8-Acetyl-3-hydroxy-2-methoxybenzo[c]chromen-6-one | 524713-48-2

• 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-Acetyl-3-hydroxy-2-methoxybenzo[c]chromen-6-one
• CAS: 524713-48-2
• 化学式: C₁₆H₁₂O₅
• 分子量: 284.268
• InChiKey: DSJJWYLTABUBAA-UHFFFAOYSA-N

物化性质

• 沸点：
  536.8±50.0 °C(Predicted)
• 密度：
  1.369±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 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：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  8-Acetyl-3-hydroxy-2-methoxybenzo[c]chromen-6-one 以85的产率得到8-Acetyl-2-methoxy-3-[(4-methoxyphenyl)methoxy]benzo[c]chromen-6-one
  参考文献：
  名称：

  ACS Catal. 2018, 8, 8324-8335

  摘要：

  DOI：
• 作为产物：
  描述：

  2-溴-5-羟基-4-甲氧基苯甲醛 在 palladium on activated charcoal sodium hydroxide 、 四(三苯基膦)钯 、 正丁基锂 、 氯化亚砜 、 ammonium formate 、 sodium hydride 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 乙醇 、 二氯甲烷 、 乙酸乙酯 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 127.66h， 生成 8-Acetyl-3-hydroxy-2-methoxybenzo[c]chromen-6-one
  参考文献：
  名称：

  Synthesis and Evaluation of a Novel Nonsteroidal-Specific Endothelial Cell Proliferation Inhibitor

  摘要：

  The identification of agents with specific antiproliferative or cytostatic activity against endothelial cells has significant value for the treatment of pathologies associated with angiogenesis, including solid tumors. Here, we describe a novel substituted dibenzo[b,d]pyran-6-one scaffold, exemplified by structures 9a and 10, and report preliminary in vitro activity data indicating that this scaffold is a promising lead for the development of specific inhibitors of endothelial cell proliferation.

  DOI：

  10.1021/jm034007d

文献信息

• Experimental and Theoretical Studies on Ru(II)-Catalyzed Oxidative C–H/C–H Coupling of Phenols with Aromatic Amides Using Air as Oxidant: Scope, Synthetic Applications, and Mechanistic Insights
  作者：Luoqiang Zhang、Lei Zhu、Yuming Zhang、Yudong Yang、Yimin Wu、Weixin Ma、Yu Lan、Jingsong You

  DOI：10.1021/acscatal.8b02816

  日期：2018.9.7

  synthesis of Palomid 529, a drug in development for the treatment of glioblastoma and neovascular age-related macular degeneration. With a combination of experimental and theoretical methods, we get more insight into the essential issues of strategy determining the reaction process. The stronger coordinating ability of 2-aryloxypyridine and the less steric hindrance of amide are pivotal to the high chemoselectivity

  我们在本文中说明了借助Zn（OTf）2的Ru（II）催化的酚与（杂）芳族酰胺的氧化邻位-C-H / C-H交叉偶联的双重螯合辅助策略。，可快速组装2'-羟基联苯-2-羧酸衍生物的丰富文库。该方案具有广泛的底物范围，优异的官能团耐受性，空气作为末端氧化剂，偶联剂的摩尔比低以及按比例放大的合成。特别是，该方法可以耐受更复杂的天然产物衍生物，从而为后期功能化提供了机会。该方案还被用作简明合成Palomid 529的关键步骤，Palomod 529是一种正在开发的用于治疗胶质母细胞瘤和新血管性年龄相关性黄斑变性的药物。结合实验和理论方法，我们对决定反应过程的策略的基本问题有更多的了解。2-芳氧基吡啶的较强的配位能力和酰胺的空间位阻较小，这是交叉偶联相对于均相偶联的高化学选择性的关键。第一个C–H键活化步骤发生在酰胺底物上，随后在2-芳氧基吡啶上的C–H键活化反应参与速率确定的步骤。
• Compositions and methods to treat skin diseases characterized by cellular proliferation and angiogenesis
  申请人：Sherris David

  公开号：US20060257337A1

  公开（公告）日：2006-11-16

  Described herein are compositions and methods for preventing and/or treating skin diseases including, but not limited to, psoriasis and atopic dermatitis as well as providing anti-aging benefits which results in reduced appearance of wrinkles and aged skin, improved skin color, treatment of photodamaged skin, improvement in skin's radiance and clarity and finish, and an overall healthy and youthful appearance of the skin, involving aberrant angiogenesis and hyperplasia employing one or more benzo[c]chromen-6-one derivatives.

  本文描述了一种预防和/或治疗皮肤疾病的组合物和方法，包括但不限于银屑病和特应性皮炎，以及提供抗衰老益处，减少皱纹和老化皮肤的出现，改善皮肤颜色，治疗光损伤皮肤，改善皮肤的光泽和清晰度以及完美度，以及使皮肤呈现整体健康和年轻外观，涉及使用一个或多个苯并[c]色素-6-酮衍生物的异常血管生成和增生。
• COMPOSITIONS AND METHODS TO TREAT DISEASES CHARACTERIZED BY CELLULAR PROLIFERATION AND ANGIOGENESIS
  申请人：Sherris I. David

  公开号：US20070197567A1

  公开（公告）日：2007-08-23

  Described herein are compositions and methods for preventing and/or treating diseases involving aberrant angiogenesis employing one or more benzo[c]chromen-6-one derivatives.

  本文描述了使用一种或多种苯并[c]色酮-6-酮衍生物预防和/或治疗涉及异常血管生成的疾病的组合物和方法。
• COMPOSITIONS AND METHODS TO TREAT SKIN DISEASES CHARACTERIZED BY CELLULAR PROLIFERATION AND ANGIOGENESIS
  申请人：SHERRIS David

  公开号：US20110268679A1

  公开（公告）日：2011-11-03

  Described herein are compositions and methods for preventing and/or treating skin diseases including, but not limited to, psoriasis and atopic dermatitis as well as providing anti-aging benefits which results in reduced appearance of wrinkles and aged skin, improved skin color, treatment of photodamaged skin, improvement in skin's radiance and clarity and finish, and an overall healthy and youthful appearance of the skin, involving aberrant angiogenesis and hyperplasia employing one or more benzo[c]chromen-6-one derivatives.

  本文描述了一种预防和/或治疗皮肤疾病的组合物和方法，包括但不限于银屑病和特应性皮炎，以及提供抗衰老效益，从而减少皱纹和老化皮肤的出现，改善皮肤颜色，治疗光损伤皮肤，改善皮肤的光泽度和清晰度，以及整体健康和年轻的外观，涉及异常血管生成和增生，并采用一种或多种苯并[c]色酮衍生物。
• COMPOSITIONS AND METHODS TO TREAT DISEASE CHARACTERIZED BY CELLULAR PROLIFERATION AND ANGIOGENESIS
  申请人：Paloma Pharmaceuticals, Inc.

  公开号：US20140105920A1

  公开（公告）日：2014-04-17

  Described herein are compositions and methods for preventing and/or treating diseases involving aberrant angiogenesis employing one or more benzo[c]chromen-6-one derivatives.

  本文描述了使用一种或多种苯并[c]色酮-6-酮衍生物预防和/或治疗涉及异常血管生成的疾病的组合物和方法。