1,4-萘二醇,5,8-二氢-6-(4-甲基-3-戊烯基)- | 177327-05-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1,4-萘二醇,5,8-二氢-6-(4-甲基-3-戊烯基)-
• 英文名称: 1,4-Naphthalenediol, 5,8-dihydro-6-(4-methyl-3-pentenyl)-
• 英文别名: 6-(4-methylpent-3-enyl)-5,8-dihydronaphthalene-1,4-diol
• CAS: 177327-05-8
• 化学式: C₁₆H₂₀O₂
• 分子量: 244.334
• InChiKey: GEOGVWFVOHPTNF-UHFFFAOYSA-N

物化性质

• 沸点：
  404.6±45.0 °C(Predicted)
• 密度：
  1.103±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-萘二醇,5,8-二氢-6-(4-甲基-3-戊烯基)- 在 吡啶 、 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 [4-Acetyloxy-6-[2-(3,3-dimethyloxiran-2-yl)ethyl]-5,8-dihydronaphthalen-1-yl] acetate
  参考文献：
  名称：

  Further antineoplastic terpenylquinones and terpenylhydroquinones

  摘要：

  Influences of the quinone/hydroquinone fragment and other structural features are considered in relation with the antineoplastic activity and selectivity of terpenylquinones/hydroquinones. Several compounds have shown IC50 values under the mu M level. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(97)10007-4
• 作为产物：
  描述：

  月桂烯 在 三氟化硼乙醚 、 silica gel 作用下， 以 正己烷 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 20.0h， 生成 1,4-萘二醇,5,8-二氢-6-(4-甲基-3-戊烯基)-
  参考文献：
  名称：

  从 1,4-苯醌合成细胞毒性 1,4-蒽醌的新途径

  摘要：

  描述了在酸存在下从对苯醌和月桂烯中获得蒽-1,4-二酮的新方法。α-月桂烯和对苯醌之间的环加成反应，然后氧化，导致 1,4-萘醌或 1,4-蒽醌，这取决于在氧化过程中是否存在用于 Diels-Alder 反应的路易斯酸；此外，溶剂中的微量酸在确定所获得的环加合物方面发挥了重要作用。合成的醌对几种肿瘤细胞系表现出细胞毒性。

  DOI：

  10.1055/s-2005-918437

文献信息

• TERPENE-QUINONE WITH ANTITUMOR ACTIVITY
  申请人：PHARMA MAR, S.A.

  公开号：EP0731078A1

  公开（公告）日：1996-09-11

  Terpene-quinones with antitumour activity, defined from a Diels-Alder cyclocondensation reaction, thereby achieving families or series of said compounds of new structure which have cytotoxic activity against cell cultures P-388, A-549, HT-29 and MEL-28, reaching IC50 levels lower than 1 microgram per millilitre.

  通过 Diels-Alder 环缩合反应确定的具有抗肿瘤活性的萜烯醌类化合物，从而获得新结构的上述化合物家族或系列，它们对细胞培养物 P-388、A-549、HT-29 和 MEL-28 具有细胞毒活性，IC50 值低于 1 微克/毫升。
• Synthesis and Biological Evaluation of Cytotoxic 6(7)-Alkyl-2-hydroxy-1, 4-naphthoquinones
  作者：José M. Miguel del Corral、Maria Angeles Castro、Marina Gordaliza、Maria Luz Martin、Alaide B. Oliveira、Simone A. Gualberto、Maria Dolores García-Grávalos、Arturo San Feliciano

  DOI：10.1002/1521-4184(200212)335:9<427::aid-ardp427>3.0.co;2-m

  日期：2002.12

  Various Diels Alder cycloaddition conditions have been used to optimise the preparation of cytotoxic 6-alkyl-1,4-naphthoquinones, which were subsequently transformed into 6(7)-alkyl-2-hydroxy-1,4-naphthoquinones. The compounds thus prepared were evaluated for their cytotoxic activity against several neoplastic cultured cell lines and some of them showed IC50 values below the muM level.
• Synthesis, anti-HIV activity, integrase enzyme inhibition and molecular modeling of catechol, hydroquinone and quinol labdane analogs
  作者：Rohan Pawar、Tiyasa Das、Sanjay Mishra、Nutan、Boskey Pancholi、Satish K. Gupta、Sujata V. Bhat

  DOI：10.1016/j.bmcl.2013.11.014

  日期：2014.1

  Labdane analogs with o-quinol, catechol and hydroquinone moiety have been synthesized using Diels-Alder reaction of methyl 3,4-dioxocyclohexa-1,5-diene-carboxylate, 3,4-dioxocyclohexa-1,5-dienecarboxylic acid and 3,6-dioxocyclohexa-1,4-dienecarboxylic acid with mono terpene 1,3-dienes, namely ocimene and myrcene. The resulting molecules and their derivatives were evaluated for their anti-HIV-1 activity using TZM-bl cell based virus infectivity assay. Two molecules 13 and 18 showed anti-HIV activity with IC50 values 5.0 (TI = 11) and 4.6 (TI = 46) mu M, respectively. The compounds 17, 18 and 20 showed efficacy against HIV-1 integrase activity and showed inhibition with IC50 13.4, 11.1 and 11.5 mu M, respectively. The HIV-1 integrase inhibition activity of these synthetic molecules was comparable with integric acid, the natural fungal metabolite. Molecular modeling studies for the HIV-1 integrase inhibition of these active synthetic molecules indicated the binding to the active site residues of the enzyme. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis and bioactivity of new antineoplastic terpenylquinones
  作者：Marina Gordaliza、JoséMa Miguel del Corral、Ma Angeles Castro、Ma Mar Mahiques、MaDolores García-Grávalos、Arturo San Feliciano

  DOI：10.1016/0960-894x(96)00326-5

  日期：1996.8

  Several monoterpenylquinones have been prepared and evaluated for their cytotoxic activity against four cell lines cultures. The size of the quinone fragment is important for the activity, being the naphtalene derivatives the most potent compounds tested. The presence of substituents on the quinone ring decreases the potency but increases the selectivity. Copyright (C) 1996 Elsevier Science Ltd
• US5744623A
  申请人：——

  公开号：US5744623A

  公开（公告）日：1998-04-28