9H-benzo[b]pyrido[4,3,2-mn]acridin-9-one | 143091-80-9

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 1-氮杂氧卟啉
• 英文名称: 9H-benzo[b]pyrido[4,3,2-mn]acridin-9-one
• 英文别名: 9H-benzo[i]pyrido[2,3,4-kl]acridin-9-one；1,8-diazabenzo[fg]naphthacen-9-one；benzosampangine；pentacyclus 13-deazaascididemin；13-deazaascididemin；deaza-ascididemin；Benzo(4,5)sampangine；2,12-diazapentacyclo[11.7.1.03,8.09,21.014,19]henicosa-1,3,5,7,9(21),10,12,14,16,18-decaen-20-one
• CAS: 143091-80-9
• 化学式: C₁₉H₁₀N₂O
• 分子量: 282.301
• InChiKey: SGZVAGOBRALNLJ-UHFFFAOYSA-N

物化性质

• 熔点：
  260-262 °C
• 沸点：
  567.8±30.0 °C(Predicted)
• 密度：
  1.414±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(2'-acetylanilino)-1,4-naphthoquinone 在 硫酸 、 氯化铵 、 溶剂黄146 作用下， 以 溶剂黄146 为溶剂， 反应 1.25h， 生成 9H-benzo[b]pyrido[4,3,2-mn]acridin-9-one
  参考文献：
  名称：

  Copyrine alkaloids: synthesis, spectroscopic characterization, and antimycotic/antimycobacterial activity of A- and B-ring-functionalized sampangines

  摘要：

  Several A- and B-ring-substituted sampangines were synthesized and evaluated for antifungal and antimycobacterial activity against AIDS-related opportunistic infection pathogens. Electrophilic halogenation provided a channel for structural elaboration of the sampangine B-ring at position 4, while the synthesis of A-ring 3-substituted sampangines and benzo[4,5]sampangine (24) were achieved from the corresponding functionalized cleistopholines. Two-dimensional NMR spectroscopy was used to rigorously characterize the A- and B-ring substituent patterns. Structure-activity relationship studies revealed the activity of the sampangines was enhanced by the presence of a substituent at position 3 or by a 4,5-benzo group.

  DOI：

  10.1021/jm00100a012

文献信息

• Fungicidal properties of sampangine and its analogs to agriculturally important fungal plant pathogens
  申请人：——

  公开号：US20040192721A1

  公开（公告）日：2004-09-30

  It has been found that sampangine and related analogs such as benzo[4,5]sampangine, 4-bromosampangine and 4-methoxysampangine may be used as effective fungicidal agents for plants. Fungicidal plant compositions and methods of using the materials for such a purpose are also provided.

  已发现sampangine及其相关类似物，如苯并［4,5］sampangine、4-溴sampangine和4-甲氧基sampangine，可用作植物的有效杀真菌剂。还提供了用于此目的的杀真菌植物组合物和使用这些材料的方法。
• Compounds and compositions useful as antifungal and antimycobacterial
  申请人：The University of Mississippi

  公开号：US05227383A1

  公开（公告）日：1993-07-13

  New analogs of sampangine and cleistopholine, compositions and methods of preparation thereof, method of treating fungal and mycobacterial infections. The compounds have the general formula: ##STR1## where the R.sub.1, R.sub.2, and R.sub.5 groups are defined herein.

  新的sampangine和cleistopholine的类似物，其组成物和制备方法，治疗真菌和分枝杆菌感染的方法。这些化合物具有一般公式：##STR1##其中R.sub.1、R.sub.2和R.sub.5基团在此处被定义。
• Sampangine and derivatives useful as an antifungal agent
  申请人：University of Mississippi

  公开号：US05128344A1

  公开（公告）日：1992-07-07

  A new compound 3-Methoxysampangine and its analogs, compositions thereof, and method of using as an antifungal agent particularly effective against Candida albicans, Cryptococcus neoformans, and Aspergillus fumigatus.

  一种新的化合物3-甲氧基三叶树碱及其类似物，其组合物，以及作为抗真菌剂使用的方法，特别对白念珠菌，新生隐球菌和烟曲霉菌具有很好的抗菌效果。
• MATERIALS FOR ORGANIC ELECTROLUMINESCENT DEVICES
  申请人：Merck Patent GmbH

  公开号：US20200199138A1

  公开（公告）日：2020-06-25

  The present invention relates to compounds suitable for use in electronic devices, and to electronic devices, especially organic electroluminescent devices, comprising these compounds.

  本发明涉及适用于电子设备的化合物，以及包括这些化合物的电子设备，特别是有机电致发光器件。
• Intramolecular Michael-type addition of azadienes to 1,4-naphthoquinones instead of Aza-Diels–Alder cycloaddition: a synthesis of ascididemin
  作者：Juan M. Cuerva、Diego J. Cárdenas、Antonio M. Echavarren

  DOI：10.1039/b202555h

  日期：2002.5.23

  α,β-Unsaturated hydrazones tethered by an amino group to 1,4-naphthoquinone or quinoline-5,8-dione do not react by intramolecular aza-Diels–Alder cycloaddition. Instead, these substrates cyclize to form benzo[b]acridine-6,11-dione or pyrido[2,3-b]acridine-5,12-dione derivatives, respectively. This route leads to a highly concise synthesis of the pyridoacridine alkaloid ascididemin.

  与氨基连接的α,β-不饱和肼酮与1,4-萘醌或喹啉-5,8-二酮并不会通过分子内氮杂Diels–Alder环加成反应。相反，这些底物会环化形成苯并[b]氨基芴-6,11-二酮或吡啶[2,3-b]氨基芴-5,12-二酮衍生物。该路线实现了吡啶氨基芴生物碱ascididemin的高效合成。