2-chloro-3-[(3,5-dimethoxyphenyl)amino]naphthalene-1,4-dione | 175885-93-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-chloro-3-[(3,5-dimethoxyphenyl)amino]naphthalene-1,4-dione
• 英文别名: 2-Chloro-3-[(3,5-dimethoxyphenyl)amino]-1,4-naphthalenedione；2-chloro-3-(3,5-dimethoxyanilino)naphthalene-1,4-dione
• CAS: 175885-93-5
• 化学式: C₁₈H₁₄ClNO₄
• 分子量: 343.766
• InChiKey: GPWAUGJZCVGZCM-UHFFFAOYSA-N

物化性质

• 沸点：
  472.1±45.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-chloro-3-[(3,5-dimethoxyphenyl)amino]naphthalene-1,4-dione 在 3-甲基吡啶 、 四丁基硫酸氢铵 、 palladium diacetate 、 sodium carbonate 、 溶剂黄146 、 对苯醌 作用下， 以 氯仿 、 水 为溶剂， 反应 64.0h， 生成 1,3-dimethoxy-5-methyl-5H-benzonaphtho<2,3-d>pyrrole-6,11-dione
  参考文献：
  名称：

  根据“ 2-苯基-萘型”结构模式设计抗肿瘤药。3. 5 H-苯并[ b ]萘并[2,3 - d ]吡咯-6,11-二酮衍生物的合成及生物活性评估

  摘要：

  合成了许多5 H-苯并[ b ]萘[2,3 - d ]吡咯-6,11-二酮衍生物。将它们的生物学活性与相应的苯并恶唑和苯并噻唑类似物进行了比较。

  DOI：

  10.1002/jhet.5570330120
• 作为产物：
  描述：

  2,3-二氯-1,4-萘醌 、 3,5-二甲氧基苯胺 在 三乙胺 作用下， 以 乙醇 为溶剂， 生成 2-chloro-3-[(3,5-dimethoxyphenyl)amino]naphthalene-1,4-dione
  参考文献：
  名称：

  Crystal structure of 2-(3,5-dimethoxyphenylamino)-3-chloronaphthalene-1,4-dione

  摘要：

  2-(3,5-Dimethoxyphenylamino)-3-chloronaphthalene-1,4-dione 化合物是由 2,3-二氯-1,4-萘醌与 3,5-二甲氧基苯胺在回流温度下发生亲核取代反应而制备的。为了确认标题化合物的结构，对其进行了单晶 X 射线衍射分析。标题化合物 C18H14ClNO4 结晶于三linic 空间群 P-1，a = 7.0016(6)埃，b = 7.7937(6)埃，c = 15.6218(11)埃，β = 97.238(4)°，V = 782.44(11)埃3，Z = 2，R1 = 0.0525，wR2 = 0.1329。

  DOI：

  10.4314/bcse.v32i3.18

文献信息

• Synthesis of Carbazolequinones by Formal [3 + 2] Cycloaddition of Arynes and 2-Aminoquinones
  作者：Jian Guo、I. N. Chaithanya Kiran、R. Santhosh Reddy、Jiangsheng Gao、Meiqiong Tang、Yuyin Liu、Yun He

  DOI：10.1021/acs.orglett.6b01090

  日期：2016.5.20

  A formal cycloaddition reaction for the synthesis of biologically and pharmaceutically important carbazolequinones via the annulation of aminoquinones with arynes has been developed. This practical and metal-free cascade reaction proceeds through successive C–C/C–N bond formations. Moreover, this novel method has been utilized for the concise synthesis of bioactive murrayaquinone A and koeniginequinone

  已经开发了一种正式的环加成反应，用于通过氨基醌与芳烃的环合反应合成生物学上和药学上重要的咔唑醌。这种实用且无金属的级联反应是通过连续的C–C / C–N键形成而进行的。此外，该新方法已被用于简明合成生物活性的墨瑞亚醌A和甲烯乙醌B及其类似物。
• Synthesis and<i>In Vitro</i>Biological Evaluation of Aminonaphthoquinones and Benzo[<i>b</i>]phenazine-6,11-dione Derivatives as Potential Antibacterial and Antifungal Compounds
  作者：Amaç Fatih Tuyun、Nilüfer Bayrak、Hatice Yıldırım、Nihal Onul、Emel Mataraci Kara、Berna Ozbek Celik

  DOI：10.1155/2015/645902

  日期：——

  A series of 2-arylamino-3-chloro-1,4-naphthoquinone derivatives (3a–h) by the reaction of 2,3-dichloro-1,4-naphthoquinone with aryl amines (2a–h) and benzo[b]phenazine-6,11-dione derivatives (4a–c) by the treatment of 2-arylamino-3-chloro-1,4-naphthoquinone derivatives (3a–h) with sodium azide were synthesized and tested for theirin vitroantibacterial and antifungal activities. The results suggest that compounds3dand3ghad potent antifungal activity againstCandida albicans(MIC = 78.12 μg/mL). All synthesized compounds (3a–h,4a–c) possessed activity againstE. faecaliswith MIC values of between 312.5 and 1250 μg/mL. Benzo[b]phenazine-6,11-dione derivatives (4a–c) were mostly active against Gram-positive bacteria. The structures of the new members of the series were established on the basis of their spectral properties (IR,¹H NMR,¹³C NMR, and mass spectrometry).

  一系列2-芳胺基-3-氯-1,4-萘醌衍生物（3a-h）通过2,3-二氯-1,4-萘醌与芳胺基（2a-h）和苯并[b]苝啉-6,11-二酮衍生物（4a-c）反应合成，方法是将2-芳胺基-3-氯-1,4-萘醌衍生物（3a-h）与叠氮化钠处理后进行检测其体外抗菌和抗真菌活性。结果表明，化合物3d和3g对白念珠菌（MIC = 78.12 μg/mL）具有强效的抗真菌活性。所有合成的化合物（3a-h，4a-c）对肠球菌具有活性，MIC值在312.5和1250 μg/mL之间。苯并[b]苝啉-6,11-二酮衍生物（4a-c）主要对革兰氏阳性细菌活性较强。这一系列新成员的结构是基于它们的光谱特性（红外光谱，1H核磁共振，13C核磁共振和质谱）确定的。
• Synthesis and Characterization of Nitrogen and Sulfur Containing 1,4-Naphthoquinones
  作者：Cigdem Sayil、Semih Kurban、Cemil Ibis

  DOI：10.1080/10426507.2013.796475

  日期：2013.12.1

  Abstract New N,S-disubstituted naphthoquinones were synthesized by reactions of S- and N-nucleophiles with 2,3-dichloro-1,4-naphthoquinone. 2-(Hexadecylthio)-3-(phenylamino)-naphthalene-1,4-dione 5a was synthesized by reaction of 2-chloro-3-(phenylamino)-naphthalene-1,4-dione 3a with hexadecanethiol 4a. The structures of the new synthesized naphthoquinone derivatives were determined by micro analyses

  摘要 通过S-和N-亲核试剂与2,3-二氯-1,4-萘醌反应合成了新的N,S-二取代萘醌。2-(Hexadecylthio)-3-(phenylamino)-naphthalene-1,4-dione 5a 是通过 2-chloro-3-(phenylamino)-naphthalene-1,4-dione 3a 与十六烷硫醇 4a 的反应合成的。新合成的萘醌衍生物的结构通过显微分析和光谱方法（FT-IR、1H NMR、13C NMR、MS 和 UV/Vis.）确定。通过使用荧光光谱和循环伏安法研究了所选化合物的光和电化学性质。图形概要
• Synthesis, Computational Study, and Evaluation of in vitro Antimicrobial, Antibiofilm, and Anticancer Activities of New Sulfanyl Aminonaphthoquinone Derivatives
  作者：Nilufer Bayrak、Hatice Yıldırım、Amac Tuyun、Emel Kara、Berna Celik、Girish Gupta、Hamid Nasiri

  DOI：10.2174/1570180813666161020164931

  日期：2016.10.20

  Background: A set of novel sulfanyl aminonaphthoquinone derivatives (5a-j) were synthesized starting from 2,3-dichloro-1,4-naphthoquinone (1). The amine substituents were introduced via a nucleophilic substitution at reflux temperature. Subsequent reactions of 2-chloro-3-arylamino-1,4-naphthoquinones (3a-d) with different thiols (4a-c) led to the formation of the desired amino-and thio-substituted products (5a-j).Methods: The purity and identity of the synthesized compounds were verified with IR, H-1 and C-13 NMR, and MS spectroscopy. In vitro antimicrobial activity was evaluated in a panel of seven bacterial strains (three Gram-positive and four Gram-negative bacteria) and one fungi with an additional study of antibiofilm activities. The anticancer activities of two selected compounds (5e and 5f) were evaluated against 60 human tumor cell lines derived from nine neoplastic diseases by National Cancer Institute (NCI).Results: As a result, compound (5e) was identified as a hit with antibacterial efficiency against human originated pathogens S. aureus with minimal inhibitory concentration (MIC) of 19.53 mu g/mL. When considering the antibiofilm activities of antibacterial molecule 5e against the S. aureus biofilms, the minimum biofilm eradication concentration (MBEC) value was 10000 mu g/mL. Concerning on anticancer activities, both compounds (5e and 5f) exhibited moderate anticancer activities on some of tumor cells, but no activity against normal peripheral blood mononuclear cells (PBMC). In addition, docking study was used to provide further insights into the experimental observations.Conclusion: Taken together, compound 5e could be considered as a promising starting point for further development.
• Design of antineoplastic agents on the basis of the “2-phenyl-naphthalene-type” structural pattern. 3. synthesis and biological activity evaluation of 5<i>H</i>-benzo[<i>b</i>]naphtho-[2,3-<i>d</i>]pyrrole-6,11-dione derivatives
  作者：Yi-Lin Luo、Ting-Chao Chou、C. C. Cheng

  DOI：10.1002/jhet.5570330120

  日期：1996.1

  A number of 5H-Benzo[b]naphtho[2,3-d]pyrrole-6,11-dione derivatives were synthesized. Their biological activity was compared with that of the corresponding benzoxazolo- and benzthiazolo-analogues.

  合成了许多5 H-苯并[ b ]萘[2,3 - d ]吡咯-6,11-二酮衍生物。将它们的生物学活性与相应的苯并恶唑和苯并噻唑类似物进行了比较。