aplidiopsamine A | 1256795-61-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: aplidiopsamine A
• 英文别名: 9-((3H-pyrrolo[2,3-c]quinolin-4-yl)methyl)-9H-purin-6-amine；9-[(3h-Pyrrolo[2,3-c]quinolin-4-yl)methyl]-9h-purin-6-amine；9-(3H-pyrrolo[2,3-c]quinolin-4-ylmethyl)purin-6-amine
• CAS: 1256795-61-5
• 化学式: C₁₇H₁₃N₇
• 分子量: 315.337
• InChiKey: GUELDSIQHALXCV-UHFFFAOYSA-N

物化性质

• 沸点：
  687.8±65.0 °C(Predicted)
• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  98.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(1H-pyrrol-3-yl)aniline 在 盐酸 、 sodium hydride 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.34h， 生成 aplidiopsamine A
  参考文献：
  名称：

  Biomimetic Synthesis and Biological Evaluation of Aplidiopsamine A

  摘要：

  The first total synthesis of Aplidiopsamine A, a rare 3H-pyrrolo[2,3-c]quinoline alkaloid from the Aplidiopsis confluata, has been achieved following the proposed biosynthesis. This biomimetic synthesis requires only five steps and proceeds in 20.8% overall yield. Biological evaluation across large panels of discrete molecular targets identified that Aplidiopsamine A is a highly selective PDE4 inhibitor, a target for numerous CNS disorders.

  DOI：

  10.1021/ol3024665

文献信息

• [EN] PYRROLOQUINOLINE ALKALOIDS AS ANTIMALARIAL AGENTS AND PROCESS FOR THE PREPARATION THEREOF<br/>[FR] ALCALOÏDES DE TYPE PYRROLOQUINOLINE COMME AGENTS ANTIPALUDIQUES ET PROCÉDÉ DE PRÉPARATION ASSOCIÉ
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2013117986A1

  公开（公告）日：2013-08-15

  The patent provides novel compounds with potential anti-malarial activity and process of synthesis thereof. Further, the process for the synthesis of known antimalarial natural products marinoquinazolinone A-F, aplidiopsamine A and their potential antimalarial analogues is disclosed.

  该专利提供了具有潜在抗疟活性的新型化合物及其合成方法。此外，还公开了用于合成已知抗疟天然产物马林喹唑啉酮A-F、阿普利地阿普胺A及它们的潜在抗疟类似物的方法。
• New class of antitubercular compounds: synthesis and anti-tubercular activity of 4-substituted pyrrolo[2,3-c]quinolines
  作者：Mahesh Akula、Jonnalagadda Padma Sridevi、P. Yogeeswari、D. Sriram、Anupam Bhattacharya

  DOI：10.1007/s00706-013-1141-1

  日期：2014.5

  AbstractModified synthesis and antitubercular activity of 4-substituted pyrrolo[2,3-c]quinolines are reported. Some of the compounds showed significant antitubercular activity, when compared to some of the existing antitubercular drugs. A compound with an imidazole moiety at position 4 shows the highest activity and least toxicity. Graphical abstract

  摘要报道了4-取代的吡咯并[2,3- c ]喹啉的合成和抗结核活性。与某些现有的抗结核药物相比，某些化合物具有显着的抗结核活性。在4位具有咪唑部分的化合物显示出最高的活性和最低的毒性。 图形概要
• PYRROLOQUINOLINE ALKALOIDS AS ANTIMALARIAL AGENTS AND PROCESS FOR THE PREPARATION THEREOF
  申请人：COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH

  公开号：US20150336947A1

  公开（公告）日：2015-11-26

  The patent provides novel compounds with potential anti-malarial activity and process of synthesis thereof. Further, the process for the synthesis of known antimalarial natural products marinoquinazolinone A-F, aplidiopsamine A and their potential antimalarial analogues is disclosed.

  该专利提供了具有潜在抗疟活性的新化合物及其合成过程。此外，还公开了天然抗疟药物Marinoquinazolinone A-F、Aplidiopsamine A及其潜在的抗疟类似物的合成方法。
• Pd-Catalyzed Imine Cyclization: Synthesis of Antimalarial Natural Products Aplidiopsamine A, Marinoquinoline A, and Their Potential Hybrid NCLite-M1
  作者：Jyoti P. Mahajan、Yogeshwar R. Suryawanshi、Santosh B. Mhaske

  DOI：10.1021/ol302676v

  日期：2012.11.16

  Palladium-catalyzed cyclization of imines has been developed to construct the extremely rare 3H-pyrrolo[2,3-c]quinoline ring system for diversity oriented first total synthesis of antimalarial marine natural product Aplidiopsamine A as well as synthesis of Marinoquinoline A and potential natural product hybrid NCLite-M1.
• Development of a Brønsted Acid-Promoted Arene–Ynamide Cyclization toward the Total Syntheses of Marinoquinolines A and C and Aplidiopsamine A
  作者：Yousuke Yamaoka、Takahiro Yoshida、Makiko Shinozaki、Ken-ichi Yamada、Kiyosei Takasu

  DOI：10.1021/jo502467m

  日期：2015.1.16

  A Bronsted acid-promoted arene-ynamide cyclization has been developed to construct the 3H-pyrrolo[2,3-c]quinolines. This reaction consists of the generation of a highly reactive keteniminium intermediate from arene-ynamide activated by a Bronsted acid and electrophilic aromatic substitution reaction to give arene-fused quinolines in high yields. This methodology enabled facile access to marinoquinolines A and C and aplidiopsamine A.