2-(1-Adamantyl)-5-bromophenol | 142650-60-0

• 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: 2-(1-Adamantyl)-5-bromophenol
• 英文别名: 2-(adamantan-1-yl)-5-bromophenol；2-(adamantan-1-yl)-5-bromo-1-phenol
• CAS: 142650-60-0
• 化学式: C₁₆H₁₉BrO
• 分子量: 307.23
• InChiKey: IOZVATPXSYDKNM-UHFFFAOYSA-N

物化性质

• 熔点：
  118 °C
• 沸点：
  383.0±35.0 °C(Predicted)
• 密度：
  1.442±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(1-Adamantyl)-5-bromophenol 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 sodium hydroxide 、 potassium acetate 、 联硼酸频那醇酯 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 5.5h， 生成 (E)-3-[4-[4-(1-adamantyl)-3-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：

  间溴苯酚 、 1-金刚烷醇 在 硫酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以16%的产率得到2-(1-Adamantyl)-5-bromophenol
  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

• Di(aromatic) compounds and their use in human and veterinary medicine
  申请人：Centre International de Recherches Dermatologiques Galderma (Cird

  公开号：US05387594A1

  公开（公告）日：1995-02-07

  Di(aromatic) compounds corresponding to the following formula: ##STR1## in which: Ar represents either ##STR2## n=1 or 2 or: ##STR3## X represents a divalent radical, Z represents O, S or a divalent radical, and R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 represent a hydrogen atom or various organic radicals, and the salts of the compounds of formula (I) when R.sub.1 is a carboxylic acid function. Use in human and veterinary medicine and in cosmetics.

  对应以下公式的二芳基化合物：##STR1## 其中：Ar代表##STR2## n=1或2或：##STR3## X代表二价基团，Z代表O、S或二价基团，R.sub.1、R.sub.2、R.sub.3、R.sub.4和R.sub.5代表氢原子或各种有机基团，以及当R.sub.1是羧酸功能时，公式（I）化合物的盐。用于人类和兽医学以及化妆品。
• Diarylselenide compounds and their use in human or veterinary medicine and in cosmetics
  申请人：Bernardon Jean-Michel

  公开号：US20060014803A1

  公开（公告）日：2006-01-19

  The invention concerns novel diarylselenide compounds corresponding to formula (I): and the use thereof in pharmaceutical compositions in human or veterinary medicine (in the treatment of dermatological, rheumatic, cardiovascular and ophthalmologic pathologies in particular), or in cosmetic compositions.

  该发明涉及与以下化学式（I）对应的新型二芳基硒化合物，以及其在人类或兽医药物中的使用（特别是在治疗皮肤病、风湿病、心血管病和眼科病变方面），或在化妆品中的使用。
• Adamantyl-substituted biaromatic compounds and pharmaceutical/cosmetic
  申请人：Centre International De Recherches Dermatologiquies Galderma

  公开号：US05877342A1

  公开（公告）日：1999-03-02

  Novel pharmaceutically/cosmetically-active adamantyl-substituted biaromatic compounds have the structural formula (I): ##STR1## wherein Ar is a radical having one of the formulae (a')-(f'): ##STR2## and are useful for the treatment of a wide variety of disease states, whether human or veterinary, for example dermatological, rheumatic, respiratory, cardiovascular, bone and ophthalmological disorders, as well as for the treatment of mammalian skin and hair conditions/disorders.

  新型具有药用/化妆活性的取代脂肪环双芳香化合物具有结构式（I）：##STR1##其中Ar是具有下列式（a'）-（f'）之一的基团：##STR2##对于治疗各种疾病状态非常有用，无论是人类还是兽医，例如皮肤病、风湿病、呼吸系统疾病、心血管疾病、骨骼疾病和眼科疾病，以及哺乳动物皮肤和毛发状况/疾病的治疗。
• Novel heteroethynylenic compounds and pharmaceutical and cosmetic compositions containing them
  申请人：——

  公开号：US20030012803A1

  公开（公告）日：2003-01-16

  The invention relates to novel heteroethynylenic compounds having the general formula (I): 1 as well as to the use of these compounds in pharmaceutical compositions intended for use in human or veterinary medicine (dermatological, rheumatic, respiratory, cardiovascular and ophthalmological complaints in particular), or alternatively in cosmetic compositions.

  本发明涉及具有通式（I）的新型杂乙炔化合物，以及这些化合物在制备用于人类或兽医药物组合物（特别是皮肤科，风湿科，呼吸科，心血管科和眼科疾病）或化妆品组合物中的应用。
• Acetylenes disubstituted with hydroxyaryl and aryl or heteroaryl groups
  申请人：Allergan, Inc.

  公开号：US05498795A1

  公开（公告）日：1996-03-12

  Compounds of the formula ##STR1## wherein R.sub.1 -R.sub.3 and R.sub.5 independently are hydrogen, lower alkyl of 1 to 6 carbons, branched chain alkyl or cycloalkyl of 3 to 15 carbons, lower alkyl substituted cycloalkyl of 3 to 15 carbons; R.sub.4 is lower alkyl of 1 to 6 carbons, branched chain alkyl or cycloalkyl of 3 to 15 carbons or lower alkyl substituted cycloalkyl of 3 to 15 carbons; X is S or O; Y is a phenyl group, or heteroaryl selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, imidazolyl and oxazolyl, said groups being substituted with the R.sub.5 group defined above; A is (CH.sub.2).sub.n where n is 0-5, lower branched chain alkyl having 3-6 carbons, cycloalkyl having 3-6 carbons, alkenyl having 2-6 carbons and 1 or 2 double bonds, alkynyl having 2-6 carbons and 1 or 2 triple bonds; B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR.sub.8, CONR.sub.9 R.sub.10, --CH.sub.2 OH, CH.sub.2 OR.sub.11, CH.sub.2 OCOR.sub.11, CHO, CH(OR.sub.12).sub.2, CHOR.sub.13 O, --COR.sub.7, CR.sub.7 (OR.sub.12).sub.2, or CR.sub.7 OR.sub.13 O, where R.sub.7 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons, R.sub.8 is an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or R.sub.8 is phenyl or lower alkylphenyl, R.sub.9 and R.sub.10 independently are hydrogen, an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5-10 carbons, or phenyl or lower alkylphenyl, R.sub.11 is lower alkyl, phenyl or lower alkylphenyl, R.sub.12 is lower alkyl, and R.sub.13 is divalent alkyl radical of 2-5 carbons, have retinoid-like biological activity.

  该化合物的公式为##STR1##其中R.sub.1 -R.sub.3和R.sub.5独立地为氢，1至6个碳的低级烷基，支链烷基或3至15个碳的环烷基，3至15个碳的低级烷基取代的环烷基；R.sub.4为1至6个碳的低级烷基，支链烷基或3至15个碳的环烷基或3至15个碳的低级烷基取代的环烷基；X为S或O；Y为苯基或从吡啶基，噻吩基，呋喃基，吡嗪基，嘧啶基，吡唑基，噻唑基，咪唑基和噁唑基中选择的杂环基，所述基团被上述R.sub.5基团取代；A为（CH.sub.2）.sub.n，其中n为0-5，低支链烷基，含有3-6个碳的环烷基，具有2-6个碳和1或2个双键的烯基，具有2-6个碳和1或2个三键的炔基；B为氢，COOH或其药学上可接受的盐，COOR.sub.8，CONR.sub.9 R.sub.10，--CH.sub.2 OH，CH.sub.2 OR.sub.11，CH.sub.2 OCOR.sub.11，CHO，CH(OR.sub.12).sub.2，CHOR.sub.13 O，--COR.sub.7，CR.sub.7 (OR.sub.12).sub.2或CR.sub.7 OR.sub.13 O，其中R.sub.7是含有1至5个碳的烷基，环烷基或烯基，R.sub.8是1至10个碳的烷基或5至10个碳的环烷基，或R.sub.8是苯基或低级烷基苯基，R.sub.9和R.sub.10独立地是氢，1至10个碳的烷基或5-10个碳的环烷基，或苯基或低级烷基苯基，R.sub.11是低级烷基，苯基或低级烷基苯基，R.sub.12是低级烷基，R.sub.13是2-5个碳的双价烷基基团，具有类视黄醇的生物活性。