7-羟基-4-苯基-3-(4-羟基苯基)香豆素 | 100242-24-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 中文名称: 7-羟基-4-苯基-3-(4-羟基苯基)香豆素
• 英文名称: 7-hydroxy-3-(4-hydroxyphenyl)-4-phenyl-2H-chromen-2-one
• 英文别名: 7-Hydroxy-4-phenyl-3-(4-hydroxyphenyl)coumarin；7-hydroxy-3-(4-hydroxyphenyl)-4-phenylchromen-2-one
• CAS: 100242-24-8
• 化学式: C₂₁H₁₄O₄
• 分子量: 330.34
• InChiKey: MLAIPUZEKYJFIL-UHFFFAOYSA-N

物化性质

• 沸点：
  427.78°C (rough estimate)
• 密度：
  1.2066 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N-二乙基氯乙胺 、 7-羟基-4-苯基-3-(4-羟基苯基)香豆素 在 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 为溶剂， 反应 8.0h， 以59%的产率得到7-(2-(diethylamino)ethoxy)-3-(4-(2-(diethylamino)ethoxy)phenyl)-4-phenyl-2H-chromen-2-one
  参考文献：
  名称：

  Cytotoxicity and DNA binding property of triphenylethylene–coumarin hybrids with two amino side chains

  摘要：

  Novel triphenylethylene-coumarin hybrids containing two amino side chains were designed and synthesized. Some of these 3,4-diphenyl coumarins, 7b-c (the double chains at 4-position on 3-, 4-phenyl, respectively), and 13b-f (the double chains at 4-position on 3-phenyl and 7-position, respectively), showed a broad-spectrum and good anti-proliferative activity against five tumor cells and low cytotoxicity in osteoblast. UV-vis, fluorescence, and circular dichroism (CD) spectroscopies and thermal denaturation exhibited that compounds 7b (R = piperidinyl), 7e (R = NEt2), and 7f (R = 4-methylpiperazinyl) had significant interactions with Ct-DNA by the intercalative mode of binding. Structure activity relationships (SARs) analysis suggested that the location of the two amino alkyl chains would play an important role both in the compounds against tumor cells proliferation and their interactions with DNA. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.084
• 作为产物：
  描述：

  2,4-二羟二苯甲酮 在 盐酸 、 水 、 potassium carbonate 作用下， 以 乙醇 、 乙酸酐 为溶剂， 反应 7.0h， 生成 7-羟基-4-苯基-3-(4-羟基苯基)香豆素
  参考文献：
  名称：

  Cytotoxicity and DNA binding property of triphenylethylene–coumarin hybrids with two amino side chains

  摘要：

  Novel triphenylethylene-coumarin hybrids containing two amino side chains were designed and synthesized. Some of these 3,4-diphenyl coumarins, 7b-c (the double chains at 4-position on 3-, 4-phenyl, respectively), and 13b-f (the double chains at 4-position on 3-phenyl and 7-position, respectively), showed a broad-spectrum and good anti-proliferative activity against five tumor cells and low cytotoxicity in osteoblast. UV-vis, fluorescence, and circular dichroism (CD) spectroscopies and thermal denaturation exhibited that compounds 7b (R = piperidinyl), 7e (R = NEt2), and 7f (R = 4-methylpiperazinyl) had significant interactions with Ct-DNA by the intercalative mode of binding. Structure activity relationships (SARs) analysis suggested that the location of the two amino alkyl chains would play an important role both in the compounds against tumor cells proliferation and their interactions with DNA. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.084

文献信息

• COMPOSITIONS AND METHODS FOR TREATMENT OF VIRAL DISEASES
  申请人：Johansen Lisa M.

  公开号：US20100009970A1

  公开（公告）日：2010-01-14

  The present invention features compositions, methods, and kits useful in the treatment of viral diseases. In certain embodiments, the viral disease is caused by a single stranded RNA virus, a flaviviridae virus, or a hepatic virus. In particular embodiments, the viral disease is viral hepatitis (e.g., hepatitis A, hepatitis B, hepatitis C, hepatitis D, hepatitis E) and the agent or combination of agents includes sertraline, a sertraline analog, UK-416244, or a UK-416244 analog. Also featured are screening methods for identification of novel compounds that may be used to treat a viral disease.

  本发明涉及用于治疗病毒性疾病的组合物、方法和试剂盒。在某些实施方式中，病毒性疾病是由单链RNA病毒、黄病毒科病毒或肝病毒引起的。在特定实施方式中，病毒性疾病是病毒性肝炎（例如甲型肝炎、乙型肝炎、丙型肝炎、丁型肝炎、戊型肝炎），药剂或药剂组合包括舍曲林、舍曲林类似物、UK-416244或UK-416244类似物。还包括用于鉴定可用于治疗病毒性疾病的新化合物的筛选方法。
• Compositions and methods for treatment of viral diseases
  申请人：Johansen Lisa M.

  公开号：US20080161324A1

  公开（公告）日：2008-07-03

  The present invention features compositions, methods, and kits useful in the treatment of viral diseases. In certain embodiments, the viral disease is caused by a single stranded RNA virus, a flaviviridae virus, or a hepatic virus. In particular embodiments, the viral disease is viral hepatitis (e.g., hepatitis A, hepatitis B, hepatitis C, hepatitis D, hepatitis E). Also featured are screening methods for identification of novel compounds that may be used to treat a viral disease.
• [EN] COMPOSITIONS AND METHODS FOR TREATMENT OF VIRAL DISEASES<br/>[FR] COMPOSITIONS ET PROCÉDÉS POUR LE TRAITEMENT DE MALADIES VIRALES
  申请人：COMBINATORX SINGAPORE PRE LTD

  公开号：WO2008033466A2

  公开（公告）日：2008-03-20

  [EN] The present invention features compositions, methods, and kits useful in the treatment of viral diseases. In certain embodiments, the viral disease is caused by a single stranded RNA virus, a flaviviridae virus, or a hepatic virus. In particular embodiments, the viral disease is viral hepatitis (e.g., hepatitis A, hepatitis B, hepatitis C, hepatitis D, hepatitis E). Also featured are screening methods for identification of novel compounds that may be used to treat a viral disease.
  [FR] La présente invention concerne des compositions, procédés et kits utiles dans le traitement de maladies virales. Dans certains modes de réalisation, la maladie virale est causée par un virus à ARN simple brin, un virus Flaviviridae, ou un virus hépatique. Dans des modes de réalisation particuliers, la maladie virale est l'hépatite virale (par exemple, hépatite A, hépatite B, hépatite C, hépatite D, hépatite E). La présente invention concerne également des procédés de criblage en vue de l'identification de nouveaux composés qui peuvent être utilisés pour traiter une maladie virale.
• Cytotoxicity and DNA binding property of triphenylethylene–coumarin hybrids with two amino side chains
  作者：Lian Zhao、Yuchao Yao、Shuai Li、Mengjiao Lv、Hua Chen、Xiaoliu Li

  DOI：10.1016/j.bmcl.2013.12.084

  日期：2014.2

  Novel triphenylethylene-coumarin hybrids containing two amino side chains were designed and synthesized. Some of these 3,4-diphenyl coumarins, 7b-c (the double chains at 4-position on 3-, 4-phenyl, respectively), and 13b-f (the double chains at 4-position on 3-phenyl and 7-position, respectively), showed a broad-spectrum and good anti-proliferative activity against five tumor cells and low cytotoxicity in osteoblast. UV-vis, fluorescence, and circular dichroism (CD) spectroscopies and thermal denaturation exhibited that compounds 7b (R = piperidinyl), 7e (R = NEt2), and 7f (R = 4-methylpiperazinyl) had significant interactions with Ct-DNA by the intercalative mode of binding. Structure activity relationships (SARs) analysis suggested that the location of the two amino alkyl chains would play an important role both in the compounds against tumor cells proliferation and their interactions with DNA. (C) 2013 Elsevier Ltd. All rights reserved.