(Z)-2-(((E)-4-(dimethylamino)benzylidene)hydrazono)thiazolidin-4-one

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (Z)-2-(((E)-4-(dimethylamino)benzylidene)hydrazono)thiazolidin-4-one
• 英文别名: (Z)-2-((E)-(4-(dimethylamino)benzylidene)hydrazono)thiazolidin-4-one；(2Z)-2-[(E)-[4-(dimethylamino)phenyl]methylidenehydrazinylidene]-1,3-thiazolidin-4-one
• 化学式: C₁₂H₁₄N₄OS
• 分子量: 262.335
• InChiKey: AOFVYOCIKCHIBD-NTUHNPAUSA-N

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：

  苄基氯甲基醚 、 (Z)-2-(((E)-4-(dimethylamino)benzylidene)hydrazono)thiazolidin-4-one 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以42%的产率得到(Z)-3-((benzyloxy)methyl)-2-(((E)-4-(dimethylamino)benzylidene)hydrazono)thiazolidin-4-one
  参考文献：
  名称：

  Design and synthesis of thiazolylhydrazone derivatives as inhibitors of chitinolytic N-acetyl-β-d-hexosaminidase

  摘要：

  N-acetyl-beta-D-hexosaminidase (Hex) is potential target for pesticide design. Here, a series of thiazolylhydrazone derivatives were designed, synthesized and evaluated as competitive inhibitors of OfHex1, a Hex from the agricultural pest Ostrinia furnacalis. The derivative 3k, with a (benzyloxy) methyl group at the N3 atom, demonstrated greater potency with a K-i of 10.2 mu M. Molecular docking analysis indicated that the (benzyloxy) methyl group of 3k was bound to a previously unexplored pocket formed by Loop478-496. Then further optimization around naphthalene ring led to find the more potency substituent phenyl. The derivative 7, with phenoxyethyl group at R-1 and a phenyl group at R-2, demonstrated an augmented potency with a K-i of 2.1 mu M. Molecular docking analysis indicated that 7 was bound to the active pocket of OfHex1 more favorably than 3k. This work suggests a novel scaffold for developing specific Hex inhibitors.

  DOI：

  10.1016/j.bmc.2018.09.014
• 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， 生成 (Z)-2-(((E)-4-(dimethylamino)benzylidene)hydrazono)thiazolidin-4-one
  参考文献：
  名称：

  Design and synthesis of thiazolylhydrazone derivatives as inhibitors of chitinolytic N-acetyl-β-d-hexosaminidase

  摘要：

  N-acetyl-beta-D-hexosaminidase (Hex) is potential target for pesticide design. Here, a series of thiazolylhydrazone derivatives were designed, synthesized and evaluated as competitive inhibitors of OfHex1, a Hex from the agricultural pest Ostrinia furnacalis. The derivative 3k, with a (benzyloxy) methyl group at the N3 atom, demonstrated greater potency with a K-i of 10.2 mu M. Molecular docking analysis indicated that the (benzyloxy) methyl group of 3k was bound to a previously unexplored pocket formed by Loop478-496. Then further optimization around naphthalene ring led to find the more potency substituent phenyl. The derivative 7, with phenoxyethyl group at R-1 and a phenyl group at R-2, demonstrated an augmented potency with a K-i of 2.1 mu M. Molecular docking analysis indicated that 7 was bound to the active pocket of OfHex1 more favorably than 3k. This work suggests a novel scaffold for developing specific Hex inhibitors.

  DOI：

  10.1016/j.bmc.2018.09.014

文献信息

• Design and synthesis of thiazolylhydrazone derivatives as inhibitors of chitinolytic N-acetyl-β-d-hexosaminidase
  作者：Huibin Yang、Tian Liu、Huitang Qi、Zhisong Huang、Zesheng Hao、Junwu Ying、Qing Yang、Xuhong Qian

  DOI：10.1016/j.bmc.2018.09.014

  日期：2018.11

  N-acetyl-beta-D-hexosaminidase (Hex) is potential target for pesticide design. Here, a series of thiazolylhydrazone derivatives were designed, synthesized and evaluated as competitive inhibitors of OfHex1, a Hex from the agricultural pest Ostrinia furnacalis. The derivative 3k, with a (benzyloxy) methyl group at the N3 atom, demonstrated greater potency with a K-i of 10.2 mu M. Molecular docking analysis indicated that the (benzyloxy) methyl group of 3k was bound to a previously unexplored pocket formed by Loop478-496. Then further optimization around naphthalene ring led to find the more potency substituent phenyl. The derivative 7, with phenoxyethyl group at R-1 and a phenyl group at R-2, demonstrated an augmented potency with a K-i of 2.1 mu M. Molecular docking analysis indicated that 7 was bound to the active pocket of OfHex1 more favorably than 3k. This work suggests a novel scaffold for developing specific Hex inhibitors.