kealiinine B | 700813-16-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: kealiinine B
• 英文别名: 6,7-dimethoxy-4-(4-methoxyphenyl)-1-methyl-1H-naphtho[2,3-d]imidazol-2-amine；6,7-dimethoxy-4-(4-methoxyphenyl)-1-methylbenzo[f]benzimidazol-2-amine
• CAS: 700813-16-7
• 化学式: C₂₁H₂₁N₃O₃
• 分子量: 363.416
• InChiKey: ADAJQGCVARDFOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  kealiinine B 、 己酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 10.5h， 以92%的产率得到N-(6,7-dimethoxy-4-(4-methoxyphenyl)-1-methyl-1H-naphtho-[2,3-d]imidazol-2-yl)hexanamide
  参考文献：
  名称：

  Marine Natural Products for Drug Discovery: First Discovery of Kealiinines A–C and Their Derivatives as Novel Antiviral and Antiphytopathogenic Fungus Agents

  摘要：

  Leucetta alkaloid kealiinines A-C and kealiinine B derivatives were designed, synthesized, and characterized on the basis of NMR and HR-MS. The anti-TMV and antiphytopathogenic fungus activities of these alkaloids were evaluated for the first time. Kealiinine B exhibited a higher anti-TMV activity than kealiinines A and C. Kealiinine B derivatives 2m (inhibitory rates: 68, 66, and 71% at 500 mu g/mL for inactivation, curative, and protection activity in vivo, respectively) and 2y (inhibitory rates: 69, 64, and 63% at 500 mu g/mL for inactivation, curative, and protection activity in vivo, respectively) showed significantly higher antiviral activity than ningnanmycin (inhibitory rates: 56, 56, and 58% at 500 mu g/mL for inactivation, curative, and protection activity in vivo, respectively), thus emerging as new lead compounds for novel antiviral agent development. Structure activity relationship research provided the basis for structural simplification of these alkaloids. Further fungicidal activity tests revealed that these alkaloids displayed broad-spectrum fungicidal activities. Compounds 2i and 2p displayed good fungicidal activities in vitro against Sclerotinia sclerotiorum and Rhizoctonia cerealis with inhibition rates of 71%/50 mg/kg and 70%/50 mg/kg, respectively.

  DOI：

  10.1021/acs.jafc.8b02238
• 作为产物：
  描述：

  6,7-dimethoxy-4-(4-methoxyphenyl)-1-methyl-1H-naphtho[2,3-d]imidazole 在 正丁基锂 、 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 10.0h， 生成 kealiinine B
  参考文献：
  名称：

  碱金属 A–C 的全合成

  摘要：

  已经使用双苄二醇的分子内 Friedel-Crafts-脱水序列完成了Leucetta衍生的生物碱、kealiinines A-C 的短全合成。前体二醇是通过一系列位置特异性格氏反应从 1-甲基-4,5-二碘咪唑获得的。然后，叠氮化物的 C2-叠氮化和氢化提供了 kealiines A-C 的报告结构。虽然1 H NMR 数据与这些材料不完全匹配，但 HPLC 数据与这些生物碱的指定结构一致。

  DOI：

  10.1021/ol302958e

文献信息

• Hypervalent Iodine(III)-Mediated Cascade Cyclization of Propargylguanidines and Total Syntheses of Kealiinine B and C
  作者：Guilong Tian、Pavel Fedoseev、Erik V. Van der Eycken

  DOI：10.1002/chem.201700934

  日期：2017.4.19

  An oxidative cascade cyclization of propargylguanidines promoted by phenyliodonium diacetate (PIDA) was developed. The protocol provides an efficient route for the synthesis of the alkaloids kealiinines B and C as well as homologues. The difference in the electronic nature of the acetylene substituent resulted in two ways of the cyclization. A plausible mechanism is proposed based on the experimental

  开发了双乙酸苯基碘鎓（PIDA）促进的炔丙基胍的氧化级联环化。该方案为合成生物碱类kealiinines B和C以及同系物提供了一条有效途径。乙炔取代基的电子性质的差异导致两种环化方式。根据实验结果提出了一种合理的机制。
• Kealiinine类衍生物及其制备和在抗植物病毒和病菌中的应用
  申请人：南开大学

  公开号：CN110483405B

  公开（公告）日：2022-11-11

  本发明涉及Kealiinine类衍生物II及其制备方法和在抗植物病毒和病菌中的应用。本发明的Kealiinine类衍生物II显示出特别优异的抗植物病毒活性，能很好地抑制烟草花叶病毒(TMV)，该类化合物同时表现出一定的抗植物病菌活性。
• Synthesis of the Reported Structures for Kealiinines B and C
  作者：Joseph B. Gibbons、Keith M. Gligorich、Bryan E. Welm、Ryan E. Looper

  DOI：10.1021/ol3019242

  日期：2012.9.21

  Syntheses of the reported structures of kealiinines B and C have been executed. An intermolecular electrophile-induced cyclization of a pendant arene on an ene-guanidine affords the tetracyclic, oxidized naphthimidazole cores.
• Marine Natural Products for Drug Discovery: First Discovery of Kealiinines A–C and Their Derivatives as Novel Antiviral and Antiphytopathogenic Fungus Agents
  作者：Gang Li、Jincheng Guo、Ziwen Wang、Yuxiu Liu、Haibin Song、Qingmin Wang

  DOI：10.1021/acs.jafc.8b02238

  日期：2018.7.18

  Leucetta alkaloid kealiinines A-C and kealiinine B derivatives were designed, synthesized, and characterized on the basis of NMR and HR-MS. The anti-TMV and antiphytopathogenic fungus activities of these alkaloids were evaluated for the first time. Kealiinine B exhibited a higher anti-TMV activity than kealiinines A and C. Kealiinine B derivatives 2m (inhibitory rates: 68, 66, and 71% at 500 mu g/mL for inactivation, curative, and protection activity in vivo, respectively) and 2y (inhibitory rates: 69, 64, and 63% at 500 mu g/mL for inactivation, curative, and protection activity in vivo, respectively) showed significantly higher antiviral activity than ningnanmycin (inhibitory rates: 56, 56, and 58% at 500 mu g/mL for inactivation, curative, and protection activity in vivo, respectively), thus emerging as new lead compounds for novel antiviral agent development. Structure activity relationship research provided the basis for structural simplification of these alkaloids. Further fungicidal activity tests revealed that these alkaloids displayed broad-spectrum fungicidal activities. Compounds 2i and 2p displayed good fungicidal activities in vitro against Sclerotinia sclerotiorum and Rhizoctonia cerealis with inhibition rates of 71%/50 mg/kg and 70%/50 mg/kg, respectively.
• Total Syntheses of Kealiinines A–C
  作者：Jayanta Das、Panduka B. Koswatta、J. Daniel Jones、Muhammed Yousufuddin、Carl J. Lovely

  DOI：10.1021/ol302958e

  日期：2012.12.21

  Short total syntheses of the Leucetta-derived alkaloids, kealiinines A–C, have been accomplished using an intramolecular Friedel–Crafts–dehydration sequence of a bis benzylic diol. The precursor diol was obtained through a series of position-specific Grignard reactions from 1-methyl-4,5-diiodoimidazole. C2-Azidation and hydrogenation of the azide then provided the reported structures of kealiinines

  已经使用双苄二醇的分子内 Friedel-Crafts-脱水序列完成了Leucetta衍生的生物碱、kealiinines A-C 的短全合成。前体二醇是通过一系列位置特异性格氏反应从 1-甲基-4,5-二碘咪唑获得的。然后，叠氮化物的 C2-叠氮化和氢化提供了 kealiines A-C 的报告结构。虽然1 H NMR 数据与这些材料不完全匹配，但 HPLC 数据与这些生物碱的指定结构一致。