(-)-trans-ethylkhellactone | 4969-82-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: (-)-trans-ethylkhellactone
• 英文别名: (9R)-10t-ethoxy-9r-hydroxy-8,8-dimethyl-9,10-dihydro-8H-pyrano[2,3-f]chromen-2-one；(9R)-10t-Aethoxy-9r-hydroxy-8,8-dimethyl-9,10-dihydro-8H-pyrano[2,3-f]chromen-2-on；trans-Ethylkhellacton；(-)-trans-Ethyl-khellactone；(9R,10S)-10-ethoxy-9-hydroxy-8,8-dimethyl-9,10-dihydropyrano[2,3-f]chromen-2-one
• CAS: 4969-82-8
• 化学式: C₁₆H₁₈O₅
• 分子量: 290.316
• InChiKey: UCLKQWHJVUDTFJ-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (-)-trans-ethylkhellactone 在 palladium on activated charcoal 、 溶剂黄146 作用下， 生成 (9R)-10t-ethoxy-9r-hydroxy-8,8-dimethyl-3,4,9,10-tetrahydro-8H-pyrano[2,3-f]chromen-2-one
  参考文献：
  名称：

  Constitution of Samidin, Dihydrosamidin and Visnadin¹

  摘要：

  DOI：

  10.1021/ja01570a062
• 作为产物：
  描述：

  (+)-沙米丁 在 sodium hydroxide 作用下， 生成 (-)-trans-ethylkhellactone
  参考文献：
  名称：

  Constitution of Samidin, Dihydrosamidin and Visnadin¹

  摘要：

  DOI：

  10.1021/ja01570a062

文献信息

• The Antagonistic Effects of Khellactones on Platelet-Activating Factor, Histamine, and Leukotriene D4.
  作者：Yoko AIDA、Toshio KASAMA、Naoki TAKEUCHI、Seisho TOBINAGA

  DOI：10.1248/cpb.43.859

  日期：——

  Khellactones of Peucedanum praeruptorum DUUN, including praeruptorins A (=Pd-Ia, 2) and B (=Pd-II, 11), had an antagonistic effect specifically on platelet aggregation induced by platelet activating factor (PAF) among various aggregating agents examined, and represent a new class of PAF antagonists. We examined the effects of twenty compounds on PAF-induced platelet aggregation and on histamine- and leukotriene D4 (LTD4)-induced contractions in isolated guinea pig ileum. Compounds 2, (±)-cis-3', 4'-diacetylkhellactone (3), (±)-cis-4'-acetyl-3'-crotonoylkhellactone (5), (±)-cis-4'-acetyl-3'-tetrolylkhellactone (6), (±)-cis-4'-acetyl-3'-tigloylkhellactone (7), (±)-cis-4'-acetyl-3'-(2"-methylbutyryl)khellactone (8), (±)-cis-3', 4'-ditigloylkhellactone (10), and 11 all strongly inhibited PAF-induced platelet aggregation. (±)-cis-4'-Acetyl-3'-(2"-methyl-2"-dodecenoyl)khellactone (9), (±)-cis-4'-ethyl-3'-tigloylkhellactone (13), (±)-cis-4'-ethyl-3'-[N-(2"-triethylammonio)ethylcarbamoyl]khellactone iodide (16), (±)-trans-3', 4'-diacetylkhellactone (18), (±)-trans-4'-acetyl-3'-crotonoylkhellactone (19), (±)-trans-4'-acetyl-3'-valerylkhellactone (20), (±)-trans-4'-acetyl-3'-isovalerylkhellactone (21), and (±)-trans-4'-acetyl-3'-tigloylkhellactone (22) were weakly inhibitory. Most of the compounds exhibited noncompetitive antagonist actions on histamine- and LTD4-induced contractions. The potencies of the antagonistic effects on histamine action were in the order 7=22≥2=8=10>6=11=13≥5>19=9 and those on LTD4 action were in the order 6=22=2>10=8>7=9=11≥13. Thus, compounds with potent PAF-antagonistic activities have the following features : cis isomers of khellactone at the C-3' and C-4' positions are more favorable than trans isomers, and the acyl moiety at the C-3' position of khellactone must be of an appropriate molecular size. In the case of histamine- and LTD4-antagonistic activities, both isomers show similar effects and acyl moieties of appropriate size are required at the C-3' and C-4' positions. These results are of interest in regard to the medicinal uses of Peucedanum species as a herbal drug.

  白花前胡所含的khellactones类化合物，包括前胡素A（=Pd-Ia，2）和前胡素B（=Pd-II，11），在各种促聚剂中，对血小板活化因子（PAF）诱导的血小板聚集具有特异性的拮抗作用，代表了一类新的PAF拮抗剂。我们研究了20种化合物对PAF诱导的血小板聚集以及对离体豚鼠回肠中组胺和白三烯D4（LTD4）诱导的收缩的影响。化合物2、(±)-顺式-3'，4'-二乙酰基khellactone（3）、(±)-顺式-4'-乙酰基-3'-丁烯酰基khellactone（5）、(±)-顺式-4'-乙酰基-3'-四羟基苯甲酰基khellactone（6）、(±)-顺式-4'-乙酰基-3'-惕各酰基khellactone（7）、(±)-顺式-4'-乙酰基-3'-(2"-甲基丁酰基)khellactone（8）、(±)-顺式-3'，4'-二惕各酰基khellactone（10）和11均强烈抑制PAF诱导的血小板聚集。(±)-顺式-4'-乙酰基-3'-(2"-甲基-2"-十二碳烯酰基)khellactone（9）、(±)-顺式-4'-乙基-3'-惕各酰基khellactone（13）、(±)-顺式-4'-乙基-3'-[N-(2"-三乙基铵)乙基氨基甲酰基]khellactone碘化物（16）、(±)-反式-3'，4'-二乙酰基khellactone（18）、(±)-反式-4'-乙酰基-3'-丁烯酰基khellactone（19）、(±)-反式-4'-乙酰基-3'-戊酰基khellactone（20）、(±)-反式-4'-乙酰基-3'-异戊酰基khellactone（21）和(±)-反式-4'-乙酰基-3'-惕各酰基khellactone（22）的抑制作用较弱。大多数化合物对组胺和LTD4诱导的收缩表现出非竞争性拮抗作用。对组胺作用的拮抗效能顺序为7=22≥2=8=10>6=11=13≥5>19=9，对LTD4作用的拮抗效能顺序为6=22=2>10=8>7=9=11≥13。因此，具有强PAF拮抗活性的化合物具有以下特点：C-3'和C-4'位置的顺式异构体比反式异构体更有利，khellactone的C-3'位置的酰基部分必须具有适当的分子大小。对于组胺和LTD4的拮抗活性，两种异构体显示出类似的效果，C-3'和C-4'位置需要适当大小的酰基部分。这些结果对于作为草药药用的Peucedanum属植物的医疗用途具有重要意义。
• The antagonist effects of compounds derived from khellactone on platelet-activating factor.
  作者：Naoki Takeuchi、Toshio Kasama、Kiyoshi Mayuzumi、Kenji Tamaru、Hiroaki Fukaya、Takayuki Ohno、Seisho Tobinaga

  DOI：10.1248/cpb.36.4221

  日期：——

  Crude coumarin constituents of Peucedanum praeruptorum Duun. including praeruptorin A (=Pd-Ia)(2) and B (=Pd-II)(11) had an antagonistic effect on a specific platelet activating factor (PAF) in the platelet aggregation induced by several aggregating agents. This provides a new class of PAF antagonists. Studies of the structure-activity relationship with khellactone (1) derivatives and PAF antagonistic activity indicate that the cis isomers of 1 at the C-3' and C-4' positions are more favorable than trans isomers, and the acyl moiety at the C-3' position of 1 requires an appropriate molecular size.

  Peucedanum praeruptorum Duun. 的粗类香豆素成分，包括 praeruptorin A (=Pd-Ia)(2) 和 B (=Pd-II)(11)，对由多个聚集剂诱导的血小板聚集中一种特定的血小板激活因子 (PAF) 产生了拮抗作用。这提供了一类新的 PAF 拮抗剂。对 khellactone (1) 衍生物与 PAF 拮抗活性之间的结构-活性关系研究表明，1 在 C-3' 和 C-4' 位点的顺式异构体比反式异构体更为有利，并且 1 在 C-3' 位点的酰基部分需要适当的分子大小。
• A Concise Route for the Synthesis of Biologically Interesting Pyranocoumarins - Seselin, (±)-<i>cis</i>-Khellactone, (±)-Quianhucoumarin D, and the (±)-5-Deoxyprotobruceol-I Regioisomer
  作者：Yong Rok Lee、Won Kyong Lee、Seok Kyun Noh、Won Seok Lyoo

  DOI：10.1055/s-2006-926329

  日期：——

  An efficient synthesis of pyranocoumarins is achieved starting from 2H-pyrans. This process provides naturally occurring seselin, cis-khellactone, quianhucoumarin D, and the 5-deoxyprotobruceol-I regioisomer.

  高效合成吡喃香豆素的过程是以2H-吡喃为起始材料。该过程提供了天然存在的塞斯林、顺式凯拉克酮、奇安胡香豆素D以及5-去氧原白头翁素I的区位异构体。
• ON KHELLACTONE
  作者：E. Späth、W. Gruber、O. Matzke

  DOI：10.1139/v53-097

  日期：1953.8.1

  A hitherto unknown minor constituent of the seeds of Ammivisnaga Lam is converted under the influence of 5% alcoholic potassium hydroxide into a compound which seems to be a coumarin. Treatment with methyl-alcoholic alkali yields a substance C₁₅H₁₆O₅, whereas treatment with ethyl-alcoholic alkali gives a substance C₁₆H₁₈O₅. Dehydrating agents convert both optically active compounds into the same optically inactive dehydration product C₁₄H_l2O₄ (Substance A). The further investigations carried out with Substance A were: oxidation, after methylation, which yielded α-hydroxyisobutyric acid; fusion with potassium hydroxide, which gave phloroglucinol. On treatment with diluted caustic alkalies two definite products, C₁₀H₆O₅, probably an acid, and C₁₁H₈O₄, a ketone, were obtained.

  迄今为止未知的Ammivisnaga Lam种子的微小成分，在5%酒精氢氧化钾的影响下转化为一种似乎是香豆素的化合物。用甲基醇性碱处理可得到一种C₁₅H₁₆O₅的物质，而用乙基醇性碱处理可得到一种C₁₆H₁₈O₅的物质。脱水剂将两种对映活性化合物转化为同一种对映不活性的脱水产物C₁₄H_l2O₄（物质A）。对物质A进行的进一步研究包括：甲基化后的氧化，产生α-羟基异丁酸；与氢氧化钾熔合，产生邻苯三酚。在用稀碱性碱处理时，得到了两种明确的产物，C₁₀H₆O₅，可能是一种酸，和C₁₁H₈O₄，一种酮。
• Natural Product-like Combinatorial Libraries Based on Privileged Structures. 3. The “Libraries from Libraries” Principle for Diversity Enhancement of Benzopyran Libraries
  作者：K. C. Nicolaou、J. A. Pfefferkorn、S. Barluenga、H. J. Mitchell、A. J. Roecker、G.-Q. Cao

  DOI：10.1021/ja0020355

  日期：2000.10.1

  As described in the preceding two papers, our interest in the construction of natural and natural product-like libraries for chemical biology studies led to the development of a new solid-phase cycloloading strategy for the construction of substituted benzopyrans. Herein, we report a parallel solution-phase method that facilitates the enhancement of both the size and diversity of these non-oligomeric benzopyran libraries using the "libraries from libraries" principle. We examine the rationale behind the use of this tandem strategy to construct discrete small molecule libraries, and describe the development of a polymer-assisted solution-phase (PASP) methodology necessary to effect the required transformations. Once developed, this chemistry is applied to two demonstration libraries.