trans-3-(1,3-benzodioxol-5-yl)prop-2-en-1-ylidene-1,3-benzothiazol-2-amine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: trans-3-(1,3-benzodioxol-5-yl)prop-2-en-1-ylidene-1,3-benzothiazol-2-amine
• 英文别名: (E,E)-3-(1,3-benzodioxol-5-yl)-N-(1,3-benzothiazol-2-yl)prop-2-en-1-imine
• 化学式: C₁₇H₁₂N₂O₂S
• 分子量: 308.36
• InChiKey: ARDNBXGECYZGRK-VNMBVSLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  72
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-[(E)-丙-1-烯基]苯并[1,3]二氧杂环戊烯 在 sodium dithionite 、 silica gel 、 溶剂黄146 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.05h， 生成 trans-3-(1,3-benzodioxol-5-yl)prop-2-en-1-ylidene-1,3-benzothiazol-2-amine
  参考文献：
  名称：

  Synthesis and SAR investigation of natural phenylpropene-derived methoxylated cinnamaldehydes and their novel Schiff bases as potent antimicrobial and antioxidant agents

  摘要：

  A series of cinnamyl compounds were synthesized from abundantly available methoxylated phenylpropenes and evaluated for their antimicrobial activity by the broth microdilution method against fourteen opportunistic bacterial and fungal human pathogens. Structure-activity relationship studies indicated that methylenedioxy cinnamaldehyde exhibited promising broad-spectrum activity against the tested microorganisms and hence was used as a lead structure to synthesize novel Schiff bases/heterocyclic compounds (23-33) under microwave irradiation. Out of these, thiazole-based Schiff bases have shown promising antibacterial activity against B. subtilis (26; MIC 0.12 mM), M. luteus (27; MIC 0.20 mM), and S. aureus (27; MIC 0.20 mM). Also, the compounds 23-33 were investigated for in vitro antioxidant activity using DPPHaEuro cent assay where compound 28 showed a maximum of 80.71 % inhibition.

  DOI：

  10.1007/s00044-013-0484-9