5-[(phenylamino)methylidene]-2-thioxo-dihydropyrimidine-4,6(1H,3H)-dion | 69791-23-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-[(phenylamino)methylidene]-2-thioxo-dihydropyrimidine-4,6(1H,3H)-dion
• 英文别名: 5-(anilinomethylene)-2-thioxohexahydro-4,6-pyrimidinedione；5-anilinomethylene-2-thio-barbituric acid；5-Anilinomethylen-2-thio-barbitursaeure；5-(anilinomethylidene)-2-sulfanylidene-1,3-diazinane-4,6-dione
• CAS: 69791-23-7
• 化学式: C₁₁H₉N₃O₂S
• 分子量: 247.277
• InChiKey: HXBBOMISRZLMIX-UHFFFAOYSA-N

物化性质

• 熔点：
  335 °C (approx, decomp)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.51
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.23
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-[(phenylamino)methylidene]-2-thioxo-dihydropyrimidine-4,6(1H,3H)-dion 、 乙酸酐 在 sodium acetate 作用下， 生成 N-(4,6-dioxo-2-thioxo-tetrahydro-pyrimidin-5-ylidenemethyl)-acetanilide
  参考文献：
  名称：

  Zenno, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1954, vol. 74, p. 199,202

  摘要：

  DOI：
• 作为产物：
  描述：

  4,6-二羟基-2-巯基嘧啶 、 N-苯基甲酰胺 生成 5-[(phenylamino)methylidene]-2-thioxo-dihydropyrimidine-4,6(1H,3H)-dion
  参考文献：
  名称：

  Ridi, Gazzetta Chimica Italiana, 1949, vol. 79, p. 175,185

  摘要：

  DOI：

文献信息

• Novel Reaction Products from Thiobarbituric Acid of Biological Interest
  作者：Ashraf A. Aly、Aboul-Fetouh E. Mourad、Alaa A. Hassan、Nasr K. Mohamed、Bahaa A. Ali、Mohamed M. El-Sayed

  DOI：10.1002/ardp.200300802

  日期：2004.3

  (1) with some π‐deficients have led to the formation of unexpected heterocyclic products such as anilinomethylenethioxopyrimidinedione, 2, 2'‐bis(pyrimidinecarbothioamide), allylthioxopyrimidinecarbothioamide, indenopyranopyrimidine and benzofuropyrimidine derivatives. A possible mechanism for the formation of these products is discussed, and the biological activity is determined.

  1, 2 - 二氢 - 2 - 硫代 - 4, 6 (1H, 5H) 嘧啶二酮 (1) 与一些 π - 缺陷的反应导致了意想不到的杂环产物的形成，如苯胺亚甲基乙硫代嘧啶二酮, 2, 2'-双 (嘧啶碳硫酰胺）、烯丙基硫代嘧啶碳硫酰胺、茚并吡喃嘧啶和苯并呋喃嘧啶衍生物。讨论了这些产品形成的可能机制，并确定了生物活性。
• PHOTOELECTRIC CONVERSION DEVICE, IMAGING DEVICE, AND METHOD FOR DRIVING PHOTOELECTRIC CONVERSION DEVICE
  申请人：FUJIFILM CORPORATION

  公开号：US20130087682A1

  公开（公告）日：2013-04-11

  A photoelectric conversion device includes, in the following order: a first electrode; an electron blocking layer; a photoelectric conversion layer containing a merocyanine dye; a hole blocking layer; and a transparent electrode as a second electrode, and an absorption maximum wavelength in a thin film absorption spectrum of the photoelectric conversion layer containing a merocyanine dye is within a range of from 400 to 520 nm.

  一种光电转换装置包括以下顺序：第一电极；电子阻挡层；包含顺-氰染料的光电转换层；空穴阻挡层；以及透明电极作为第二电极。其中，包含顺-氰染料的光电转换层在薄膜吸收光谱中的吸收峰最大波长在400到520纳米范围内。
• New thiobarbituric acid scaffold-based small molecules: Synthesis, cytotoxicity, 2D-QSAR, pharmacophore modelling and in-silico ADME screening
  作者：Heba S.A. El-Zahabi、Maha M.A. Khalifa、Yomna M.H. Gado、Amel M. Farrag、Mahmoud M. Elaasser、Nesreen A. Safwat、Reham R. AbdelRaouf、Reem K. Arafa

  DOI：10.1016/j.ejps.2019.01.023

  日期：2019.3

  A series of twenty five new thiobarbituric acid derivatives, viz. 3a-h, 4-7, 8a-c, 9, 10a-c, 11 and 12a-d, were designed and synthesized as potential cytotoxic agents. In-vitro screening of the new compounds against the three human cancer cell lines Caco-2, HepG-2 and MCF-7 was performed to assess their intrinsic activity. Compound 12d exhibited potent sub-micromolar activity against HepG-2 and MCF-7 (IC50 = 0.07 and 0.08 mu M, respectively). In-silico pharmacophore modelling of this chemotype compounds disclosed a five features' pharmacophore model representing essential steric and electronic fingerprints essential for activity. Finally, a 2D-QSAR model was devised to quantitatively correlate the 2D molecular feature descriptors of this series of thiobarbiturates with their cytotoxic activity against MCF-7. Finally, in silico evaluation of the physicochemical and ADME properties of these derivatives was performed.
• Ridi, Gazzetta Chimica Italiana, 1949, vol. 79, p. 175,185
  作者：Ridi

  DOI：——

  日期：——
• PESTOV, D. V.;KAPUSTINA, G. V.;SLESAREV, V. I., 1989) 5 S., ONIITEHXIM G. CHERKASSY, 22-XP89
  作者：PESTOV, D. V.、KAPUSTINA, G. V.、SLESAREV, V. I.

  DOI：——

  日期：——