2,3-dihydro-5-hydroxy-6,8,8-trimethyl-2-phenyl-4H-1-benzopyran-4,7(8H)-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2,3-dihydro-5-hydroxy-6,8,8-trimethyl-2-phenyl-4H-1-benzopyran-4,7(8H)-dione
• 英文别名: 5-hydroxy-6,8,8-trimethyl-2-phenyl-2,3-dihydrochromene-4,7-dione
• 化学式: C₁₈H₁₈O₄
• 分子量: 298.339
• InChiKey: CLTODYVARKMPCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-Cyclohexene-1,3-dione,2-[(2E)-1-hydroxy-3-phenyl-2-propenylidene]-5-methoxy-4,6,6-trimethyl-,(2E)- 在 盐酸 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 1.0h， 以40%的产率得到champanone B
  参考文献：
  名称：

  Total synthesis and bioactivity of unique flavone desmosdumotin B and its analogs

  摘要：

  The first total synthesis of a unique flavone natural product, desmosdumotin B (1), was accomplished. Furthermore, three novel flavonoids, 6-8, and a novel chalcone, 9, were synthesized. The new compounds were evaluated as in vitro inhibitors of human cancer cell growth. The synthetic 1 showed significant cytotoxic activity against a multi-drug resistant cell line (KB-VIN) with an ED50 value of 2.0 mu g/mL compared to > 40 mu g/mL against the parental KB cell line. Flavone 7 displayed selective activity against 1A9 ovarian carcinoma with an ED50 value of 0.7 mu g/mL. Selected 1-analogs and synthetic intermediates were also screened for antitumor-promoting effects as inhibitors of EBV-EA activation. Among them, trihydroxyacetophenone derivatives 11 and 14 showed good activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.04.070

文献信息

• Desmosdumotins, the Method for Preparing the Same and Use as Anti-Tumor or Anti-AIDS Agents
  申请人：Wu Jiuhong

  公开号：US20090233998A1

  公开（公告）日：2009-09-17

  This invention discloses the method for preparing desmosdumotin C, the series of desmosdumotin C derivatives and their manufactures, and the total synthesis of desmosdumotin B. The invention also discloses uses of the derivatives and pharmaceutical compositions containing the same in preparation of medicines for treatment of tumor or AIDS.

  本发明揭示了制备desmosdumotin C的方法、desmosdumotin C衍生物系列及其制备方法，以及desmosdumotin B的全合成方法。本发明还揭示了衍生物的用途和含有它们的制药组合物，用于制备治疗肿瘤或艾滋病的药物。
• Novel cyclopeptide and unique flavone from Desmos rostrata. Total synthesis of desmorostratone
  作者：Ngoc Tuan Nguyen、Van Cuong Pham、Marc Litaudon、Françoise Guéritte、Bernard Bodo、Van Tuyen Nguyen、Van Hung Nguyen

  DOI：10.1016/j.tet.2009.06.017

  日期：2009.8

  Two new compounds, a cyclic peptide desmocyclopeptide (1) and a special flavone desmorostratone (2) were isolated from the stem bark of Desmos rostrata, along with two known compounds, desmosdumotins B (3) and C (4). Their Structures were established on the basis of the spectral data, including mass spectrometry and 2D NMR. The total synthesis of desmorostratone (2) was performed in order to confirm its structure as well as that of desmosdumotin C (4), which was a tautomeric mixture in the solution. Finally, cytotoxity of these compounds were evaluated. Desmosdumotin C (4) displayed a moderate inhibition activity against KB cell line with an IC50 of 19.2 mu M, whereas the other products showed a weak inhibition against the same cell line target. (c) 2009 Elsevier Ltd. All rights reserved.
• US7834216B2
  申请人：——

  公开号：US7834216B2

  公开（公告）日：2010-11-16
• Total synthesis and bioactivity of unique flavone desmosdumotin B and its analogs
  作者：Kyoko Nakagawa-Goto、Kenneth F. Bastow、Jiu-Hong Wu、Harukuni Tokuda、Kuo-Hsiung Lee

  DOI：10.1016/j.bmcl.2005.04.070

  日期：2005.6

  The first total synthesis of a unique flavone natural product, desmosdumotin B (1), was accomplished. Furthermore, three novel flavonoids, 6-8, and a novel chalcone, 9, were synthesized. The new compounds were evaluated as in vitro inhibitors of human cancer cell growth. The synthetic 1 showed significant cytotoxic activity against a multi-drug resistant cell line (KB-VIN) with an ED50 value of 2.0 mu g/mL compared to > 40 mu g/mL against the parental KB cell line. Flavone 7 displayed selective activity against 1A9 ovarian carcinoma with an ED50 value of 0.7 mu g/mL. Selected 1-analogs and synthetic intermediates were also screened for antitumor-promoting effects as inhibitors of EBV-EA activation. Among them, trihydroxyacetophenone derivatives 11 and 14 showed good activity. (c) 2005 Elsevier Ltd. All rights reserved.