2-nitrophenalenone | 73693-16-0

• 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-nitrophenalenone
• 英文别名: 2-Nitrophenalenon；2-nitro-1H-phenalen-1-one；2-nitroperinaphthenone；2-Nitrophenalen-1-one
• CAS: 73693-16-0
• 化学式: C₁₃H₇NO₃
• 分子量: 225.203
• InChiKey: NYEBMUGPMLUXNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 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：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  萘嵌苯酮 在 硫酸 、 硝酸 作用下， 以30%的产率得到2-nitrophenalenone
  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

• [DE] DIREKTZIEHENDE HAARFÄRBEMITTEL UND DEREN VERWENDUNG<br/>[EN] DIRECT HAIR DYE AND THE USE THEREOF<br/>[FR] AGENT DE COLORATION POUR LES CHEVEUX MONTANT DIRECTEMENT SUR LA FIBRE ET LEUR UTILISATION
  申请人：HENKEL KOMMANDITGESELLSCHAFT AUF AKTIEN

  公开号：WO1999060992A1

  公开（公告）日：1999-12-02

  (DE) Die Erfindung betrifft Mittel zum Färben und Tönen keratinischer Fasern, insbesondere menschlicher Haare, die als direktziehenden Farbstoff mindestens eine Verbindung der Formel (I), in der R1-R8 voneinander unabhängig stehen für Wasserstoff, eine C1-4-Alkylgruppe, eine Allylgruppe, eine C1-4-Alkoxygruppe, eine C1-4-Monohydroxylakylgruppe, eine C2-4-Dihydroxyalkylgruppe, eine Hydroxygruppe, ein Halogenatom, eine Nitrogruppe, eine Cyanogruppe oder eine NR9R10-Gruppe, in der R9 und R10 voneinander unabhängig stehen für Wasserstoff, eine C1-4-Alkylgruppe, eine Allylgruppe, eine C1-4-Hydroxyalkylgruppe oder eine C2-4-Dihydroxyalkylgruppe, wobei mindestens 5 Substituenten Wasserstoff sind, oder deren physiologisch verträglichen Salze enthalten. Diese Verbindungen zeichnen sich insbesondere durch ein verbessertes Aufziehvermögen der Farbstoffmoleküle auf das Haar und/oder einen verbesserten Glanz des gefärbten Haares aus.(EN) The invention relates to agents for dying and tinting keratin fibers, especially human hair, which, as a direct dye, comprise at least one compound of formula (I) in which R1-R8, independent of one another, represent hydrogen, a C1-C4 alkyl group, an allyl group, a C1-C4 alkoxyl group, a C1-C4 monohydroxyalkyl group, a C2-C4 dihydroxyalkyl group, a hydroxyl group, a halogen atom, a nitro group, a cyano group or an NR9R10 group, in which R9 and R10, independent of one another, represent hydrogen, a C1-C4 alkyl group, an allyl group, a C1-C4 hydroxyalkyl group or a C2-C4 dihydroxyalkyl group, whereby at least five substituents are hydrogen or contain physiologically compatible salts thereof. These compounds are characterized in that the dye molecules exhibit an improved ability of attaching to the hair and/or the dyed hair exhibits an improved shine.(FR) L'invention concerne des agents utilisés pour colorer ou teinter les fibres kératiniques, en particulier les cheveux, qui contiennent, comme colorant montant directement sur la fibre, au moins un composé correspondant à la formule (I) ou bien ses sels physiologiquement tolérés. Dans ladite formule, R1-R8 représentent, indépendamment l'un de l'autre, hydrogène, un groupe alkyle C1-4, un groupe allyle, un groupe alcoxy C1-4, un groupe monohydroxyalkyle C1-4, un groupe dihydroxyalkyle C2-4, un groupe hydroxy, un atome d'halogène, un groupe nitro, un groupe cyano ou un groupe NR9R10 où R9 et R10 représentent, indépendamment l'un de l'autre, hydrogène, un groupe alkyle C1-4, un groupe allyle, un groupe hydroxyalkyle C1-4 ou un groupe dihydroxyalkyle C2-4, au moins 5 substituants représentant hydrogène. Ces composés se caractérisent par une capacité améliorée des molécules de colorant à monter sur les cheveux et/ou par un éclat amélioré des cheveux colorés.

  该发明涉及用于染色和定型头发（特别是人类头发）的中间体，这些中间体作为直接染料，至少包含一个具有下述公式的化合物（I），其中根据下列情况，R1-R8各独立代表：氢、C1-C4烷基、烯丙基、C1-C4氧基、C1-C4羟基甲基、C2-C4二羟基丙基、羟基、卤素原子、硝基、亚硝基或按如下情况独立代表：R9和R10；氢、C1-C4烷基、烯丙基、C1-C4羟基丙基或C2-C4二羟基丙基，其中要求至少五个取代基为氢或包含生理相容性盐类。这些化合物的特征是，染色分子的吸附能力得以改善，并且/或染色后的头发光泽度得到提高。
• 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.
• Solodar', S. L.; Kochkin, V. A., Journal of Organic Chemistry USSR (English Translation), 1981, vol. 17, p. 725 - 731
  作者：Solodar', S. L.、Kochkin, V. A.

  DOI：——

  日期：——
• DOKUNIXIN N. S.; SOLODAR S. L.; VINOGRADOV L. M., ZH. ORGAN. XIMII, 1979, 15, HO 11, 2360-2366
  作者：DOKUNIXIN N. S.、 SOLODAR S. L.、 VINOGRADOV L. M.

  DOI：——

  日期：——
• SOLODAR S. L.; KOCHKIN V. A., ZH. ORGAN. XIMII, 1981, 17, HO 4, 828-834
  作者：SOLODAR S. L.、 KOCHKIN V. A.

  DOI：——

  日期：——