3'-(adamantan-1-yl)-4'-tert-butyldimethylsilyloxybiphenyl-4-aldehyde | 459423-14-4

• 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'-tert-butyldimethylsilyloxybiphenyl-4-aldehyde
• 英文别名: 3’-(adamantan-1-yl)-4’-tert-butyldimethylsilyloxybiphenyl-4-aldehyde；4-[3-(1-adamantyl)-4-(t-butyldimethylsilyloxy)phenyl]-benzaldehyde；4-(3-(1-adamantyl)-4-tert-butyldimethyl-silyloxyphenyl)benzaldehyde；4-[3-(1-adamantyl)-4-[tert-butyl(dimethyl)silyl]oxyphenyl]benzaldehyde
• CAS: 459423-14-4
• 化学式: C₂₉H₃₈O₂Si
• 分子量: 446.705
• InChiKey: UZDMDWSDHSQNCL-UHFFFAOYSA-N

物化性质

• 沸点：
  532.4±50.0 °C(Predicted)
• 密度：
  1.069±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.02
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3'-(adamantan-1-yl)-4'-tert-butyldimethylsilyloxybiphenyl-4-aldehyde 生成 methyl (E)-3-[4-[3-(1-adamantyl)-4-[tert-butyl(dimethyl)silyl]oxyphenyl]phenyl]prop-2-enoate
  参考文献：
  名称：

  Retinoid derivatives with antiangiogenic, antitumoral and proapoptotic activities

  摘要：

  描述了式（I）化合物，其中R，R'，R''，A和D具有文本中描述的含义，作为治疗具有异常血管生成和抗肿瘤特征的病理的有用药剂。

  公开号：

  US08101793B2
• 作为产物：
  描述：

  2-(1-金刚烷基)-4-溴苯酚 在 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 sodium carbonate 、 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 2.0h， 生成 3'-(adamantan-1-yl)-4'-tert-butyldimethylsilyloxybiphenyl-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

• [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。
• 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.

  本发明涉及一些杂环化合物，其具有公式（I），可用于治疗癌症和其他疾病，其中：1 （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，杂环芳基，取代杂环芳基，芳基或取代芳基残基； （c）Ar3是芳基，取代芳基，杂环芳基或取代杂环芳基残基； （d）Ar4是芳基，取代芳基，杂环芳基或取代杂环芳基残基； （e）R5是氢，羟基，烷基或取代烷基； （f）- - - - -代表存在或不存在的键；和 （g）W，X，Y和Z独立地或一起是C（O）—，C（S），S，O或NH；或其药学上可接受的盐。
• Synthesis and Structure−Activity Relationships of a New Series of Retinoid-Related Biphenyl-4-ylacrylic Acids Endowed with Antiproliferative and Proapoptotic Activity
  作者：Raffaella Cincinelli、Sabrina Dallavalle、Raffaella Nannei、Serena Carella、Daniele De Zani、Lucio Merlini、Sergio Penco、Enrico Garattini、Giuseppe Giannini、Claudio Pisano、Loredana Vesci、Paolo Carminati、Valentina Zuco、Chiara Zanchi、Franco Zunino

  DOI：10.1021/jm049440h

  日期：2005.7.1

  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.
• Retinoid derivatives with antiangiogenic, antitumoral and proapoptotic activities
  申请人：Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.

  公开号：US08101793B2

  公开（公告）日：2012-01-24

  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 characterized by altered angiogenesis and as antitumorals.

  描述了式（I）化合物，其中R，R'，R''，A和D具有文本中描述的含义，作为治疗具有异常血管生成和抗肿瘤特征的病理的有用药剂。