2,5-dioxopyrrolidin-1-yl 2-naphthoate | 56374-47-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,5-dioxopyrrolidin-1-yl 2-naphthoate
• 英文别名: N-hydroxysuccinimidyl 2-naphthoate；2-naphthoic acid；naphthalene-2-carboxylic acid 2,5-dioxo-pyrrolidin-1-yl ester；2-naphthalenecarboxylic acid N-hydroxysuccinimide ester；2,5-Pyrrolidinedione, 1-[(2-naphthalenylcarbonyl)oxy]-；(2,5-dioxopyrrolidin-1-yl) naphthalene-2-carboxylate
• CAS: 56374-47-1
• 化学式: C₁₅H₁₁NO₄
• 分子量: 269.257
• InChiKey: ITIHGMYTWCAPQI-UHFFFAOYSA-N

物化性质

• 沸点：
  440.8±28.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,5-dioxopyrrolidin-1-yl 2-naphthoate 以95%的产率得到(S)-3-(1H-Indol-3-yl)-2-[(naphthalene-2-carbonyl)-amino]-propionic acid
  参考文献：
  名称：

  Carbamic acid compounds comprising an amide linkage as hdac inhibitors

  摘要：

  这项发明涉及抑制HDAC活性的某些活性碳酸酰胺化合物，其化学式为（1），其中：A是芳基；Q1是至少有2个碳原子骨架的芳基前导基团；J是选择自以下的酰胺键：—NR1C(═O)—和—C(═O)NR1—；R1是酰胺取代基；Q2是酸前导基团；以及其药学上可接受的盐、溶剂化合物、酰胺、酯、醚、化学保护形式和前药。本发明还涉及包含这种化合物的药物组合物，以及在体外和体内使用这种化合物和组合物来抑制HDAC，例如，抑制增殖性疾病，如癌症和牛皮癣。

  公开号：

  US20040092598A1
• 作为产物：
  描述：

  2-萘甲酸 以82%的产率得到2,5-dioxopyrrolidin-1-yl 2-naphthoate
  参考文献：
  名称：

  Carbamic acid compounds comprising an amide linkage as hdac inhibitors

  摘要：

  这项发明涉及抑制HDAC活性的某些活性碳酸酰胺化合物，其化学式为（1），其中：A是芳基；Q1是至少有2个碳原子骨架的芳基前导基团；J是选择自以下的酰胺键：—NR1C(═O)—和—C(═O)NR1—；R1是酰胺取代基；Q2是酸前导基团；以及其药学上可接受的盐、溶剂化合物、酰胺、酯、醚、化学保护形式和前药。本发明还涉及包含这种化合物的药物组合物，以及在体外和体内使用这种化合物和组合物来抑制HDAC，例如，抑制增殖性疾病，如癌症和牛皮癣。

  公开号：

  US20040092598A1

文献信息

• Discovery of a potent anti-tumor agent through regioselective mono-N-acylation of 7H-pyrrolo[3,2-f]quinazoline-1,3-diamine
  作者：Jingjin Chen、Alina Kassenbrock、Bingbing X. Li、Xiangshu Xiao

  DOI：10.1039/c3md00134b

  日期：——

  7H-Pyrrolo[3,2-f]quinazoline-1,3-diamine (1) is a privileged chemical scaffold with significant biological activities. However, the currently accessible chemical space derived from 1 is rather limited. Here we expanded the chemical space related to 1 by developing efficient methods for regioselective monoacylation at N1, N3 and N7, respectively. With this novel methodology, a focused library of mono-N-acylated pyrroloquinazoline-1,3-diamines was prepared and screened for anti-breast cancer activity. The structure–activity relationship (SAR) results showed that N3-acylated compounds were in general more potent than N1-acylated compounds while N7-acylation significantly reduced their solubility. Among the compounds evaluated, 7f possessed 8-fold more potent activity than 1 in MDA-MB-468 cells. More importantly, 7f was not toxic to normal human cells. These results suggest that 7f is a novel compound as a potential anti-breast cancer agent without harming normal cells.

  7H-吡咯并[3,2-f]喹唑啉-1,3-二胺（1）是一种具有显著生物活性的优势化学骨架。然而，目前可获得的源自1的化学空间相当有限。本文通过开发高效的方法，分别实现了对N1、N3和N7位点的区域选择性单酰化，从而扩展了与1相关的化学空间。利用这种新颖的方法，制备并筛选了一个针对乳腺癌活性的单N-酰化吡咯喹唑啉-1,3-二胺的聚焦库。结构-活性关系（SAR）结果显示，N3-酰化化合物通常比N1-酰化化合物更有效，而N7-酰化显著降低了化合物的溶解性。在评估的化合物中，7f在MDA-MB-468细胞中比1具有8倍的更强活性。更重要的是，7f对正常人类细胞无毒性。这些结果表明，7f是一种新型化合物，可能作为一种不损害正常细胞的潜在乳腺癌治疗药物。
• Modulation of intramolecular heterodimer-induced fluorescence quenching of tricarbocyanine dye for the development of fluorescent sensor
  作者：Tomoya Hirano、Jun Akiyama、Shuichi Mori、Hiroyuki Kagechika

  DOI：10.1039/c0ob00207k

  日期：——

  Various approaches have been used to modulate the fluorescence changes of sensors in the presence of target analytes, including intramolecular interaction between fluorophores or between fluorophore and other molecular species, like resonance energy transfer (RET). Here, we focus on fluorescence quenching by intramolecular heterodimer complex formation, which can be modulated over a shorter distance range than RET. We synthesized several conjugates of tricarbocyanine, which is a near-infrared fluorophore, with several quencher candidates via flexible short linker structure, and examined their fluorescence properties. Of our synthesized compounds, the dabcyl group proved to be the best quencher via heterodimer complex formation. The fluorescence of tricarbocyanine–dabcyl conjugates in aqueous media was almost completely quenched, and there was a dramatic fluorescence enhancement when heterodimer formation was blocked. These results suggested a design approach to develop fluorescence sensors for probing proximity relationships and structural transitions.

  各种方法被用来调节传感器在目标分析物存在时的荧光变化，包括荧光团之间或荧光团与其他分子物种之间的分子内作用力，例如共振能量转移（RET）。在这里，我们重点关注通过分子内异源二聚体复合物形成的荧光淬灭，这种方式的调节距离范围比RET更短。我们合成了几种三氰基钙调素的共轭物，这是一种近红外荧光团，与几种淬灭剂候选物通过灵活的短链结构结合，并检查了它们的荧光性质。在我们合成的化合物中，dabcyl基团通过异源二聚体复合物形成被证明是最佳淬灭剂。在水相介质中，三氰基钙调素–dabcyl共轭物的荧光几乎完全被淬灭，当异源二聚体形成被阻断时，荧光显著增强。这些结果暗示了一种设计方法，以开发用于探测近距离关系和结构转变的荧光传感器。
• Benextramine-neuropeptide Y receptor interactions: contribution of the benzylic moieties to [3H]neuropeptide Y displacement activity
  作者：Michael B. Doughty、Chandra S. Chaurasia、Ke Li

  DOI：10.1021/jm00054a012

  日期：1993.1

  6-aminohexanoic acid, followed by deprotection of the t-Boc groups with 4 N HCl in dioxane. Acylation of this symmetric diamine with N-hydroxysuccinimide esters of appropriately substituted benzoic acids, followed by reduction of the resultant tetraamides with diborane in refluxing THF, afforded the target compounds. The BXT analog lacking the benzylic group (i.e., compound 11) had no [3H]NPY displacement activity

  使用溶液相肽合成方法合成了N，N'-双[6-[（[2-甲氧基苄基）氨基]己-1-基]胱胺的类似物（benextramine，BXT，2），并分析了取代特异性结合的活性1 nM N- [丙酰-3H]神经肽Y（[3H] NPY）来自大鼠脑中对苯乙胺敏感的神经肽Y（NPY）结合位点。我们对这些类似物的新合成方法开始于，将胱胺与叔丁氧羰基（t-Boc）保护的6-氨基己酸的N-羟基琥珀酰亚胺酯酰化，然后用在二恶烷中的4 N HCl脱保护t-Boc基团。用适当取代的苯甲酸的N-羟基琥珀酰亚胺酯将该对称的二胺酰化，然后在回流的THF中用乙硼烷还原所得的四酰胺，得到目标化合物。缺乏苄基的BXT类似物（即化合物11）在浓度高达1.4 x 10（-3）M时没有[3H] NPY置换活性。邻位，间位和对位的活性范围是9倍在对苯达拉明敏感的NPY大鼠大脑结合位点的甲氧基，氯代和羟基苯达拉明类似物的区域异构体与在α-
• [EN] PROCESS FOR CONVERSION OF PHENOLS TO CARBOXAMIDES VIA THE SUCCINIMIDE ESTERS<br/>[FR] PROCEDE DE CONVERSION DE PHENOLS EN CARBOXAMIDES VIA LES SUCCINIMIDE ESTERS
  申请人：RENSSELAER POLYTECH INST

  公开号：WO2004007449A1

  公开（公告）日：2004-01-22

  A process for converting an aryl triflate, heteroaryl triflate, aryl halide or heteroaryl halide to an N-hydroxysuccinimido este is disclosed. The process involves reacting the triflate or halide with carbon monoxide and N-hydroxysuccinimide in a solvent in the presence of a palladium catalyst and a base.

  揭示了一种将芳基三氟甲磺酸酯、杂环芳基三氟甲磺酸酯、芳基卤代物或杂环芳基卤代物转化为N-羟基琥珀酰亚胺酯的方法。该方法涉及在溶剂中，在钯催化剂和碱的存在下，将三氟甲磺酸酯或卤代物与一氧化碳和N-羟基琥珀酸亚胺反应。
• Detecting a peroxide-based explosive via molecular gelation
  作者：Jing Chen、Weiwei Wu、Anne J. McNeil

  DOI：10.1039/c2cc33486k

  日期：——

  A convenient and portable triacetone triperoxide (TATP) sensor was developed utilizing a thiol-to-disulfide oxidation to trigger a solution-to-gel phase transition. Using this method, TATP can be detected visually without any instrumentation.

  利用硫醇到二硫化物的氧化反应触发溶液到凝胶的相变，开发出了一种方便携带的三丙酮三过氧化物（TATP）传感器。使用这种方法，无需任何仪器即可直观地检测 TATP。