2-(benzo[d][1,3]dioxol-5-ylmethoxy)isoindoline-1,3-dione | 2014-62-2

• 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-(benzo[d][1,3]dioxol-5-ylmethoxy)isoindoline-1,3-dione
• 英文别名: 2-(benzo[1,3]dioxol-5-ylmethoxy)isoindole-1,3-dione；2-(1,3-Benzodioxol-5-ylmethoxy)isoindole-1,3-dione
• CAS: 2014-62-2
• 化学式: C₁₆H₁₁NO₅
• 分子量: 297.267
• InChiKey: AWOACMOPIMPIAF-UHFFFAOYSA-N

物化性质

• 熔点：
  178-179 °C
• 沸点：
  475.0±55.0 °C(Predicted)
• 密度：
  1.51±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：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(benzo[d][1,3]dioxol-5-ylmethoxy)isoindoline-1,3-dione 在 一水合肼 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 O-(benzo[d][1,3]dioxol-5-ylmethyl)hydroxylamine
  参考文献：
  名称：

  [3 + 2] O-异氰酸酯的环加成物充当不带电荷的1,3-偶极当量。

  摘要：

  1,3-偶极子通常用于[3 + 2]环加成反应，而等电不带电偶极子变体仍未开发。与传统的1,3-偶极子相反，不带电荷的偶极子等价物形成两性离子环加合物，可用于构建进一步的分子复杂性。在这项工作中，氧取代的异氰酸酯的第一个环加成反应（O-异氰酸酯）通过实验和DFT计算进行了研究。通过与烯烃的分子内和分子间环加成反应，这种独特的环加成反应策略可提供一类新型的杂环氮杂-氧鎓叶立德。这使得可以对瞬态氮杂-氧鎓叶立德中间体的反应性进行系统的研究，该中间体可以经历N-O键裂解，然后插入亚硝基CH并通过改变烯烃或烯烃的结构形成β-内酰胺或异恶唑烷酮。O-异氰酸酯试剂。

  DOI：

  10.1002/anie.202007942
• 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-(benzo[d][1,3]dioxol-5-ylmethoxy)isoindoline-1,3-dione
  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

• Design, Synthesis, and in vitro Antibacterial Activity of Fluoroquinolone Derivatives Containing a Chiral 3-(Alkoxyimino)-2-(aminomethyl)azetidine Moiety
  作者：Kai Lv、Yexin Sun、Lanyin Sun、Zengquan Wei、Huiyuan Guo、Jinwei Wu、Mingliang Liu

  DOI：10.1002/cmdc.201200210

  日期：2012.7

  A series of novel (R)/(S)‐7‐(3‐alkoxyimino‐2‐aminomethyl‐1‐azetidinyl)fluoroquinolone derivatives were synthesized and evaluated for their in vitro antibacterial activity against representative strains. Our results reveal that 12 of the target compounds generally show better activity (MIC: <0.008–0.5 μg mL−1) against the tested Gram‐positive strains including MRSA and MRSE than levofloxacin (LVFX,

  合成了一系列新颖的（R）/（S）-7-（3-烷氧基亚氨基-2-氨基甲基-1-氮杂环丁烷基）氟喹诺酮衍生物，并评估了它们对代表性菌株的体外抗菌活性。我们的结果表明，该目标化合物的12通常显示出更好的活性（MIC：<0.008-0.5微克毫升-1）相对于被测试的革兰氏阳性菌株，包括MRSA和MRSE比左氧氟沙星（LVFX，MIC：0.125-8微克毫升-1）。它们的活性类似于吉非沙星（GMFX，MIC：<0.008–4μgmL -1）。但是，它们对革兰氏阴性菌株的活性通常不如两种参考药物强。此外，针对金黄色葡萄球菌的临床菌株，包括MRSA和表皮葡萄球菌包括MRSE，化合物16 w，y和z的MIC 50值（0.06–16μgmL -1）和MIC 90值（0.5–32μgmL -1）为2-8和2-16倍小于LVFX，分别与16瓦特（MIC 90范围：0.5-4微克毫升-1）中的溶液也被发现是活性高于GMFX（MIC
• Alkylation of Allyl/Alkenyl Sulfones by Deoxygenation of Alkoxyl Radicals
  作者：Jia-Bin Han、Ao Guo、Xiang-Ying Tang

  DOI：10.1002/chem.201806138

  日期：2019.2.26

  challenging deoxygenation of alkoxyl radicals from readily accessible alcohol derivatives was developed, affording facile synthesis of functionalized alkenes with good functional group tolerance under mild reaction conditions. Because alkoxyl radicals can easily undergo β‐fragmentations or hydrogen abstractions, this new strategy for deoxygenation of alkoxyl radicals is highly valuable. Moreover, mechanistic

  从容易获得的醇衍生物开发了具有挑战性的烷氧基自由基脱氧剂，可在温和的反应条件下轻松合成具有良好官能团耐受性的官能化烯烃。由于烷氧基自由基很容易发生β片段分解或夺氢现象，因此这种使烷氧基自由基脱氧的新策略非常有价值。此外，机理研究表明，电子中性膦可作为脱氧剂。
• Asymmetric synthesis of pyrrolo[2,3–b]indole scaffolds by organocatalytic [3 + 2] dearomative annulation
  作者：Heng-Zhi Tian、Sheng-Feng Wu、Guo-Qiang Lin、Xing-Wen Sun

  DOI：10.1016/j.tetlet.2022.153969

  日期：2022.8

  An organocatalytic approach for the stereoselective synthesis of pyrrolo[2,3–b]indoles is presented. The developed methodology is based on the [3 + 2] dearomative annulation reaction between 3-nitroindoles and fumaric acid amide esters. Products bearing three adjacent stereogenic centers, one being quaternary, were formed with excellent yields, good diastereoselectivities and decent enantioselectivities

  提出了一种立体选择性合成吡咯并[2,3- b ]吲哚的有机催化方法。开发的方法基于 3-硝基吲哚和富马酸酰胺酯之间的 [3 + 2] 脱芳环反应。具有三个相邻立体中心（一个是四元中心）的产物以优异的收率、良好的非对映选择性和良好的对映选择性形成。
• Resveratrol Analogs and Prodrugs Differently Affect the Survival of Breast Cancer Cells Impairing Estrogen/Estrogen Receptor α/Neuroglobin Pathway
  作者：Emiliano Montalesi、Patrizio Cracco、Filippo Acconcia、Marco Fiocchetti、Giovanna Iucci、Chiara Battocchio、Elisabetta Orlandini、Lidia Ciccone、Susanna Nencetti、Maurizio Muzzi、Sandra Moreno、Iole Venditti、Maria Marino

  DOI：10.3390/ijms24032148

  日期：——

  Breast cancer is the first leading tumor in women in terms of incidence worldwide. Seventy percent of cases are estrogen receptor (ER) α-positive. In these malignancies, 17β-estradiol (E2) via ERα increases the levels of neuroglobin (NGB), a compensatory protein that protects cancer cells from stress-induced apoptosis, including chemotherapeutic drug treatment. Our previous data indicate that resveratrol (RSV), a plant-derived polyphenol, prevents E2/ERα-induced NGB accumulation in this cellular context, making E2-dependent breast cancer cells more prone to apoptosis. Unfortunately, RSV is readily metabolized, thus preventing its effectiveness. Here, four different RSV analogs have been developed, and their effect on the ERα/NGB pathway has been compared with RSV conjugated with highly hydrophilic gold nanoparticles as prodrug to evaluate if RSV derivatives maintain the breast cancer cells’ susceptibility to the chemotherapeutic drug paclitaxel as the original compound. Results demonstrate that RSV conjugation with gold nanoparticles increases RSV efficacy, with respect to RSV analogues, reducing NGB levels and enhancing the pro-apoptotic action of paclitaxel, even preventing the anti-apoptotic action exerted by E2 treatment on these cells. Overall, RSV conjugation with gold nanoparticles makes this complex a promising agent for medical application in breast cancer treatment.

  乳腺癌是全球发病率最高的女性肿瘤。70%的病例雌激素受体（ER）α呈阳性。在这些恶性肿瘤中，17β-雌二醇（E2）通过ERα增加了神经球蛋白（NGB）的水平，而神经球蛋白是一种补偿蛋白，可保护癌细胞免受压力诱导的细胞凋亡（包括化疗药物治疗）。我们以前的数据表明，白藜芦醇（RSV）是一种植物多酚，在这种细胞环境下可防止 E2/ERα 诱导的 NGB 积累，使依赖 E2 的乳腺癌细胞更容易凋亡。遗憾的是，RSV 很容易被代谢掉，因此无法发挥其功效。在此，我们开发了四种不同的 RSV 类似物，并将它们对 ERα/NGB 通路的作用与 RSV 与作为原药的高亲水性金纳米粒子共轭进行了比较，以评估 RSV 衍生物是否能像原始化合物一样保持乳腺癌细胞对化疗药物紫杉醇的敏感性。结果表明，与 RSV 类似物相比，RSV 与金纳米粒子共轭可提高 RSV 的药效，降低 NGB 水平，增强紫杉醇的促凋亡作用，甚至阻止 E2 处理对这些细胞产生的抗凋亡作用。总之，RSV 与金纳米粒子的结合使这种复合物成为一种很有希望应用于乳腺癌治疗的药物。
• Design, synthesis and antifungal activities of novel pyrrole alkaloid analogs
  作者：Ming-Zhong Wang、Han Xu、Tuan-Wei Liu、Qi Feng、Shu-Jing Yu、Su-Hua Wang、Zheng-Ming Li

  DOI：10.1016/j.ejmech.2011.01.031

  日期：2011.5

  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.