(Z)-5-(2-fluorobenzylidene)-2-thioxothiazolidin-4-one | 917985-95-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-5-(2-fluorobenzylidene)-2-thioxothiazolidin-4-one
• 英文别名: (5Z)-5-[(2-fluorophenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 917985-95-6
• 化学式: C₁₀H₆FNOS₂
• mdl: MFCD04969004
• 分子量: 239.294
• InChiKey: PPZBKJKFBVRKKK-YVMONPNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-5-(2-fluorobenzylidene)-2-thioxothiazolidin-4-one 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 33.17h， 生成 (Z)-2-(5-(2-fluorobenzyliden)-4-oxo-4,5-dihydrothiazol-2-ylamino)-3-phenyl-N-tosylpropanamide
  参考文献：
  名称：

  Structure-based design of rhodanine-based acylsulfonamide derivatives as antagonists of the anti-apoptotic Bcl-2 protein

  摘要：

  A series of novel rhodanine-based acylsulfonamide derivatives were designed, synthesized, and evaluated as small-molecule inhibitors of anti-apoptotic Bcl-2 protein. These compounds exhibit potent antiproliferative activity in three human tumor cell lines (Hep G2, PC-3 and B16-F10). Among them, the most potent compounds 10 and 11 bind to Bcl-2 with a K-i of 20 and 25 nM, respectively. Docking studies demonstrated that these two compounds orient similarly at the binding site of Bcl-2, and the calculated binding affinities (Glide XP score) of compound 10 is more negative than that of compound 11. The binding interactions of compounds with high binding affinity to Bcl-2 protein were analyzed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.079
• 作为产物：
  描述：

  罗丹宁 、 2-氟苯甲醛 以 neat (no solvent) 为溶剂， 生成 (Z)-5-(2-fluorobenzylidene)-2-thioxothiazolidin-4-one
  参考文献：
  名称：

  (Z)-5-[(5-Methyl-1H-imidazol-4-yl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one monohydrate: a three-dimensional hydrogen-bonded framework structure

  摘要：

  标题化合物的有机成分 C8H7N3OS2-H2O 中的非 H 原子几乎共面，因为两个环平面之间的二面角仅为 1.8 (2)°；在连接两个环的甲基 C 原子上有 127.8 (3)° 的宽 C-C-C 角。分子组分通过 N-H...O 和 O-H...N 两种类型的双中心氢键以及一个三中心 O-H...（N,S）系统连接成一个三维框架结构。与一些 (Z)-5- 芳基亚甲基-2-硫代亚甲基-1,3-噻唑烷-4-酮进行了比较。

  DOI：

  10.1107/s0108270112043260

文献信息

• Synthesis and Characterization of (Z)-5-Arylmethylidene-rhodanines with Photosynthesis-Inhibiting Properties
  作者：Veronika Opletalova、Jan Dolezel、Katarina Kralova、Matus Pesko、Jiri Kunes、Josef Jampilek

  DOI：10.3390/molecules16065207

  日期：——

  A series of rhodanine derivatives was prepared. The synthetic approach, analytical and spectroscopic data of all synthesized compounds are presented. Lipophilicity of all the discussed rhodanine derivatives was analyzed using the RP-HPLC method. The compounds were tested for their ability to inhibit photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts and reduce chlorophyll content in freshwater alga Chlorella vulgaris. Structure-activity relationships between the chemical structure, physical properties and biological activities of the evaluated compounds are discussed. For majority of the tested compounds the lipophilicity of the compound and not electronic properties of the R1 substituent were decisive for PET-inhibiting activity. The most potent PET inhibitor was (5Z)-5-(4-bromobenzylidene)-2-thioxo-1,3-thiazolidin-4-one (IC50 = 3.0 μmol/L) and the highest antialgal activity was exhibited by (5Z)-5-(4-chlorobenzylidene)-2-thioxo-1,3-thiazolidin-4-one (IC50 = 1.3 μmol/L).

  一系列硫代酮衍生物被制备。展示了所有合成化合物的合成方法、分析及光谱数据。通过反相高效液相色谱法（RP-HPLC）分析了所有讨论的硫代酮衍生物的亲脂性。对这些化合物在菠菜（Spinacia oleracea L.）叶 chloroplasts 中抑制光合电子传递（PET）的能力以及在淡水藻类小球藻（Chlorella vulgaris）中降低叶绿素含量进行了测试。讨论了评估化合物的化学结构、物理性质与生物活性之间的构效关系。在大多数测试化合物中，化合物的亲脂性而非R1取代基的电子性质是决定PET抑制活性的关键。最强效的PET抑制剂是(5Z)-5-(4-溴苯甲叉基)-2-硫代-1,3-噻唑烷-4-酮（IC50 = 3.0 μmol/L），而最高的抗藻活性则由(5Z)-5-(4-氯苯甲叉基)-2-硫代-1,3-噻唑烷-4-酮（IC50 = 1.3 μmol/L）表现。
• (<i>Z</i>)-5-[(5-Methyl-1<i>H</i>-imidazol-4-yl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one monohydrate: a three-dimensional hydrogen-bonded framework structure
  作者：Alberto Insuasty、Braulio Insuasty、Justo Cobo、Christopher Glidewell

  DOI：10.1107/s0108270112043260

  日期：2012.11.15

  The non-H atoms in the organic component of the title compound, C₈H₇N₃OS₂·H₂O, are almost coplanar, as the dihedral angle between the two ring planes is only 1.8 (2)°; there is a wide C—C—C angle of 127.8 (3)° at the methine C atom linking the two rings. The molecular components are linked into a three-dimensional framework structure by two-centre hydrogen bonds of N—H...O and O—H...N types, together with a three-centre O—H...(N,S) system. Comparisons are made with some (Z)-5-arylmethylidene-2-sulfanylidene-1,3-thiazolidin-4-ones.

  标题化合物的有机成分 C8H7N3OS2-H2O 中的非 H 原子几乎共面，因为两个环平面之间的二面角仅为 1.8 (2)°；在连接两个环的甲基 C 原子上有 127.8 (3)° 的宽 C-C-C 角。分子组分通过 N-H...O 和 O-H...N 两种类型的双中心氢键以及一个三中心 O-H...（N,S）系统连接成一个三维框架结构。与一些 (Z)-5- 芳基亚甲基-2-硫代亚甲基-1,3-噻唑烷-4-酮进行了比较。
• Rhodanine Derivatives¹
  作者：Frances C. Brown、Charles K. Bradsher、Sara M. Bond、Marny Potter

  DOI：10.1021/ja01149a510

  日期：1951.5
• Selective small molecule inhibitors of the potential breast cancer marker, human arylamine N-acetyltransferase 1, and its murine homologue, mouse arylamine N-acetyltransferase 2
  作者：Angela J. Russell、Isaac M. Westwood、Matthew H.J. Crawford、James Robinson、Akane Kawamura、Christina Redfield、Nicola Laurieri、Edward D. Lowe、Stephen G. Davies、Edith Sim

  DOI：10.1016/j.bmc.2008.11.032

  日期：2009.1

  The identification, synthesis and evaluation of a series of rhodanine and thiazolidin-2,4-dione derivatives as selective inhibitors of human arylamine N-acetyltransferase 1 and mouse arylamine N-acetyltransferase 2 is described. The most potent inhibitors identified have submicromolar activity and inhibit both the recombinant proteins and human NAT1 in ZR-75 cell lysates in a competitive manner. H-1 NMR studies on purified mouse Nat2 demonstrate that the inhibitors bind within the putative active site of the enzyme. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis and antifungal activity of (Z)-5-arylidenerhodanines
  作者：Maximiliano Sortino、Paula Delgado、Sabina Juárez、Jairo Quiroga、Rodrigo Abonía、Braulio Insuasty、Manuel Nogueras、Laura Rodero、Francisco M. Garibotto、Ricardo D. Enriz

  DOI：10.1016/j.bmc.2006.09.038

  日期：2007.1.1

  An efficient microwave-assisted synthesis of new (Z)-5-arylidenerhodanines under solvent-free conditions is described and their in vitro antifungal activity was evaluated following the CLSI (formerly NCCLS) guidelines against a panel of both standardized and clinical opportunistic pathogenic fungi. An analysis of the structure-activity relationship (SAR) along with computational studies showed that the most active compounds (F- and CF3-substituted rbodanines) possess high log P values and low polarizability. Mechanism-based assays suggest that active compounds neither would bind to ergosterol nor would produce a damage to the fungal membrane. (c) 2006 Elsevier Ltd. All rights reserved.