5-[(4-oxo-4H-chromen-3-yl)methylene]-1,3-thiazolidine-2,4-dione | 897630-85-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 5-[(4-oxo-4H-chromen-3-yl)methylene]-1,3-thiazolidine-2,4-dione
• 英文别名: 5-[(4-oxo-4H-chromen-3-yl)methylene]thiazolidine-2,4-dione
• CAS: 897630-85-2
• 化学式: C₁₃H₇NO₄S
• 分子量: 273.269
• InChiKey: RRGNBDARMIMGAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.12
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  76.38
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-[(4-oxo-4H-chromen-3-yl)methylene]-1,3-thiazolidine-2,4-dione 在 sodium ethanolate 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以70%的产率得到5-[5-(2-hydroxyphenyl)-1H-pyrazol-4-y1]methylene-1,3-thiazolidine-2,4-dione
  参考文献：
  名称：

  合成生物活性杂芳基噻唑烷-2,4-二酮的新方法

  摘要：

  3-甲酰基色酮（1）与噻唑烷-2,4-二酮（2）的缩合得到5- [4-氧代-4H-铬-3-基）亚甲基] -1,3-噻唑烷-2,4-二酮（ 3）。3与水合肼，苯肼和盐酸羟胺反应，得到相应的吡唑和异恶唑衍生物4-7。使化合物3与硫脲，胍和氰基胍反应，得到相应的嘧啶衍生物8-10。嘧啶并[1,2-a]嘧啶12，苯并[1,5]二氮杂卓15，吡啶[1,2-b] [1,2,4]三氮杂卓16、1,2,4-三唑并[3,4-由3的反应制得b] [1,3,4] thiadiazepine 19和1,2,4-triazino [3,2-b] [1,3,4] thiadiazepine 20连接的thiazolidine-2,4-dione具有N，N-和N，S-双功能亲核试剂。3对碳亲核试剂的化学反应性产生了连接噻唑烷-2,4-二酮22-25的新杂环部分。

  DOI：

  10.1590/s0103-50532011000600019
• 作为产物：
  描述：

  2'-羟基苯乙酮 在 sodium acetate 、 溶剂黄146 、 三氯氧磷 作用下， 反应 12.0h， 生成 5-[(4-oxo-4H-chromen-3-yl)methylene]-1,3-thiazolidine-2,4-dione
  参考文献：
  名称：

  Thiazolidine-2,4-diones derivatives as PPAR-γ agonists: Synthesis, molecular docking, in vitro and in vivo antidiabetic activity with hepatotoxicity risk evaluation and effect on PPAR-γ gene expression

  摘要：

  A library of conjugates of chromones and 2,4-thiazolidinedione has been synthesized by Knoevenagel condensation followed by reduction using hydrogen gas and Pd/C as a catalyst. Compounds 5c and 5e were most effective in lowering the blood glucose level comparable to standard drug pioglitazone. Compound 5e exhibited potent PPAR-gamma transactivation of 48.72% in comparison to pioglitazone (62.48%). All the molecules showed good glide score against the PPAR-gamma target in molecular docking study. PPAR-gamma gene expression was significantly increased by compound 5e (2.56-fold) in comparison to standard drug pioglitazone. Compounds 5e and 5c did not cause any damage to the liver and may be considered as promising candidates for the development of new antidiabetic agents. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.05.034

文献信息

• Synthesis and aldose reductase inhibitory activity of some new chromonyl-2,4-thiazolidinediones
  作者：Oya Bozdağ-Dündar、Begüm Evranos、Net Daş-Evcimen、Mutlu Sarıkaya、Rahmiye Ertan

  DOI：10.1016/j.ejmech.2008.01.004

  日期：2008.11

  As it is known that still, there were no any confident ARIs on the market and they have several side effects, we need to approve new ARIs to reduce diabetic complications especially which have effect on the cataract formation. In this study, a new series of chromonl-2,4-thiazolidinediones (Ia-e, IIa-e, IIIa-e) were prepared by Knoevenagel reaction with substituted 3-formylchromones (3a-e) and unsubstituted (1) or substituted 2,4-thiazolidinedione (2). The synthesized compounds were tested for their ability to inhibit rat kidney AR by an in vitro spectrophotometric assay. Compound IIIe showed the highest inhibitory activity (82.43 +/- 0.76%). Compounds la-e and IIIa-d also showed significant inhibitory activity (42.40 +/- 5.78, 52.71 +/- 3.31, 49.69 +/- 1.55, 50.80 +/- 3.62, 46.70 +/- 2.33, 49.44 +/- 4.53, 61.17 +/- 4.74, 68.58 +/- 2.05, 77.28 +/- 0.26%, respectively). (C) 2008 Elsevier Masson SAS. All rights reserved.
• Thiazolidine-2,4-diones derivatives as PPAR-γ agonists: Synthesis, molecular docking, in vitro and in vivo antidiabetic activity with hepatotoxicity risk evaluation and effect on PPAR-γ gene expression
  作者：Syed Nazreen、Mohammad Sarwar Alam、Hinna Hamid、Mohammad Shahar Yar、Abhijeet Dhulap、Perwez Alam、M.A.Q. Pasha、Sameena Bano、Mohammad Mahboob Alam、Saqlain Haider、Chetna Kharbanda、Yakub Ali、K.K. Pillai

  DOI：10.1016/j.bmcl.2014.05.034

  日期：2014.7

  A library of conjugates of chromones and 2,4-thiazolidinedione has been synthesized by Knoevenagel condensation followed by reduction using hydrogen gas and Pd/C as a catalyst. Compounds 5c and 5e were most effective in lowering the blood glucose level comparable to standard drug pioglitazone. Compound 5e exhibited potent PPAR-gamma transactivation of 48.72% in comparison to pioglitazone (62.48%). All the molecules showed good glide score against the PPAR-gamma target in molecular docking study. PPAR-gamma gene expression was significantly increased by compound 5e (2.56-fold) in comparison to standard drug pioglitazone. Compounds 5e and 5c did not cause any damage to the liver and may be considered as promising candidates for the development of new antidiabetic agents. (C) 2014 Elsevier Ltd. All rights reserved.
• A new approach for the synthesis of bioactive heteroaryl thiazolidine-2,4-diones
  作者：Magdy Ahmed Ibrahim、Mohamed Abdel-Megid Abdel-Hamed、Naser Mohamed El-Gohary

  DOI：10.1590/s0103-50532011000600019

  日期：——

  thiazolidine-2,4-dione (2) afforded 5-[4-oxo-4H-chromen-3-yl)methylene]-1,3-thiazolidine-2,4-dione (3). Reaction of 3 with hydrazine hydrate, phenyl hydrazine and hydroxylamine hydrochloride gave the corresponding pyrazole and isoxazole derivatives 4-7. Compound 3 was subjected to react with thiourea, guanidine and cyanoguanidine to give the corresponding pyrimidine derivatives 8-10. Pyrimido[1,2-a]pyrimidine 12

  3-甲酰基色酮（1）与噻唑烷-2,4-二酮（2）的缩合得到5- [4-氧代-4H-铬-3-基）亚甲基] -1,3-噻唑烷-2,4-二酮（ 3）。3与水合肼，苯肼和盐酸羟胺反应，得到相应的吡唑和异恶唑衍生物4-7。使化合物3与硫脲，胍和氰基胍反应，得到相应的嘧啶衍生物8-10。嘧啶并[1,2-a]嘧啶12，苯并[1,5]二氮杂卓15，吡啶[1,2-b] [1,2,4]三氮杂卓16、1,2,4-三唑并[3,4-由3的反应制得b] [1,3,4] thiadiazepine 19和1,2,4-triazino [3,2-b] [1,3,4] thiadiazepine 20连接的thiazolidine-2,4-dione具有N，N-和N，S-双功能亲核试剂。3对碳亲核试剂的化学反应性产生了连接噻唑烷-2,4-二酮22-25的新杂环部分。