3-chloro-4-hydroxynaphthalene-1,2-dione | 1526-73-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-chloro-4-hydroxynaphthalene-1,2-dione
• 英文别名: 3-chloro-2-hydroxy-naphthalene-1,4-dione；3-chloro-1,4-dihydro-1,4-dioxo-2-hydroxynaphthalene；2-chloro-3-hydroxy-[1,4]-naphthoquinone；2-chloro-3-hydroxynaphthalene-1,4-dione；2-chloro-3-hydroxy-1,4-naphthoquinone；2-hydroxy-3-chloro-1,4-naphthoquinone；3-chloro-2-hydroxy-1,4-naphthoquinone
• CAS: 1526-73-4
• 化学式: C₁₀H₅ClO₃
• mdl: MFCD00043767
• 分子量: 208.601
• InChiKey: FIGWNRLKJUUMTF-UHFFFAOYSA-N

物化性质

• 熔点：
  216.5°C
• 沸点：
  299.56°C (rough estimate)
• 密度：
  1.3609 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  1.36
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

安全信息

• 海关编码：
  2914700090

反应信息

• 作为反应物：
  描述：

  3-chloro-4-hydroxynaphthalene-1,2-dione 在 氢碘酸 作用下， 以 二氯甲烷 为溶剂， 生成 2-羟基-1,4-萘醌
  参考文献：
  名称：

  Regiocontrolled synthesis and HIV inhibitory activity of unsymmetrical binaphthoquinone and trimeric naphthoquinone derivatives of conocurvone

  摘要：

  Unsymmetrical biquinone and trimeric quinone derivatives were synthesized using halotriflate-biselectrophilic naphthoquinones through stepwise regioselective quinone substitution chemistry and evaluated for their ability to inhibit the cytopathogenic effects of HIV-1 using an MTT colorimetric assay. Compounds were also screened for their ability to inhibit the activity of HIV-1 integrase in vitro. Pyranylated trimeric quinones and biquinones exhibited both antiviral activity and integrase inhibitory activity. Conocurvone 1 and trimeric quinone 21 were the most potent HIV integrase inhibitors in the series. All of the biquinones showed HIV inhibitory activity. Simple methoxy substituted biquinones did not inhibit HIV-1 integrase. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2006.04.034
• 作为产物：
  描述：

  1,1,3,4-tetrchloroteralin-2-one 在 sodium hydroxide 作用下， 生成 3-chloro-4-hydroxynaphthalene-1,2-dione
  参考文献：
  名称：

  Zincke; Kegel, Chemische Berichte, 1888, vol. 21, p. 3552

  摘要：

  DOI：

文献信息

• Design, Synthesis and Antimalarial Activity of Some New 2-Hydroxy-1,4-naphthoquinone-4-hydroxyaniline Hybrid Mannich Bases
  作者：Dipshikha Sharma、Dipak Chetia、Mithun Rudrapal

  DOI：10.14233/ajchem.2016.19478

  日期：——

  In this study, some novel 2-hydroxy-1,4-naphthoquinone-4-hydroxyaniline hybrid Mannich bases were designed, synthesized and evaluated for in vitro antimalarial activity. The design strategy of novel hybrid molecules involves fusion between the pharmacophoric moieties of lawsone (2-hydroxy-1,4-naphthoquinone, a residue from atovaquone) and Mannich substituted 4-hydroxyaniline (4-aminophenol, a residue from amodiaquine) on the basis of molecular hybridization strategy. Newly designed compounds, 5a-f were also studied for drug-likeness assessment based on Lipinski’s rule of five. All the synthesized compounds exhibited some degree of in vitro antimalarial activity against the chloroquine-sensitive strain (RKL-2) of P. falciparum at the tested dose (1 mg/mL), which was considerably less than that of the standard drug, chloroquine (0.1 mg/mL). However, compounds with propyl, 5a (IC50 0.453 μg/mL) and morpholinyl, 5f (IC50 0.391 μg/mL) substitutions showed comparatively better activity than rest of the synthesized analogues. Compound 5f (IC50 0.993 μg/mL) was found to possess higher antimalarial effectiveness than compound 5a (IC50 2.92 μg/mL) against resistant strain (RKL-9) of P. falciparum. The activity of these compounds against the resistant strain was also less than that of chloroquine (IC50 0.299 μg/mL). From results, it is clear that compounds having substitutions like smaller alkyl groups (n-propyl, 5a; isopropyl, 5b) or saturated heterocyclic moiety (morpholinyl, 5f) possess superior antimalarial activity in comparison to other compounds substituted with bulky alkyl (diisopropyl, 5c; n-butyl, 5d) or aryl (phenyl, 5e) moieties. Further, since all the compounds exhibited favourable drug-like properties a reasonable correlation therefore appears to exist between their drug-likeness and antimalarial activities.

  在本研究中，我们设计、合成了一些新颖的2-羟基-1,4-萘醌-4-羟基苯胺杂化Mannich碱，并评估了它们在体外抗疟活性。新型杂化分子设计策略涉及基于分子杂交策略将lawhone（2-羟基-1,4-萘醌，阿托喹酮的残留部分）和 Mannich取代的4-羟基苯胺（4-氨基苯酚，阿莫地喹的残留部分）的药效团部分融合。根据Lipinski的五规则，还研究了新设计的化合物5a-f的类药性评估。所有合成的化合物在测试剂量（1 mg/mL）下对氯喹敏感的P. falciparum菌株（RKL-2）显示出一定程度的体外抗疟活性，这远低于标准药物氯喹（0.1 mg/mL）的活性。然而，具有丙基、5a（IC50 0.453 μg/mL）和吗啉基、5f（IC50 0.391 μg/mL）取代的化合物显示出相对较好的活性相比其他合成的类似物。化合物5f（IC50 0.993 μg/mL）对耐药菌株（RKL-9）的P. falciparum具有比化合物5a（IC50 2.92 μg/mL）更高的抗疟效果。这些化合物对耐药菌株的活性也低于氯喹（IC50 0.299 μg/mL）。从结果中可以清楚地看出，与其他用大体积烷基（二异丙基，5c；正丁基，5d）或芳基（苯基，5e）取代的化合物相比，具有较小烷基（正丙基，5a；异丙基，5b）或饱和杂环基团（吗啉基，5f）取代的化合物具有更优越的抗疟活性。此外，由于所有化合物都表现出良好的类药性，因此它们与抗疟活性之间似乎存在合理相关性。
• [EN] NAPTHOQUINONES, PRO-DRUGS, AND METHODS OF USE THEREOF<br/>[FR] NAPHTOQUINONES, PROMÉDICAMENTS, ET LEURS PROCÉDÉS D'UTILISATION
  申请人：UNIV TEXAS

  公开号：WO2017106624A1

  公开（公告）日：2017-06-22

  Provided herein are naphthoquinones compounds such as those with a hydrogen bond donating group of the formula (I): wherein: R1, R2, R3, R4, R5, and n are as defined herein. Also provided herein are pharmaceutical composition of the present compounds and methods of treatment using the compounds including their use in the treatment of cancer.

  提供在本说明书中的萘醌化合物，例如具有式(I)中的氢键供体基团的那些：其中：R1、R2、R3、R4、R5和n如本文所述定义。此外，还提供了本化合物的药物组合物以及使用这些化合物进行治疗的方法，包括它们在癌症治疗中的应用。
• Chlorination of Quinonoid Compounds Using Dichlorine Monoxide
  作者：Prakash C. Thapliyal、K. P. Singh、Rajinder N. Khanna

  DOI：10.1080/00397919408011701

  日期：1994.4

  Abstract Dichlorine monoxide is a selective reagent for the monochlorination at the active quinonoid position in benzoquinones and naphthoquinones.

  摘要 一氧化二氯是苯醌类和萘醌类中活性醌类位置单氯化的选择性试剂。
• Sulfur-containing derivatives of 1,4-naphthoquinone, part 1: Disulfide synthesis
  作者：Maryna V. Stasevych、Maxym Yu. Plotnikov、Mykola O. Platonov、Svitlana I. Sabat、Rostyslav Ya. Musyanovych,、Volodymyr P. Novikov

  DOI：10.1002/hc.20112

  日期：——

  Disulfides of 1,4-naphthoquinone were synthesized, and different methods of their synthesis were investigated. High yields and purity of disulfides were obtained from the oxidation of thiol derivatives. The latter were prepared in high yields and purity from isothiuronic salts. The obtained disulfides are syntho- nes for compounds with a wide spectrum of biological activity. © 2005 Wiley Periodicals

  合成了 1,4-萘醌的二硫化物，并研究了它们的不同合成方法。从硫醇衍生物的氧化中获得高产率和纯度的二硫化物。后者由异硫脲酸盐以高产率和纯度制备。获得的二硫化物是具有广泛生物活性的化合物的合成物。© 2005 Wiley Periodicals, Inc. 杂原子化学 16:205–211, 2005; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20112
• Molecular structures and biological activities of (N)-n-alkylammonium 2-chloro-3-oxido-1,4-naphthoquinone salts
  作者：Dinkar Choudhari、Dipali N. Lande、Aditi Bagade、Shridhar P. Gejji、Debamitra Chakravarty、Kisan M. Kodam、Sunita Salunke-Gawali

  DOI：10.1016/j.molstruc.2017.05.083

  日期：2017.10

  structures and vibrational spectra of (N)-n-alkylammonium 2-chloro-3-oxido-1,4-naphthoquinone salts (alkyl = methyl to octyl, CS-1 to CS-8) possessing X-H⋯Y (X = N, C and Y O, Cl) hydrogen bonding and diverse noncovalent interactions have been characterized. Except for the CS-2 and CS-7 rest of the compounds facilitate π⋯π and Cl⋯π interactions. The compound CS-3 showed the presence of Cl⋯O interactions

  摘要 具有 XH⋯的 (N)-n-烷基铵 2-chloro-3-oxido-1,4-naphthoquinone 盐（烷基 = 甲基到辛基，CS-1 到 CS-8）的单晶 X 射线结构和振动光谱Y (X = N, C 和 YO, Cl) 氢键和多种非共价相互作用已被表征。除了 CS-2 和 CS-7 之外，其余化合物促进 π⋯π 和 Cl⋯π 相互作用。化合物CS-3表现出Cl⋯O相互作用的存在。得到的电子结构和光谱特性与密度泛函理论一致。这些复合物显示出显着的抗增殖和抗真菌活性。

表征谱图