4-chloro-7H-naphtho[1,2,3-ij][2,7]naphthyridin-7-one | 143858-48-4

• 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: 4-chloro-7H-naphtho[1,2,3-ij][2,7]naphthyridin-7-one
• 英文别名: 4-chlorosampangine；3-chlorosampangine；12-chloro-10,16-diazatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9,11,13(17),14-octaen-8-one
• CAS: 143858-48-4
• 化学式: C₁₅H₇ClN₂O
• 分子量: 266.686
• InChiKey: SDPVMTFZFDHZEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• 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：

  sampangine 在 N-氯代丁二酰亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以53%的产率得到4-chloro-7H-naphtho[1,2,3-ij][2,7]naphthyridin-7-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

• 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类似物，其组成和制备方法，以及治疗真菌和分枝杆菌感染的方法。该化合物具有以下通式：##STR1##其中R.sub.1，R.sub.2和R.sub.5基团在此定义。
• Antimycobacterial method
  申请人：The University of Mississippi

  公开号：US05530004A1

  公开（公告）日：1996-06-25

  New analogs of sampangine and cleistopholine, compositions and methods of preparation thereof, method of treating fungal and mycobacterial infections.

  新的sampangine和cleistopholine类似物，其组合物和制备方法，以及治疗真菌和分枝杆菌感染的方法。
• Zjawiony, Jordan K.; Srivastava, Anita R.; Hufford, Charles D., Heterocycles, 1994, vol. 39, # 2, p. 779 - 800
  作者：Zjawiony, Jordan K.、Srivastava, Anita R.、Hufford, Charles D.、Clark, Alice M.

  DOI：——

  日期：——
• CuCl₂-Promoted 6-<i>endo-dig</i> Chlorocyclization and Oxidative Aromatization Cascade: Efficient Construction of 1-Azaanthraquinones from <i>N</i>-Propargylaminoquinones
  作者：Na Fei、Hao Yin、Shaozhong Wang、Huaqin Wang、Zhu-Jun Yao

  DOI：10.1021/ol201542h

  日期：2011.8.19

  An efficient synthetic methodology was developed to assemble 1-azaanthraquinones from N-propargylaminoquinones by copper(II)-promoted sequential 6-endo-dig chlorocyclization and oxidative aromatization. The approach can be extended to preprare chlorinated alkaloids such as cleistophine and sampangine. A possible mechanism involving carbon-carbon bond formation triggered by regioselective electrophilic activation and carbon-chlorine bond formation via reductive elimination was proposed.
• SAMPANGINE DERIVATIVES USEFUL AS ANTIFUNGAL AND ANTIMYCOBACTERIAL AGENTS
  申请人：THE UNIVERSITY OF MISSISSIPPI

  公开号：EP0588796B1

  公开（公告）日：2001-04-04