preussomerin D | 134111-68-5

• 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 D
• 英文别名: (1S,2R,4R,5R,12R)-5,7-dihydroxy-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-heptaen-15-one
• CAS: 134111-68-5
• 化学式: C₂₀H₁₂O₇
• 分子量: 364.311
• InChiKey: PEMPTCPFSPBRLS-WAPOTWQKSA-N

物化性质

• 沸点：
  729.5±60.0 °C(Predicted)
• 密度：
  1.85±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  27
• 可旋转键数：
  0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  97.8
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  preussomerin D 、 乙酸酐 在 4-二甲氨基吡啶 作用下， 以 丙酮 为溶剂， 以67%的产率得到[(1S,2R,4R,5R,12R)-7-acetyloxy-15-oxo-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-heptaen-5-yl] acetate
  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：——
• INHIBITION OF ISOPRENOID BIOSYNTHETIC PATHWAYS TO TREAT NEUROINFLAMMATORY DISORDERS
  申请人：TABACZYNSKI David A.

  公开号：US20160303146A1

  公开（公告）日：2016-10-20

  This invention provides methods and pharmaceutical compositions that can treat neuroinflammatory disease by reducing the production of pyrophosphate intermediates produced during the biosynthesis of isoprenoids. The pyrophosphate compounds being inhibited are normally produced through the mevalonate and non-mevalonate pathways of the host vertebrate organisms and their symbiotic and pathogenic microorganisms. The methods involve administering to a patient an inhibitor of the mevalonate-dependent pathway, an inhibitor of the non-mevalonate pathway, or combination of such inhibitors.
• INHIBITION OF ISOPRENOID BIOSYNTHETIC PATHWAYS TO TREAT AUTOIMMUNE DISORDERS
  申请人：TABACZYNSKI David A.

  公开号：US20160375041A1

  公开（公告）日：2016-12-29

  The invention provides methods and pharmaceutical compositions that can treat autoimmune disease by reducing the production of pyrophosphate intermediates produced during the biosynthesis of isoprenoids. The pyrophosphate compounds being inhibited are normally produced through the mevalonate and non-mevalonate pathways of the host vertebrate organisms and their symbiotic and pathogenic microorganisms. The methods involve administering to a patient an inhibitor of the mevalonate-dependent pathway, an inhibitor of the non-mevalonate pathway, or combination of such inhibitors.
• US6673937B2
  申请人：——

  公开号：US6673937B2

  公开（公告）日：2004-01-06