(5E)-2-疏基-5-(2-硝基亚苄基)-1,3-噻唑-4(5H)-酮 | 6308-22-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (5E)-2-疏基-5-(2-硝基亚苄基)-1,3-噻唑-4(5H)-酮
• 英文名称: (5Z)-5-(2-nitrobenzylidene)-2-thioxo-1,3-thiazolidin-4-one
• 英文别名: (Z)-5-(2-nitrobenzylidene)-2-thioxothiazolidin-4-one；5-[(2-nitrophenyl)methylene]-2-thioxo-4-thiazolidinone；(5E)-2-mercapto-5-(2-nitrobenzylidene)-1,3-thiazol-4(5H)-one；(5Z)-5-[(2-nitrophenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 6308-22-1
• 化学式: C₁₀H₆N₂O₃S₂
• mdl: MFCD04969015
• 分子量: 266.301
• InChiKey: CTTRUEBEEFZQBL-YVMONPNESA-N

物化性质

• 溶解度：
  二甲基亚砜：≥ 77.5 mg/mL（291.03 mM）

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 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：
  132
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2934999090

制备方法与用途

生物活性

AKOS B018304 是一种对位被极性取代的芳基亚烷基衍生物，是一种有效的低微摩尔活性的 CHIKV 抑制剂。

体外研究

AKOS B018304（化合物6）是一种具有对位极性取代的芳基亚烷基衍生物。

反应信息

• 作为反应物：
  描述：

  4-bromo-3-methyl-1-phenylpyrazol-5-one 、 (5E)-2-疏基-5-(2-硝基亚苄基)-1,3-噻唑-4(5H)-酮 生成 (5Z)-3-(3-methyl-5-oxo-1-phenyl-4H-pyrazol-4-yl)-5-[(2-nitrophenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
  参考文献：
  名称：

  MITRA, P.;MITTRA, A. S., J. INDIAN CHEM. SOC., 1984, 61, N 1, 77-78

  摘要：

  DOI：
• 作为产物：
  描述：

  邻硝基苯甲醛 在 三乙胺 作用下， 以 乙醇 为溶剂， 生成 (5E)-2-疏基-5-(2-硝基亚苄基)-1,3-噻唑-4(5H)-酮
  参考文献：
  名称：

  药物病理生理 Mtb 蛋白靶点的分子建模：合成一些 2-thioxo-1, 3-thiazolidin-4-one 衍生物作为抗结核剂

  摘要：

  摘要 合成了20种新型2-thioxo-1,3-thiazolidin-4-one衍生物(5a-5t)并评价了它们的抗结核活性。化合物的结构通过红外、核磁共振和质谱方法确认。此外，对化合物5a进行了单晶X射线衍射。所有合成的化合物均通过 Alamar Blue 测定法筛选其对 MTB（H37RV，ATCC 编号：27294）的体外抗分枝杆菌活性。化合物5r、5k、5t显示出最有效的体外活性，MIC分别为0.05、0.1、0.2μg/ml浓度，其比标准品更有效。进行分子对接和动力学模拟以找出标题化合物的合理机制。

  DOI：

  10.1016/j.molstruc.2017.07.009

文献信息

• Thiazolidinone derivatives as hypoglycemic agents and for treating Alzheimer's disease
  申请人：ELI LILLY AND COMPANY

  公开号：EP0587377A2

  公开（公告）日：1994-03-16

  Provided are methods for treating hyperglycemia and Alzheimer's disease utilizing certain rhodanine derivatives. Certain of the rhodanine derivatives utilized in the instant methods are novel and, accordingly, such compounds, process for preparing same and pharmaceutical formulations thereof, are also provided.

  本发明提供了利用某些罗丹宁衍生物治疗高血糖和阿尔茨海默病的方法。在本方法中使用的某些罗丹宁衍生物是新颖的，因此还提供了此类化合物、其制备工艺和药物制剂。
• Compounds useful as hypoglycemic agents and for treating Alzheimer's disease
  申请人：ELI LILLY AND COMPANY

  公开号：EP0915090A1

  公开（公告）日：1999-05-12

  Provided are methods for treating hyperglycemia and Alzheimer's disease utilizing certain rhodanine derivatives. Certain of the rhodanine derivatives utilized in the instant methods are novel and, accordingly, such compounds, process for preparing same and pharmaceutical formulations thereof, are also provided.

  本发明提供了利用某些罗丹宁衍生物治疗高血糖和阿尔茨海默病的方法。在本方法中使用的某些罗丹宁衍生物是新颖的，因此还提供了此类化合物、其制备工艺和药物制剂。
• Exploration of inhibitors for diaminopimelate aminotransferase
  作者：Chenguang Fan、Matthew D. Clay、Michael K. Deyholos、John C. Vederas

  DOI：10.1016/j.bmc.2010.02.001

  日期：2010.3

  Bacteria and higher plants make L-lysine from diaminopimelic acid (DAP). In mammals L-lysine is an essential amino acid that must be acquired from the diet as the biosynthetic pathway is absent for this key constituent of proteins. Recently, LL-diaminopimelate aminotransferase (LL-DAP-AT), a pyridoxal-5'-phosphate (PLP)-dependent enzyme, was reported to catalyze a key step in the route to L-lysine in plants and Chlamydia. Specific inhibitors of this enzyme could thus potentially serve as herbicides or antibiotics that are non-toxic to mammals. In this work, 29,201 inhibitors were screened against LL-DAP-AT and the IC50 values were determined for the top 46 compounds. An aryl hydrazide and rhodanine derivatives were further modified to generate 20 analogues that were also tested against LL-DAP-AT. These analogues provide additional structure-activity relationships (SAR) that are useful in guiding further design of inhibitors. (C) 2010 Elsevier Ltd. All rights reserved.
• The synthesis and SAR of rhodanines as novel class C β-lactamase inhibitors
  作者：Eugene B Grant、Deodialsingh Guiadeen、Ellen Z Baum、Barbara D Foleno、Haiyong Jin、Deborah A Montenegro、Erin A Nelson、Karen Bush、Dennis J Hlasta

  DOI：10.1016/s0960-894x(00)00444-3

  日期：2000.10

  beta-Lactam antibiotics such as the cephalosporins and penicillins have diminished clinical effectiveness due to the hydrolytic activity of diverse beta-lactamases, especially those in molecular classes A and C. A structure-activity relationship (SAR) study of a high-throughput screening lead resulted in the discovery of a potent and selective non-beta-lactam inhibitor of class C beta-lactamases. (C) 2000 Elsevier Science Ltd. All rights reserved.
• SENCZUK, L.;SENCZUK, M.;URBANOWICZ, M., POL. J. CHEM., 1982, 56, N 10-12, 1549-1552
  作者：SENCZUK, L.、SENCZUK, M.、URBANOWICZ, M.

  DOI：——

  日期：——