrovascular disorders and then the compounds are useful as an inhibiting agent for cerebral edema or a therapeutic agent for cerebrovascular disorders. Moreover, because the compounds do hardly show a behavior suppressing action, which is considered to be side effect in treating cerebrovascular disorders at the acute stage, they are an excellent therapeutic agent for, in particular, the acute stage cerebrovascular disorders. Moreover, the compounds show a cerebral protective activity (an anti-anoxic activity), an activity of increasing cerebral blood flow, and an activity of inhibiting lipid peroxidation, and these activities may lead to the increased utility as a therapeutic agent for cerebrovascular disorders.

  N-(12-硝基氧代十二烷基)-6-(4-乙基或异丙基-1-哌嗪基)吡啶-3-羧酰胺或其生理学上可接受的盐。该化合物具有出色的抑制脑水肿的活性，特别是缺血性脑水肿和延迟性神经元死亡的抑制活性（神经细胞中钙离子流入的抑制活性）。脑水肿是伴随脑血管疾病的病理状况，特别是急性期脑血管疾病，然后该化合物可用作脑水肿的抑制剂或脑血管疾病的治疗剂。此外，由于该化合物几乎不显示抑制行为，这被认为是治疗急性期脑血管疾病的副作用，因此它是一种优秀的治疗剂，特别是针对急性期脑血管疾病。此外，该化合物显示出脑保护活性（抗缺氧活性），增加脑血流的活性和抑制脂质过氧化的活性，这些活性可能导致其作为脑血管疾病治疗剂的增加实用性。
• PYRIDINECARBOXAMIDE DERIVATIVES
  申请人：Nisshin Flour Milling Co., Ltd.

  公开号：EP0882716A1

  公开（公告）日：1998-12-09

  N-(12-Nitroxydodecyl)-6-(4-ethyl or isopropyl-1-piperazinyl)pyridine-3-carboxamide or physiologically acceptable salts thereof. The said compounds have excellent inhibiting activity of cerebral edema, especially ischemic cerebral edema, and inhibiting activity of delayed neuronal death (an inhibiting activity of Ca-influx in neuronal cells). Cerebral edema is a pathologic condition accompanying cerebrovascular disorders, especially the acute stage cerebrovascular disorders and then the compounds are useful as an inhibiting agent for cerebral edema or a therapeutic agent for cerebrovascular disorders. Moreover, because the compounds do hardly show a behavior suppressing action, which is considered to be side effect in treating cerebrovascular disorders at the acute stage, they are an excellent therapeutic agent for, in particular, the acute stage cerebrovascular disorders. Moreover, the compounds show a cerebral protective activity (an anti-anoxic activity), an activity of increasing cerebral blood flow, and an activity of inhibiting lipid peroxidation, and these activities may lead to the increased utility as a therapeutic agent for cerebrovascular disorders.

  N-(12-硝基十二烷基)-6-(4-乙基或异丙基-1-哌嗪基)吡啶-3-甲酰胺或其生理上可接受的盐类。 上述化合物对脑水肿（尤其是缺血性脑水肿）有很好的抑制作用，对延迟神经元死亡（抑制神经元细胞中 Ca 的流入）也有很好的抑制作用。脑水肿是脑血管疾病，尤其是急性期脑血管疾病的一种病理状态，因此，这些化合物可作为脑水肿的抑制剂或脑血管疾病的治疗剂。此外，由于这些化合物在急性期治疗脑血管疾病时几乎不表现出被认为具有副作用的行为抑制作用，因此，它们尤其是急性期脑血管疾病的极佳治疗剂。此外，这些化合物还具有脑保护活性（抗缺氧活性）、增加脑血流量的活性和抑制脂质过氧化的活性，这些活性可能会增加其作为脑血管疾病治疗剂的效用。