1-(adamantyl-1-yl)-3-(4-bromophenyl)propenone | 174315-50-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 1-(adamantyl-1-yl)-3-(4-bromophenyl)propenone
• 英文别名: (E)-1-(1-adamantyl)-3-(4-bromophenyl)prop-2-en-1-one
• CAS: 174315-50-5
• 化学式: C₁₉H₂₁BrO
• 分子量: 345.279
• InChiKey: KTPIUKVFNGQVRL-ZZXKWVIFSA-N

物化性质

• 熔点：
  135 °C
• 沸点：
  458.2±20.0 °C(Predicted)
• 密度：
  1.378±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(adamantyl-1-yl)-3-(4-bromophenyl)propenone 在 palladium diacetate 、 lithium hydroxide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 54.0h， 生成 (E)-3-[4-[3-(1-adamantyl)-5-hydroxyphenyl]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：

  1-金刚烷甲酮 、 对溴苯甲醛 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 72.0h， 以85%的产率得到1-(adamantyl-1-yl)-3-(4-bromophenyl)propenone
  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

• Kozlov, N. G.; Skakovskii, E. D.; Korotyshova, G. P., Russian Journal of General Chemistry, 1997, vol. 67, # 10, p. 1602 - 1605
  作者：Kozlov, N. G.、Skakovskii, E. D.、Korotyshova, G. P.

  DOI：——

  日期：——
• KOZLOV, N. S.;SHMANAJ, G. S.;KOROTYSHOVA, G. P., VESTSI AN BSSR. CEP. XIM. N.,(1991) N, S. 60-65
  作者：KOZLOV, N. S.、SHMANAJ, G. S.、KOROTYSHOVA, G. P.

  DOI：——

  日期：——
• CYCLIC AZINE COMPOUND HAVING ADAMANTYL GROUP, PRODUCTION METHOD, AND ORGANIC ELECTROLUMINESCENT DEVICE CONTAINING IT AS CONSTITUENT COMPONENT
  申请人：TOSOH CORPORATION

  公开号：US20160372678A1

  公开（公告）日：2016-12-22

  An azine compound represented by the formula (1), a method for its production and an organic electroluminescent device containing it as a constituent component. wherein Ad each independently represents a 1-adamantyl group, etc., p and q are each independently 0 or 1, Ar 1 and Ar 2 are each independently a single bond (but only when p is 1, or q is 1), or a pyridyl group which may be substituted by a phenyl group, etc., incidentally, Ad groups on Ar 1 and Ar 2 are each independently bonded to said pyridyl group, etc., Ar 2 is each independently a C 3-13 heteroaromatic group which may be substituted by a fluorine atom, etc., X 1 , X 2 , X 3 and X 4 are each independently a single bond, etc., m and n are each independently 0, 1 or 2, Z is a nitrogen atom, etc., n+p+q is 1, 2 or 3.
• US9812652B2
  申请人：——

  公开号：US9812652B2

  公开（公告）日：2017-11-07
• 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.