cis-10-ethoxy-9-hydroxy-8,8-dimethyl-9,10-dihydro-8H-pyrano[2,3-f]chromen-2-one

• 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: cis-10-ethoxy-9-hydroxy-8,8-dimethyl-9,10-dihydro-8H-pyrano[2,3-f]chromen-2-one
• 英文别名: (+/-)-cis-4'-ethylkhellactone；(+/-)-cis-Ethylkhellacton；(-)-cis-Ethyl-khellactone；(9S,10S)-10-ethoxy-9-hydroxy-8,8-dimethyl-9,10-dihydropyrano[2,3-f]chromen-2-one
• 化学式: C₁₆H₁₈O₅
• 分子量: 290.316
• InChiKey: UCLKQWHJVUDTFJ-GJZGRUSLSA-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：

  cis-10-ethoxy-9-hydroxy-8,8-dimethyl-9,10-dihydro-8H-pyrano[2,3-f]chromen-2-one 在 吡啶 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 生成 (+/-)-cis-3'--4'-ethylkhellactone
  参考文献：
  名称：

  The antagonist effects of compounds derived from khellactone on platelet-activating factor.

  摘要：

  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。

  DOI：

  10.1248/cpb.36.4221
• 作为产物：
  描述：

  邪蒿素 在 indium(III) chloride 、 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 cis-10-ethoxy-9-hydroxy-8,8-dimethyl-9,10-dihydro-8H-pyrano[2,3-f]chromen-2-one
  参考文献：
  名称：

  A Concise Route for the Synthesis of Biologically Interesting Pyranocoumarins - Seselin, (±)-cis-Khellactone, (±)-Quianhucoumarin D, and the (±)-5-Deoxyprotobruceol-I Regioisomer

  摘要：

  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。

  DOI：

  10.1055/s-2006-926329

文献信息

• 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。
• Dihydropyranocoumarins from roots of Peucedanum japonicum
  作者：Yasumasa Ikeshiro、Izumi Mase、Yutaka Tomita

  DOI：10.1016/0031-9422(92)80463-o

  日期：1992.12

  Two new angular-type dihydropyranocoumarins, peujaponisin and (-)-visnadin, were isolated from the roots of Pencedanum japonicum and the structures determined as 3'(S)-senecioyloxy-4'(S)-isovaleryloxy-3',4'-dihydroseselin and 3'(S)-2-methylbutyryloxy-4'(S)-acetoxy-3',4'-dihydroseselin, respectively, by spectroscopic analysis and chemical reactions.
• 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。
• 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。