2-chloro-7-(4-methylpent-3-en-1-yl)naphthalene-1,4-dione | 500217-72-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-chloro-7-(4-methylpent-3-en-1-yl)naphthalene-1,4-dione
• 英文别名: 2-chloro-7-(4'-methyl-3'-pentenyl)-1,4-naphthoquinone；2-Chloro-7-(4-methylpent-3-enyl)naphthalene-1,4-dione
• CAS: 500217-72-1
• 化学式: C₁₆H₁₅ClO₂
• 分子量: 274.747
• InChiKey: SYWNSADOMRVCLA-UHFFFAOYSA-N

物化性质

• 沸点：
  406.8±45.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-chloro-7-(4-methylpent-3-en-1-yl)naphthalene-1,4-dione 在 Lindlar's catalyst 氢气 、 silver(l) oxide 作用下， 以 乙酸乙酯 、 乙醚 为溶剂， 反应 24.0h， 生成 2-chloro-7-(4-methylpentyl)-1,4-naphthoquinone
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Cytotoxic 6(7)-Alkyl-2-hydroxy-1, 4-naphthoquinones

  摘要：

  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.

  DOI：

  10.1002/1521-4184(200212)335:9<427::aid-ardp427>3.0.co;2-m
• 作为产物：
  描述：

  2-甲基-6-亚甲基-1,7-辛二烯 、 2,5-二氯-1,4-苯醌 在 二氧化锰 SiO2 、 乙酸乙酯 、 hexanes 、 hexanes EtOAc 作用下， 以 苯 为溶剂， 反应 48.0h， 以to provide chloronapthylquinone 6 (15.21 g, 82%)的产率得到2-chloro-7-(4-methylpent-3-en-1-yl)naphthalene-1,4-dione
  参考文献：
  名称：

  SERINIQUINONES, MELANOMA-SPECIFIC ANTICANCER AGENTS

  摘要：

  提供了丝氨醌衍生物及其治疗癌症的方法，特别是治疗黑色素瘤和前列腺癌。

  公开号：

  US20150148314A1

文献信息

• [EN] SERINIQUINONES, MELANOMA-SPECIFIC ANTICANCER AGENTS<br/>[FR] SÉRIQUINONES, AGENTS ANTICANCÉREUX SPÉCIFIQUES DES MÉLANOMES
  申请人：UNIV CALIFORNIA

  公开号：WO2014018919A1

  公开（公告）日：2014-01-30

  Accordingly, there are provided, inter alia, derivatives of seriniquinone and methods useful for the treatment of cancer, and in particular treatment of melanoma and prostate cancer.

  因此，提供了丝氨醌衍生物以及用于治疗癌症的方法，特别是治疗黑色素瘤和前列腺癌的方法。
• Synthesis and antifungal activity of terpenyl-1,4-naphthoquinone and 1,4-anthracenedione derivatives
  作者：Ma Ángeles Castro、Ana Ma Gamito、Verónica Tangarife-Castaño、Bibiana Zapata、José Ma Miguel del Corral、Ana C. Mesa-Arango、Liliana Betancur-Galvis、Arturo San Feliciano

  DOI：10.1016/j.ejmech.2013.06.018

  日期：2013.9

  strategy used to obtain the quinone derivatives was initially based on the Diels–Alder cycloaddition between myrcene and several p-benzoquinone derivatives, followed by cyclisation of the prenyl side chain in the case of anthracene-1,4-diones. The most promising compounds, displaying MIC values in the low μg/mL range, were those bearing one or two chlorine atoms attached to the quinone ring. Time-kill curves

  进行的27简单和杂环稠合的异戊烯基-1,4-萘醌和1,4-蒽二酮类抗真菌评价体外针对人病原性酵母菌（念珠菌属）和丝状真菌（曲霉属，镰孢属，和毛癣菌属）。最初用于获得醌衍生物的合成策略是基于月桂烯和几种对映体之间的Diels-Alder环加成反应-苯醌衍生物，在蒽-1,4-二酮的情况下，异戊二烯侧链的环化。MIC值在低μg/ mL范围内的最有希望的化合物是那些带有一个或两个氯原子连接在醌环上的化合物。确定的最有效化合物的时间杀灭曲线显示出其抑菌作用模式与伊曲康唑相似。
• A Novel Synthetic Route to Cytotoxic 1,4-Anthraquinones from 1,4-Benzoquinones
  作者：Mª Angeles Castro、José Mª Miguel del Corral、Marina Gordaliza、Pablo A. García、Ana Mª Gamito、Simone A. Gualberto、Ronan Batista、Arturo San Feliciano

  DOI：10.1055/s-2005-918437

  日期：——

  A new procedure to obtain anthracene-1,4-diones from p-benzoquinones and myrcene, in the presence of acids, is described. The cycloaddition reaction between α-myrcene and p-benzoquinones, followed by oxidation, led to 1,4-naphthoquinones or 1,4-anthraquinones depending upon whether the Lewis acid used in the Diels-Alder reaction, was present or absent during oxidation; furthermore, traces of acid in

  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。
• New cytotoxic furoquinones obtained from terpenyl-1,4-naphthoquinones and 1,4-anthracenediones
  作者：José M. Miguel del Corral、M. Angeles Castro、Alaide B. Oliveira、Simone A. Gualberto、Carmen Cuevas、Arturo San Feliciano

  DOI：10.1016/j.bmc.2006.06.053

  日期：2006.11

  A series of new furoterpenyl-1,4-naphtho(anthra)quinones have been prepared via oxidative cyclization of the corresponding 2-hydroxy-3-butenyl-1,4-naphtho(anthra)quinones. Depending on the reaction conditions the 1,2-quinones or the 1,4-quinones were obtained. Several new furo-1,4-anthraquinones were also obtained by condensation of 2,3-dichloroquinones with 1,3-dicarbonyls. The compounds synthesized have been evaluated for their cytotoxicity against neoplastic cell lines, some of them being effective below the micromolar level. (c) 2006 Elsevier Ltd. All rights reserved.
• US9481662B2
  申请人：——

  公开号：US9481662B2

  公开（公告）日：2016-11-01