4'-(hydroxy[1,1',3',3'']terphenyl-4-yl)aldehyde | 862651-00-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4'-(hydroxy[1,1',3',3'']terphenyl-4-yl)aldehyde
• 英文别名: 4-(4-Hydroxy-3-phenylphenyl)benzaldehyde
• CAS: 862651-00-1
• 化学式: C₁₉H₁₄O₂
• 分子量: 274.319
• InChiKey: CBUXTYIFKHNINU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4'-(hydroxy[1,1',3',3'']terphenyl-4-yl)aldehyde 在 lithium hydroxide 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 23.0h， 生成 (E)-3-[4-(4-hydroxy-3-phenylphenyl)phenyl]prop-2-enoic acid
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of a New Series of Retinoid-Related Biphenyl-4-ylacrylic Acids Endowed with Antiproliferative and Proapoptotic Activity

  摘要：

  Atypical retinoids (AR) represent a class of proapoptotic agents with promising potential in the treatment of neoplastic diseases. In the present work 4'-hydroxybiphenyl-4-ylacrylic acids were studied as a novel series of AR. The synthesized compounds were evaluated for their antiproliferative activity in a human promyelocytic leukemia cell line (NB4) and in an ovarian carcinoma cell system including IGROV-1, carrying a functional wild-type p53, and a cisplatin-resistant subline, IGROV-1/Pt-1. The presence of a bulky lipophilic group at position 3' (adamantan-1-yl being the best) and the E configuration of the acrylic moiety appear essential for activity below 1 mu M. No substitution on the rings or on the double bond improved the activity. A qualitative correlation between the log P and molecular volume of the 3'-substituent and the antiproliferative activity was found. From the study of a few selected compounds, it appears that the presence of the carboxylic group is an essential requirement for apoptogenic properties but not for antiproliferative activity, this being maintained in amide derivatives. On the other hand, compounds able to induce apoptosis produced a detectable level of genotoxic damage. This observation supports the hypothesis that the genotoxic stress is a critical event mediating apoptosis induction by compounds of this class. Among the compounds investigated, E-3-(3'-adamantan-1-yl-4'-hydroxybiphenyl-4-yl)acrylic acid (2) was chosen for further investigation.

  DOI：

  10.1021/jm049440h
• 作为产物：
  描述：

  邻苯基苯酚 、 alkaline earth salt of/the/ methylsulfuric acid 在 四(三苯基膦)钯 、 chloroamine-T 、 sodium carbonate 、 sodium iodide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 20.5h， 生成 4'-(hydroxy[1,1',3',3'']terphenyl-4-yl)aldehyde
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of a New Series of Retinoid-Related Biphenyl-4-ylacrylic Acids Endowed with Antiproliferative and Proapoptotic Activity

  摘要：

  Atypical retinoids (AR) represent a class of proapoptotic agents with promising potential in the treatment of neoplastic diseases. In the present work 4'-hydroxybiphenyl-4-ylacrylic acids were studied as a novel series of AR. The synthesized compounds were evaluated for their antiproliferative activity in a human promyelocytic leukemia cell line (NB4) and in an ovarian carcinoma cell system including IGROV-1, carrying a functional wild-type p53, and a cisplatin-resistant subline, IGROV-1/Pt-1. The presence of a bulky lipophilic group at position 3' (adamantan-1-yl being the best) and the E configuration of the acrylic moiety appear essential for activity below 1 mu M. No substitution on the rings or on the double bond improved the activity. A qualitative correlation between the log P and molecular volume of the 3'-substituent and the antiproliferative activity was found. From the study of a few selected compounds, it appears that the presence of the carboxylic group is an essential requirement for apoptogenic properties but not for antiproliferative activity, this being maintained in amide derivatives. On the other hand, compounds able to induce apoptosis produced a detectable level of genotoxic damage. This observation supports the hypothesis that the genotoxic stress is a critical event mediating apoptosis induction by compounds of this class. Among the compounds investigated, E-3-(3'-adamantan-1-yl-4'-hydroxybiphenyl-4-yl)acrylic acid (2) was chosen for further investigation.

  DOI：

  10.1021/jm049440h

文献信息

• NOVEL TRISPHENOL COMPUND
  申请人：Yoshitomo Akira

  公开号：US20120220805A1

  公开（公告）日：2012-08-30

  A trisphenol compound is expressed by formula (1), wherein R represents an alkyl group or alkoxyl group with 1 to 8 carbon atoms, phenyl group or hydroxyl group; R 1 represents an alkyl group or alkoxyl group with 1 to 8 carbon atoms, or phenyl group; R 2 represents an alkyl group or alkoxyl group with 1 to 8 carbon atoms; R 3 represents a hydrogen atom or alkyl group with 1 to 8 carbon atoms; a represents 0, 1, 2, or 3; b represents 1 or 2; and c and d represent 0, 1, 2, 3, or 4; where the sum of b and c is 5 or less; R's may be either the same or different when a is 2 or more; R 1 's may be either the same or different when c is 2 or more; and R 2 's may be either the same or different when d is 2 or more.

  一种三酚化合物由式（1）表示，其中R代表具有1至8个碳原子的烷基基团或烷氧基基团，苯基或羟基；R1代表具有1至8个碳原子的烷基基团或烷氧基基团，或苯基；R2代表具有1至8个碳原子的烷基基团或烷氧基基团；R3代表氢原子或具有1至8个碳原子的烷基基团；a代表0、1、2或3；b代表1或2；c和d代表0、1、2、3或4；其中b和c的和小于或等于5；当a大于等于2时，R可能相同也可能不同；当c大于等于2时，R1可能相同也可能不同；当d大于等于2时，R2可能相同也可能不同。
• US8816135B2
  申请人：——

  公开号：US8816135B2

  公开（公告）日：2014-08-26