4-(7-methoxychroman-3-yl)phenol | 89019-86-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 4-(7-methoxychroman-3-yl)phenol
• 英文别名: 4-(7-methoxy-3,4-dihydro-2H-chromen-3-yl)phenol
• CAS: 89019-86-3
• 化学式: C₁₆H₁₆O₃
• 分子量: 256.301
• InChiKey: KNNAWQXWSNKMRD-UHFFFAOYSA-N

物化性质

• 沸点：
  412.7±45.0 °C(Predicted)
• 密度：
  1.198±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(7-methoxychroman-3-yl)phenol 在 potassium carbonate 、 magnesium 作用下， 以 乙醚 、 丙酮 为溶剂， 生成 5-[4-(7-methoxychroman-3-yl)phenoxy]-2-methylpentan-2-ol
  参考文献：
  名称：

  Design and synthesis of 3-arylbenzopyran based non-steroidal vitamin-D₃mimics as osteogenic agents

  摘要：

  在小鼠头盖骨成骨细胞中，1 pM浓度下增强成骨细胞分化，且无固有毒性。

  DOI：

  10.1039/c6md00469e
• 作为产物：
  描述：

  大豆甙元 在 palladium on activated charcoal 、 氢气 、 sodium carbonate 作用下， 以 乙醇 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-(7-methoxychroman-3-yl)phenol
  参考文献：
  名称：

  在温和条件下轻松合成与雌马酚相连的 1-杂（芳基）-1,2,3-三唑

  摘要：

  摘要 我们在此报告了一种在极其温和的条件下利用铜催化的叠氮化物-炔环加成反应合成与雌马酚相连的 1-杂（芳基）-1,2,3-三唑的简便方法。该开发协议的显着特点包括：易于分离过程、产品的良好收率和杂芳基三唑的附属物多样性。图形概要

  DOI：

  10.1080/00397911.2020.1792932

文献信息

• Induction of targeted osteogenesis with 3-aryl- 2H -benzopyrans and 3-aryl- 3H -benzopyrans: Novel osteogenic agents
  作者：Atul Gupta、Imran Ahmad、Jyoti Kureel、Mohammad Hasanain、Praveen Pandey、Sarita Singh、Aijaz A. John、Jayanta Sarkar、Divya Singh

  DOI：10.1016/j.jsbmb.2016.01.010

  日期：2016.4

  Development of target oriented chemotherapeutics for treatment of chronic diseases have been considered as an important approach in drug development. Following this approach, in our efforts for exploration of new osteogenic leads, substituted 3-aryl-2H-benzopyran and 3-aryl-3H-benzopyran derivatives (19, 20a-e, 21, 22a-e, 26, 27, 28a-e, 29, 31a-b, 32 and 33) have been characterized as estrogen receptor-(3 selective osteogenic (bone forming) agents. The synthesized compounds were evaluated for osteogenic activity using mouse calvarial osteoblast cells. Four compounds viz 20b, 22a, 27and 32 showed significant osteogenic activity at EC50 values 1.35, 34.5, 407 and 29.5 pM respectively. Out of these, 20b and 32 were analyzed for their bone mineralization efficacy and osteogenic gene expression by qPCR. The results showed that 20b and 32 significantly increased mineral nodule formation and the transcript levels of BMP-2, RUNX-2 and osteocalcin at 100 pM concentrations respectively. Further mechanistic studies of 20b and 32 using transiently knocked down expression of ER-alpha and beta in mouse osteoblast (MOBs) showed that 20b and 32 exerts osteogenic efficacy via activation of estrogen receptor-beta preferentially. Additionally, compounds showed significant anticancer activity in a panel of cancer cell lines within the range of (IC50) 6.54-27.79 mu M. The most active molecule, 22b inhibited proliferation of cells by inducing apoptosis and arresting cell cycle at sub-G(0) phase with concomitant decrease in cells at S phase. (C) 2016 Elsevier Ltd. All rights reserved.
• Synthesis of amide derivatives of 3-aryl-3H-benzopyrans as osteogenic agent concomitant with anticancer activity
  作者：Sarita Singh、Surendra Chandra Verma、Vinay Kumar、Kriti Sharma、Diksha Singh、Sana Khan、Neelam Gupta、Romila Singh、Feroz Khan、Debabrata Chanda、Durga Prasad Mishra、Divya Singh、Partha Roy、Atul Gupta

  DOI：10.1016/j.bioorg.2023.106380

  日期：2023.4
• Design and synthesis of 3-arylbenzopyran based non-steroidal vitamin-D₃mimics as osteogenic agents
  作者：Mohd. Imran Ahmad、Dushyant Singh Raghuvanshi、Sarita Singh、Aijaz A. John、Ravi Prakash、Kripa Shankar Nainawat、Divya Singh、Shubhandra Tripathi、Ashok Sharma、Atul Gupta

  DOI：10.1039/c6md00469e

  日期：——

  27benhanced osteoblast differentiation at 1 pM in mouse calvarial osteoblast cells without inherent toxicity.

  在小鼠头盖骨成骨细胞中，1 pM浓度下增强成骨细胞分化，且无固有毒性。
• A facile access for the synthesis of 1-hetero(aryl)-1,2,3-triazoles linked to equol under mild conditions
  作者：Muthipeedika Nibin Joy、Nikolai Beliaev、Tetyana V. Beryozkina、Vasiliy A. Bakulev

  DOI：10.1080/00397911.2020.1792932

  日期：2020.10.17

  Abstract We herein report a convenient methodology for the synthesis of 1-hetero(aryl)-1,2,3-triazoles linked with equol by utilizing copper-catalyzed azide-alkyne cycloaddition reaction under exceptionally mild conditions. The salient features of this developed protocol include: easy isolation process, good to excellent yield of the products and appendage diversity of heteroaryl triazoles. Graphical

  摘要 我们在此报告了一种在极其温和的条件下利用铜催化的叠氮化物-炔环加成反应合成与雌马酚相连的 1-杂（芳基）-1,2,3-三唑的简便方法。该开发协议的显着特点包括：易于分离过程、产品的良好收率和杂芳基三唑的附属物多样性。图形概要