3-butylthiazolidine-2,4-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 3-butylthiazolidine-2,4-dione
• 英文别名: 3-Butyl-1,3-thiazolidine-2,4-dione
• 化学式: C₇H₁₁NO₂S
• mdl: MFCD17010960
• 分子量: 173.236
• InChiKey: FKVULACBYWDJMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.714
• 拓扑面积：
  62.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-乙基-1H-吲哚-2,3-二酮 、 3-butylthiazolidine-2,4-dione 以 水 为溶剂， 反应 24.0h， 以97%的产率得到3-butyl-5-(1-ethyl-3-hydroxy-2-oxoindolin-3-yl)thiazolidine-2,4-dione
  参考文献：
  名称：

  Thiazolidinedione–Isatin Conjugates via an Uncatalyzed Diastereoselective Aldol Reaction on Water

  摘要：

  An uncatalyzed aldol reaction of N-substituted thiazolidinediones with isatin derivatives has been developed "on water" to afford a new class of pharmacologically important thiazolidinedione-isatin conjugates in excellent yields and diastereoselectivities. The isatin-thiazolidine conjugate undergoes a catalyst-free stereoselective transfer aldol reaction on water. Single-crystal X-ray studies reveal that the aldol products can self-assemble to form supramolecular DNA "zipper" like structures through intermolecular hydrogen bonds and aromatic pi-pi interactions.

  DOI：

  10.1021/jo402515d
• 作为产物：
  描述：

  2,4-噻唑烷二酮 、 氯丁烷 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以73%的产率得到3-butylthiazolidine-2,4-dione
  参考文献：
  名称：

  Thiazolidinedione–Isatin Conjugates via an Uncatalyzed Diastereoselective Aldol Reaction on Water

  摘要：

  An uncatalyzed aldol reaction of N-substituted thiazolidinediones with isatin derivatives has been developed "on water" to afford a new class of pharmacologically important thiazolidinedione-isatin conjugates in excellent yields and diastereoselectivities. The isatin-thiazolidine conjugate undergoes a catalyst-free stereoselective transfer aldol reaction on water. Single-crystal X-ray studies reveal that the aldol products can self-assemble to form supramolecular DNA "zipper" like structures through intermolecular hydrogen bonds and aromatic pi-pi interactions.

  DOI：

  10.1021/jo402515d

文献信息

• MACROPHAGE IDENTIFICATION AGENT, AND IDENTIFICATION METHOD, SORTING METHOD, EVALUATION METHOD, SCREENING METHOD AND KIT USING THE MACROPHAGE IDENTIFIER AGENT
  申请人：CANON KABUSHIKI KAISHA

  公开号：US20160018389A1

  公开（公告）日：2016-01-21

  An object of the present invention is to provide an identification method for a macrophage subtype using an organic compound. Another object of the present invention is to provide a macrophage identification agent containing an organic compound in which a spectral characteristic obtained when the organic compound is added is different depending on a macrophage subtype. Still another object of the present invention is to provide an evaluation method for a macrophage subtype using a macrophage identification agent, an analysis method for correlation between a macrophage subtype and a test substance, a screening method for correlation between a macrophage subtype and a test substance, and a kit. An identification method for a macrophage subtype utilizing that a spectral characteristic obtained with an organic compound added is different depending on a macrophage subtype is provided.

  本发明的一个目的是提供一种利用有机化合物对巨噬细胞亚型进行识别的方法。本发明的另一个目的是提供一种巨噬细胞识别试剂，其中当添加有机化合物时得到的光谱特征取决于巨噬细胞亚型而不同。本发明的另一个目的是提供一种利用巨噬细胞识别试剂进行巨噬细胞亚型评估的方法，一种用于巨噬细胞亚型与测试物之间相关性分析的方法，一种用于巨噬细胞亚型与测试物之间相关性筛选的方法，以及一种试剂盒。提供了一种利用添加有机化合物得到的光谱特征不同取决于巨噬细胞亚型的巨噬细胞亚型识别方法。
• Macrophage identification agent, and identification method, sorting method, evaluation method, screening method and kit using the macrophage identifier agent
  申请人：CANON KABUSHIKI KAISHA

  公开号：US10041937B2

  公开（公告）日：2018-08-07

  An object of the present invention is to provide an identification method for a macrophage subtype using an organic compound. Another object of the present invention is to provide a macrophage identification agent containing an organic compound in which a spectral characteristic obtained when the organic compound is added is different depending on a macrophage subtype. Still another object of the present invention is to provide an evaluation method for a macrophage subtype using a macrophage identification agent, an analysis method for correlation between a macrophage subtype and a test substance, a screening method for correlation between a macrophage subtype and a test substance, and a kit. An identification method for a macrophage subtype utilizing that a spectral characteristic obtained with an organic compound added is different depending on a macrophage subtype is provided.

  本发明的一个目的是提供一种利用有机化合物识别巨噬细胞亚型的方法。本发明的另一个目的是提供一种含有有机化合物的巨噬细胞识别剂，其中添加有机化合物时获得的光谱特性因巨噬细胞亚型的不同而不同。本发明的另一个目的是提供一种使用巨噬细胞鉴定剂的巨噬细胞亚型的评估方法、巨噬细胞亚型与测试物质之间相关性的分析方法、巨噬细胞亚型与测试物质之间相关性的筛选方法和试剂盒。本发明提供了一种巨噬细胞亚型的鉴别方法，该方法利用了添加有机化合物后获得的光谱特性随巨噬细胞亚型的不同而不同的特点。
• Thiazolidinone–Peptide Hybrids as Dengue Virus Protease Inhibitors with Antiviral Activity in Cell Culture
  作者：Christoph Nitsche、Verena N. Schreier、Mira A. M. Behnam、Anil Kumar、Ralf Bartenschlager、Christian D. Klein

  DOI：10.1021/jm400828u

  日期：2013.11.14

  The protease of dengue virus is a promising target for antiviral drug discovery. We here report a new generation of peptide hybrid inhibitors of dengue protease that incorporate N-substituted 5-arylidenethiazolidinone heterocycles (rhodanines and thiazolidinediones) as N-terminal capping groups of the peptide moiety. The compounds were extensively characterized with respect to inhibition of various proteases, inhibition mechanisms, membrane permeability, antiviral activity, and cytotoxicity in cell culture. A sulfur/oxygen exchange in position 2 of the capping heterocycle (thiazolidinedione-capped vs rhodanine-capped peptide hybrids) has a significant effect on these properties and activities. The most promising in vitro affinities were observed for thiazolidinedione-based peptide hybrids containing hydrophobic groups with K-i values between 1.5 and 1.8 mu M and competitive inhibition mechanisms. Rhodanine-capped peptide hybrids with hydrophobic substituents have, in correlation with their membrane permeability, a more pronounced antiviral activity in cell culture than the thiazolidinediones.
• Structural exploration, synthesis and pharmacological evaluation of novel 5-benzylidenethiazolidine-2,4-dione derivatives as iNOS inhibitors against inflammatory diseases
  作者：Liang Ma、Heying Pei、Lei Lei、Linhong He、Jinying Chen、Xiaolin Liang、Aihua Peng、Haoyu Ye、Mingli Xiang、Lijuan Chen

  DOI：10.1016/j.ejmech.2014.12.036

  日期：2015.3

  In our previous work, 3I inhibited the LPS-induced iNOS activity and NO production in RAW 264.7 cells and improved joint inflammation and cartilage destruction in inflammatory model. In this study, we synthesized 59 derivatives and bioisosteres on the basis of 3I by Knoevenagel condensation and biologically evaluated for the study of structure-activity relationship (SAR). We found that 7-44 suppressed the iNOS activity (IC50 25.2 mu M) and LPS-induced NO production (IC50 45.6 mu M) in RAW 264.7 cells. As for the SAR study, the dimethoxylphenyl group of 7-44 was potential for a further modification. At a dose of 10 mg/kg, oral administration of 7-44 possessed protective properties in both carrageenan-induced paw edema of male ICR mice and adjuvant-induced arthritis of Lewis female rats. Although the activity of 7-44 was slightly inferior, the PK profiles of 7-44 were superior to those of 3I. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Hu, Yi; Chen, Zhen-Chu; Le, Zhang-Gao, Journal of Chemical Research, 2004, # 4, p. 276 - 278
  作者：Hu, Yi、Chen, Zhen-Chu、Le, Zhang-Gao、Zheng, Qin-Guo

  DOI：——

  日期：——