(E)-4-((2-(benzo[d]thiazol-2-yl)hydrazono)methyl)-2-methoxyphenol | 1316315-03-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (E)-4-((2-(benzo[d]thiazol-2-yl)hydrazono)methyl)-2-methoxyphenol
• 英文别名: 4-(Benzothiazol-2-yl-hydrazonomethyl)-2-methoxy-phenol；4-[(E)-(1,3-benzothiazol-2-ylhydrazinylidene)methyl]-2-methoxyphenol
• CAS: 1316315-03-3
• 化学式: C₁₅H₁₃N₃O₂S
• 分子量: 299.353
• InChiKey: YGYUCPKKRGUHKY-CXUHLZMHSA-N

物化性质

• 熔点：
  201-202 °C
• 沸点：
  498.5±55.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)
• 溶解度：
  1.6 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  95
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  香草醛 、 2-肼基苯并噻唑 以 乙醇 为溶剂， 以85%的产率得到(E)-4-((2-(benzo[d]thiazol-2-yl)hydrazono)methyl)-2-methoxyphenol
  参考文献：
  名称：

  Synthesis and Antitumor Evaluation of (E)-2-Benzothiazole Hydrazones

  摘要：

  合成了一系列11种（E）-2-苯并噻唑肼，并评估了它们对三种肿瘤癌细胞的体外抗癌活性：HL-60（白血病）、MDAMB-435（乳腺癌）和HCT-8（结肠）。其中，3e和3f对HL-60显示出良好的细胞毒性活性。结果还表明，化合物3f似乎对HL-60细胞系具有选择性，表现为一个优良的抗白血病先导分子原型。

  DOI：

  10.2174/157018010792062740

文献信息

• Synthesis and Antitumor Evaluation of (E)-2-Benzothiazole Hydrazones
  作者：Antonio Francisco Nogueira、Elisa Carvalho Azevedo、Vitor Francisco Ferreira、Ana Jersia Araujo、Evelyne Alves dos Santos、Claudia Pessoa、Leticia Veras Costa-Lotufo、Raquel Carvalho Montenegro、Manoel Odorico de Moraes、Thatyana Rocha Alves Vasconcelos

  DOI：10.2174/157018010792062740

  日期：2010.10.1

  A series of eleven (E)-2-benzothiazole hydrazones were synthesized and evaluated for their in vitro anticancer activities against three neoplastic cancer cells: HL-60 (leukemia), MDAMB-435 (breast) and HCT-8 (colon). Two of them, 3e and 3f, showed good cytotoxicity activity for HL-60. The results also demonstrated that compound 3f seems to be selective to HL-60 cell line, appearing as a good prototype for an antileukemia lead molecule.

  合成了一系列11种（E）-2-苯并噻唑肼，并评估了它们对三种肿瘤癌细胞的体外抗癌活性：HL-60（白血病）、MDAMB-435（乳腺癌）和HCT-8（结肠）。其中，3e和3f对HL-60显示出良好的细胞毒性活性。结果还表明，化合物3f似乎对HL-60细胞系具有选择性，表现为一个优良的抗白血病先导分子原型。
• Synthesis and anticancer activity of (E)-2-benzothiazole hydrazones
  作者：Eric B. Lindgren、Monique A. de Brito、Thatyana R.A. Vasconcelos、Manuel O. de Moraes、Raquel C. Montenegro、Julliane D. Yoneda、Kátia Z. Leal

  DOI：10.1016/j.ejmech.2014.08.039

  日期：2014.10

  Benzothiazole hydrazones have been synthesized and evaluated for their in vitro antiproliferative activity against three human cancer cell lines: HL-60 (leukemia), MDAMB-435 (breast) and HCT-8 (colon). The good cytotoxicity for the three cancer cell lines and theoretical profile of compounds 3o and 3p pointed them as promising lead molecules for anticancer drug design. (c) 2014 Elsevier Masson SAS. All rights reserved.
• Synthesis, antioxidant and cytoprotective evaluation of potential antiatherogenic phenolic hydrazones. A structure–activity relationship insight
  作者：Corinne Vanucci-Bacqué、Chantal Carayon、Corinne Bernis、Caroline Camare、Anne Nègre-Salvayre、Florence Bedos-Belval、Michel Baltas

  DOI：10.1016/j.bmc.2014.05.034

  日期：2014.8

  A novel series of hydrazones derived from substituted benzaldehydes have been synthesized as potential antiatherogenic agents. Several methods were used for exploring their antioxidant and cytoprotective properties, such as their scavenging effect on 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical, the inhibition of superoxide anion (O₂(·-)) generation and the measurement of cell-induced low-density lipoprotein oxidation (monitored by the formation of TBARS). The cytoprotective efficacy was also evaluated by measuring the cell viability (monitored by the MTT assay) in the presence of cytotoxic oxidized LDL. In this report, we discuss the relationship between the chemical structure of phenolic hydrazones and their antioxidant and cytoprotective activities, for subsequent application as antiatherogenic agents. This SAR study confirms that the phenolic frame is not the only prerequisite for antioxidant activity and N-methylbenzothiazole hydrazone moiety magnifies the dual required properties in two most interesting derivatives.