2-((2-hydroxyethyl)thio)naphthalene-1,4-dione | 83293-77-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-((2-hydroxyethyl)thio)naphthalene-1,4-dione
• 英文别名: 2-(2-hydroxyethylthio)-1,4-naphthoquinone；2-(2-hydroxy-ethylsulfanyl)-[1,4]naphthoquinone；2-(2-Hydroxy-aethylmercapto)-[1,4]naphthochinon；NSC 148596；2-(2-Hydroxyethylsulfanyl)naphthalene-1,4-dione
• CAS: 83293-77-0
• 化学式: C₁₂H₁₀O₃S
• 分子量: 234.276
• InChiKey: IBLOZMPODBITIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  79.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-((2-hydroxyethyl)thio)naphthalene-1,4-dione 在 C₄H₉CO₃H 、 五氯化钼 作用下， 以 苯 为溶剂， 反应 0.5h， 以95%的产率得到2-(2-hydroxyethylsulfinyl)-1,4-naphthoquinone
  参考文献：
  名称：

  Tolstikov, G. A.; Shul'ts, E. E.; Vafina, G. F., Journal of Organic Chemistry USSR (English Translation), 1989, vol. 25, # 6.2, p. 1109 - 1121

  摘要：

  DOI：
• 作为产物：
  描述：

  2-巯基乙醇 、 1,4-萘醌 以 丙酮 为溶剂， 以75 %的产率得到2-((2-hydroxyethyl)thio)naphthalene-1,4-dione
  参考文献：
  名称：

  脂肪醇的 α-sp3-CH 与 1,4-萘醌的 sp2-CH 键的光驱动碳-碳偶联

  摘要：

  在这里，在催化剂、金属、碱和无试剂条件下，脂肪伯醇与 1,4-萘醌的 α-选择性 C sp3 -H 键官能化产生了由蓝色 LED 光驱动的 C sp 2 -C sp 2偶联产物. 在该转化过程中，三个 C-H 键（两个 sp 3 -CH、一个 sp 2 -C-H 和一个 O-H）断裂并形成四个新键，从而产生荧光 2-acylated-1,4-naphthohydroquinones .

  DOI：

  10.1021/acs.orglett.2c03066

文献信息

• Synthetic Naphthoquinone Derivatives as Anticancer Agents in Ovarian Cancer: Cytotoxicity Assay and Investigation of Possible Biological Mechanisms Action
  作者：Renata Dalmaschio Daltoé、Leticia Batista Azevedo Rangel、Maicon Delarmelina、Klesia Pirola Madeira、Marcella Leite Porto、Silvana Santos Meirelles、Isabella dos Santos Guimarães、Éclair Venturini Filho、Alan Reinke Pereira、Rafael de Queiroz Ferreira、Gabriel Fernandes Souza dos Santos、Izabela de França Schaffel、José Walkimar de Mesquita Carneiro、Artur M. S. Silva、Sandro José Greco

  DOI：10.1002/cbdv.202200807

  日期：2023.2

  naphthoquinone derivatives were synthesized in yields ranging from 52 to 96% using easy, fast, and low-cost methodologies. All naphthoquinone derivatives were screened for their in vitro anti-proliferative activities against OVCA A2780 cancer cell lines. Amongst all analysed compounds, derivatives 3–5 presented the most prominent cytotoxic potential. Naphthoquinones 3 and 4, bearing sulfur-containing

  在这项研究中，使用简单、快速和低成本的方法合成了八种萘醌衍生物，产率在 52% 到 96% 之间。筛选了所有萘醌衍生物对 OVCA A2780 癌细胞系的体外抗增殖活性。在所有分析的化合物中，衍生物3 – 5具有最突出的细胞毒性潜力。带有含硫基团的萘醌3和4被确定为具有产生 ROS 的高潜力，特别是超氧阴离子。此外，3和4化合物导致 G0/G1 期细胞群减少，并诱导超过 90% 的细胞群发生凋亡。化合物5在这些过程中没有任何作用。最后，测试了化合物3 – 5对 PI3K 和 MAPK 的抑制能力。化合物3和4不抑制 PI3K 酶。另一方面，萘醌-多酚5只能抑制表达 pERK 的细胞百分比。
• Mechanism of charge transfer in the molecular DPQ complex studied by time-resolved fluorescence spectroscopy
  作者：V. V. Borovkov、R. P. Evstigneeva、I. A. Struganova、V. F. Kamalov、B. N. Toleutaev

  DOI：10.1021/j100170a011

  日期：1991.8

  The pathways of charge separation in the dimethylaniline-mesoporphyrin II-naphthoquinone triad DPQ and its Zn complex were established. The rate constants of electron transfer from P and ZnP to Q were measured to be k = 1.5 x 10(9) s-1 and k > 5 x 10(10) s-1, respectively, from the results of picosecond fluorescence spectroscopy. The transformation of the DPQ and DZnPQ triads to the reduced form by NaBH4 treatment results in blocking of the electron-transfer channel from both P and ZnP to Q. The transformation of the DPQ and DZnPQ triads to the reduced forms by NaBH4 results in blocking of the electron-transfer channel from both P and ZnP to Q. The role of structural and conformational changes of triads in the electron-transfer process is discussed.
• Synthesis, Antitumor Activity and Docking of 2,3-(Substituted)-1,4-Naphthoquinone Derivatives Containing Nitrogen, Oxygen and Sulfur
  作者：Maicon Delarmelina、Renata D. Daltoé、Murilo F. Cerri、Klesia P. Madeira、Leticia B. A. Rangel、Valdemar Lacerda Júnior、Wanderson Romão、Alex G. Taranto、Sandro J. Greco

  DOI：10.5935/0103-5053.20150157

  日期：——

  Eleven 2,3-(substituted)-1,4-naphthoquinone derivatives were synthesized in yields ranging from 52-89%. These derivatives were evaluated for their cytotoxic effects on human lungs (H460), triple-negative breast (MDA-MB-231) and ovarian (A2780) cancer cell lines. Compounds 5f and 8 showed IC50 values of 3.048 x 10(-5) mol L-1 and 4.24 x 10(-6) mol L-1 for H460; 5c and 8 showed IC50 values of 2.16 x 10(-5) mol L-1 and 1.60 x 10(-5) mol L-1 for MDA-MB-231, and 5g and 8 showed IC50 values of 2.68 x 10(-6) mol L-1 and 3.89 x 10(-6) mol L-1 for A2780. Additionally, we conducted a docking study with the four most active compounds and the therapeutic targets PI3K and topoisomerase II showing the pharmacophoric conformation of these compounds.
• TOLSTIKOV, G. A.;SHULTS, EH. EH.;VAFINA, G. F.;SPIRIXIN, L. V.;PANASENKO,+, ZH. ORGAN. XIMII, 25,(1989) N, S. 1231-1246
  作者：TOLSTIKOV, G. A.、SHULTS, EH. EH.、VAFINA, G. F.、SPIRIXIN, L. V.、PANASENKO,+

  DOI：——

  日期：——
• CD45 and Methods and Compounds Related Thereto
  申请人：Panchal Rekha

  公开号：US20120135013A1

  公开（公告）日：2012-05-31

  Disclosed herein are compounds, compositions and methods for preventing, reducing or inhibiting an amount of protein tyrosine phosphatase receptor type C (CD45) expressed or activity of CD45 in a cell or a subject. Also disclosed are methods for preventing, inhibiting or treating an infection in a cell or a subject immunizing a subject or enhancing a subject's immune response against an infection preventing, reducing or inhibiting the susceptibility of a cell or a subject to an infection or subsequent pathogenesis and morbidity due to the infection and preventing, reducing, and inhibiting apoptosis caused by or resulting from a biological agent in a cell or a subject which comprises preventing, reducing or inhibiting an amount of protein tyrosine phosphatase receptor type C (CD45) expressed or activity of CD45 in the cell or the subject.