2-aminophenalenone | 55077-97-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 非那烯类
• 英文名称: 2-aminophenalenone
• 英文别名: 2-Amino-phenalenon；2-Amino-1H-phenalen-1-one；2-aminophenalen-1-one
• CAS: 55077-97-9
• 化学式: C₁₃H₉NO
• 分子量: 195.221
• InChiKey: IHVMVTBHISOISX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-aminophenalenone 在 氯 作用下， 以 四氯化碳 、 氯苯 为溶剂， 反应 0.5h， 以36%的产率得到2-amino-3-chloro-1H-phenalen-1-one
  参考文献：
  名称：

  Phenalenones. III. The Anomalous Diazotization of 3-Substituted 2-Aminophenalenones

  摘要：

  对 3-取代的 2-氨基-1H-苯丙烯-1-酮（取代基=Cl、Br、PhS 或 OH）进行重氮化反应，可得到 2-重氮-1H-苯丙烯-1,3(2H)-二酮。该反应极有可能涉及瞬时重氮氢氧化物中间体的分子内重排，以及随之而来的 3 位取代基的消除。

  DOI：

  10.1246/bcsj.54.939
• 作为产物：
  描述：

  2-nitrophenalenone 在 1% Pd/C 、 氢气 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以98%的产率得到2-aminophenalenone
  参考文献：
  名称：

  Structure−Activity Relationship in the Interaction of Substituted Perinaphthenones with Mycosphaerella fijiensis

  摘要：

  The levels of native fungitoxic perinaphthenone phytoalexins in susceptible Musa varieties (banana), which are commercially grown in large plantations, are too low to provide plants with long-lasting protection against highly pathogenic fungi. Novel strategies for plant protection are necessary to reduce crop losses and to prevent the development of resistant fungal strains. The synthesis of novel fungicides based on the structures of perinaphthenone natural products is considered to be a promising strategy. Thirteen substituted, perinaphthenones, among them two known natural products (1, 2) and 11 synthetics (3-13), were evaluated for their activity against Mycosphaerella fijiensis, and their half-maximal inhibitory concentrations (IC50) were calculated to establish structure-activity relationships (SAR). A SAR trend was hypothesized, leading to the design of a new compound, 4-methoxy-2-nitro-1H-phenalen-1-one (14); the new compound displayed significantly enhanced in vitro activity against M. fijiensis compared to other perinaphthenone derivatives. The activity of 14 was comparable to that of two commercial fungicides.

  DOI：

  10.1021/jf901052e

文献信息

• Design, synthesis and evaluation of amino-substituted 1H-phenalen-1-ones as anti-leishmanial agents
  作者：Mónica Blanco Freijo、Atteneri López-Arencibia、José E. Piñero、Grant McNaughton-Smith、Teresa Abad-Grillo

  DOI：10.1016/j.ejmech.2017.10.032

  日期：2018.1

  Screening of a designed collection of mono-substituted amino-IH-phenalen-1-ones against promastigote forms of L. donovani and L. amazonensis, identified seven compounds with anti-leishmanial activities comparable or better than the commonly prescribed anti-leishmanial drug, miltefosine. Structure activity analysis revealed that appendages containing a basic tertiary nitrogen were favored, and that the position of the appendage also affected their potency. Like miltefosine, several of these active compounds significantly reduced the mitochondrial membrane potential in promastigotes. Further studies in amastigotes of L. amazonensis revealed that compounds 14, 15 and 33 were more active and more selective than miltefosine, with sub-micromolar potencies and selectivity indices > 100. (C) 2017 Elsevier Masson SAS. All rights reserved.
• DE677967
  申请人：——

  公开号：——

  公开（公告）日：——
• Solodar', S. L.; Kochkin, V. A., Journal of Organic Chemistry USSR (English Translation), 1980, vol. 16, # 10, p. 1809 - 1812
  作者：Solodar', S. L.、Kochkin, V. A.

  DOI：——

  日期：——
• Solodar', S. L.; Kochkin, V. A., Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, # 2, p. 370 - 380
  作者：Solodar', S. L.、Kochkin, V. A.

  DOI：——

  日期：——
• Naphthindenones
  申请人：GEN ANILINE WORKS INC

  公开号：US02174751A1

  公开（公告）日：1939-10-03