8-bromo-6-chloro-4-hydroxy-chromen-2-one | 1175095-14-3

• 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-bromo-6-chloro-4-hydroxy-chromen-2-one
• 英文别名: 8-Bromo-6-chloro-4-hydroxy-2H-1-benzopyran-2-one；8-bromo-6-chloro-4-hydroxychromen-2-one
• CAS: 1175095-14-3
• 化学式: C₉H₄BrClO₃
• 分子量: 275.486
• InChiKey: ZLDIAJQXMMRMPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-bromo-6-chloro-4-hydroxy-chromen-2-one 、 2-(N,N-二甲氨基)苯甲醛 在 吗啉 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以63%的产率得到3-(3-bromo-5-chloro-2-hydroxybenzoyl)-3-((8-bromo-6-chloro-4-hydroxy-2-oxo-2H-chromen-3-yl)methyl)-1-methyl-3,4-dihydroquinolin-2(1H)-one
  参考文献：
  名称：

  通过氢化物转移/ N-脱烷基/ N-酰化反应进行氧化还原触发的3,4-二氢喹啉-2（1 H）-one衍生物的可转换合成

  摘要：

  通过氧化还原-中性氢化物转移/ N-脱烷基/ N-酰化策略发展了3-非，3-单，3,3'-二取代的3,4-二氢喹啉-2（1 H）-ones的可转换合成分别由邻氨基苯甲醛与4-羟基香豆素和Meldrum酸组成。合成3,3'-高度官能化的3,4-二氢喹啉-2（1 H）-1的空前策略已实现，其中通过迈克尔加成通过o -QM原位利用释放的HCHO 。此外，通过简明合成CYP11B2抑制剂已很好地说明了该方案的合成效用。

  DOI：

  10.1021/acs.orglett.0c03863
• 作为产物：
  描述：

  3'-溴-5'-氯-2'-羟基苯乙酮 、 碳酸二乙酯 在 sodium hydride 作用下， 以 甲苯 、 kerosene 为溶剂， 生成 8-bromo-6-chloro-4-hydroxy-chromen-2-one
  参考文献：
  名称：

  Discovery of novel 5-(2-hydroxyphenyl)-2-phthalide-3(3H)-pyrazolones as balanced multifunctional agents against Alzheimer's disease

  摘要：

  DOI：

  10.1016/j.ejmech.2023.115216

文献信息

• [EN] CHROMENE DERIVATIVES AND USE THEREOF AS HIF HYDROXYLASE ACTIVITY INHIBITORS<br/>[FR] DÉRIVÉS DE CHROMÈNE ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE L'ACTIVITÉ DE L'HYDROXYLASE HIF
  申请人：FIBROGEN INC

  公开号：WO2009100250A1

  公开（公告）日：2009-08-13

  The present invention relates to novel compounds of formula (I), methods, and compositions capable of decreasing HIF hydroxylase activity, thereby increasing the stability and/or activity of hypoxia inducible factor (HIF).

  本发明涉及公式（I）的新化合物，以及能够降低HIF羟化酶活性的方法和组合物，从而增加缺氧诱导因子（HIF）的稳定性和/或活性。
• DABCO-catalyzed one-pot three component synthesis of dihydropyrano[3,2-c]chromene substituted quinazolines and their evaluation towards anticancer activity
  作者：Sumathi Vodnala、A.K.D. Bhavani、Ramakrishna Kamutam、V.G.M. Naidu、Promila、Ch. Prabhakar

  DOI：10.1016/j.bmcl.2016.07.003

  日期：2016.8

  A facile DABCO promoted one-pot three component synthesis of a new series of C-C linked bis-heterocycle containing dihydropyrano[c]chromene as highly fused oxa-heteryl group at C-2 position of quinazoline was developed. Quinazoline-2-carbaldehyde, substituted 4-hydroxycoumarin and ethyl cyanoacetate were used as key components in the Knoevenagel-Michael addition reaction to get the titled compounds

  开发了一种简便的DABCO促进了一系列新的CC连接的双杂环的单锅三组分合成，该双环的双环含有二氢吡喃并[c]苯甲基作为喹唑啉C-2位的高度稠合的氧杂杂环基。喹唑啉-2-甲醛，取代的4-羟基香豆素和氰基乙酸乙酯用作Knoevenagel-Michael加成反应的关键组分，得到标题化合物。筛选了这些化合物对MDA-MB 231和MDA-MB 453乳腺癌细胞系的抗癌活性。
• CHROMENE DERIVATIVES AND USE THEREOF AS HIF HYDROXYLASE ACTIVITY INHIBITORS
  申请人：Ho Wen-bin

  公开号：US20100331400A1

  公开（公告）日：2010-12-30

  The present invention relates to novel compounds of formula (I), methods, and compositions capable of decreasing HIF hydroxylase activity, thereby increasing the stability and/or activity of hypoxia inducible factor (HIF).

  本发明涉及一种新的化合物（I）的方法和组合物，能够降低HIF羟化酶活性，从而增加缺氧诱导因子（HIF）的稳定性和/或活性。
• Compounds exhibiting efflux inhibitor activity and composition and uses thereof
  申请人：Wempe Fitzpatrick Michael

  公开号：US20070254859A1

  公开（公告）日：2007-11-01

  At least one compound chosen from compounds of Formula I: a pharmaceutically acceptable salt or ester thereof, a solvate thereof, a chelate thereof, a non-covalent complex thereof, a prodrug thereof, and mixtures of any of the foregoing, wherein: n is a number from 1 to 900, wherein the individual units may be the same or different; W is chosen from alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, aralkyl and substituted aralkyl; each of R 2 , R 3 , R 4 and R 5 is independently chosen from —H, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, aralkyl and substituted aralkyl; Z′ is chosen from —O—, —N—, —NO—, —NR 4 —, —S—, —SO— and —SO 2 —, wherein R 4 is defined as above; each of X, X′, Y and Z is independently chosen from —CR 4 R 5 —, —NH—, —NR 4 —, —NO—, —O—, —NOR 4 —, —S—, —SO—, —SO 2 —, wherein R 4 and R 5 are defined as above; R 1 is chosen from a tocopherol, a steroid and a flavonoid; and R 6 is chosen from any R 1 , alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, aralkyl and substituted aralkyl.
• US8324405B2
  申请人：——

  公开号：US8324405B2

  公开（公告）日：2012-12-04