6-氯-2-羟基-[1,4]萘醌 | 74237-21-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 6-氯-2-羟基-[1,4]萘醌
• 英文名称: 6-chloro-2-hydroxy-[1,4]naphthoquinone
• 英文别名: 6-chloro-2-hydroxynaphthalene-1,4-dione；6-Chlor-2-hydroxy-[1,4]naphthochinon；6-chloro-2-hydroxy-1,4-naphthoquinone
• CAS: 74237-21-1
• 化学式: C₁₀H₅ClO₃
• 分子量: 208.601
• InChiKey: ZJPOEIQBAPCMMA-UHFFFAOYSA-N

物化性质

• 熔点：
  210-212 °C
• 沸点：
  401.1±45.0 °C(Predicted)
• 密度：
  1.611±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.16
• 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

反应信息

• 作为反应物：
  描述：

  6-氯-2-羟基-[1,4]萘醌 在 二氢吡啶 、 C₃₀H₃₄N₄OS 、 三乙胺 、 L-脯氨酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 36.58h， 生成 (6R,8S)-8-benzyl-2-chloro-6-nitro-9,10-dioxo-6,7,8,9-tetrahydro-5H-5,8-methano benzo[7]annulen-5-yl acetate
  参考文献：
  名称：

  用于合成硝基甲烷苯并[7]环烯的有机催化对映选择性迈克尔-羟醛[3+2]环化

  摘要：

  已经报道了通过双功能硫脲催化的对映选择性 Michael-Aldol[3+2] 环化，并以良好的收率合成了一系列具有潜在生物活性的硝基甲烷苯并 [7] 环烯，并具有优异的对映选择性和非对映选择性。

  DOI：

  10.1002/ejoc.202100974
• 作为产物：
  描述：

  (2-Acetyl-4-chloro-phenyl)-acetic acid ethyl ester 在 乙醇 、 氧气 、 sodium 作用下， 生成 6-氯-2-羟基-[1,4]萘醌
  参考文献：
  名称：

  .beta.-Lapachone: synthesis of derivatives and activities in tumor models

  摘要：

  In order to find a 3,4-dihydro-2H-naphtho[1,2-b]pyran-5,6-dione more potent than the naturally occurring 2,2-dimethyl derivative [beta-lapachone (10a)], we synthesized a series of analogous compounds with modifications at position 2 of the pyran ring or at positions 8 and 9 of the benzene ring. Of the compounds tested in vitro for inhibition of RNA-dependent DNA polymerase and in mice infected with Rauscher leukemia, all retained good enzyme activity. Inhibition of the reverse transcriptase activity of the 2,2-substituted derivatives 10b-e was as strong as 10a. However, only the 2-methyl-2-phenyl derivative 10e proved to be about as potent as the 2,2-dimethyl reference compound 10a in prolonging the mean survival time of mice with Rauscher leukemia virus induced leukemia.

  DOI：

  10.1021/jm00374a010

文献信息

• [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。
• Palladium-catalyzed enol/enolate directed oxidative annulation: functionalized naphthofuroquinone synthesis and bioactivity evaluation
  作者：Shuaipeng Lv、Haitao Liu、Jie Kang、Yun Luo、Ting Gong、Zhengqi Dong、Guibo Sun、Chunnian He、Xiaobo Sun、Lei Wang

  DOI：10.1039/c9cc05233j

  日期：——

  A palladium-promoted oxidative annulation reaction for the synthesis of structurally diverse naphthoquinone-containing heterocycles has been developed, providing switchable access to 1,2-naphthofuroquinones and densely functionalized cyclobutene-fused 1,4-naphthofuroquinones by selective enol/enolate-directed processes. The synthetic application was extended by late-stage functionalization of an anti-HIV

  已经开发了用于合成结构多样的含萘醌的杂环的钯促进的氧化环化反应，通过选择性的烯醇/烯醇酸酯定向方法提供了可转换的途径来接近1,2-萘呋喃醌和稠密官能化的环丁烯稠合的1,4-萘呋喃醌。合成的应用通过抗HIV药物的后期功能化得以扩展。1,2-萘呋喃醌合成的实用价值在内皮保护性先导化合物的开发中得到了强调。
• Palladium(II)-Catalyzed Oxidative Annulation of 2-Hydroxynaphthalene-1,4-diones and Internal Alkynes via C–H Functionalization
  作者：Peng Sun、Jiaojiao Yang、Jinsong Peng、Baichuan Mo、Xin Chen、Xiang Li、Chunxia Chen

  DOI：10.1021/acs.joc.9b03153

  日期：2020.5.15

  An efficient Pd(II)-catalyzed oxidative annulation of 2-hydroxynaphthalene-1,4-diones and internal alkynes has been developed with high step efficiency. A broad range of functional groups are compatible with this reaction, thus providing a new entry to diverse naphtho[2,3-b]furan-4,9-dione derivatives in good to high yields.

  已经开发了一种高效的Pd（II）催化的2-羟基萘-1,4-二酮和内部炔烃的氧化环化反应，具有较高的步长效率。各种各样的官能团都可与该反应相容，从而以高至高收率提供了新的各种萘并[2,3-b]呋喃-4,9-二酮衍生物的入口。
• Naphthoquinone anti-psoriatic agents
  申请人：Syntex (U.S.A.) Inc.

  公开号：US04255405A1

  公开（公告）日：1981-03-10

  The 2,3-diesters of 6-substituted-2,3-dihydroxy-1,4-naphthoquinones exhibit useful anti-psoriatic activity in mammals.

  6-取代-2,3-二羟基-1,4-萘醌的2,3-二酯在哺乳动物中显示出有用的抗银屑病活性。
• Synthesis, Characterization and Cytotoxic Investigations of Novel C3-Dihydrofuran Substituted 1H-benzo[g]chromene-2,5,10-triones besides Antimicrobial study
  作者：Venkata Swamy Tangeti、D. Vasundhara、M. Naresh Kumar、Himabindu Mylapalli、Kaja Srinivas Pavan Kumar

  DOI：10.14233/ajchem.2017.20209

  日期：——

  A series of novel C3-dihydrofuran substituted 1H-benzo[g]chromene-2,5,10-triones were synthesized and characterized by spectral analysis. The target molecules were screened for their antimicrobial and anticancer activities and structure and activity relationship (SAR) was investigated. Structure and activity relationship studies revealed that the compounds 6p, 6q, 6s, 6t were found to be more active in antimicrobial screening. Antiproliferative properties were evaluated against human cancer cell lines, namely, laryngeal carcinoma (Hep2), lung adenocarcinoma (A549) and cervical cancer (HeLa). The best among them, C3-dihydrofuran substituted 1H-benzo[g]chromene-2,5,10-trione with methoxy group substitution at ring A and B were selected for further structure activity relationship. Among the derivatives, (2S,3S)-propyl-4-acetyl-5-(7,9-dimethoxy-2,5,10-trioxo-5,10-dihydro-2H-benzo[g]chromen-3-yl)-3-(3,5-dimethoxyphenyl)-2,3-dihydrofuran-2-carboxylate (6t) showed most potent cytotoxic activity against all the three cancer cell lines. Toxicity studies revealed that dihydrofuran substituted 1H-benzo[g] chromene-2,5,10-triones (6a-t) are specifically target the cancer cell lines.

  合成了一系列新型C3-二氢呋喃取代的1H-苯并[g]色烯-2,5,10-三酮，并通过光谱分析对其进行了表征。针对这些靶分子进行了抗微生物和抗癌活性的筛选，并研究了其结构与活性关系（SAR）。结构与活性关系研究显示，化合物6p、6q、6s、6t在抗微生物筛选中表现更为活跃。抗增殖特性则针对人类癌细胞系进行评估，包括喉癌（Hep2）、肺腺癌（A549）和宫颈癌（HeLa）。在这些化合物中，C3-二氢呋喃取代的1H-苯并[g]色烯-2,5,10-三酮A和B环上有甲氧基取代的化合物被选为进一步的结构活性关系研究。在这些衍生物中，(2S,3S)-丙基-4-乙酰基-5-(7,9-二甲氧基-2,5,10-三氧-5,10-二氢-2H-苯并[g]色烯-3-基)-3-(3,5-二甲氧基苯基)-2,3-二氢呋喃-2-羧酸酯（6t）对所有三种癌细胞系表现出最强的细胞毒活性。毒性研究表明，二氢呋喃取代的1H-苯并[g]色烯-2,5,10-三酮（6a-t）特异性靶向癌细胞系。