4-{[(E)-6-Methyl-benzothiazol-2-ylimino]-methyl}-phenol | 96717-91-8

• 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: 4-{[(E)-6-Methyl-benzothiazol-2-ylimino]-methyl}-phenol
• 英文别名: 4-[(6-Methyl-1,3-benzothiazol-2-yl)iminomethyl]phenol
• CAS: 96717-91-8
• 化学式: C₁₅H₁₂N₂OS
• 分子量: 268.339
• InChiKey: XYPOXBHUUKXRTF-UHFFFAOYSA-N

物化性质

• 沸点：
  469.7±47.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 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：
  73.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-{[(E)-6-Methyl-benzothiazol-2-ylimino]-methyl}-phenol 在 吡啶 作用下， 以 苯 为溶剂， 生成 Morpholin-4-yl-acetic acid 4-{[(E)-6-methyl-benzothiazol-2-ylimino]-methyl}-phenyl ester
  参考文献：
  名称：

  Dash; Mahapatra; Panda, Journal of the Indian Chemical Society, 1984, vol. 61, # 11-12, p. 1061 - 1064

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氨基-6-甲基苯并噻唑 、 对羟基苯甲醛 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 4-{[(E)-6-Methyl-benzothiazol-2-ylimino]-methyl}-phenol
  参考文献：
  名称：

  作为细菌酶 MurA 新型抑制剂的吡咯烷二酮类的鉴定和生化表征

  摘要：

  为了开发新型抗生素，针对细胞壁肽聚糖生物合成的早期步骤似乎是一种有前途的策略，但尚未得到充分利用。MurA 是该途径中的第一个酶，是临床使用的不可逆抑制剂磷霉素的靶标。然而，其结合位点的突变可能会导致细菌耐药性。我们在此报道了一系列新型可逆的基于吡咯烷二酮的 MurA 抑制剂，它们同样抑制野生型 (WT) MurA 和磷霉素抗性 MurA C115D 突变体，显示出磷霉素对 WT MurA 抑制的累加效应。对于最有效的抑制剂46 (IC 50 = 4.5 μM)，使用天然质谱和蛋白质 NMR 光谱分析了抑制模式。该化合物类对人体细胞无毒，并且在人 S9 级分、人血浆和细菌细胞裂解液中高度稳定。总而言之，这种新型化合物类别可能会进一步开发为抑制细胞壁合成的抗生素候选药物。

  DOI：

  10.1021/acs.jmedchem.2c01275

文献信息

• Synthesis and Characterization of Thermotropic Liquid Crystals Consisting Heterocyclic Benzothiazole Core System
  作者：Kok-Leei Foo、Sie-Tiong Ha、Siew-Ling Lee

  DOI：10.14233/ajchem.2014.17135

  日期：——

  A new series of rod-shaped mesomorphic compounds, 6-methyl-2-(4-alkoxybenzylidenamino)benzothiazoles bearing a fused thiazole ring and imine central linkage, were prepared and their molecular structures were confirmed via mass spectrometric, IR and NMR spectroscopic techniques. The mesomorphic properties were identifed using differential scanning calorimetry, polarizing optical microscopy and X-ray diffraction analysis. All compounds showed enantiotropic mesomorphism. Whilst the lower members of the series, butyloxy, hexyloxy and octyloxy derivatives exhibited nematic phase, the medium members (decyloxy derivative) exhibited nematic and smectic A phases. The higher members (C12, C14, C16 and C18 derivatives) displayed smectic A phase only.

  制备了一系列新的棒状介形化合物--6-甲基-2-（4-烷氧基亚苄基氨基）苯并噻唑，它们具有融合的噻唑环和亚胺中心连接，并通过质谱、红外光谱和核磁共振光谱技术确认了它们的分子结构。利用差示扫描量热法、偏振光学显微镜和 X 射线衍射分析确定了它们的介形性质。所有化合物都表现出了对映体介形性。该系列的低级成员，丁氧基、己氧基和辛氧基衍生物表现出向列相，而中级成员（癸氧基衍生物）则表现出向列相和共晶 A 相。较高的成员（C12、C14、C16 和 C18 衍生物）仅表现出胶凝 A 相。
• Mesomorphic behavior of new benzothiazole liquid crystals having Schiff base linker and terminal methyl group
  作者：Sie Tiong Ha、Kok Leei Foo、Hong Cheu Lin、Masato M. Ito、Kazuma Abe、Kenji Kunbo、S. Sreehari Sastry

  DOI：10.1016/j.cclet.2012.04.025

  日期：2012.7

  spectrometric analysis. Enantiotropic nematic phase was observed for shorter members. Smectic A phase only emerged from octyloxy derivative onwards. The terminal methyl group at the benzothiazole fragment and the Schiff base linkage influenced the mesomorphic behavior of the present series.

  摘要合成了一系列同源的杂环，即6-甲基-2-（4-烷氧基苄叉基氨基）苯并噻唑，并利用FT-IR，1H和13C NMR及质谱分析对其进行了表征。对于较短的成员，观察到对映向列相。近晶A相仅从辛氧基衍生物开始出现。苯并噻唑片段的末端甲基和席夫碱键影响了本系列的介观行为。
• The Synthesis, Characterization, Acid Dissociation, and Theoretical Calculation of Several Novel Benzothiazole Schiff Base Derivatives
  作者：Kamuran Görgün、Handan Can Sakarya、Müjgan Özkütük

  DOI：10.1021/je500679w

  日期：2015.3.12

  Schiff base derivatives of benzothiazoles were synthesized using substituted 2-aminobenzothiazoles and different substituted benzaldehydes. The structures of the synthesized Schiff bases were determined using Fourier transform infrared spectroscopy, H-1 NMR, C-13 NMR, and elemental analyses. The acid dissociation behavior, which was visible in UV-visible absorption spectra, of the 10 novel benzothiazole Schiff bases was studied. The acidity constants (pKa), the structures, and the protonation mechanisms of the studied molecules were obtained. The substituent effect on both phenyl rings of these synthesized benzothiazole Schiff base derivatives was observed, and the experimentally calculated deprotonation values were between 11.47 and 8.91, and the protonation values were between 4.54 and 3.52. Also, the protonation sites of synthesized benzothiazole Schiff base were investigated using H-1 NMR and FT-IR. The theoretical calculations were performed with the CACHE semiempirical method (AM1, PM3, and PM5). The best correlation between the experimental and theoretical pKa and acidity values of the compounds was obtained using the PM5 calculation method.