8-iodo-7-methoxy-4-methylcoumarin | 110533-92-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 8-iodo-7-methoxy-4-methylcoumarin
• 英文别名: 8-iodo-7-methoxy-4-methyl-2H-chromen-2-one；8-iodo-7-methoxy-4-methylchromen-2-one
• CAS: 110533-92-1
• 化学式: C₁₁H₉IO₃
• 分子量: 316.095
• InChiKey: ZHOFLVSEEMXJFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-iodo-7-methoxy-4-methylcoumarin 在 sodium hydroxide 、 dipotassium peroxodisulfate 作用下， 生成 6-hydroxy-8-iodo-7-methoxy-4-methyl-coumarin
  参考文献：
  名称：

  Iodination of 7-Hydroxy-, and 5-Hydroxy-4-methylcoumarin and Their Methyl Ethers

  摘要：

  DOI：

  10.1021/jo01105a041
• 作为产物：
  描述：

  羟甲香豆素 在 ammonium hydroxide 、 碘 、 potassium carbonate 、 potassium iodide 作用下， 以 水 、 丙酮 为溶剂， 反应 29.5h， 生成 8-iodo-7-methoxy-4-methylcoumarin
  参考文献：
  名称：

  Grignard试剂合成Osthole衍生物及其对蚊子的杀幼虫活性

  摘要：

  修饰了臭虫的结构，以改善其对蚊子的杀幼虫活性。已经开发了一种使用格氏试剂的新型高效合成osthole衍生物的方法，该方法利用CuI和LiCl作为促进剂，并覆盖了广泛的底物，从而以中等至良好的收率（高达83％）提供了相应的产品。生物活性评估表明，几种产品表现出的活性比蛇窝更好。

  DOI：

  10.1002/cjoc.201500620

文献信息

• Palladium-catalyzed synthesis of 8-allyl or 8-prenylcoumarins by using organotin reagents as multicoupling nucleophiles
  作者：Qiang Yin、Han Yan、Yaqin Zhang、Yige Wang、Guojin Zhang、Yuxiang He、Weihua Zhang

  DOI：10.1002/aoc.2944

  日期：2013.2

  In this study, 8‐iodocoumarin derivatives underwent a direct Stille cross‐coupling reaction with several organotin compounds in the presence of a catalytic amount of Pd(PPh3)4 in DMF at 80 °C. The cross‐coupling reaction proceeded smoothly under mild conditions and permitted the formation of 8‐allyl or 8‐prenylcoumarin compounds in good yields. Copyright © 2012 John Wiley & Sons, Ltd.

  在这项研究中，在80°C的DMF中催化量的Pd（PPh 3）4存在下，8-碘docoumarin衍生物与几种有机锡化合物直接进行了Stille交叉偶联反应。交叉偶联反应在温和条件下进行得很顺利，并以高收率形成了8个烯丙基或8个异戊烯基香豆素化合物。版权所有©2012 John Wiley＆Sons，Ltd.
• Phototoxicity of 7-oxycoumarins with keratinocytes in culture
  作者：Christophe Guillon、Yi-Hua Jan、Diane E. Heck、Thomas M. Mariano、Robert D. Rapp、Michele Jetter、Keith Kardos、Marilyn Whittemore、Eric Akyea、Ivan Jabin、Jeffrey D. Laskin、Ned D. Heindel

  DOI：10.1016/j.bioorg.2019.103014

  日期：2019.8

  Seventy-one 7-oxycoumarins, 66 synthesized and 5 commercially sourced, were tested for their ability to inhibit growth in murine PAM212 keratinocytes. Forty-nine compounds from the library demonstrated light-induced lethality. None was toxic in the absence of UVA light. Structure-activity correlations indicate that the ability of the compounds to inhibit cell growth was dependent not only on their physiochemical characteristics, but also on their ability to absorb UVA light. Relative lipophilicity was an important factor as was electron density in the pyrone ring. Coumarins with electron withdrawing moieties - cyan and fluoro at C-3 - were considerably less active while those with bromines or iodine at that location displayed enhanced activity. Coumarins that were found to inhibit keratinocyte growth were also tested for photo-induced DNA plasmid nicking. A concentration-dependent alteration in migration on neutral gels caused by nicking was observed.
• [EN] COMPOSITIONS AND METHODS FOR TREATING TRINUCLEOTIDE REPEAT DISORDERS<br/>[FR] COMPOSITIONS ET PROCÉDÉS POUR TRAITER DES MALADIES À EXPANSION DE TRIPLETS
  申请人：MASSACHUSETTS INST TECHNOLOGY

  公开号：WO2007124171A2

  公开（公告）日：2007-11-01

  [EN] This invention relates to compositions and methods for treating disorders resulting from protein-misfolding. We describe exemplary compounds, which may be contained in pharmaceutical compositions, the screening methods by which they were discovered, and their use as therapeutic or prophylactic agents.
  [FR] L'invention concerne des compositions et des procédés pour traiter des troubles résultant d'un mauvais repliement de protéines. Cette invention se rapporte en outre à des composés exemplaires qui peuvent figurer dans des compositions pharmaceutiques, aux procédés de criblage qui ont permis de découvrir ces composés, ainsi qu'à l'utilisation desdits composés en tant qu'agents thérapeutiques ou prophylactiques.