2,3-dihydro-5-methoxy-2-phenylmethylene-1H-indenone | 75258-84-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2,3-dihydro-5-methoxy-2-phenylmethylene-1H-indenone
• 英文别名: 5-Methoxy-2-[1-phenyl-meth-(E)-ylidene]-indan-1-one；5-Methoxy-2-benzylidene-1-indanone；2-benzylidene-5-methoxy-3H-inden-1-one
• CAS: 75258-84-3
• 化学式: C₁₇H₁₄O₂
• 分子量: 250.297
• InChiKey: PMDOZLNQFMRWIN-UHFFFAOYSA-N

物化性质

• 沸点：
  447.6±45.0 °C(Predicted)
• 密度：
  1.210±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-dihydro-5-methoxy-2-phenylmethylene-1H-indenone 在 palladium on activated charcoal 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 为溶剂， 反应 14.5h， 生成 9a-benzyl-7-methoxy-1,2,8,9,9a-tetrahydro-3H-fluoren-3-one
  参考文献：
  名称：

  A Structure-Guided Approach to an Orthogonal Estrogen-Receptor-Based Gene Switch Activated by Ligands Suitable for in Vivo Studies

  摘要：

  A strategy to obtain a fully orthogonal estrogen-receptor-based gene switch responsive to molecules with acceptable pharmacological properties is presented. From a series of tetrahydrofluorenones active on the wild-type estrogen receptor (ER) an inactive analogue is chosen as a new lead compound. Coevolution of receptor mutants and ligands leads to an ER-based gene switch suitable for studies in animal models.

  DOI：

  10.1021/jm060516e
• 作为产物：
  描述：

  5-甲氧基-1-茚酮 、 苯甲醛 生成 2,3-dihydro-5-methoxy-2-phenylmethylene-1H-indenone
  参考文献：
  名称：

  体内结构-活性关系研究支持双特异性磷酸酶的变构靶向

  摘要：

  探测DUSP6的变构抑制：我们使用转基因斑马鱼来识别的类似物（呈现体内结构-活性关系（SAR）途径Ë）-2-苄基-3-（环己基）-2,3-二氢-1- ħ茚‐1-one (BCI) 作为双特异性磷酸酶 6 (DUSP6) 的新型变构抑制剂。一种化合物 BCI-215 表现出与母体化合物 BCI 相似的活性，但缺乏生物体或细胞毒性。

  DOI：

  10.1002/cbic.201402000

文献信息

• In Vivo Structure-Activity Relationship Studies Support Allosteric Targeting of a Dual Specificity Phosphatase
  作者：Vasiliy N. Korotchenko、Manush Saydmohammed、Laura L. Vollmer、Ahmet Bakan、Kyle Sheetz、Karl T. Debiec、Kristina A. Greene、Christine S. Agliori、Ivet Bahar、Billy W. Day、Andreas Vogt、Michael Tsang

  DOI：10.1002/cbic.201402000

  日期：2014.7.7

  Probing allosteric inhibition of DUSP6: We present an in vivo structure–activity relationship (SAR) approach using transgenic zebrafish to identify analogues of (E)‐2‐benzylidene‐3‐(cyclohexylamino)‐2,3‐dihydro‐1H‐inden‐1‐one (BCI) as novel allosteric inhibitors of dual specificity phosphatase 6 (DUSP6). One compound, BCI‐215, exhibited similar activity to parent compound BCI but lacked organismal

  探测DUSP6的变构抑制：我们使用转基因斑马鱼来识别的类似物（呈现体内结构-活性关系（SAR）途径Ë）-2-苄基-3-（环己基）-2,3-二氢-1- ħ茚‐1-one (BCI) 作为双特异性磷酸酶 6 (DUSP6) 的新型变构抑制剂。一种化合物 BCI-215 表现出与母体化合物 BCI 相似的活性，但缺乏生物体或细胞毒性。
• Orthogonal gene switches
  申请人：Ciliberto Gennaro

  公开号：US20070087346A1

  公开（公告）日：2007-04-19

  The present invention relates to an orthogonal gene switch for regulating the expression of a desired gene. The gene switch comprises a chimeric transcription factor that does not respond to endogenous ligands, and a ligand that is capable of activating the chimeric transcription factor but not endogenous transcription factors. The present invention also relates to the method of constructing the orthogonal gene switch.

  本发明涉及一种正交基因开关，用于调节所需基因的表达。该基因开关包括一个嵌合转录因子，不响应内源性配体，以及一种配体，能够激活嵌合转录因子，但不能激活内源性转录因子。本发明还涉及构建正交基因开关的方法。
• CN115417871
  申请人：——

  公开号：——

  公开（公告）日：——
• A Structure-Guided Approach to an Orthogonal Estrogen-Receptor-Based Gene Switch Activated by Ligands Suitable for in Vivo Studies
  作者：Olaf Kinzel、Daniela Fattori、Ester Muraglia、Paola Gallinari、Maria Chiara Nardi、Chantal Paolini、Giuseppe Roscilli、Carlo Toniatti、Odalys Gonzalez Paz、Ralph Laufer、Armin Lahm、Anna Tramontano、Riccardo Cortese、Raffaele De Francesco、Gennaro Ciliberto、Uwe Koch

  DOI：10.1021/jm060516e

  日期：2006.9.1

  A strategy to obtain a fully orthogonal estrogen-receptor-based gene switch responsive to molecules with acceptable pharmacological properties is presented. From a series of tetrahydrofluorenones active on the wild-type estrogen receptor (ER) an inactive analogue is chosen as a new lead compound. Coevolution of receptor mutants and ligands leads to an ER-based gene switch suitable for studies in animal models.
• In vitro Anti-Trypanosomal Activities of Indanone-Based Chalcones
  作者：Richard M. Beteck、Lesetje J. Legoabe、Michelle Isaacs、Heinrich C. Hoppe

  DOI：10.1055/a-0775-0737

  日期：2019.6

  Human African trypanosomiasis is a neglected infectious disease that affects mostly people living in the rural areas of Africa. Current treatment options are limited to just four drugs that have been in use of four to nine decades. The life-threatening toxic side-effects associated with the use of these drugs are disconcerting. Poor efficacy, low oral bioavailability, and high cost are other shortcomings of current HAT treatments. Evaluating the potentials of known hits for other therapeutic areas may be a fast and convenient method to discover new hit compounds against alternative targets. A library of 34 known indanone based chalcones was screened against T.b. brucei and nine potent hits, having IC50 values between 0.5–8.9 µM, were found. The SAR studies of this series could provide useful information in guiding future exploration of this class of compounds in search of more potent, safe, and low cost anti-trypanosomal agents. Graphical Abstract

  人类非洲锥虫病是一种被忽视的传染病，主要影响生活在非洲农村地区的人群。目前的治疗选择仅限于四种药物，这些药物已经使用了四到九十年。与使用这些药物相关的危及生命的毒副作用令人担忧。目前非洲锥虫病治疗的其他缺点包括疗效差、口服生物利用度低和成本高。评估已知药物对其他治疗领域的潜力可能是一种快速和便捷的方法，以发现针对其他靶点的新药物化合物。对包含34种已知基于茚酮的查尔酮的化合物库进行了筛选，针对T.b. brucei，找到了九种有效化合物，IC50值介于0.5-8.9 µM之间。这一系列的结构活性关系研究可能为引导未来探索这一类化合物以寻找更有效、安全和低成本的抗锥虫药物提供有用信息。【图形摘要】