preussomerin A | 129240-52-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: preussomerin A
• 英文别名: (1S,2R,4R,5R,12R,15S)-3,11,21,22-tetraoxaheptacyclo[10.9.1.11,6.112,16.02,4.010,24.020,23]tetracosa-6,8,10(24),13,16(23),17,19-heptaene-5,7,15-triol
• CAS: 129240-52-4
• 化学式: C₂₀H₁₄O₇
• 分子量: 366.327
• InChiKey: YYUIJBSRPPKHNR-YIHIMSTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  27
• 可旋转键数：
  0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  101
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  preussomerin A 在 sodium acetate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 4.0h， 以50%的产率得到preussomerin G
  参考文献：
  名称：

  The preussomerins: novel antifungal metabolites from the coprophilous fungus Preussia isomera Cain

  摘要：

  Preussomerins A-F (1-6), a series of new aromatic bis-ketals with antifungal and antibacterial activities, have been isolated from the coprophilous fungus Preussia isomera (CBS 415.82). Preussomerins A-F were obtained from ethyl acetate extracts of liquid cultures of P. isomera by silica gel chromatography and reversed-phase HPLC. The structures of preussomerins B-F (2-6) were proposed on the basis of extensive NMR experiments and by comparison with the data for preussomerin A (1), whose structure was confirmed by single-crystal X-ray diffraction analysis. The isolation process was guided by in vitro bioassays for antifungal antagonism toward other coprophilous fungi.

  DOI：

  10.1021/jo00014a007

文献信息

• Synthesis and methods of use of new antimitotic agents
  申请人：——

  公开号：US20020049221A1

  公开（公告）日：2002-04-25

  Oxidative cyclization of bis-naphthyl ethers allows concise total syntheses of palmarumycin CP, and deoxypreussomerin A in 8-9 steps and 15-35% overall yield from 5-hydroxy-8-methoxy-1 -tetralone. A small library of palmarumycin analogs was created. Biological evaluation of these naphthoquinone spiroketals against MCF-7 and MDA-MB-23 1 human breast cancer cells revealed several low-micromolar growth inhibitors. A number of the analogs inhibit the thioredoxin -thioredoxin reductase system.

  通过双萘醚的氧化环化反应，可以从 5-hydroxy-8-methoxy-1 -tetralone（5-羟基-8-甲氧基-1-四氢萘酮）出发，以 8-9 个步骤和 15-35% 的总收率，简便地全合成出棕榈霉素 CP 和脱氧普鲁索梅林 A。我们建立了一个小型的香豆素类似物库。对这些萘醌螺环酮类化合物针对 MCF-7 和 MDA-MB-23 1 人类乳腺癌细胞进行的生物学评估发现了几种低微摩生长抑制剂。其中一些类似物可抑制硫氧还蛋白-硫氧还蛋白还原酶系统。
• WEBER, HOLLY A.;GLOER, JAMES B., J. ORG. CHEM., 56,(1991) N4, C. 4355-4360
  作者：WEBER, HOLLY A.、GLOER, JAMES B.

  DOI：——

  日期：——
• Weber, Holly A.; Baenziger, Norman C.; Gloer, James B., Journal of the American Chemical Society, 1990, vol. 112, # 18, p. 6718 - 6719
  作者：Weber, Holly A.、Baenziger, Norman C.、Gloer, James B.

  DOI：——

  日期：——
• US6673937B2
  申请人：——

  公开号：US6673937B2

  公开（公告）日：2004-01-06
• The preussomerins: novel antifungal metabolites from the coprophilous fungus Preussia isomera Cain
  作者：Holly A. Weber、James B. Gloer

  DOI：10.1021/jo00014a007

  日期：1991.7

  Preussomerins A-F (1-6), a series of new aromatic bis-ketals with antifungal and antibacterial activities, have been isolated from the coprophilous fungus Preussia isomera (CBS 415.82). Preussomerins A-F were obtained from ethyl acetate extracts of liquid cultures of P. isomera by silica gel chromatography and reversed-phase HPLC. The structures of preussomerins B-F (2-6) were proposed on the basis of extensive NMR experiments and by comparison with the data for preussomerin A (1), whose structure was confirmed by single-crystal X-ray diffraction analysis. The isolation process was guided by in vitro bioassays for antifungal antagonism toward other coprophilous fungi.