3,5-bis(tetrahydro-2H-pyran-2-yloxy)benzaldehyde | 268232-54-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,5-bis(tetrahydro-2H-pyran-2-yloxy)benzaldehyde
• 英文别名: 3,5-Bis[(tetrahydro-2H-pyran-2-yl)oxy]-benzaldehyde；3,5-bis(oxan-2-yloxy)benzaldehyde
• CAS: 268232-54-8
• 化学式: C₁₇H₂₂O₅
• 分子量: 306.359
• InChiKey: AUPXTEMIFWYDDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,5-bis(tetrahydro-2H-pyran-2-yloxy)benzaldehyde 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 正丁基锂 、 三甲胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 环己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 5-[(4-hydroxyphenyl)ethynyl]-1,3-benzenediol
  参考文献：
  名称：

  白藜芦醇类似物的合成及其抗氧化活性评价

  摘要：

  邮箱：[e-mail]；[e-mail] (JT Lee) 2013 年 12 月 18 日接收，2014 年 1 月 14 日接受 关键词：芪、白藜芦醇类似物、抗氧化剂、ABTS 活性氧（ROS）是指体内产生的自由基，氧分子是由-正常代谢过程中的产物，通过碳水化合物、脂肪和蛋白质的氧化产生能量。自由基如超氧阴离子自由基（O

  DOI：

  10.5012/bkcs.2014.35.5.1549
• 作为产物：
  描述：

  3,5-二羟基苯甲酸甲酯 在 4-甲基苯磺酸吡啶 、 pyridinium chlorochromate 作用下， 以 氯仿 为溶剂， 反应 18.0h， 生成 3,5-bis(tetrahydro-2H-pyran-2-yloxy)benzaldehyde
  参考文献：
  名称：

  白藜芦醇的新类似物：结肠癌细胞增殖和代谢的抑制

  摘要：

  白藜芦醇是存在于红葡萄皮中的植物化学物质，因此是红酒以及各种浆果和坚果中的一种。它是一种抗氧化剂，在临床前的啮齿类动物致癌模型中显示出化学预防癌症的特性。白藜芦醇的生物利用度低，因为它会迅速代谢为葡萄糖醛酸和硫酸盐。酚的共轭代谢产物的药理活性通常远低于其代谢祖细胞的药理活性。因此，旨在减慢酚的代谢结合速率的化学合成操作可以产生具有提高的生物利用度和功效的类似物。在这里，我们描述了一系列新的白藜芦醇类似物的Wittig-Horner-Emmons反应的合成，其中苯酚部分被羟甲基和/或甲氧基系统地取代。II期代谢酶制剂对缺少酚基团的类似物进行孵育时，几乎不会生成或仅生成少量的缀合物。新的类似物中有四个抑制人源性HCA-7结肠癌细胞的生长，但效力比白藜芦醇低得多。

  DOI：

  10.1016/j.tet.2013.05.042

文献信息

• Natural Product-like Combinatorial Libraries Based on Privileged Structures. 1. General Principles and Solid-Phase Synthesis of Benzopyrans
  作者：K. C. Nicolaou、J. A. Pfefferkorn、A. J. Roecker、G.-Q. Cao、S. Barluenga、H. J. Mitchell

  DOI：10.1021/ja002033k

  日期：2000.10.1

  report a novel strategy for the design and construction of natural and natural product-like libraries based on the principle of privileged structures, a term originally introduced to describe structural motifs capable of interacting with a variety of unrelated molecular targets. The identification of such privileged structures in natural products is discussed, and subsequently the 2,2-dimethylbenzopyran

  在此，我们报告了一种基于特权结构原理设计和构建天然和天然产物类库的新策略，该术语最初用于描述能够与各种不相关的分子靶标相互作用的结构基序。讨论了天然产物中此类特权结构的鉴定，随后选择 2,2-二甲基苯并吡喃部分作为通过该策略构建类天然产物库的初始模板。最初，采用独特的环加载策略开发了苯并吡喃基序的新型固相合成，该策略依赖于使用新的聚苯乙烯基溴化硒树脂。一旦确定了这些苯并吡喃的加载、加工和裂解，
• Vitamin D analogues
  申请人：Galderma Research & Development S.N.C.

  公开号：US06689922B1

  公开（公告）日：2004-02-10

  The invention concerns novel bi-aromatic compounds having the formula: which are analogs of vitamin D, the process of preparing them, as well as their use in pharmaceutical compositions in human or veterinary medicine, particularly in dermatology, cancer treatment, treatment of auto-immune diseases, and in organ or tissue transplants. Cosmetic compositions and methods of use are also included.

  这项发明涉及具有以下公式的新型双芳香化合物：这些化合物是维生素D的类似物，涉及它们的制备过程，以及它们在人类或兽医药学中的药用组合物中的使用，特别是在皮肤病学、癌症治疗、自身免疫疾病治疗以及器官或组织移植中。还包括化妆品组合物和使用方法。
• Synthesis of 16β-derivatives of 3-(2-bromoethyl)-estra-1,3,5(10)-trien-17β-ol as inhibitors of 17β-HSD1 and/or steroid sulfatase for the treatment of estrogen-dependent diseases
  作者：Maxime Lespérance、Jenny Roy、Adrien Djiemeny Ngueta、René Maltais、Donald Poirier

  DOI：10.1016/j.steroids.2021.108856

  日期：2021.8

  key role of a bromoethyl side chain added at the C3-position of a 16β-carbamoyl-benzyl-E2 nucleus to covalently inhibit 17β-HSD1. To extend the structure–activity relationship study to the C16β-position of this new selective irreversible inhibitor (PBRM), we synthesized a series of analog compounds by changing the nature of the C16β-side chain but keeping the 2-bromoethyl group at position C3. We determined

  17β-羟基类固醇脱氢酶 1 型 (17β-HSD1) 和类固醇硫酸酯酶 (STS) 参与人体中最有效的雌激素雌二醇 (E2) 的合成。已知这些酶在雌激素依赖性疾病的进展中发挥关键作用，例如乳腺癌和子宫内膜异位症。因此，抑制 17β-HSD1 和/或 STS 代表了调节雌激素依赖性肿瘤或病变生长的有希望的途径。我们最近确定了在 16β-氨基甲酰基-苄基-E2 核的 C3 位添加溴乙基侧链以共价抑制 17β-HSD1 的关键作用。为了将构效关系研究扩展到这种新型选择性不可逆抑制剂 (PBRM) 的 C16β 位，我们通过改变C16β-侧链的性质但将2-溴乙基保持在C3位，合成了一系列类似化合物。我们确定了它们在 T-47D 细胞中的 17β-HSD1 抑制作用（E1 转化为 E2），但我们没有获得比 PBRM 更强的 17β-HSD1 抑制剂。化合物发现16和17更可能与催化位点结合，并显示出有希望但中等的抑制活性，估计
• Anti-diabetic activity of fused PPARγ-SIRT1 ligands with limited body-weight gain by mimicking calorie restriction and decreasing SGK1 expression
  作者：Celine Pirat、Catherine Dacquet、Veronique Leclerc、Nathalie Hennuyer、Monique Beucher-Gaudin、Ghislaine Zanirato、Anne Géant、Bart Staels、Alain Ktorza、Amaury Farce、Daniel-Henri Caignard、Pascal Berthelot、Nicolas Lebegue

  DOI：10.1016/j.ejmech.2017.06.006

  日期：2017.9

  A series of benzothiazol-2-one containing alpha-ethoxyphenylpropionic acid derivatives incorporating resveratrol or butein scaffolds were designed as fused full PPAR gamma agonist ligands and SIRT1-activating compounds for the treatment of type 2 diabetes (T2D) and its complications. Compound 14d displayed the best in vitro pharmacological profile with full PPAR gamma agonist activity (Emax = 98%, EC50 = 200 nM), SIRTI enzymatic activation (+128%) and SGK1 expression inhibition (- 57%) which is known to limit side effects as fluid retention and body-weight gain. Compound 14d showed high efficacy in an ob/ob mice model with significant decreases in serum triglyceride, glucose and insulin levels but mostly with limited body-weight gain by mimicking calorie restriction (CR) and inhibiting SGKI expression. (C) 2017 Elsevier Masson SAS. All rights reserved.
• ——
  作者：Christelle Pouget、Catherine Fagnere、Jean‐Philippe Basly、Anne‐Elise Besson、Yves Champavier、Gerard Habrioux、Albert‐Jose Chulia

  DOI：10.1023/a:1014490817731

  日期：——

  Purpose. Aromatase inhibitors are known to prevent the conversion of androgens to estrogens and play a significant role in the treatment of estrogen dependent diseases such as breast cancer. Some flavonoids have been reported as potent aromatase inhibitors: therefore. in an effort to develop novel anti breast cancer agents. B ring substituted flavanones with a 7-methoxy group on A ring were synthesized and tested to assess their ability to inhibit aromatase activity and to determine the optimal B ring substitution pattern.Methods. A series of flavanones was prepared by cyclisation of 2'-hydroxychalcones previously obtained by Claisen-Schmidt condensation and the aromatase inhibitory activity or these compounds was investigated using human placental microsomes and radiolabeled [1.2,6,7-H-3]-androstenedione as substrate.Results. Almost all flavanones exhibited inhibitory effect on the aromatase activity but their potency was dependent on their B ring subtitution pattern. Hydroxylation at position 3' and/or 4' enhanced the anti-aromatase activity thus, 3'.4'-dihydroxy-7-methoxyflavanone was found to he twice more potent than aminoglutethimide. the first aromatase inhibitor clinically used.Conclusions. These results indicated that these flavanones could be considered as potential anti breast cancer agents through the inhibition of aromatase activity and allowed us to select some of these Compounds as skeleton for the development of flavonoid structurally-related aromatase inhibitors.