2-[(4-硝苄基)氧代]-1H-异吲哚-1,3(2H)-二酮 | 30777-85-6

• 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
• 中文名称: 2-[(4-硝苄基)氧代]-1H-异吲哚-1,3(2H)-二酮
• 英文名称: N-(p-Nitrobenzyloxy)-phthalimid
• 英文别名: 2-[(4-nitrobenzyl)oxy]-1H-isoindole-1,3(2H)-dione；2-[(4-nitrophenyl)methoxy]isoindole-1,3-dione
• CAS: 30777-85-6
• 化学式: C₁₅H₁₀N₂O₅
• mdl: MFCD00517030
• 分子量: 298.255
• InChiKey: KICBTWPSVKJQLP-UHFFFAOYSA-N

物化性质

• 熔点：
  195-198°C
• 沸点：
  502.8±52.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.066
• 拓扑面积：
  92.4
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2925190090

反应信息

• 作为反应物：
  描述：

  2-[(4-硝苄基)氧代]-1H-异吲哚-1,3(2H)-二酮 在 碳酸氢钠 、 一水合肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 N-(2-Amino-ethyl)-O-(4-nitro-benzyl)-hydroxylamine
  参考文献：
  名称：

  1-Benzyloxy-4,5-dihydro-1H-imidazol-2-yl-amines, a novel class of NR1/2B subtype selective NMDA receptor antagonists

  摘要：

  Screening of the Roche compound depository led to the identification of (1-benzyloxy-4,5-dihydro-1H-imidazol-2-yl)-butyl amine 4, a structurally novel NR1/2B Subtype selective NMDA receptor antagonist. The structure-activity relationships developed in this series resulted in the discovery of a novel class of potent and selective NMDA receptor blockers displaying activity in vivo. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00713-3
• 作为产物：
  描述：

  苯酐 在 吡啶 、 盐酸羟胺 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-[(4-硝苄基)氧代]-1H-异吲哚-1,3(2H)-二酮
  参考文献：
  名称：

  Design, synthesis and antifungal activities of novel pyrrole alkaloid analogs

  摘要：

  A series of novel analogs of pyrrole alkaloid were designed and synthesized by a facile method and their structures were characterized by H-1 NMR, C-13 NMR and high-resolution mass spectrometry (HRMS). The structure of compound 2a was identified by 2D NMR including heteronuclear multiple-quantum coherence (HMQC), heteronuclear multiple-bond correlation (HMBC) and H-H correlation spectrometry (H-H COSY) spectra. Their antifungal activities against five fungi were evaluated, and the results indicated that some of the title compounds showed moderate fungicidal activities in vitro against Alternaria solani, Cercospora arachidicola, Fusarium omysporum, Gibberella zeae and Physalospora piricola at the dosage of 50 mu g mL(-1). Compound 2a and 3a exhibited good activities against P. piricola at low dosage. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.01.031

文献信息

• Photoinduced Electron-Transfer-Promoted Redox Fragmentation of <i>N</i>-Alkoxyphthalimides
  作者：Maria Zlotorzynska、Glenn M. Sammis

  DOI：10.1021/ol202740w

  日期：2011.12.2

  new photoinduced electron-transfer-promoted redox fragmentation of N-alkoxyphthalimides has been developed. Mechanistic experiments have established that this reaction proceeds through a unique concerted intramolecular fragmentation process. This distinctive mechanism imparts many synthetic advantages, which are highlighted in the redox fragmentation of various heterocyclic substrates.

  已经开发了一种新的光诱导的N-烷氧基邻苯二甲酰亚胺电子转移促进的氧化还原片段化。机理实验已经确定，该反应通过独特的协同分子内断裂过程进行。这种独特的机理赋予了许多合成优势，这些优势在各种杂环底物的氧化还原片段化中得到了彰显。
• 4-Alkyloxyimino-cytosine nucleotides: tethering approaches to molecular probes for the P2Y6 receptor
  作者：P. Suresh Jayasekara、Matthew O. Barrett、Christopher B. Ball、Kyle A. Brown、Eszter Kozma、Stefano Costanzi、Lucia Squarcialupi、Ramachandran Balasubramanian、Hiroshi Maruoka、Kenneth A. Jacobson

  DOI：10.1039/c3md00132f

  日期：——

  4-Alkyloxyimino derivatives of pyrimidine nucleotides display high potency as agonists of certain G protein-coupled P2Y receptors (P2YRs). In an effort to functionalize a P2Y6R agonist for fluorescent labeling, we probed two positions (N4 and γ-phosphate of cytidine derivatives) with various functional groups, including alkynes for click chemistry. Functionalization of extended imino substituents at the 4 position of the pyrimidine nucleobase of CDP preserved P2Y6R potency generally better than γ-phosphoester formation in CTP derivatives. Fluorescent Alexa Fluor 488 conjugate 16 activated the human P2Y6R expressed in 1321N1 human astrocytoma cells with an EC50 of 9 nM, and exhibited high selectivity for this receptor over other uridine nucleotide-activated P2Y receptors. Flow cytometry detected specific labeling with 16 to P2Y6R-expressing but not to wild-type 1321N1 cells. Additionally, confocal microscopy indicated both internalized 16 (t1/2 of 18 min) and surface-bound fluorescence. Known P2Y6R ligands inhibited labeling. Theoretical docking of 16 to a homology model of the P2Y6R predicted electrostatic interactions between the fluorophore and extracellular portion of TM3. Thus, we have identified the N4-benzyloxy group as a structurally permissive site for synthesis of functionalized congeners leading to high affinity molecular probes for studying the P2Y6R.

  4-烷氧亚氨基嘧啶核苷酸衍生物作为某些G蛋白偶联P2Y受体（P2YRs）的激动剂显示出高度效力。为了对P2Y6R激动剂进行荧光标记，我们在两个位置（胞苷衍生物的N4位和γ-磷酸基团）上探查了包括炔烃在内的各种功能团，用于点击化学反应。在CDP的嘧啶核碱4位上进行扩展亚氨基取代，相比于CTP衍生物中的γ-磷酸酯形成，通常更好地保持了P2Y6R的效力。荧光染料Alexa Fluor 488的共轭物16激活了在1321N1人星形胶质瘤细胞中表达的人P2Y6R，其EC50为9 nM，并且对这种受体的选择性远高于其他由尿嘧啶核苷酸激活的P2Y受体。流式细胞术检测到16对表达P2Y6R的细胞有特异性标记，而对野生型1321N1细胞无标记。此外，共聚焦显微镜显示16被内化（半衰期18分钟）并有表面结合的荧光。已知的P2Y6R配体抑制标记。16与P2Y6R的同源模型的理论对接预测了荧光团与TM3的外部部分之间的静电相互作用。因此，我们确定了N4-苄氧基团作为合成功能化类似物的结构容许位点，从而得到用于研究P2Y6R的高亲和力分子探针。
• Total synthesis of antitumor agent at-125, (αS,5S)-α-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid
  作者：Jack E. Baldwin、Jin K. Cha、Lawrence I. Kruse

  DOI：10.1016/s0040-4020(01)96774-2

  日期：1985.1

  A short and efficient total synthesis of racemic AT-125 and its racemic threo isomer proceeds via an intramolecular Michael cyclization of a protected α,β-dehydroglutamic acid γ-hydroxamate. Separation of diastereomers and deprotection to racemic AT-125 followed by enzymatic resolution of the N-chloroacetamide with hog-kidney acylase provides the natural αS,5S isomer.

  外消旋AT-125及其外消旋苏式异构体的短而有效的全合成通过受保护的α，β-脱氢谷氨酸γ-异羟肟酸酯的分子内迈克尔环化进行。分离非对映异构体并将其脱保护为外消旋AT-125，然后用猪肾酰化酶酶促拆分N-氯乙酰胺，即可提供天然αS，5 S异构体。
• Design, synthesis and evaluation of oxime-functionalized nitrofuranylamides as novel antitubercular agents
  作者：Yi-Lei Fan、Jian-Bing Wu、Xing Ke、Zhong-Ping Huang

  DOI：10.1016/j.bmcl.2018.07.046

  日期：2018.10

  H37Rv and drug-resistant clinical isolates. Among them, two compounds 7a and 7b exhibited excellent activity against the three tested strains. Both of them were comparable to the first-line anti-TB agents INH and RIF against MTB H37Rv, and were far more potent than INH and RIF against MDR-TB 16833 and 16995 strains. Thus, both of them could act as leads for further optimization.

  设计，合成了一系列肟官能化的硝基呋喃酰胺，并评估了它们对MTB H37Rv和耐药临床分离株的体外抗分枝杆菌活性。其中，两种化合物7a和7b对三种测试菌株表现出优异的活性。它们两者均与针对MTB H37Rv的一线抗结核病药物INH和RIF相当，并且比针对MDR-TB 16833和16995菌株的INH和RIF更有力。因此，它们两者都可以作为进一步优化的线索。
• Synthesis and anti-tumor activity evaluation of salinomycin C20-<i>O</i>-alkyl/benzyl oxime derivatives
  作者：Bo Li、Jun Wu、Lei Tang、Xu Lian、Zhongwen Li、Wenfang Duan、Tong Qin、Xintong Zhao、Yuhua Hu、Chi Zhang、Tianlei Li、Jie Hao、Wenxuan Zhang、Jihong Zhang、Song Wu

  DOI：10.1039/d1ob02292j

  日期：——

  Seventeen C20-O-alkyl/benzyl oxime derivatives were synthesized by a concise and effective method. Most of these derivatives showed tens to several hundred nanomolar IC50 values against HT-29 colorectal, HGC-27 gastric and MDA-MB-231 breast cancer cells, whose antiproliferative activity is 15–240 fold better than that of salinomycin. The C20-oxime etherified derivatives can coordinate potassium ions

  通过简洁有效的方法合成了17种C20- O-烷基/苄基肟衍生物。这些衍生物中的大多数对HT-29结肠直肠癌、HGC-27胃癌和MDA-MB-231乳腺癌细胞显示出数十至数百纳摩尔的IC 50值，其抗增殖活性比盐霉素高15-240倍。C20-肟醚化衍生物可以配位钾离子，并进一步调节HT-29细胞中的胞质Ca 2+浓度。效力的显着提高应归因于改性衍生物更好的离子结合和转运能力。此外，C20- O-烷基/苄基肟衍生物显示出比盐霉素更好的选择性指数 (SI)，表明它们具有较低的神经毒性风险。