2-benzyloxy-3-chloro-1,4-naphthoquinone | 81288-68-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-benzyloxy-3-chloro-1,4-naphthoquinone
• 英文别名: 2-benzyl-3-chloro-[1,4]naphthoquinone；2-Benzyl-3-chlor-[1,4]naphthochinon；2-Benzyl-3-chloronaphthalene-1,4-dione
• CAS: 81288-68-8
• 化学式: C₁₇H₁₁ClO₂
• 分子量: 282.726
• InChiKey: JJNVENAGJVMIEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-benzyloxy-3-chloro-1,4-naphthoquinone 在 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以47%的产率得到3-benzyl-4-hydroxynaphthalene-1,2-dione
  参考文献：
  名称：

  1,4-Naphthoquinone Cations as Antiplasmodial Agents: Hydroxy-, Acyloxy-, and Alkoxy-Substituted Analogues

  摘要：

  Cations of hydroxy-substituted 1,4-naphthoquinones were synthesized and evaluated as antiplasmodial agents against Plasmodium falciparum. The atovaquone analogues were found to be inactive as antagonists of parasite growth, which was attributed to ionization of the acidic hydroxyl moiety. Upon modification to an alkoxy substituent, the antiplasmodial activity was restored in the sub-100 nM range. Optimal inhibitors were found to possess IC50 values of 17.4 49.5 nM against heteroresistant P. falciparum W2.

  DOI：

  10.1021/ml300242v
• 作为产物：
  描述：

  苯乙酰氯 在 sodium hydroxide 、 乙醚 、 双氧水 、 溶剂黄146 作用下， 生成 2-benzyloxy-3-chloro-1,4-naphthoquinone
  参考文献：
  名称：

  Naphthoquinone Antimalarials. XXIII. Bz-Substituted Derivatives

  摘要：

  DOI：

  10.1021/ja01179a010

文献信息

• [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。
• Allylation of Quinones via Photoinduced Electron-Transfer Reactions from Allylstannanes
  作者：Kazuhiro Maruyama、Hiroshi Imahori

  DOI：10.1246/bcsj.62.816

  日期：1989.3

  Photochemical reactions of quinones with allylstannanes provided four types of products: adducts of allyl group to the carbonyl oxygens of quinones, adducts of allyl group to the olefinic carbons, adducts of allyl group to the carbonyl carbons, and hydroquinones. An electron-transfer mechanism was confirmed by 1H-CIDNP (Chemically Induced Dynamic Nuclear Polarization) method. This study suggests that

  醌与烯丙基锡烷的光化学反应提供了四种类型的产物：烯丙基与醌的羰基氧的加合物、烯丙基与烯烃碳的加合物、烯丙基与羰基碳的加合物和对苯二酚。通过1H-CIDNP（化学诱导动态核极化）方法证实了电子转移机制。该研究表明 a) 从烯丙基锡烷到醌的光致电子转移产生相应的醌阴离子自由基和锡阳离子自由基，b) 锡阳离子自由基裂解产生烯丙基自由基和锡阳离子，以及 c) 烯丙基自由基攻击醌阴离子自由基导致最终产物烯丙基化醌的形成。
• GUPTA, R. B.;FRANCK, R. W., SYNLETT.,(1990) N, C. 355-357
  作者：GUPTA, R. B.、FRANCK, R. W.

  DOI：——

  日期：——
• DENISOV, V. YA.;POZDNYAKOV, O. V., IZV. VUZOV. XIMIYA I XIM. TEXNOL., 1981, 24, N 12, 14-1480
  作者：DENISOV, V. YA.、POZDNYAKOV, O. V.

  DOI：——

  日期：——