6-{[(1,2-Benzothiazol-3-yl)amino]methylidene}-2-methoxycyclohexa-2,4-dien-1-one | 647026-36-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 6-{[(1,2-Benzothiazol-3-yl)amino]methylidene}-2-methoxycyclohexa-2,4-dien-1-one
• 英文别名: 2-(1,2-benzothiazol-3-yliminomethyl)-6-methoxyphenol
• CAS: 647026-36-6
• 化学式: C₁₅H₁₂N₂O₂S
• 分子量: 284.338
• InChiKey: VHVPTQFEHXIWHV-UHFFFAOYSA-N

物化性质

• 熔点：
  145-147 °C(Solv: benzene (71-43-2))
• 沸点：
  403.7±45.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  83
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-氨基-1,2-苯并异噻唑 、 邻香草醛 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 0.25h， 以75%的产率得到6-{[(1,2-Benzothiazol-3-yl)amino]methylidene}-2-methoxycyclohexa-2,4-dien-1-one
  参考文献：
  名称：

  Synthesis and biological evaluation of benzo[d]isothiazole, benzothiazole and thiazole Schiff bases

  摘要：

  Three new series of benzo[d]isothiazole, benzothiazole and thiazole Schiff bases were synthesized and tested in vitro with the aim of identifying novel lead compounds active against emergent and re-emergent human and cattle infectious diseases (AIDS, hepatitis B and C, tuberculosis. bovine viral diarrhoea) or against drug-resistant cancers (leukaemia, carcinoma, melanoma, MDR tumors) for which no definitive cure or efficacious vaccine is available at present. In particular, these compounds were evaluated in vitro against representatives of different virus classes, such as a HIV-1 (Retrovirus), a HBV (Hepadnavirus) and the single-stranded RNA(+) viruses Yellow fever virus (YFV) and Bovine viral diarrhoea virus (BVDV), both belonging to Flaviviridae. Title compounds were also tested against representatives of Gram-positive and Gram-negative bacteria (Staphylococcus aureus, Salmonella spp.), various atypic mycobacterial strains Mycobacterium fortuitom and Mycobacterium smegmatis), yeast (Candida albicans) and mould (Aspergillus fumigatus). None of the compounds showed antiviral or antimicrobial activity. The benzo[ci]isothiazole compounds showed a marked Cytotoxicity (CC50 = 4-9 muM) against the human CD4(+) lymphocytes (MT-4) that were used to support HIV-1 growth. For this reason, the most cytotoxic compounds of this series were evaluated for their antiproliferative activity against a panel of human cell lines derived from haematological and solid tumors. The results highlighted that all the benzo[d]isothiazole derivatives inhibited the growth of leukaemia cell lines, whereas only one of the above mentioned compounds (1e) showed antiproliferative activity against two solid tumor-derived cell lines. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00493-0

文献信息

• Synthesis and biological evaluation of benzo[d]isothiazole, benzothiazole and thiazole Schiff bases
  作者：Paola Vicini、Athina Geronikaki、Matteo Incerti、Bernadetta Busonera、Graziella Poni、Carla Alba Cabras、Paolo La Colla

  DOI：10.1016/s0968-0896(03)00493-0

  日期：2003.11

  Three new series of benzo[d]isothiazole, benzothiazole and thiazole Schiff bases were synthesized and tested in vitro with the aim of identifying novel lead compounds active against emergent and re-emergent human and cattle infectious diseases (AIDS, hepatitis B and C, tuberculosis. bovine viral diarrhoea) or against drug-resistant cancers (leukaemia, carcinoma, melanoma, MDR tumors) for which no definitive cure or efficacious vaccine is available at present. In particular, these compounds were evaluated in vitro against representatives of different virus classes, such as a HIV-1 (Retrovirus), a HBV (Hepadnavirus) and the single-stranded RNA(+) viruses Yellow fever virus (YFV) and Bovine viral diarrhoea virus (BVDV), both belonging to Flaviviridae. Title compounds were also tested against representatives of Gram-positive and Gram-negative bacteria (Staphylococcus aureus, Salmonella spp.), various atypic mycobacterial strains Mycobacterium fortuitom and Mycobacterium smegmatis), yeast (Candida albicans) and mould (Aspergillus fumigatus). None of the compounds showed antiviral or antimicrobial activity. The benzo[ci]isothiazole compounds showed a marked Cytotoxicity (CC50 = 4-9 muM) against the human CD4(+) lymphocytes (MT-4) that were used to support HIV-1 growth. For this reason, the most cytotoxic compounds of this series were evaluated for their antiproliferative activity against a panel of human cell lines derived from haematological and solid tumors. The results highlighted that all the benzo[d]isothiazole derivatives inhibited the growth of leukaemia cell lines, whereas only one of the above mentioned compounds (1e) showed antiproliferative activity against two solid tumor-derived cell lines. (C) 2003 Elsevier Ltd. All rights reserved.