2-((benzo[d]thiazol-2-ylimino)methyl)phenol | 16779-08-1

• 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: 2-((benzo[d]thiazol-2-ylimino)methyl)phenol
• 英文别名: 2-((benzothiazol-2-ylimino)methyl)phenol；2-Salicylidenamino-benzothiazol；2-Salicylidenamino-benzothiazol, N-(o-Hydroxybenzyliden)-2-aminobenzthiazol；2-(Benzothiazol-2-yliminomethyl)-phenol；2-(1,3-benzothiazol-2-yliminomethyl)phenol
• CAS: 16779-08-1
• 化学式: C₁₄H₁₀N₂OS
• 分子量: 254.312
• InChiKey: QHXJLHSKVDZVOA-UHFFFAOYSA-N

物化性质

• 熔点：
  145.5-146 °C(Solv: ethanol (64-17-5))
• 沸点：
  442.6±47.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  2-((benzo[d]thiazol-2-ylimino)methyl)phenol 在 sodium tetrahydroborate 作用下， 以 1,4-二氧六环 为溶剂， 生成 2-(o-Hydroxybenzyl)-amino-benzothiazol
  参考文献：
  名称：

  Shimidzu,N.; Uno,T., Chemical and pharmaceutical bulletin, 1973, vol. 21, p. 184 - 190

  摘要：

  DOI：
• 作为产物：
  描述：

  苯并噻唑 在 盐酸羟胺 作用下， 生成 2-((benzo[d]thiazol-2-ylimino)methyl)phenol
  参考文献：
  名称：

  Conte,M. et al., Bulletin de la Societe Chimique de France, 1967, p. 2834 - 2841

  摘要：

  DOI：

文献信息

• Mixed Ligand Complexes with 4-Aminoantipyrine Derivatives to Combat Natural Antioxidant System: Synthesis, Characterization and Biological Studies
  作者：J. Joseph、G. Ayisha Bibin Rani

  DOI：10.14233/ajchem.2015.17108

  日期：——

  Novel 4-aminoantipyrine based mixed ligand metal complexes with the Schiff bases of L1 (L1- 4-aminoantipyrine with furfuraldehyde and L2/L3/L4/L5 are and L2-2-aminophenol with salicylaldehyde, L3-2-aminophenol with cinnamaldehyde, L4-2-aminobenzothiazole with salicylaldehyde, L5-2-aminobenzothiazole with cinnamaldehyde) were synthesized. The structures of the mixed ligand complexes were established by analytical and spectral techniques. They were screened for in vitro antimicrobial activity against of bacteria and fungi by disc diffusion method. The interaction of metal complexes with calf thymus-DNA (CT-DNA) was investigated by UV-visible, cyclic voltammetry, viscosity and thermal denaturation studies. DNA interaction studies suggest that metal complex binds to calf thymus-DNA through intercalation mode. Superoxide dismutase activity of these complexes has also been studied. The free ligands and their metal complexes have been tested for in vitro antioxidant activity by the reduction of 1,1-diphenyl-2-picryl hydrazyl (DPPH). The antioxidant activities of the complexes were studied and compared with the activity of ascorbic acid. Copper(II) complex showed superior antioxidant activity than other complexes.

  基于新型的4-氨基安替比林的混合配体金属配合物与L1（L1-4-氨基安替比林与糠醛）、L2/L3/L4/L5（L2-2-氨基苯酚与水杨醛、L3-2-氨基苯酚与肉桂醛、L4-2-氨基苯并噻唑与水杨醛、L5-2-氨基苯并噻唑与肉桂醛）的席夫碱被合成。通过分析和光谱技术确定了混合配体配合物的结构。它们通过纸片扩散法被筛选用于体外抗菌活性，以对抗细菌和真菌。通过紫外-可见光谱、循环伏安法、粘度和热变性研究，调查了金属配合物与小牛胸腺DNA（CT-DNA）的相互作用。DNA相互作用研究表明，金属配合物通过嵌插模式与小牛胸腺DNA结合。这些配合物的超氧化物歧化酶活性也已被研究。自由配体及其金属配合物通过还原1,1-二苯基-2-苦基肼（DPPH）进行了体外抗氧化活性测试。研究了配合物的抗氧化活性，并与抗坏血酸的活性进行了比较。铜(II)配合物显示出比其他配合物更优越的抗氧化活性。
• Ultrasound-Assisted One-pot Synthesis of Bis-azetidinones in the Presence of Zeolite
  作者：Venkateshwarlu Jetti、Praveen Chidurala、Ramakanth Pagadala、Jyotsna S. Meshram、Chowdam Ramakrishna

  DOI：10.1002/jhet.1922

  日期：2014.8

  the sustainable chemical research industry. In this work, an attempt was made to synthesize bis-azetidin-2-ones () by Staudinger reaction ([2 + 2] ketene-imine cycloaddition reaction) in the presence of zeolite by using both conventional and under ultrasound irradiation. The synthesized compounds have been elucidated on the basis of their elemental analysis and spectral data (IR, 1H NMR, 13C NMR, and

  声化学方法是可持续化学研究行业的一项创新任务。在这项工作中，尝试合成双氮杂环丁烷-2-酮（通过使用常规和超声辐射在沸石存在下通过施陶丁格反应（[2 + 2]烯酮-亚胺环加成反应））。已根据其元素分析和光谱数据（IR，1 H NMR，13 C NMR和质谱）阐明了合成的化合物，以评估其在超声波下的性能。观察到，通过声化学方法在1-2小时内完全转化为氮杂环丁烷-2-酮，而在常规方法下在15-46小时内完全转化为氮杂环丁烷-2-酮。最后，已经观察到，与常规方法相比，使用声化学方法合成2-氮杂环丁酮是一种节能且环保的技术。
• Synthesis, DNA binding, antioxidant and cytotoxic activities of ruthenium(II) complexes of a Schiff base ligand
  作者：Subbaiyan Sathiyaraj、Krishnan Sampath、Ray J. Butcher、Chinnasamy Jayabalakrishnan

  DOI：10.1007/s11243-013-9690-z

  日期：2013.4

  The binding of the free ligand and its complexes with CT-DNA was studied using electronic absorption spectroscopy. In addition, the free ligand and its complexes were subjected to antioxidant activity tests, which showed that they all possess significant scavenging effects against DPPH and OH radicals. The in vitro cytotoxicities of the compounds were assessed using tumor (HeLa and MCF-7) cell lines

  三种钌 (II) 配合物 [Ru(CO)Cl(PPh3)L]、[Ru(CO)Cl(AsPh3)L] 和 [Ru(CO)Cl(Py)L]，由 2 -(苯并噻唑-2-亚氨基甲基)-苯酚 (HL) 与 [RuHCl(CO)B(EPh3)2]，其中 B = PPh3、AsPh3 或吡啶，E = P 或 As。所有配合物均已通过物理化学和光谱方法进行表征。游离配体HL的结构由单晶X射线衍射确定。使用电子吸收光谱研究游离配体及其复合物与 CT-DNA 的结合。此外，对游离配体及其配合物进行了抗氧化活性测试，结果表明它们均具有显着的清除DPPH和OH自由基的作用。使用肿瘤（HeLa 和 MCF-7）细胞系评估化合物的体外细胞毒性。
• A benzimidazole/benzothiazole-based electrochemical chemosensor for nanomolar detection of guanine
  作者：Hemant Sharma、Narinder Singh、Doo Ok Jang

  DOI：10.1039/c4ra12892c

  日期：——

  The electrochemical detection of guanine was accomplished using benzimidazole/benzothiazole-based imine-linked Co(iii) complexes with platinum electrodes.

  使用铂电极完成了基于苯并咪唑/苯并噻唑基亚胺连接的钴（III）配合物对鸟嘌呤的电化学检测。
• Synthesis and Crystal Structure of Charge Transfer Complex (CTC) of 2-Aminobenzothiazole with Its Schiff Base
  作者：Huihong Li、Jing Li、Hongxia Chen、Yong Zhang、Dan Huang

  DOI：10.1007/s10870-011-0185-5

  日期：2011.12

  A novel charge transfer complex (CTC), C14H10N2OS·C7H6N2S was synthesized by the reaction of 2-aminobenzothiazole (ABT) with its derivative Schiff base (2-((benzo[d]thiazol-2-ylimino) methyl) phenol is abbreviated as BYMBP) in THF. This complex was characterized by 1HNMR, 13CNMR, IR and UV–vis. Crystal structure of the complex has been determined by X-ray diffraction. The crystal is triclinic, space group P-1 with the unit cell parameters a = 9.7732(5), b = 9.9936(4), c = 11.0193(7) Å and α = 71.901(9), β = 78.686(10), γ = 70.397(9)°, Z = 2, R = 0.0499. wR 2 = 0.1190. The structure of the title complex was fully optimized at the RB3LYP/6-311++g(d,p) level of theory and CTC’s π–π stacking interaction, bond lengths (Å) and angles (°) were calculated. A novel 1:1 complex was synthesized because of π–π stacking , C–H⋯π and C–H⋯N interactions in its molecule.

  一个新型电荷转移复合物（CTC），C14H10N2OS·C7H6N2S，是通过2-氨基苯噻唑（ABT）与其衍生物施夫碱（2-((苯并[d]噻唑-2-亚基)甲基)酚，简称为BYMBP）在四氢呋喃（THF）中反应合成的。该复合物通过1H NMR、13C NMR、红外光谱（IR）和紫外-可见光谱（UV-vis）进行了表征。该复合物的晶体结构通过X射线衍射确定。晶体为三斜晶系，空间群为P-1，晶胞参数为a = 9.7732(5) Å，b = 9.9936(4) Å，c = 11.0193(7) Å，α = 71.901(9)°，β = 78.686(10)°，γ = 70.397(9)°，Z = 2，R = 0.0499，wR² = 0.1190。该复合物的结构在RB3LYP/6-311++g(d,p)理论水平下进行了完全优化，并计算了CTC的π–π堆积相互作用、键长（Å）和角度（°）。由于分子中的π–π堆积、C–H⋯π和C–H⋯N相互作用，合成了一个新型的1:1复合物。