4-Oxo-2-<4-dimethylamino-benzylidenhydrazono>-thiazolidin | 22068-82-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-Oxo-2-<4-dimethylamino-benzylidenhydrazono>-thiazolidin
• 英文别名: 4-dimethylamino-benzaldehyde (4-oxo-thiazolidin-2-ylidene)-hydrazone；Thiazolidin-2,4-dion-2-(4-dimethylamino-benzylidenhydrazon)；(2E)-2-[[4-(dimethylamino)phenyl]methylidenehydrazinylidene]-1,3-thiazolidin-4-one
• CAS: 22068-82-2
• 化学式: C₁₂H₁₄N₄OS
• mdl: MFCD00704638
• 分子量: 262.335
• InChiKey: AOFVYOCIKCHIBD-UHFFFAOYSA-N

物化性质

• 熔点：
  242 °C
• 沸点：
  422.4±47.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  82.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-Oxo-2-<4-dimethylamino-benzylidenhydrazono>-thiazolidin 、 氯化苄 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以38%的产率得到(Z)-3-benzyl-2-(((E)-4-(dimethylamino)benzylidene)hydrazono)thiazolidin-4-one
  参考文献：
  名称：

  Thiazolylhydrazone dervatives as inhibitors for insect N-acetyl-β-d-hexosaminidase and chitinase

  摘要：

  Insect chitinase and N-acetyl-beta-D-hexosaminidases (Hex) are potential targets for developing new pesticides. Here, a series of thiazolylhydrazones I (with substituted group R(1 )at N3) and II (with substituted group R-1 at N2) were designed, synthesised and evaluated as competitive inhibitors of OfHex1 and OfChi-h, from the agricultural pest Ostrinia furnacalis. Derivatives I-3d and II-3d, with phenoxyethyl group at R-1, demonstrated the best inhibitory activities against OfHex1 and Of Chi-h. Molecular docking analysis indicated that the branched conformation compound II-3d (K-i = 1.5 mu mol/L) formed more hydrogen bonds with OfHex1 than the stretched conformation compound I-3d (K-i = 5.9 mu mol/L). The differences in compounds' binding conformations with OfChi-h explained differences in inhibitory activity of compounds I-3d (K-i =1.9 mu mol/L) and II-3d (K-i = 4.1 mu mol/L). This work suggests a novel scaffold for developing specific Hex and Chi-h inhibitors. (C) 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2019.11.035
• 作为产物：
  描述：

  对二甲氨基苯甲醛 在 sodium acetate 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 20.0h， 生成 4-Oxo-2-<4-dimethylamino-benzylidenhydrazono>-thiazolidin
  参考文献：
  名称：

  Thiazolylhydrazone dervatives as inhibitors for insect N-acetyl-β-d-hexosaminidase and chitinase

  摘要：

  Insect chitinase and N-acetyl-beta-D-hexosaminidases (Hex) are potential targets for developing new pesticides. Here, a series of thiazolylhydrazones I (with substituted group R(1 )at N3) and II (with substituted group R-1 at N2) were designed, synthesised and evaluated as competitive inhibitors of OfHex1 and OfChi-h, from the agricultural pest Ostrinia furnacalis. Derivatives I-3d and II-3d, with phenoxyethyl group at R-1, demonstrated the best inhibitory activities against OfHex1 and Of Chi-h. Molecular docking analysis indicated that the branched conformation compound II-3d (K-i = 1.5 mu mol/L) formed more hydrogen bonds with OfHex1 than the stretched conformation compound I-3d (K-i = 5.9 mu mol/L). The differences in compounds' binding conformations with OfChi-h explained differences in inhibitory activity of compounds I-3d (K-i =1.9 mu mol/L) and II-3d (K-i = 4.1 mu mol/L). This work suggests a novel scaffold for developing specific Hex and Chi-h inhibitors. (C) 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2019.11.035

文献信息

• Thiocyanoacetate. III. The Synthesis of 2-Hydrazono-4-thiazolidinone Derivatives
  作者：Satoshi Kambe、Toshio Hayashi

  DOI：10.1246/bcsj.45.952

  日期：1972.3
• Buu-Hoi et al., Journal of the Chemical Society, 1956, p. 713,714
  作者：Buu-Hoi et al.

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• Taniyama et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1955, vol. 75, p. 382,385
  作者：Taniyama et al.

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  日期：——
• Gheorghiu et al., Revue de Chimie, Academie de la Republique Populaire Roumaine, 1956, vol. 1, # 1, p. 97,122
  作者：Gheorghiu et al.

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• Stoicescu-Crivetz; Mandasescu, 1953, vol. 4, p. 307,310
  作者：Stoicescu-Crivetz、Mandasescu

  DOI：——

  日期：——