4-Cyclohexene-1,3-dione,2-[(2E)-1-hydroxy-3-phenyl-2-propenylidene]-5-methoxy-4,6,6-trimethyl-,(2E)- | 426823-13-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-Cyclohexene-1,3-dione,2-[(2E)-1-hydroxy-3-phenyl-2-propenylidene]-5-methoxy-4,6,6-trimethyl-,(2E)-
• 英文别名: desmosdumotin C
• CAS: 426823-13-4
• 化学式: C₁₉H₂₀O₄
• 分子量: 312.365
• InChiKey: TYOLMDXXIKMMEZ-RICRECKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-Cyclohexene-1,3-dione,2-[(2E)-1-hydroxy-3-phenyl-2-propenylidene]-5-methoxy-4,6,6-trimethyl-,(2E)- 在 硫酸 、 碘 、 二甲基亚砜 作用下， 以71%的产率得到desmosdumotin B
  参考文献：
  名称：

  Novel cyclopeptide and unique flavone from Desmos rostrata. Total synthesis of desmorostratone

  摘要：

  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.

  DOI：

  10.1016/j.tet.2009.06.017
• 作为产物：
  描述：

  2-acetyl-3,5-dihydroxy-4,6,6-trimethylcyclohexa-2,4-dienone 在 氢氧化钾 作用下， 以 甲醇 、 乙醚 、 乙醇 、 水 、 乙酸乙酯 为溶剂， 反应 26.0h， 生成 4-Cyclohexene-1,3-dione,2-[(2E)-1-hydroxy-3-phenyl-2-propenylidene]-5-methoxy-4,6,6-trimethyl-,(2E)-
  参考文献：
  名称：

  First Total Synthesis of Desmosdumotin C^†

  摘要：

  Desmosdumotin C (1), a novel compound isolated from the roots of Desmos dumosus, was synthesized from 2,4,6-trihydroxyacetophenone (2), confirming the assigned structure of the natural product.

  DOI：

  10.1081/scc-200063907

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。
• Antitumor Agents 260. New Desmosdumotin B Analogues with Improved In Vitro Anticancer Activity
  作者：Kyoko Nakagawa-Goto、Kenneth F. Bastow、Tzu-Hsuan Chen、Susan L. Morris-Natschke、Kuo-Hsiung Lee

  DOI：10.1021/jm701208v

  日期：2008.6.1

  Sixteen analogues (3-16, 33, and 48) of the unique flavonoid desmosdumotin B (1) were prepared and evaluated as in vitro inhibitors of the human KB cancer cell line and its MDR subclone, KB-VIN. 6,8,8-Triethyl analogues 10-13 showed enhanced KB-VIN selectivity. In particular, 4'-alkyl derivatives 11 (4'-Me) and 12 (4'-Et) showed significant ED50 values of 0.03 and 0.025 mu g/mL, respectively, against KB-VIN with selectivities of > 460- and 320-fold compared with that of KB. This report is the first to describe compounds showing such high activity against MDR cells versus non-MDR cells. The unique activity of 1-analogues is likely MDR-mediated because cotreatment with verapamil, a P-gp inhibitor, partially reversed the selective toxicity of both 1 and 10. Interestingly, only 1-analogues with a naphthalene B-ring (8 and 14) showed significant cytotoxic activity against KB; and other cancer cell lines. Thus, 1-analogues might be a new class of potent drug candidates, especially as 11 and 12 express direct selective action against tumors expressing MDR.
• 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.
• US7834216B2
  申请人：——

  公开号：US7834216B2

  公开（公告）日：2010-11-16
• 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.