5-(2-nitrobenzylidene)-4-thiazolidinone-2-thioxo | 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
• 英文名称: 5-(2-nitrobenzylidene)-4-thiazolidinone-2-thioxo
• 英文别名: 5-(2-nitrobenzylidene)rhodanine；5-(2-nitro-benzylidene)-2-thioxo-thiazolidin-4-one；5-(2-Nitro-benzyliden)-2-thioxo-thiazolidin-4-on；(5E)-5-[(2-nitrophenyl)methylidene]-2-sulfanyl-1,3-thiazol-4-one；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-UHFFFAOYSA-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：

  5-(2-nitrobenzylidene)-4-thiazolidinone-2-thioxo 在 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 为溶剂， 反应 32.0h， 生成 (S,E)-N-(4-((3-chlorophenyl)amino)quinazolin-6-yl)-1-(5-(2-nitrobenzylidene)-4-oxo-4,5-dihydrothiazol-2-yl)pyrrolidine-2-carboxamide
  参考文献：
  名称：

  Combination of 4-anilinoquinazoline and rhodanine as novel epidermal growth factor receptor tyrosine kinase inhibitors

  摘要：

  A type of novel rhodanine-based 4-anilinoquinazoline, which designed the combination between quinazoline as the backbone and various substituted biological rhodanine groups as the side chain, have been synthesized, and their antiproliferative activities were also evaluated firstly. These compounds displayed good antiproliferative activity and EGFR-TK inhibitory activity. Among them, compound 8d showed good inhibitory activity (IC50 = 2.7 mu M for Hep G2, IC50 = 3.1 mu M for A549) and molecular docking of 8d into EGFR TK active site was also performed, this inhibitor well fitting the active site might well explain its excellent inhibitory activity. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.04.065
• 作为产物：
  描述：

  罗丹宁 、 邻硝基苯甲醛 生成 5-(2-nitrobenzylidene)-4-thiazolidinone-2-thioxo
  参考文献：
  名称：

  THE CONDENSATION OF RHODANINE WITH AROMATIC DIALDEHYDES AND SOME RELATED COMPOUNDS

  摘要：

  已研究了罗丹宁及其3-乙基和3-苯基衍生物与对苯二甲醛、吡啶-2,6-二甲醛和邻苯二甲醛的缩合反应。已制备了29种含有芳香环中亲电取代基的5-芳基亚醛罗丹宁。

  DOI：

  10.1139/v58-229

文献信息

• THE CONDENSATION OF RHODANINE WITH AROMATIC DIALDEHYDES AND SOME RELATED COMPOUNDS
  作者：Frederick J. Allan、G. Graham Allan、J. B. Thomson

  DOI：10.1139/v58-229

  日期：1958.11.1

  The condensation of rhodanine and its 3-ethyl and 3-phenyl derivatives with terephthaldehyde, pyridine-2,6-dicarboxaldehyde, and phthaldehyde has been investigated. Twenty-nine 5-arylidene-rhodanines containing an electrophilic substituent in the aromatic ring have been prepared.

  已研究了罗丹宁及其3-乙基和3-苯基衍生物与对苯二甲醛、吡啶-2,6-二甲醛和邻苯二甲醛的缩合反应。已制备了29种含有芳香环中亲电取代基的5-芳基亚醛罗丹宁。
• N-Glucopyranosyl-5-aralkylidenerhodanines: Synthesis and Antibacterial and Antiviral Activities
  作者：William O. Foye、Phichai Tovivich

  DOI：10.1002/jps.2600661126

  日期：1977.11

  N-glycoside formation. A number of the rhodanine derivatives, especially those with nitro or chloro groups in the aromatic ring, showed antibacterial activity. N-beta-D-Glucopyranosyl-5-(4-nitrobenzylidene) rhodanine showed antiviral activity by inhibition of viral RNA synthesis. Some effect on blood sugar levels also was observed with several rhodanines.

  合成了一系列的N-（2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖基）-5-芳烷基亚乙基金丹宁，并且除去了乙酰基基团，得到了N-β-D-吡喃葡萄糖基-5-芳烷基亚芳基但不通过酸水解裂解若丹宁环。在甲醇中用氨水进行碱水解会裂解为N-葡萄糖基硫脲，为N-糖苷的形成提供了证据。许多若丹宁衍生物，特别是在芳族环中具有硝基或氯基的那些，均显示出抗菌活性。N-β-D-Glucopyranosyl-5-（4-硝基亚苄基）若丹宁通过抑制病毒RNA合成表现出抗病毒活性。几种罗丹宁对血糖水平也有一定影响。
• Bondzynski, Monatshefte fur Chemie, 1887, vol. 8, p. 350
  作者：Bondzynski

  DOI：——

  日期：——
• Senczuk, Lidia; Senczuk, Malgorzata; Urbanowicz, Malgorzata, Polish Journal of Chemistry, 1982, vol. 56, # 10-12, p. 1549 - 1552
  作者：Senczuk, Lidia、Senczuk, Malgorzata、Urbanowicz, Malgorzata

  DOI：——

  日期：——
• Synthesis, properties, and perspectives of gem-diphosphono substituted-thiazoles
  作者：Wafaa M. Abdou、Neven A. Ganoub、Athina Geronikaki、Eman Sabry

  DOI：10.1016/j.ejmech.2007.07.005

  日期：2008.5

  A series of substituted arylidene thiazoles were allowed to react with Wittig-Homer (WH) reagent, tetraethyl methyl-1,1-bisphosphonate, to produce via Michael addition reaction the corresponding heteroarylmethylenebisphosphonates (BPs) in different yields according to the experimental conditions. Acid hydrolysis of the new BPs was undertaken to obtain the corresponding bisphosphonic acids. Prediction and the in vivo activity of the products in the rat adjuvant model are also discussed in terms of structure-activity relationships (SAR). (C) 2007 Elsevier Masson SAS. All rights reserved.