3'-(adamantan-1-yl)-4'-hydroxybiphenyl-4-aldehyde | 459423-09-7

• 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: 3'-(adamantan-1-yl)-4'-hydroxybiphenyl-4-aldehyde
• 英文别名: 4-[3-(1-adamantyl)-4-hydroxyphenyl]benzaldehyde
• CAS: 459423-09-7
• 化学式: C₂₃H₂₄O₂
• 分子量: 332.442
• InChiKey: CXAQNQSRZVDVJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  3'-(adamantan-1-yl)-4'-hydroxybiphenyl-4-aldehyde 在 aluminum oxide 、 potassium fluoride 、 三甲基溴硅烷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 [(E)-2-[4-[3-(1-adamantyl)-4-hydroxyphenyl]phenyl]ethenyl]phosphonic 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：

  4-甲酰基苯硼酸 、 2-(1-金刚烷基)-4-溴苯酚 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 3.0h， 以30%的产率得到3'-(adamantan-1-yl)-4'-hydroxybiphenyl-4-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

• Heterocyclic derivatives for the treatment of cancer and other proliferative diseases
  申请人：——

  公开号：US20020143182A1

  公开（公告）日：2002-10-03

  The invention relates to certain heterocyclic compounds useful for the treatment of cancer and other diseases, having the Formula (I): 1 wherein: (a) m is an integer 0 or 1; (b) R 12 is an alkyl, a substituted alkyl, a cycloalkyl, a substituted cycloalkyl, a heterocyclic, a substituted heterocyclic, a heteroaryl, a substituted heteroaryl, an aryl or a substituted aryl residue; (c) Ar 3 is an aryl, a substituted aryl, a heteroaryl or a substituted heteroaryl residue; (d) Ar 4 is an aryl, a substituted aryl, a heteroaryl or a substituted heteroaryl residue; (e) R 5 is hydrogen, hydroxy, alkyl or substituted alkyl; (f) - - - - - represents a bond present or absent; and (g) W, X, Y and Z are independently or together C(O)—, C(S), S, O, or NH; or a pharmaceutically acceptable salt thereof.

  该发明涉及某些对治疗癌症和其他疾病有用的杂环化合物，其具有以下式（I）： 1 其中： (a) m是整数0或1； (b) R12是烷基，取代烷基，环烷基，取代环烷基，杂环基，取代杂环基，杂芳基，取代杂芳基，芳基或取代芳基残基； (c) Ar3是芳基，取代芳基，杂芳基或取代杂芳基残基； (d) Ar4是芳基，取代芳基，杂芳基或取代杂芳基残基； (e) R5是氢，羟基，烷基或取代烷基； (f) - - - - - 代表存在或不存在的键；以及 (g) W、X、Y和Z独立或一起是C(O)、C(S)、S、O或NH；或其药学上可接受的盐。
• 2-Substituted thiazolidinone and oxazolidinone derivatives for the inhibition of phosphatases and the treatment of cancer
  申请人：——

  公开号：US20040097566A1

  公开（公告）日：2004-05-20

  The present invention relates to certain substituted heterocycles, including 2-substituted thiazolidinone and 2-substituted oxazolidinone compounds. These compounds are useful in the treatment of diseases related to uncontrolled cellular proliferation, such as cancer or precancerous conditions. The compounds are also useful for modulating lipid and/or carbohydrate metabolism, and treating Type II diabetes, hyperglycemia or obesity, and for treating inflammatory diseases such as arthritis. Some disclosed embodiments of the invention relate to compounds having the structures indicated below, or a pharmaceutically acceptable salt thereof. 1

  本发明涉及某些取代杂环化合物，包括2-取代噻唑烷酮和2-取代噁唑烷酮化合物。这些化合物在治疗与细胞无法控制增殖相关的疾病，如癌症或癌前病变方面非常有用。这些化合物还可用于调节脂质和/或碳水化合物代谢，治疗II型糖尿病、高血糖或肥胖症，以及治疗炎症性疾病，如关节炎。本发明的某些实施例涉及具有下面所示结构的化合物或其药学上可接受的盐。1
• Retinoid Derivatives With Antiangiogenic, Antitumoral And Proapoptotic Activities
  申请人：Dallavalle Sabrina

  公开号：US20080021088A1

  公开（公告）日：2008-01-24

  Described and claimed are compounds of Formula (I) in which R, R′, R″, A, and D have the meanings described in the text, as useful agents in the cure of pathologies characterized by altered angiogenesis and as antitumorals.

  描述和声明的是化合物式（I）的化合物，其中R、R'、R"、A和D在文本中所描述的含义，作为治疗由异常血管生成特征的病理状况和抗肿瘤剂的有用药物。
• EP1385465A2
  申请人：——

  公开号：EP1385465A2

  公开（公告）日：2004-02-04
• EP1385465A4
  申请人：——

  公开号：EP1385465A4

  公开（公告）日：2005-09-07