2-imino-3-(pyridin-2-yl)thiazolidin-4-one | 406175-53-9

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2-imino-3-(pyridin-2-yl)thiazolidin-4-one
• CAS: 406175-53-9
• 化学式: C₈H₇N₃OS
• 分子量: 193.229
• InChiKey: MTBYWGCKSQFYGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  57.05
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-苄氧基苯甲醛 、 2-imino-3-(pyridin-2-yl)thiazolidin-4-one 在 sodium acetate 、 溶剂黄146 作用下， 反应 3.0h， 以82%的产率得到5-(4-(benzyloxy)benzylidene)-2-imino-3-(pyridin-2-yl)thiazolidin-4-one
  参考文献：
  名称：

  Design and development of novel Mycobacterium tuberculosis l-alanine dehydrogenase inhibitors

  摘要：

  In the present study, we used crystal structure of MTB L-AlaDH protein complex with N-6-methyl adenosine for structure based virtual screening of in house database to identify new small molecule inhibitors for MTB-L-AlaDH. Two molecules identified as better leads and were modified synthetically to obtain thirty novel analogues belonging to 2-iminothiazolidine-4-ones and 4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamides. Among the screened compounds four (4n, 40,12 and 14) emerged as potent inhibitors displaying IC50 values ranging from 0.58 +/- 0.02 to 1.74 +/- 0.03 mu M against MTB-L-AlaDH and were non-cytotoxic at 50 mu M. Some of these synthesized compounds also exhibited good activity against nutrient starved dormant MTB cells. The most potent inhibitors were found to stabilize the protein which was confirmed biophysically through differential scanning fluorimetry. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.12.046
• 作为产物：
  描述：

  2-氨基吡啶 在 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 5.0h， 生成 2-imino-3-(pyridin-2-yl)thiazolidin-4-one
  参考文献：
  名称：

  Structural exploration, synthesis and pharmacological evaluation of novel 5-benzylidenethiazolidine-2,4-dione derivatives as iNOS inhibitors against inflammatory diseases

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2014.12.036

文献信息

• Synthesis of Some Novel 5-(Arylidene)-2-imino-3(pyridin-2-yl)thiazolidin-4-one Derivatives
  作者：Akbar Mobinikhaledi、Naser Foroughifar、Somayeh Faghihi

  DOI：10.1080/10426500802387401

  日期：2009.7.13

  potassium thiocyanate gave 2-imino-3-(pyridin-2-yl)thiazolidin-4-one ( 4 ) as an intermediate compound for the synthesis of pyridin-2-yl substituted 2-imino-thiazolidine-4-one derivatives. Cyclocondensation reaction of ( 4 ) with a series of aromatic aldehydes gave 5-arylidene derivatives of pyridin-2-yl substituted 2-imino-thiazolidine-4-ones 5a–j . 1 H and 13C NMR spectroscopy, as well as elemental

  在无水苯中用氯乙酰氯处理 2-氨基吡啶 (1) 得到 2-氯-N-(吡啶-2-基)乙酰胺 (3)，进一步与硫氰酸钾反应得到 2-亚氨基-3-(吡啶- 2-yl)thiazolidin-4-one (4) 作为合成 pyridin-2-yl 取代的 2-imino-thiazolidine-4-one 衍生物的中间体化合物。(4) 与一系列芳香醛的环缩合反应得到吡啶-2-基取代的 2-亚氨基-噻唑烷-4-酮 5a-j 的 5-亚芳基衍生物。1 H 和 13C NMR 光谱以及元素分析用于鉴定这些新化合物。