3-methyl-2-(phenylthio)-1,4-naphthoquinone | 70691-68-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-methyl-2-(phenylthio)-1,4-naphthoquinone
• 英文别名: 2-methyl-3-thiophenyl-1,4-naphthoquinone；2-methyl-3-phenylthio-1,4-naphthalenedione；2-methyl-3-(phenylthio) naphthalene-1,4-dione；2-Methyl-3-phenylmercapto-[1,4]naphthochinon；2-methyl-3-phenylsulfanyl-[1,4]naphthoquinone；2-phenylthio-3-methyl-1,4-naphthoquinone；2-Methyl-3-(phenylsulfanyl)naphthoquinone；2-methyl-3-phenylsulfanylnaphthalene-1,4-dione
• CAS: 70691-68-8
• 化学式: C₁₇H₁₂O₂S
• 分子量: 280.347
• InChiKey: SUWHTOFNNOUEAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 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：
  59.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,4-环己二烯 、 3-methyl-2-(phenylthio)-1,4-naphthoquinone 在 palladium on charcoal 吡啶 、 2-二甲氨基吡啶 、 乙酸酐 作用下， 以 四氢呋喃 为溶剂， 生成 2-phenylthio-3-methyl-1,4-diacetoxynaphthalene
  参考文献：
  名称：

  Naphthalene anti-psoriatic agents

  摘要：

  哺乳动物的银屑病可以通过局部施用具有以下公式的萘酚来缓解：##STR1## 其中：R.sup.1 是烷氧基，烷基硫醚基，可选地取代的苯氧基或可选地取代的苯硫醚基；R.sup.2 是氢，低级烷基，可选地取代的苯基或可选地取代的苯烷基；R.sup.3 是低级烷基，低级烷氧基，或卤素，m是0，1或2，或者R.sup.3是可选地取代的苯基，可选地取代的苯基低级烷基，可选地取代的苯基低级烷氧基，氨基，低级烷基氨基，低级二烷基氨基，氰基，或S(0).sub.n R，其中R是低级烷基；可选地取代的苯基；可选地取代的苯基低级烷基；或可选地取代的含有三个至九个环原子并含有一个或两个选自氮、氧和硫的杂原子的杂环芳基，以及它们的药物可接受的酸加成盐；且m是1，n是0，1或2；W是含有一至七个碳原子的烷基，可选地取代的苯基或可选地取代的苄基。

  公开号：

  US05091558A1
• 作为产物：
  描述：

  甲萘醌 、 二苯二硫醚 在 1,3-双(二苯基膦)丙烷 、 H₃N*C₂H₆O₆S₂ 、 tetrabutylammonium tetrafluoroborate 、 silver(I) acetate 作用下， 以 二甲基亚砜 为溶剂， 反应 48.0h， 以88%的产率得到3-methyl-2-(phenylthio)-1,4-naphthoquinone
  参考文献：
  名称：

  Silver-Catalyzed Direct Thiolation of Quinones by Activation of Aryl Disulfides to Synthesize Quinonyl Aryl Thioethers

  摘要：

  A silver-catalyzed coupling reaction of quinones with aryl disulfides for the synthesis of quinonyl aryl thio ethers is described. In the presence of AgOAc (0.2 equiv)/dppp (0.24 equiv) as the catalyst, (NH4)(2)S2O8 (3.0 equiv) as the oxidant, and Bu4NBF4 (1.0 equiv) as the additive, the reaction is simple, provides high yield (up to 88% yield), and possesses a broad substrate scope. The reaction is believed to proceed via direct activation of disulfides evidenced by observation of a metathesis reaction between two different disulfides placed together under the reaction conditions and C-13 NMR spectroscopy analysis.

  DOI：

  10.1021/acs.joc.5b00247

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。
• Exploring synthetic avenues for the effective synthesis of selenium- and tellurium-containing multifunctional redox agents
  作者：Susanne Mecklenburg、Saad Shaaban、Lalla A. Ba、Torsten Burkholz、Thomas Schneider、Britta Diesel、Alexandra K. Kiemer、Anne Röseler、Katja Becker、Jörg Reichrath、Alexandra Stark、Wolfgang Tilgen、Muhammad Abbas、Ludger A. Wessjohann、Florenz Sasse、Claus Jacob

  DOI：10.1039/b907831b

  日期：——

  Various human illnesses, including several types of cancer and infectious diseases, are related to changes in the cellular redox homeostasis. During the last decade, several approaches have been explored which employ such disturbed redox balances for the benefit of therapy. Compounds able to modulate the intracellular redox state of cells have been developed, which effectively, yet also selectively, appear to kill cancer cells and a range of pathogenic microorganisms. Among the various agents employed, certain redox catalysts have shown considerable promise since they are non-toxic on their own yet develop an effective, often selective cytotoxicity in the presence of the ‘correct’ intracellular redox partners. Aminoalkylation, amide coupling and multicomponent reactions are suitable synthetic methods to generate a vast number of such multifunctional catalysts, which are chemically diverse and, depending on their structure, exhibit various interesting biological activities.

  人类的各种疾病，包括几种癌症和传染病，都与细胞氧化还原平衡的变化有关。过去十年间，人们探索了几种方法，利用这种紊乱的氧化还原平衡来进行治疗。目前已开发出能够调节细胞内氧化还原状态的化合物，这些化合物能够有效但也有选择性地杀死癌细胞和一系列病原微生物。在所使用的各种药剂中，某些氧化还原催化剂显示出相当大的前景，因为它们本身无毒，但在 "正确的 "细胞内氧化还原伙伴存在的情况下，会产生有效的、通常是选择性的细胞毒性。氨基烷基化、酰胺偶联和多组分反应是生成大量此类多功能催化剂的合适合成方法。
• Visible Light-Mediated Thiolation of Substituted 1,4-Naphthoquinones Using Eosin Y as a Photoredox Catalyst
  作者：Bhawana Nagar、Basab Bijayi Dhar

  DOI：10.1021/acs.joc.1c02924

  日期：2022.3.4

  (isolated yield of ≥75%) for thiolation of substituted 1,4-naphthoquinones using various aromatic and aliphatic thiols at room temperature is described herein. The rate-determining step of the reaction is thiyl radical generation, and the radical was characterized by high-resolution mass spectrometry. Cost effectiveness, operational simplicity, a short reaction time, high atom economy, and a very good yield

  在伊红 Y 存在下，本文描述了在室温下使用各种芳香族和脂肪族硫醇对取代的 1,4-萘醌进行硫醇化的可见光诱导的一步程序（分离产率≥75%）。该反应的限速步骤是硫自由基的产生，该自由基通过高分辨质谱进行表征。成本效益、操作简单、反应时间短、原子经济性高和非常好的产率使得这种光氧化还原介导的过程成为过渡金属（例如，Cu、Ag 和 Pd）催化的醌与硫醇或二硫化物。
• Heterocyclic effect for optical properties of naphthoquinone-based pigment: 2-methyl-3-heteroarylthio-1,4-naphthalenedione
  作者：Akihiro Sako、Koji Okuda、Nobuo Tajima、Reiko Kuroda、Yoshitane Imai

  DOI：10.1016/j.tet.2017.02.053

  日期：2017.4

  naphthoquinone-based heterocyclic pigments, 2-methyl-3-[(1-methyl-1H-imidazol-2-yl)thio-1,4-naphthalenedione, (4-methyl-4H-1,2,4-triazol-3-yl)thio-1,4-naphthalenedione, and (1-methyl-1H-tetrazol-5-yl)thio]-1,4-naphthalenedione, are synthesized, and their optical properties in both solution and solid states are investigated. Depending on the heteroarylthio ring in the pigment, variation in optical properties is observed

  三种新型萘醌基杂环颜料，即2-甲基-3-[（1-甲基-1H-咪唑-2-基）硫代-1,4-萘二酮，（4-甲基-4H-1,2,4-三唑）合成了-3-基）硫-1,4-萘二酮和（1-甲基-1H-四唑-5-基）硫基] -1,4-萘二酮，它们在溶液和固态下的光学性质均为调查。取决于颜料中的杂芳硫基环，观察到光学性质的变化，例如溶液和固态中每种颜料的特征色。含有1-甲基-1H-四唑-5-基环的非手性颜料在固态下表现出手性空间基团和CD信号。
• Naphthoquinone Antimalarials. XXIII. Bz-Substituted Derivatives
  作者：Louis F. Fieser、Russell H. Brown

  DOI：10.1021/ja01179a010

  日期：1949.11.19