5-(adamant-1-yl)-2,4-dihydroxybenzaldehyde | 173190-69-7

• 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: 5-(adamant-1-yl)-2,4-dihydroxybenzaldehyde
• 英文别名: 5-(1-adamantyl)-2,4-dihydroxybenzaldehyde；2,4-dihydroxy-5-(1-adamantyl)benzaldehyde；2,4-Dihydroxy-5-(1-adamantyl)-benzaldehyde
• CAS: 173190-69-7
• 化学式: C₁₇H₂₀O₃
• 分子量: 272.344
• InChiKey: XGKWOFXNGNVFOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(adamant-1-yl)-2,4-dihydroxybenzaldehyde 在 potassium carbonate 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 6.0h， 生成 (E)-3-(5-(adamantan-1-yl)-2,4-bis(methoxymethoxy)phenyl)-1-(2-hydroxy-5-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Discovery of new chalone adamantyl arotinoids having RXRα-modulating and anticancer activities

  摘要：

  DOI：

  10.1016/j.bioorg.2021.104961
• 作为产物：
  描述：

  1-金刚烷醇 、 2,4-二羟基苯甲醛 在 硫酸 作用下， 以 二氯甲烷 为溶剂， 生成 5-(adamant-1-yl)-2,4-dihydroxybenzaldehyde
  参考文献：
  名称：

  Adamantyl-substituted biaromatic compounds and pharmaceutical/cosmetic

  摘要：

  新型具有药用/化妆活性的取代脂环烷基双芳香化合物具有结构式(I)：其中Ar是具有下列式(a')-(f')之一的基团：并且适用于治疗各种疾病状态，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，以及治疗哺乳动物皮肤和毛发状况/疾病。

  公开号：

  US05786379A1

文献信息

• Adamantyl-substituted polycyclic acetylene compounds and
  申请人：Centre International de Recherches Dermatologiques Galderma

  公开号：US05574036A1

  公开（公告）日：1996-11-12

  Novel pharmaceutically/cosmetically-active adamantyl-substituted polycyclic acetylene 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/化妆活性的脂环己基取代多环乙炔化合物具有结构式(I)：其中Ar是具有式(a)-(f)之一的基团，对于治疗广泛的疾病状态是有用的，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，以及治疗哺乳动物的皮肤和毛发状况/疾病。
• Use of adamantyl-substituted polycyclic acetylene compounds in skin and
  申请人：Centre International De Recherches Dermatologiques Galderma

  公开号：US05798354A1

  公开（公告）日：1998-08-25

  Novel pharmaceutically/cosmetically-active adamantyl-substituted polycyclic acetylene 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.

  具有药理/美容活性的新型亚胺基取代的多环乙炔化合物具有结构式(I)：##STR1## 其中Ar是具有以下式子之一的基团(a)-(f)：##STR2## 并且可用于治疗各种疾病状态，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，以及用于治疗哺乳动物皮肤和毛发状况/疾病。
• Composés bi-aromatiques acétylénés à groupement adamantyle, compositions pharmaceutiques et cosmétiques les contenant et utilisations
  申请人：CENTRE INTERNATIONAL DE RECHERCHES DERMATOLOGIQUES GALDERMA, ( CIRD GALDERMA)

  公开号：EP0679631A1

  公开（公告）日：1995-11-02

  L'invention concerne de nouveaux composés bi-aromatiques acétylénés à groupement adamantyle qui présentent comme formule générale (I) : ainsi que l'utilisation de ces derniers dans des compositions pharmaceutiques destinées à un usage en médecine humaine ou vétérinaire (affections dermatologiques, rhumatismales, respiratoires, cardiovasculaires et ophtalmologiques notamment), ou bien encore dans des compositions cosmétiques.

  本发明涉及带有金刚烷基的新型乙炔化双芳香族化合物，其通式为(I)： 以及后者在用于人类或兽类医药（尤其是皮肤病、风湿病、呼吸系统疾病、心血管疾病和眼科疾病）的药物组合物或化妆品组合物中的用途。
• Inhibition of IκB Kinase-β and Anticancer Activities of Novel Chalcone Adamantyl Arotinoids
  作者：Paula Lorenzo、Rosana Alvarez、Maria A. Ortiz、Susana Alvarez、F. Javier Piedrafita、Ángel R. de Lera

  DOI：10.1021/jm800285f

  日期：2008.9.11

  On the basis of the observations that chalcone 7 (MX781) and some related adamantyl arotinoids (AdArs) inhibit I kappa B alpha kinase beta (IKK beta) activity, inhibit cell growth, and induce apoptosis in cancer cells, a new series of AdArs structurally related to 7 have been designed and synthesized. Modifications were intended to reduce or eliminate RAR activity, and we evaluated the effect of the novel analogues of 7 on IKK beta activity and proliferation of a variety of cancer cell lines (leukemia, Jurkat; prostate, PC-3; breast carcinomas, T47D, MDA-MB-468). Consistent with the design principles, the biological activities of these AdArs do not appear to be RAR-mediated, since most analogues are unable to activate RAR-mediated transactivation and exhibit significantly diminished antagonist activity. All compounds are capable of inducing apoptosis in Jurkat cells, as demonstrated by elevated DEVDase activity and externalization of phosphatidylserine. Several of the analogues elicit stronger growth inhibitory activity against prostate (PC-3) and breast (MDA-MB-468) carcinoma cells, which contain elevated basal IKK activity; this antiproliferative activity correlates with increased inhibition of recombinant IKK beta in vitro, suggesting that the anticancer activities of these AdArs might be related to the inhibition of' IKK/NF kappa B signaling.
• Composés biaromatiques portant un groupement adamantyl en ortho, compositions pharmaceutiques et cosmétiques les contenant et utilisations
  申请人：CENTRE INTERNATIONAL DE RECHERCHES DERMATOLOGIQUES GALDERMA (C.I.R.D. GALDERMA)

  公开号：EP0776885B1

  公开（公告）日：1999-10-27