(+/-)-quianhucoumarin D

• 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: (+/-)-quianhucoumarin D
• 英文别名: qianhucomarin D；(+/-)-9r,10c-diacetoxy-8,8-dimethyl-9,10-dihydro-8H-pyrano[2,3-f]chromen-2-one；(+/-)-9r,10c-Diacetoxy-8,8-dimethyl-9,10-dihydro-8H-pyrano[2,3-f]chromen-2-on；Qianhucoumarin D；[(9S,10S)-9-acetyloxy-8,8-dimethyl-2-oxo-9,10-dihydropyrano[2,3-f]chromen-10-yl] acetate
• 化学式: C₁₈H₁₈O₇
• 分子量: 346.337
• InChiKey: YJOWXMGENDGFDH-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1a,9c-dihydro-2,2-dimethyl-2H,8H-oxireno[c]pyrano[2,3-f][1]benzopyran-8-one 在 吡啶 、 甲醇 、 硼酸三钠 、 氢氧化钾 、 硫酸 作用下， 生成 (+/-)-quianhucoumarin D
  参考文献：
  名称：

  Schroeder et al., Chemische Berichte, 1959, vol. 92, p. 2338,2362

  摘要：

  DOI：

文献信息

• イソサミジン類縁体およびサミジン類縁体の製造方法
  申请人：公立大学法人大阪府立大学

  公开号：JP2018145120A

  公开（公告）日：2018-09-20

  【課題】イソサミジン類縁体あるいはサミジン類縁体の工業的規模での簡便な製造方法の提供。【解決手段】下式（１）で示される化合物を行う工程、１）セネシオイル化、及び、2）アセチル化を行う工程を含む製造方法。［ＸはＯ等；Ｒ１は各々独立してＣ１〜３アルキル基等；Ｒ２はＨ等；Ｒ３はＣ１〜３アルキル基；ｍは０〜２の整数；ｎは１又は２；記号＊は不斉中心を表す］【選択図】なし

  提供工业规模下简便的制造方法，包括进行以下步骤：1）Senecioylation，和2）Acetylation。【X为O等；R1为各自独立的C1-3烷基等；R2为H等；R3为C1-3烷基；m为0-2的整数；n为1或2；符号*表示不对称中心】【选择图】无
• 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。
• Anti-AIDS Agents. 15. Synthesis and Anti-HIV Activity of Dihydroseselins and Related Analogs
  作者：Li Huang、Yoshiki Kashiwada、L. Mark Cosentino、Sharon Fan、Chin-Ho Chen、Andrew T. McPhail、Toshihiro Fujioka、Kunihide Mihashi、Kuo-Hsiung Lee

  DOI：10.1021/jm00049a014

  日期：1994.11

  derivatives, seselin (3) and (+/-)-cis-(4), (+)-cis- (5), and (+/-)-trans-dihydroseselin-3',4'-diol (7) were also tested for their in vitro anti-HIV activity. An optically pure compound, 3',4'-di-O-(-)-camphanoyl-(+)-cis-khellactone (16), showed potent inhibitory activity and remarkable selectivity against HIV replication. The EC50 value and in vitro therapeutic index (TI) of 16 are 4 x 10(-4) microM and

  为了评估其抗HIV活性，合成了42种基于Suksdorfin（1）结构的二氢香豆素。这些合成衍生物包括3'，4'-二-O-酰基-和3'-或4'-O-酰基-顺式-二氢芝麻素（8-21）和3'，4'-反式-二氢芝麻素与O-酰基和/或在3'和4'位置（6、22-43）的O-烷基。还制备了两个4'-叠氮基（44、45）和三个4'-烷基酰胺基（46、48、49）衍生物。通过使用光学纯试剂，合成了三对非对映异构体，并将其分离为光学纯化合物（14、15、16、17、38、39）。塞斯林（3）和（+/-）-顺-（4），（+）-顺-（5）和（+/-）-反-二氢塞塞林3'，4'与上述合成衍生物一起还测试了-二醇（7）的体外抗HIV活性。光学纯的化合物3'，4' -di-O-（-）-camphanoyl-（+）-cis-khellactone（16）具有较强的抑制活性，并且对HIV复制具有明显的选择性。EC50值和体外治疗指数（TI）为16分别为4
• 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。
• Synthesis and Cytotoxic Activity of Pyranocoumarins of the Seselin and Xanthyletin Series
  作者：Prokopios Magiatis、Eleni Melliou、Alexios-Leandros Skaltsounis、Sofia Mitaku、Stéphane Léonce、Pierre Renard、Alain Pierré、Ghanem Atassi

  DOI：10.1021/np9800295

  日期：1998.8.1

  The synthesis of known (3-6) and new (7-10 and 14-22) coumarins in the seselin and xanthyletin series is described. The cytotoxic activity of compounds 3-22 was carried out in vitro on L-1210 cells. The most active compounds were 9, 16, 18, and 20 in the seselin series and 10, 17, and 19 in the xanthyletin series. Structure-activity relationships are discussed.