(5Z)-2-thioxo-3-allyl-5-[(pyridine-2-yl)methylene]-imidazole-4(4H)-one | 1336986-85-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (5Z)-2-thioxo-3-allyl-5-[(pyridine-2-yl)methylene]-imidazole-4(4H)-one
• 英文别名: (5Z)-3-prop-2-enyl-5-(pyridin-2-ylmethylidene)-2-sulfanylideneimidazolidin-4-one
• CAS: 1336986-85-6
• 化学式: C₁₂H₁₁N₃OS
• 分子量: 245.305
• InChiKey: IAWAFWBQRQGHDJ-NTMALXAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  77.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5Z)-2-thioxo-3-allyl-5-[(pyridine-2-yl)methylene]-imidazole-4(4H)-one 在 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  具有意外结构的混合价铜（I，II）双核配合物：合成，生物学性质和抗癌活性

  摘要：

  我们已经合成和表征了一组新的双核混合价Cu（I，II）配合物，其中包含具有异常结构的取代的2-烷硫基-5-芳基亚甲基-4 H-咪唑啉-4-酮。这些复合物显示出对多种细胞系具有细胞毒性。我们发现这些化合物不嵌入DNA，抑制聚合酶（主要是端粒酶）的数量，积累在细胞核中，并引起DNA降解。初步研究表明，铅化合物可抑制小鼠乳腺腺癌的生长。

  DOI：

  10.1021/jm500154f
• 作为产物：
  描述：

  吡啶-2-甲醛 、 3-丙-2-烯基-2-巯基咪唑烷-4-酮 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以93%的产率得到(5Z)-2-thioxo-3-allyl-5-[(pyridine-2-yl)methylene]-imidazole-4(4H)-one
  参考文献：
  名称：

  Conversion of 2-thiohydantoins and their derivatives to the corresponding hydantoins in the processes of complexation reactions with copper(II) chloride dihydrate

  摘要：

  The treatment of 5-pyridylmethylene-substituted 2-thiohydantoins or 2-alkylthio-3,5-dihydro-4H-imidazole-4-ones with CuCl(2)2H(2)O affords the mononuclear or polymeric copper(II) complexes of the corresponding hydantoins. A presumable mechanism of hydantoin moiety formation involves Lewis acid catalyzed nucleophilic substitution of a sulfur-containing leaving group in the organic ligand by a water molecule from CuCl2H2O. The copper complexes Cu(L-1-H)Cl(H2O) (7; L-1 = (Z)-3-allyl-5-(pyridine-2-ylmethylene)imidazole-2,4(4H)-dione) and Cu(L-2-H)(2) (9; L-2 = Z)-3-allyl-5-(5'-bromo-pyridine-2-ylmethylene)imidazole-2,4(4H)-dione) were characterized by X-ray diffraction. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2014.03.045

文献信息

• TELOMERASE INHIBITORS AND A METHOD FOR THE PREPARATION THEREOF
  申请人：UCHREZHDENIE KHIMICHESKIJJ FAKUL'TET GOSUDARSTVENNOE UCHEBNO-NAUCHNOE

  公开号：US20130109861A1

  公开（公告）日：2013-05-02

  The invention relates to the field of organic and medicinal chemistry, and molecular biology, and concerns a method for the preparation of a new class of telomerase-inhibiting compounds, which can be utilized for studying telomerases and catalytic sub-units of telomerases, and reverse transcriptases, and foe studying and treating neoplastic and viral diseases. Telomerase-inhibiting coordination compounds of derivatives of imidazol-4-one are characterized by general formula

  本发明涉及有机化学、药物化学和分子生物学领域，涉及一种制备新型端粒酶抑制剂化合物的方法，可用于研究端粒酶和催化亚单位，以及反转录酶，用于研究和治疗肿瘤和病毒性疾病。咪唑-4-酮衍生物的端粒酶抑制配位化合物的一般式如下：
• Conversion of 2-thiohydantoins and their derivatives to the corresponding hydantoins in the processes of complexation reactions with copper(II) chloride dihydrate
  作者：Elena K. Beloglazkina、Alexander G. Majouga、Andrei V. Mironov、Anna V. Yudina、Olga Yu. Kuznetsova、Nikolai V. Zyk

  DOI：10.1016/j.poly.2014.03.045

  日期：2014.7

  The treatment of 5-pyridylmethylene-substituted 2-thiohydantoins or 2-alkylthio-3,5-dihydro-4H-imidazole-4-ones with CuCl(2)2H(2)O affords the mononuclear or polymeric copper(II) complexes of the corresponding hydantoins. A presumable mechanism of hydantoin moiety formation involves Lewis acid catalyzed nucleophilic substitution of a sulfur-containing leaving group in the organic ligand by a water molecule from CuCl2H2O. The copper complexes Cu(L-1-H)Cl(H2O) (7; L-1 = (Z)-3-allyl-5-(pyridine-2-ylmethylene)imidazole-2,4(4H)-dione) and Cu(L-2-H)(2) (9; L-2 = Z)-3-allyl-5-(5'-bromo-pyridine-2-ylmethylene)imidazole-2,4(4H)-dione) were characterized by X-ray diffraction. (C) 2014 Elsevier Ltd. All rights reserved.
• Mixed Valence Copper(I,II) Binuclear Complexes with Unexpected Structure: Synthesis, Biological Properties and Anticancer Activity
  作者：Alexander G. Majouga、Maria I. Zvereva、Maria P. Rubtsova、Dmitry A. Skvortsov、Andrei V. Mironov、Dulat M. Azhibek、Olga O. Krasnovskaya、Vasily M. Gerasimov、Anna V. Udina、Nikolay I. Vorozhtsov、Elena K. Beloglazkina、Leonid Agron、Larisa V. Mikhina、Alla V. Tretyakova、Nikolay V. Zyk、Nikolay S. Zefirov、Alexander V. Kabanov、Olga A. Dontsova

  DOI：10.1021/jm500154f

  日期：2014.7.24

  We have synthesized and characterized a panel of new binuclear mixed valence Cu(I,II) complexes containing substituted 2-alkylthio-5-arylmethylene-4H-imidazolin-4-ones with unusual structure. These complexes are shown to be cytotoxic for various cell lines. We have found that these compounds did not intercalate DNA, inhibited number of polymerases (telomerase predominantly), accumulated in the cell

  我们已经合成和表征了一组新的双核混合价Cu（I，II）配合物，其中包含具有异常结构的取代的2-烷硫基-5-芳基亚甲基-4 H-咪唑啉-4-酮。这些复合物显示出对多种细胞系具有细胞毒性。我们发现这些化合物不嵌入DNA，抑制聚合酶（主要是端粒酶）的数量，积累在细胞核中，并引起DNA降解。初步研究表明，铅化合物可抑制小鼠乳腺腺癌的生长。