2-氯-3-丙氧基萘-1,4-二酮 | 84369-93-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-氯-3-丙氧基萘-1,4-二酮
• 英文名称: 2-chloro-3-propoxy-1,4-naphthoquinone
• 英文别名: 2-chloro-3-propoxynaphthalene-1,4-dione
• CAS: 84369-93-7
• 化学式: C₁₃H₁₁ClO₃
• 分子量: 250.682
• InChiKey: LHRLRJXHMDGYQJ-UHFFFAOYSA-N

物化性质

• 沸点：
  389.6±42.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-氯-3-丙氧基萘-1,4-二酮 、 苯胺 在 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium tert-butylate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以67%的产率得到2-(phenylamino)-3-propoxynaphthalene-1,4-dione
  参考文献：
  名称：

  Discovery of Novel 2-Aniline-1,4-naphthoquinones as Potential New Drug Treatment for Leber’s Hereditary Optic Neuropathy (LHON)

  摘要：

  Leber's hereditary optic neuropathy (LHON) is a rare genetic mitochondrial disease and the primary cause of chronic visual impairment for at least 1 in 10 000 individuals in the U.K. Treatment options remain limited, with only a few drug candidates and therapeutic approaches, either approved or in development. Recently, idebenone has been investigated as drug therapy in the treatment of LHON, although evidence for the efficacy of idebenone is limited in the literature. NAD(P)H:quinone oxidoreductase 1 (NQO1) and mitochondrial complex III were identified as the major enzymes involved in idebenone activity. Based on this mode of action, computer-aided techniques and structure-activity relationship (SAR) optimization studies led to the discovery of a series naphthoquinone-related small molecules, with comparable adenosine 5'-triphosphate (ATP) rescue activity to idebenone. Among these, three compounds showed activity in the nanomolar range and one, 2-((4-fluoro-3-(trifluoromethyl)phenyl)amino)-3-(methylthio)naphthalene-1,3-dione (1), demonstrated significantly higher potency ex vivo, and significantly lower cytotoxicity, than idebenone.

  DOI：

  10.1021/acs.jmedchem.0c00942
• 作为产物：
  描述：

  2,3-二氯-1,4-萘醌 生成 2-氯-3-丙氧基萘-1,4-二酮
  参考文献：
  名称：

  CLARK, N. G., PESTIC. SCI., 1984, 15, N 3, 235-240

  摘要：

  DOI：

文献信息

• Synthesis of 2-Alkoxy 1,4-Naphthoquinone Derivatives as Antiplatelet, Antiinflammatory, and Antiallergic Agents.
  作者：Jin-Cherng Lien、Li-Jiau Huang、Che-Ming Teng、Jih-Pyang Wang、Sheng-Chu Kuo

  DOI：10.1248/cpb.50.672

  日期：——

  In our continuing search for novel antiplatelet, antiallergic, and antiinflammatory agents, 2-alkoxy derivatives of 1,4-naphthoquinone were prepared. Some of these compounds showed significant antiplatelet, antiallergic, and antiinflammatory activities. Among them, 2-propoxy-1,4-naphthoquinone and 2-butoxy-1,4-naphthoquinone exhibited potent inhibitory effect on neutrophil superoxide anion formation

  在我们不断寻找新的抗血小板药，抗过敏药和抗炎药的过程中，制备了1,4-萘醌的2-烷氧基衍生物。这些化合物中的一些显示出显着的抗血小板，抗过敏和抗炎活性。其中，2-丙氧基-1,4-萘醌和2-丁氧基-1,4-萘醌对中性粒细胞超氧阴离子的形成具有有效的抑制作用。这两种化合物值得进一步探索。
• Alkoxy and Enediyne Derivatives Containing 1,4-Benzoquinone Subunits—Synthesis and Antitumor Activity
  作者：Monika Kadela-Tomanek、Ewa Bębenek、Elwira Chrobak、Małgorzata Latocha、Stanisław Boryczka

  DOI：10.3390/molecules22030447

  日期：——

  4-benzoquinone subunit. This fragment occurs in three enediyne antibiotics, dynemicin A, deoxydynemicin A, and uncilamicin, which exhibit high biological activity. A series of alkoxy derivatives containing 1,4-naphthoquinone, 5,8-quinolinedione, and 2-methyl-5,8-quinolinedione moieties was synthesized. Moreover, the 1,4-benzoquinone subunit was contacted with an enediyne fragment. All obtained compounds were characterized

  生物体产生的化合物最常作为药物和制备新的半合成衍生物的原料。最大的一组天然化合物由含有 1,4-苯醌亚基的产品组成。该片段出现在三种烯二炔抗生素中，dynemicin A、deoxydynemicin A 和 uncilamicin，它们表现出很高的生物活性。合成了一系列含有 1,4-萘醌、5,8-喹啉二酮和 2-甲基-5,8-喹啉二酮部分的烷氧基衍生物。此外，1,4-苯醌亚基与烯二炔片段接触。所有获得的化合物都通过光谱和光谱方法进行表征。将所得烷烃、烯烃、炔烃和烯二炔衍生物作为抗肿瘤剂进行测试。根据 1,4-苯醌亚基的类型和使用的肿瘤细胞系，它们显示出高细胞毒活性。合成的衍生物符合利平斯基五法则并且通过血脑屏障具有低渗透性。
• Substituted 1,4-naphthoquinones vs. the ascitic sarcoma 180 of mice
  作者：Ernest M. Hodnett、Chinda Wongwiechintana、William J. Dunn、Pam Marrs

  DOI：10.1021/jm00358a021

  日期：1983.4

  Twelve 1,4-naphthoquinones have been tested against the ascitic form of sarcoma 180 in Swiss mice. Statistical analysis shows that the most important molecular parameter determining their effectiveness in prolonging the life of mice bearing this tumor is their redox potentials. Although the toxicities of the compounds are also related to the redox potentials in the same way, the therapeutic indexes can be increased by adding substituents of greater lipophilicity. The naphthoquinones differ greatly in antitumor activities and may inhibit the growth of malignant cells by different mechanisms.
• Discovery of Novel 2-Aniline-1,4-naphthoquinones as Potential New Drug Treatment for Leber’s Hereditary Optic Neuropathy (LHON)
  作者：Carmine Varricchio、Kathy Beirne、Pascale Aeschlimann、Charles Heard、Malgorzata Rozanowska、Marcela Votruba、Andrea Brancale

  DOI：10.1021/acs.jmedchem.0c00942

  日期：2020.11.25

  Leber's hereditary optic neuropathy (LHON) is a rare genetic mitochondrial disease and the primary cause of chronic visual impairment for at least 1 in 10 000 individuals in the U.K. Treatment options remain limited, with only a few drug candidates and therapeutic approaches, either approved or in development. Recently, idebenone has been investigated as drug therapy in the treatment of LHON, although evidence for the efficacy of idebenone is limited in the literature. NAD(P)H:quinone oxidoreductase 1 (NQO1) and mitochondrial complex III were identified as the major enzymes involved in idebenone activity. Based on this mode of action, computer-aided techniques and structure-activity relationship (SAR) optimization studies led to the discovery of a series naphthoquinone-related small molecules, with comparable adenosine 5'-triphosphate (ATP) rescue activity to idebenone. Among these, three compounds showed activity in the nanomolar range and one, 2-((4-fluoro-3-(trifluoromethyl)phenyl)amino)-3-(methylthio)naphthalene-1,3-dione (1), demonstrated significantly higher potency ex vivo, and significantly lower cytotoxicity, than idebenone.
• CLARK, N. G., PESTIC. SCI., 1984, 15, N 3, 235-240
  作者：CLARK, N. G.

  DOI：——

  日期：——