methyl E-3-(3'-adamantan-1-yl-4'-hydroxybiphenyl-4-yl)acrylate | 496858-32-3

• 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: methyl E-3-(3'-adamantan-1-yl-4'-hydroxybiphenyl-4-yl)acrylate
• 英文别名: methyl E-3-(3’-adamantan-1-yl-4’-hydroxybiphenyl-4-yl) acrylate；adarotene methyl ester；methyl E-4-(3-(1-adamantyl)-4-hydroxyphenyl)cinnamate；(E)-3-(3'-adamantan-1-yl-4'-hydroxy-biphenyl-4-yl)-acrylic acid methyl ester；(E)-3-(3'-adamantan-1-yl-4'-hydroxybiphenyl-4-yl)-acrylic acid methyl ester；methyl (E)-3-[4-[3-(1-adamantyl)-4-hydroxyphenyl]phenyl]prop-2-enoate
• CAS: 496858-32-3
• 化学式: C₂₆H₂₈O₃
• 分子量: 388.507
• InChiKey: UHRMRPFHRRLXNO-RUDMXATFSA-N

物化性质

• 熔点：
  >240 °C
• 沸点：
  553.5±50.0 °C(Predicted)
• 密度：
  1.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  methyl E-3-(3'-adamantan-1-yl-4'-hydroxybiphenyl-4-yl)acrylate 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以94%的产率得到阿达罗汀
  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：

  3-(金刚烷-1-基)-4'-溴-[1,1'-联苯]-4-醇 以98的产率得到methyl E-3-(3'-adamantan-1-yl-4'-hydroxybiphenyl-4-yl)acrylate
  参考文献：
  名称：

  J. Med. Chem. 2003, 46, 909-912

  摘要：

  DOI：

文献信息

• [EN] PHENOL DERIVATIVES FOR USE AS ANTIMICROBIAL, ANTIBACTERIAL, BACTERICIDE<br/>[FR] DÉRIVÉS DE PHÉNOL DESTINÉS À ÊTRE UTILISÉS COMME ANTIMICROBIENS, ANTIBACTÉRIENS, ET BACTÉRICIDES
  申请人：SPECIAL PRODUCTS LINE S P A

  公开号：WO2020178053A1

  公开（公告）日：2020-09-10

  Phenol derivatives of general formula (I) and (II), wherein meanings of the substituents are indicated in the description, their pharmaceutically acceptable salts, together with the processes for their preparation, their use as antimicrobial, antibacterial, bactericide agents and the corresponding pharmaceutical compositions are disclosed.

  通式（I）和（II）的酚衍生物，其中取代基的含义在描述中指明，它们的药用盐，以及它们的制备方法，它们作为抗微生物、抗菌、杀菌剂的用途以及相应的药物组成物被披露。
• [EN] NEW RETINOID DERIVATIVES ENDOWED WITH CYTOTOXIC AND/OR ANTIANGIOGENIC PROPERTIES<br/>[FR] NOUVEAUX DÉRIVÉS DE RÉTINOÏDES PRÉSENTANT DES PROPRIÉTÉS CYTOTOXIQUES ET/OU ANTI-ANGIOGÈNES
  申请人：SIGMA TAU IND FARMACEUTI

  公开号：WO2010072727A1

  公开（公告）日：2010-07-01

  The present invention relates to new retinoid derivatives of Formula (I), and to pharmaceutical compositions containing them for the treatment of patients affected by pathologies such as arthritic conditions, tumours, metastatic cancer, diabetic retinopathy, psoriasis, chronic inflammatory diseases or atherosclerosis.

  本发明涉及公式(I)的新视黄醇衍生物，以及含有它们的药物组合物，用于治疗患有关节炎、肿瘤、转移性癌症、糖尿病性视网膜病变、银屑病、慢性炎症性疾病或动脉粥样硬化等病症的患者。
• [EN] RETINOID DERIVATIVES WITH ANTIANGIOGENIC, ANTITUMORAL AND PROAPOPTOTIC ACTIVITIES<br/>[FR] DERIVES RETINOIDES A ACTIVITE ANTIANGIOGENIQUE, ANTITUMORALE ET PROAPOPTOTIQUE
  申请人：SIGMA TAU IND FARMACEUTI

  公开号：WO2003011808A1

  公开（公告）日：2003-02-13

  Are described 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 characterised by altered angiogenesis and as antitumorals.

  描述了式(I)中的化合物，其中R、R'、R''、A和D的含义如文本所述，作为治疗具有改变血管生成的病理和抗肿瘤药物的有用剂型。
• Retinoid derivatives with antiangiogenic, antitumoral and proapoptotic activities
  申请人：——

  公开号：US20040235757A1

  公开（公告）日：2004-11-25

  Are described 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 characterised by altered angiogenesis and as antitumorals.

  化合物的公式（I）中的R，R'，R''，A和D的含义如文本所述，可用作治疗具有改变的血管生成的病理特征和抗肿瘤剂的有用药剂。
• 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。