(Z)-2-(((E)-naphthalen-1-ylmethylene)hydrazono)thiazolidin-4-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (Z)-2-(((E)-naphthalen-1-ylmethylene)hydrazono)thiazolidin-4-one
• 英文别名: (2E)-2-[(E)-1-naphthylmethylenehydrazono]thiazolidin-4-one；(2E)-2-[(E)-naphthalen-1-ylmethylidenehydrazinylidene]-1,3-thiazolidin-4-one
• 化学式: C₁₄H₁₁N₃OS
• 分子量: 269.327
• InChiKey: BSMOMGJTALEJMD-OVCLIPMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  79.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  氯甲烷 、 (Z)-2-(((E)-naphthalen-1-ylmethylene)hydrazono)thiazolidin-4-one 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以20%的产率得到(Z)-3-methyl-2-(((E)-naphthalen-1-ylmethylene)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：

  1-naphthaldehyde thiosemicarbazone 、 溴乙酸乙酯 在 sodium acetate 作用下， 以 甲醇 为溶剂， 以83%的产率得到(Z)-2-(((E)-naphthalen-1-ylmethylene)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