preussomerin G | 134111-72-1

• 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 G
• 英文别名: (1S,2R,4S,12R)-7-hydroxy-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-5,15-dione
• CAS: 134111-72-1
• 化学式: C₂₀H₁₀O₇
• 分子量: 362.295
• InChiKey: YMTRIUFFDHMDKK-WTGUMLROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  27
• 可旋转键数：
  0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  94.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-甲基-3-(2,4,5-三甲基-3,6-二氧代环己-1,4-二烯-1-基)丁酸 、 preussomerin G 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以38%的产率得到[(1S,2R,4S,12R)-5,15-dioxo-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-7-yl] 3-methyl-3-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanoate
  参考文献：
  名称：

  由真菌化合物合成生物还原酯。

  摘要：

  已经合成了四种新的生物还原酯（7-10）。它们的结构由三甲基锁构成，该三锁含醌丙酸与真菌细胞毒性化合物具有酯键；preussomerin G（1），preussomerin I（2），phaseolinone（3）和phomenone（4）。合成的酯旨在通过还原性缺氧和过表达而通过还原性活化作用专门作用于癌细胞。因此，在整个正常细胞中分布期间，毒性将降低。在癌细胞系中使用已报道的还原酶（即BC-1细胞和NCI-H187）以及不含还原酶的癌细胞来确定其抗癌活性。KB单元格。当考虑每种细胞系时，结果表明结构修饰产生的7-10比其母体化合物（1-4）引起的细胞毒性更小。7和8对NCI-H187具有强烈的细胞毒性（IC50 <或= 5 microg / ml），而9和10对BC-1细胞具有中等的细胞毒性（IC50 = 6-10 microg / ml）。进一步研究了代表的酚酯（8）和​​醇酯（9）

  DOI：

  10.1248/cpb.55.930
• 作为产物：
  描述：

  preussomerin E 在 sodium acetate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 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

• Unified Route to the Palmarumycin and Preussomerin Natural Products. Enantioselective Synthesis of (−)-Preussomerin G
  作者：Anthony G. M. Barrett、Frank Blaney、Andrew D. Campbell、Dieter Hamprecht、Thorsten Meyer、Andrew J. P. White、David Witty、David J. Williams

  DOI：10.1021/jo0110247

  日期：2002.5.1

  inhibitor (-)-preussomerin G has been synthesized, achieving the first enantioselective route for accessing this family of natural products. Highlights of the synthetic work include an asymmetric epoxidation of a cyclic enone in excellent yield and enantiomeric excess and a potentially biomimetic oxidative spirocyclization for the introduction of the bis-spiroketal array unique to the preussomerin natural

  通过鉴定出其中三种天然产物的绝对立体化学，已经实现了八烷基金霉素家族的八个成员的总合成。另外，已经合成了ras-法呢基转移酶抑制剂（-）-前体小体G，实现了获得该天然产物家族的第一对映选择性途径。合成工作的重点包括以极佳的收率和对映异构体过量进行环状烯酮的不对称环氧化，以及潜在的仿生氧化螺环化反应，以引入早螺旋体天然产物所独有的双螺酮阵列。
• 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。
• Preussomerins and Deoxypreussomerins: Novel Inhibitors of Ras Farnesyl-Protein Transferase
  作者：Sheo B. Singh、Deborah L. Zink、Jerrold M. Liesch、Richard G. Ball、Michael A. Goetz、Evon A. Bolessa、Robert A. Giacobbe、Keith C. Silverman、Gerald F. Bills

  DOI：10.1021/jo00100a035

  日期：1994.10

  Farnesylation of Ras (p21) by farnesyl-protein transferase (FPTase) precedes association of Ras with the plasma membrane which is essential for Ras-mediated cell-transforming activity. Our continuing search for FPTase inhibitors led us to isolate a number of novel preussomerins and deoxypreussomerins from the extracts of a dung-inhabiting coelomycetous fungus from Chaco Province, Argentina. Isolation, structure elucidation, chemistry, and structure-activity relationships of the natural products and derivatives have been described.
• Total Syntheses of (±)-Preussomerins G and I
  作者：Shannon Chi、Clayton H. Heathcock

  DOI：10.1021/ol990020+

  日期：1999.7.1

  Preussomerins G and I (2 and 3) have been synthesized for the first time. The key reaction in the synthesis is a possibly biomimetic tautomerization reaction depicted in Scheme 3 and the foregoing graphic. The driving force for this interesting rearrangement is primarily derived from the increase in resonance energy associated with converting a naphthalene ring into two isolated benzene rings.
• 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：——