(+/-)-nuevamine | 99265-24-4

• 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: (+/-)-nuevamine
• 英文别名: 8,9-dimethoxy-5,11b-dihydro-6H-1,3-dioxa-6a-aza-indeno[5,6-c]fluoren-7-one；6,7-Dimethoxy-16,18-dioxa-10-azapentacyclo[11.7.0.02,10.03,8.015,19]icosa-1(20),3(8),4,6,13,15(19)-hexaen-9-one
• CAS: 99265-24-4
• 化学式: C₁₉H₁₇NO₅
• 分子量: 339.348
• InChiKey: OMDLUUQOGBOMJH-UHFFFAOYSA-N

物化性质

• 熔点：
  193-194 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  533.8±50.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-Chlor-4,5-dimethoxy-isobenzofuran-3-on 在 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 96.0h， 生成 (+/-)-nuevamine
  参考文献：
  名称：

  异吲哚异喹啉生物碱的合成。（±）-新胺结构的修订

  摘要：

  报道了一种简单有效的合成异吲哚异喹啉的方法，并指定了生物碱（±）-新胺的新结构。

  DOI：

  10.1016/s0040-4039(00)98873-7

文献信息

• Propylphosphonic anhydride (T3P®) mediated synthesis of 3-oxoisoindoline-1-carboxamides from 2-formylbenzoic acid, amines, and isocyanides. Preparation of isoindolinone alkaloids
  作者：Valentina Varga、Mátyás Milen、Péter Ábrányi-Balogh

  DOI：10.1016/j.tetlet.2018.08.063

  日期：2018.10

  Propylphosphonic anhydride (T3P®) was successfully applied to the synthesis of an isoindolinone library by the utilization of an Ugi four-center, three-component reaction (Ugi-4C-3CR). The use of T3P® significantly shortened the required reaction time and the corresponding products were obtained in good to high yields. Moreover, a side-reaction was observed when phenylethylamine derivatives and tryptamine

  通过利用Ugi四中心三组分反应（Ugi-4C-3CR），丙基膦酸酐（T3P®）成功应用于异吲哚啉酮文库的合成。T3P®的使用大大缩短了所需的反应时间，并以高至高收率获得了相应的产物。此外，当使用苯乙胺衍生物和色胺作为胺组分时，观察到副反应。将后者反应用于微波辅助的一锅法合成异喹啉生物碱（±）-新胺。出乎意料的是，在存在T3P®的情况下，传统的Ugi四组分反应（Ugi-4CR）无法成功。在这种情况下，从多组分反应中产生了除羧酸之外的α-氨基酰胺。
• Synthesis of Condensed Tetrahydroisoquinoline Class of Alkaloids by Employing TfOH-Mediated Imide Carbonyl Activation
  作者：Jayaraman Selvakumar、Ramana Sreenivasa Rao、Vijayan Srinivasapriyan、Srinivasan Marutheeswaran、Chinnasamy Ramaraj Ramanathan

  DOI：10.1002/ejoc.201403617

  日期：2015.4

  isoindoloisoquinolinones, pyrroloisoquinolinones, and benzo[a]quinolizinones were successfully assembled from the corresponding imides by using a TfOH-mediated (TfOH = trifluoromethanesulfonic acid) imide carbonyl activation and cyclization strategy. By employing this simple method, the isoquinoline alkaloids crispine A, trolline/oleracein E, and erythrinarbine were successfully synthesized in racemic form. The reaction

  通过使用 TfOH 介导的（TfOH = 三氟甲磺酸）酰亚胺羰基活化和环化策略，从相应的酰亚胺成功组装了基于异喹啉的多环内酰胺，例如异吲哚异喹啉酮、吡咯并异喹啉酮和苯并 [a] 喹啉酮。通过使用这种简单的方法，异喹啉生物碱松脆 A、三乙醇胺/油茶素 E 和红菊素以外消旋形式成功合成。不对称 N-苯乙基邻苯二甲酰亚胺与 TfOH 的反应显示出优异的区域选择性，这通过 DFT 计算得到了合理化。
• A General, Concise Strategy that Enables Collective Total Syntheses of over 50 Protoberberine and Five Aporhoeadane Alkaloids within Four to Eight Steps
  作者：Shiqiang Zhou、Rongbiao Tong

  DOI：10.1002/chem.201601245

  日期：2016.5.17

  reported. This synthesis represents the most efficient and shortest route to date, featuring three catalytic processes: CuI‐catalyzed redox‐A3 reaction, Pd‐catalyzed reductive carbocyclization, and PtO2‐catalyzed hydrogenation. Importantly, this new strategy to the tetracyclic framework has also been applied to the collective concise syntheses of >30 natural protoberberines (without 13‐methyl group) and

  报告了一种简洁，催化和通用的策略，该策略允许在四个步骤中为每个分子高效地合成22种天然13-甲基原小ber碱。该合成代表了迄今为止最有效，最短的路线，具有三个催化过程：CuI催化的氧化还原A 3反应，Pd催化的还原碳环化和PtO 2催化的氢化。重要的是，这种针对四环框架的新策略也已应用于30多种天然原小ber碱（无13-甲基）和5种金刚烷烷生物碱的集体简明合成中。
• Brønsted acid assisted activation of imide carbonyl group: regioselective synthesis of isoindoloisoquinolinone alkaloid (±)-nuevamine
  作者：Jayaraman Selvakumar、Chinnasamy Ramaraj Ramanathan

  DOI：10.1039/c1ob06349a

  日期：——

  Activation of imide carbonyl group with trifluoromethanesulfonic acid facilitates the intramolecular cyclization of phenethylphthalimides to give a fused isoindoloisoquinolinone skeleton. The first one pot regioselective synthesis of isoindoloisoquinolinone alkaloid (±)-nuevamine has been successfully executed using this methodology.

  用三氟甲磺酸活化酰亚胺羰基有助于苯乙基邻苯二甲酰亚胺的分子内环化，从而得到融合的异吲哚异喹啉酮骨架。利用这种方法，首次成功地进行了异吲哚异喹啉酮生物碱 (±)-nuevamine 的一锅区域选择性合成。
• Synthesis and biological evaluation of isoindoloisoquinolinone, pyroloisoquinolinone and benzoquinazolinone derivatives as poly(ADP-ribose) polymerase-1 inhibitors
  作者：Arumugam Suyavaran、Chitteti Ramamurthy、Ramachandran Mareeswaran、Yagna Viswa Shanthi、Jayaraman Selvakumar、Selvaraj Mangalaraj、Muthuvel Suresh Kumar、Chinnasamy Ramaraj Ramanathan、Chinnasamy Thirunavukkarasu

  DOI：10.1016/j.bmc.2014.12.017

  日期：2015.2

  A series of novel fused isoquinolinones with isoindoloisoquinolinone, pyroloisoquinolinone, and benzoquinalizinone skeletons were synthesized from corresponding phenethylimides. The isoquinolinone derivatives were evaluated for their protective effect on chicken erythrocytes subjected to oxidative damage. The effect of isoquinolinone derivatives were analysed by estimation of cell viability, antioxidant enzyme activities, DNA damage (comet assay), PARP-1 inhibition assay and molecular docking of the compounds with PARP-1 active site. The compounds CRR-271, CRR-288 and CRR-224+225 showed significant protective effect at 100 mu M concentration. The PARP-1 inhibition assay revealed the IC50 values of CRR-271, CRR-288 and CRR-224+225 as <200 nM, further molecular docking studies shows higher binding energies with PARP-1 active site. Interesting findings in this study suggest that the novel isoquinolinone derivatives inhibit PARP-1 activity and protect cells against oxidative DNA damage, which could be implemented in the treatment of inflammatory diseases. (C) 2014 Elsevier Ltd. All rights reserved.