seriniquinone | 22200-69-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: seriniquinone
• 英文别名: 12-thiapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(13),2(11),4,6,8,15,17,19-octaene-3,10,14,21-tetrone
• CAS: 22200-69-7
• 化学式: C₂₀H₈O₄S
• 分子量: 344.347
• InChiKey: PWUWIMAXHCTYJA-UHFFFAOYSA-N

物化性质

• 熔点：
  288 °C
• 沸点：
  612.3±54.0 °C(Predicted)
• 密度：
  1.578±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（升温时高达15mg/ml）或DMF（高达15mg/ml）

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  96.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  seriniquinone 在 盐酸 、 tin(ll) chloride 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 以72%的产率得到
  参考文献：
  名称：

  [EN] SERINIQUINONES, MELANOMA-SPECIFIC ANTICANCER AGENTS
  [FR] SÉRIQUINONES, AGENTS ANTICANCÉREUX SPÉCIFIQUES DES MÉLANOMES

  摘要：

  因此，提供了丝氨醌衍生物以及用于治疗癌症的方法，特别是治疗黑色素瘤和前列腺癌的方法。

  公开号：

  WO2014018919A1
• 作为产物：
  描述：

  2,3-二溴-1,4-萘醌 在 双氧水 、 三乙胺 、 二硫代乙酰胺 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 seriniquinone
  参考文献：
  名称：

  Matsuoka, Masaru; Iwamoto, Akihiro; Kitao, Teijiro, Journal of Heterocyclic Chemistry, 1991, vol. 28, # 5, p. 1445 - 1447

  摘要：

  DOI：

文献信息

• Single dish gradient screening of small molecule localization
  作者：Paolo Beuzer、Joshua Axelrod、Lynnie Trzoss、Willam Fenical、Ramesh Dasari、Antonio Evidente、Alexander Kornienko、Hu Cang、James J. La Clair

  DOI：10.1039/c6ob01418f

  日期：——

  Understanding trafficking in cells and tissues is one of the most critical steps in exploring the mechanisms and modes of action (MOAs) of a small molecule. Typically, deciphering the role of concentration presents one of the most difficult challenges associated with this task. Herein, we present a practical solution to this problem by developing concentration gradients within single dishes of cells

  了解细胞和组织的运输是探索小分子作用机制和模式 (MOA) 的最关键步骤之一。通常，破译注意力的作用是与此任务相关的最困难的挑战之一。在此，我们通过在单个细胞培养皿中形成浓度梯度来提出解决该问题的实用解决方案。我们通过评估由两类天然产物开发的荧光标记探针来演示该方法，这些天然产物已被 STORM 超分辨率显微镜鉴定为潜在的抗癌先导化合物。
• SERINIQUINONES, MELANOMA-SPECIFIC ANTICANCER AGENTS
  申请人：The Regents of the University of California, a California corporation

  公开号：US20150148314A1

  公开（公告）日：2015-05-28

  There are provided, inter alia, derivatives of seriniquinone and methods useful for the treatment of cancer, and in particular treatment of melanoma and prostate cancer.

  提供了丝氨醌衍生物及其治疗癌症的方法，特别是治疗黑色素瘤和前列腺癌。
• Comparative analysis of p-terphenylquinone and seriniquinone derivatives as reactive oxygen species-modulating agents
  作者：Haruna Nagao、Masayuki Ninomiya、Hodaka Sugiyama、Atsuya Itabashi、Kaho Uno、Kaori Tanaka、Mamoru Koketsu

  DOI：10.1016/j.bmcl.2022.128992

  日期：2022.11

  Quinones are widespread in plants, animals, insects, and microorganisms. Several anticancer agents contain quinone structures as critical parts to show remarkable potential and distinctive modes of actions. The purpose of this study was to investigate the structure–activity relationships of microbial quinones and their derivatives as anticancer agents. A series of p-terphenylquinone and seriniquinone

  醌广泛存在于植物、动物、昆虫和微生物中。几种抗癌剂含有醌结构作为关键部分，显示出显着的潜力和独特的作用模式。本研究的目的是研究微生物醌及其衍生物作为抗癌剂的结构-活性关系。由此制备了一系列对三联苯醌和丝氨酸醌衍生物。合成醌的处理对人白血病 HL-60 细胞具有剂量依赖性的抗增殖活性。此外，丝氨酸醌衍生物会升高细胞活性氧（ROS）水平，从而引发随后的细胞凋亡事件。我们的研究结果强调了丝氨酸醌衍生物作为氧化还原循环诱导的 ROS 调节抗癌剂的巨大潜力。
• Wilputte; Martin, Bulletin des Societes Chimiques Belges, 1956, vol. 65, p. 874,891
  作者：Wilputte、Martin

  DOI：——

  日期：——
• Tetrathiafulvalene quinones, hydroquinones and esters
  作者：William H Watson、Etim E Eduok、Ram P Kashyap、Mariusz Krawiec

  DOI：10.1016/s0040-4020(01)89885-9

  日期：1993.4

  Benzocyclohexa-2,5-diene-1,4-dione-1,3-thiole-2-thione (2) was synthesized starting with 2,3-dichloronapthoquinone (1). Compounds 3 and 4 were also obtained; however, the yield of 2 can be increased through control of the temperature and reaction time. Reaction of 2 with triethylphosphite gave 5 and the tetrathiafulvalene ester 6. The tetrathiafulvalenequinone (9) was obtained by hydrolysis of 6 followed by oxidation of & Compound 9 was obtained more directly by hydrogenation of 2 followed by coupling with triethylphosphite and oxidation. Chloranil was used to prepare the dithiafulvene quinone 12 which was reduced, coupled with triethylphosphite to form, presumably, polymer 13. The reactions were repeated using the hexanoic acid esters of the corresponding hydroquinone thiafulvalenes. The crystal structures of 2, 3, 4, 5, 6a and 10 were determined by X-ray diffraction. Cyclic voltammetry studies show the tetrathiafulvalene quinones reduce like quinones, but do not exhibit the oxidation properties of tetrathiafulvalenes.