2-chloro-3-(4-methylpiperazin-1-yl)naphthalene-1,4-dione | 6312-48-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-chloro-3-(4-methylpiperazin-1-yl)naphthalene-1,4-dione
• 英文别名: 3-chloro-2-(4-methylpiperazin-1-yl)-1,4-naphthoquinone；2-chloro-3-(4-methyl-piperazin-1-yl)-[1,4]naphthoquinone；1-Methyl-4-(2-chlor-1,4-naphthochinonyl-(3))-piperazin
• CAS: 6312-48-7
• 化学式: C₁₅H₁₅ClN₂O₂
• 分子量: 290.749
• InChiKey: GUNUJEHGUYLPRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-chloro-3-(4-methylpiperazin-1-yl)naphthalene-1,4-dione 在 sodium azide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 以59%的产率得到3-Azido-2-(4-methylpiperazino)-1,4-naphthoquinone
  参考文献：
  名称：

  Reaction of 2-(4-alkylpiperazino)-3-chloro-1,4-naphthoquinones with sodium azide

  摘要：

  It was shown that 2-(4-alkylpiperazino)-3-chloro-1,4-naphthoquinones react on heating with NaN3 in DMF to form new heterocyclic quinones - 1,2,3,4-tetrahydro-13-alkyl-3,1-(iminoethano)benzo[g]quinoxaline-5,10-diones as well as the corresponding 2-(4-alkylpiperazino)-3-aminonaphthoquinones and naphthimidazopyrazinediones.

  DOI：

  10.1007/bf00958261
• 作为产物：
  描述：

  溴甲烷 、 3-chloro-2-(piperazin-1-yl)-1,4-naphthoquinone 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 2-chloro-3-(4-methylpiperazin-1-yl)naphthalene-1,4-dione
  参考文献：
  名称：

  Synthesis of photoactive 1-methyl-1-R-4-(1,4-dioxo-1,4-dihydronaphthalen-2-yl)piperazinium salts

  摘要：

  Photoactive 4-(1,4-dioxo-1,4-dihydronaphthalen-2-yl)piperazinium salts were synthesized by alkylation of 3-chloro-2-(piperazin-1-yl)-and 2-arylamino-3-(4-methylpiperazin-1-yl)-1,4-naphthoquinones. Light sensitivities of materials obtained by adsorption of the synthesized piperazinium salts from solution onto oxidized aluminum support were estimated.

  DOI：

  10.1134/s1070428011120086

文献信息

• An investigation of nucleophilic substitution reactions of 2,3-dichloro-1,4-naphthoquinone with various nucleophilic reagents
  作者：Cemil Ibis、Hassen Shntaif、Hakan Bahar、Sahinler Ayla

  DOI：10.2298/jsc141124021i

  日期：——

  Novel N- , N,S- and N,O- substituted naphthoquinone compounds were prepared by the reactions of 2,3-dichloro-1,4-naphthoquinone (1) and the corresponding nucleophiles in the presence of chloroform and triethylamine or ethanol solution of Na2CO3. The structures of the novel naphthoquinone compounds were characterized by micro analysis, FT-IR, 1H NMR, 13C NMR, MS and cyclic voltammetry.

  通过 2,3-二氯-1,4-萘醌 (1) 与相应的 N,S,O-取代萘醌化合物 通过 2,3-二氯-1,4-萘醌 (1) 与相应的亲核物在氯仿和三乙胺或乙醇存在下的反应 在氯仿和三乙胺或乙醇 Na2CO3 溶液中发生反应。新型萘醌化合物的结构通过显微分析、傅立叶变换 通过微量分析、傅立叶变换红外光谱、1H NMR、13C NMR、质谱和循环 伏安法对新型萘醌化合物的结构进行了表征。
• [EN] NAPHTHAQUINONE METHYLTRANSFERASE INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE NAPHTAQUINONE MÉTHYLTRANSFÉRASE ET LEURS UTILISATIONS
  申请人：SLOAN KETTERING INST CANCER

  公开号：WO2015172076A1

  公开（公告）日：2015-11-12

  Provided herein are compounds of (I), and pharmaceutically acceptable salts, solvates, hydrates, polymorphs, co-crystals, tautomers, stereoisomers, and prodrugs thereof. Also provided are pharmaceutical compositions and methods involving the inventive compounds for the treatment of proliferative diseases (e.g., cancer (e.g., leukemia, breast cancer, melanoma, metastatic cancer) and diseases associated with inappropriate SET8 activity. Also provided are methods for inhibiting SET8 and methods for labelling SET8.

  本文提供了化合物(I)及其药用可接受的盐、溶剂合物、水合物、多型体、共晶体、互变异构体、立体异构体和其前药。还提供了涉及创新化合物用于治疗增殖性疾病（例如，癌症（例如，白血病、乳腺癌、黑色素瘤、转移性癌症）和与不当的SET8活性相关的疾病）的药物组合物和方法。还提供了用于抑制SET8的方法和用于标记SET8的方法。
• Reactions of quinones with some amino alcohols, thiols and a UV-Vis study
  作者：Cemil Ibis、Sibel Sahinler Ayla、Elvira Babayeva

  DOI：10.1080/10426507.2020.1714619

  日期：2020.6.2

  4-naphthoquinone (DCNQ) with amino-1,2-propanediol and some thiols were investigated. Novel N-, N,S-, and S,O- substituted derivatives were obtained and the structures of all compounds were characterized by spectroscopic methods (FT-IR, 1H NMR, 13C NMR, Mass spectroscopy) and microanalysis. The absorption behaviors of novel compounds were also investigated with UV-Vis spectroscopy in different solvents, such

  摘要 在本研究中，研究了 2,3-二氯-1,4-萘醌 (DCNQ) 与氨基-1,2-丙二醇和一些硫醇的反应。获得了新的 N-、N,S- 和 S,O- 取代衍生物，所有化合物的结构都通过光谱方法（FT-IR、1H NMR、13C NMR、质谱）和微量分析表征。还用紫外-可见光谱研究了新化合物在不同溶剂（如乙醇、四氢呋喃和氯仿）中的吸收行为。图形概要
• ‘On water’ assisted synthesis and biological evaluation of nitrogen and sulfur containing hetero-1,4-naphthoquinones as potent antifungal and antibacterial agents
  作者：Vishnu K. Tandon、Hardesh K. Maurya、Manoj K. Verma、Rohitashw Kumar、Praveen K. Shukla

  DOI：10.1016/j.ejmech.2010.02.023

  日期：2010.6

  2-Chloro-3-(4-methylpiperazin-1-yl)naphthalene-1,4-dione (3a), 2-chloro-3-(pyrrolidin-1-yl)naphthalene-1,4-dione (3b), 2-chloro-3-(piperidin-1-yl)naphthalene-1,4-dione (3c), 2-chloro-3-morpholinonaphthalene-1,4-dione (3d), 2-chloro-3-(2-phenylhydrazinyl)naphthalene-1,4-dione (3e), 2-(allylamino)-3-chloronaphthalene-1,4-dione (3f), 2-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-ylthio)acetic acid (3g), 2-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-ylthio)succinic acid (3h), methyl 2-(3-chloro-1,4-choxo-1,4-dihydronaphthalen-2-ylthio)acetate (3i), 2-chloro-3-(2-mercaptoethylthio)naphthalene-1,4-dione (3j), 3-hydroxy-4-methyl-4H-naphtho[2,3-b][1,4]thiazine-5,10-dione (3k) and compounds 31-q have been synthesized by a green methodology approach using water as solvent and evaluated for their antifungal and antibacterial activity. The antifungal profile of 3a-n indicated that compounds 3a-d, 3j, 3e and 3k have potent antifungal activity. Amongst the most promising antifungal compounds, 3a-g, 3j, 3k showed better antifungal activity than clinically prevalent antifungal drugs Fluconazole and Amphotericin-B against Trichophyton mentagraphytes and compounds 3j and 3k have been found to be lead antifungal bicyclic and tricyclic 1,4-naphthoquinones. Compound 3k also exhibited pronounced antibacterial activity.
• BEREZHNAYA, V. N.;SHISHKINA, R. P., IZV. AN CCCP. CEP. XIM.,(1990) N, S. 2103-2107
  作者：BEREZHNAYA, V. N.、SHISHKINA, R. P.

  DOI：——

  日期：——