6,7,8,9-tetrahydroradicicol | 88929-18-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6,7,8,9-tetrahydroradicicol
• 英文别名: Tetrahydroradicicol；(4R,6R,8R)-16-chloro-17,19-dihydroxy-4-methyl-3,7-dioxatricyclo[13.4.0.06,8]nonadeca-1(15),16,18-triene-2,13-dione
• CAS: 88929-18-4
• 化学式: C₁₈H₂₁ClO₆
• 分子量: 368.814
• InChiKey: ZGZOBNGYHLFQFW-DFKRKDTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  96.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6,7,8,9-tetrahydroradicicol 在 甲醇 、 cerium(III) chloride hexahydrate 、 sodium tetrahydroborate 作用下， 反应 0.58h， 以32.7%的产率得到(4R,6R,8R,13R)-16-chloro-13,17,19-trihydroxy-4-methyl-3,7-dioxatricyclo[13.4.0.06,8]nonadeca-1(15),16,18-trien-2-one
  参考文献：
  名称：

  Synthesis and structure–activity relationships of radicicol derivatives and WNT-5A expression inhibitory activity

  摘要：

  WNT-5A, a secretory glycoprotein, is related to the proliferation of dermal papilla cells. To develop a hair-growth stimulant, we have been searching for inhibitors of WNT-5A expression. We identified radicicol (1) as an active compound, and synthesized several radicicol derivatives. Among them, 6,7-dihydro-10 alpha-hydroxy radicicol (31) was found to function as a new potent WNT-5A expression inhibitor with relatively low toxicity and excellent stability. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.04.060
• 作为产物：
  描述：

  根赤壳菌素 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 0.17h， 以1.6 mg的产率得到Hexahydroradicicol
  参考文献：
  名称：

  Search for Hsp90 Inhibitors with Potential Anticancer Activity:  Isolation and SAR Studies of Radicicol and Monocillin I from Two Plant-Associated Fungi of the Sonoran Desert

  摘要：

  In an effort to discover small molecule inhibitors of Hsp90, we have screened over 500 EtOAc extracts of Sonoran desert plant-associated fungi using a two-stage strategy consisting of a primary cell-based heat shock induction assay (HSIA) followed by a secondary biochemical luciferase refolding assay (LRA). Bioassay-guided fractionation of extracts active in these assays derived from Chaetomium chiversii and Paraphaeosphaeria quadriseptata furnished the Hsp90 inhibitors radicicol (1) and monocillin 1 (2), respectively. In SAR studies, 1, 2, and their analogues, 3-16, were evaluated in these assays, and the antiproliferative activity of compounds active in both assays was determined using the breast cancer cell line MCF-7. Radicicol and monocillin 1 were also evaluated in a solid-phase competition assay for their ability to bind Hsp90 and to deplete cellular levels of two known Hsp90 client proteins with relevance to breast cancer, estrogen receptor (ER), and the type 1 insulin-like growth factor receptor (IGF-1R). Some inferences on SAR were made considering the crystal structure of the N-terminus of yeast Hsp90 bound to 1 and the observed biological activities of 1-16. Isolation of radicicol and monocillin 1 in this study provides evidence that we have developed an effective strategy for discovering natural product-based Hsp90 inhibitors with potential anticancer activity.

  DOI：

  10.1021/np058095b

文献信息

• MACROCYCLIC COMPOUNDS USEFUL AS INHIBITORS OF KINASES AND HSP90
  申请人：Université de Strasbourg

  公开号：EP2136799B1

  公开（公告）日：2017-10-04
• Assay for identifying compounds which affect stability of mrna
  申请人：Katelic Tania

  公开号：US20070190532A1

  公开（公告）日：2007-08-16

  The present invention relates to an assay for the identification of biologically active compounds, in particular to a reporter gene assay for the identification of compounds, which have an effect on mRNA stability. More particularly, the present invention relates to a reporter gene expression system and cell lines comprising said expression system. The invention further relates to compounds which destabilise mRNA.
• ASSAY FOR IDENTIFYING COMPOUNDS WHICH AFFECT STABILITY OF MRNA
  申请人：Kastelic Tania

  公开号：US20090068654A1

  公开（公告）日：2009-03-12

  The present invention relates to an assay for the identification of biologically active compounds, in particular to a reporter gene assay for the identification of compounds, which have an effect on mRNA stability. More particularly, the present invention relates to a reporter gene expression system and cell lines comprising said expression system. The invention further relates to compounds which destabilise mRNA.
• US7598079B2
  申请人：——

  公开号：US7598079B2

  公开（公告）日：2009-10-06