3,5-di-tert-butylsalicylidene benzoylhydrazine | 606937-93-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5-di-tert-butylsalicylidene benzoylhydrazine
• 英文别名: N’-(3,5-di-tert-butyl-2-hydroxyphenylmethylidene)benzoyl hydrazone；3,5-Di-t-butylsalicylidene benzoylhydrazine；N-[(3,5-ditert-butyl-2-hydroxyphenyl)methylideneamino]benzamide
• CAS: 606937-93-3
• 化学式: C₂₂H₂₈N₂O₂
• 分子量: 352.477
• InChiKey: UEHOZCUBIBMWLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  61.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,5-di-tert-butylsalicylidene benzoylhydrazine 、 copper diacetate 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  摘要：

  Series of new binuclear copper(II) complexes with acylhydrazones and azomethines of substituted derivatives of salicylaidehyde containing bulky tert-butyl substituents were synthesized. The target dimerization of the monomeric fragments of the complexes caused by the steric factors was shown to predetermine the specific features of their magnetochemical behavior. The calculated exchange parameters for the complexes based on acy1hydrazones range from -110 to -138 cm(-1) and those for the complexes based on azomethines lie in the interval from -400 to -500 cm(-1).

  DOI：

  10.1023/a:1021642530810
• 作为产物：
  描述：

  3,5-二叔丁基水杨醛 、 苯甲酰肼 以 甲醇 为溶剂， 反应 0.13h， 生成 3,5-di-tert-butylsalicylidene benzoylhydrazine
  参考文献：
  名称：

  共配体和溶剂对 ONO Schiff 碱 V(IV) 氧化配合物性质的影响

  摘要：

  摘要 描述了四种八面体几何形状的 V(IV/V) 配合物，具有三齿 ONO Schiff 碱配体、氧化和双齿（麦芽酚、1,10-菲咯啉或 2,2'-联吡啶）共配体。席夫碱由 3,5-二-叔丁基-2-羟基苯甲醛和酰肼（苯甲酰肼、2-羟基苯甲酰肼和苯乙酸酰肼）形成。所有配合物的 X 射线单晶结构显示它们是 1:1 异构体的混合物，ONO 配体的 5 和 6 元环与 VO 的位置​​不同，不包括 1。VO 带的位置在发现红外光谱取决于 VO 和易位的供体原子键距离。两种配合物3和3a被分离为非溶剂化和溶剂化复合物，溶剂分子的配位极大地改变了结构参数。循环伏安测量显示钒氧化还原系统的不可逆过程和共配体的可逆过程。讨论了配合物在溶液中的稳定性。

  DOI：

  10.1016/j.molstruc.2018.12.047

文献信息

• Aroylhydrazone derivative as fluorescent sensor for highly selective recognition of Zn2+ ions: syntheses, characterization, crystal structures and spectroscopic properties
  作者：Xiaohong Peng、Xiaoliang Tang、Wenwu Qin、Wei Dou、Yanling Guo、Jiangrong Zheng、Weisheng Liu、Daqi Wang

  DOI：10.1039/c0dt01590c

  日期：——

  complexes [Zn(HL1)C2H5OH]∞ (1) and [Cu(HL1)(H2O)]CH3OH (2) have been synthesized and characterized in terms of their crystal structures, absorption and emission spectra. H3L1 displays high selectivity for Zn2+ over Na+, K+, Mg2+, Ca2+ and other transition metal ions in Tris–HCl buffer solution (pH = 7.13, EtOH–H2O = 8 : 2 v/v). To obtain insight into the relation between the structure and selectivity

  新型Zn 2+荧光化学传感器N ′-（3,5-二叔丁基水杨基）-2-羟基苯甲酰肼（H 3 L 1）及其配合物[Zn（HL 1）C 2 H 5 OH] ∞（1）和[Cu（HL 1）（H 2 O）] CH 3 OH（2）的合成和表征为它们的晶体结构，吸收和发射光谱。H 3 L 1对Zn 2+的Na +，K +，Mg 2 +，Ca 2+和其他过渡金属离子具有较高的选择性。特里斯–HCl缓冲溶液（pH = 7.13， 乙醇–高氧2= 8：2 v / v）。为了了解结构和选择性之间的关系，需要使用类似的配体3,5-二叔丁基水杨基苯甲酰肼（H 2 L 2），它与H 3 L 1相比，在水杨酰肼中没有羟基取代基，及其配合物[Zn 2（HL 2）2（CH 3 COO）2（C 2 H 5 OH）]（3），[Co（L 2）2 ] [Co（DMF）4（C 2 H 5 OH）（H 2 O）]（4），[Fe（HL 2）2
• Novel di-tertiary-butyl phenylhydrazones as dual cyclooxygenase-2/5-lipoxygenase inhibitors: Synthesis, COX/LOX inhibition, molecular modeling, and insights into their cytotoxicities
  作者：Shibnath Ghatak、Alok Vyas、Suniti Misra、Paul O’Brien、Ajit Zambre、Victor M. Fresco、Roger R. Markwald、K. Venkateshwara Swamy、Zahra Afrasiabi、Amitava Choudhury、Madhukar Khetmalas、Subhash Padhye

  DOI：10.1016/j.bmcl.2013.11.015

  日期：2014.1

  Although dual inhibition of Cyclooxygenase-2 (COX-2) and 5-Lipoxygenase (5-LOX) enzymes is highly effective than targeting COX or LOX alone, there are only a few reports of examining such compounds in case of colorectal cancers (CRC). In the present work we report that the novel di-tert-butyl phenol-based dual inhibitors DTPSAL, DTPBHZ, DTPINH, and DTPNHZ exhibit significant cytotoxicity against human CRC cell lines. Molecular docking studies revealed a good fit of these compounds in the COX-2 and 5-LOX protein cavities. The inhibitors show significant inhibition of COX-2 and 5-LOX activities and are effective against a panel of human colon cancer cell lines including HCA-7, HT-29, SW480 and intestinal Apc10.1 cells as well as the hyaluronan synthase-2 (Has2) enzyme over-expressing colon cancer cells, through inhibition of the Hyaluronan/CD44v6 cell survival pathway. Western blot analysis and qRT-PCR analyses indicated that the di-tert-butyl phenol-based dual inhibitors reduce the expression of COX-2, 5-LOX, and CD44v6 in human colon cancer HCA-7 cells, while the combination of CD44v6shRNA and DTPSAL has an additional inhibitory effect on CD44v6 mRNA expression. The synergistic inhibitory effect of Celecoxib and Licofelone on CD44v6 mRNA expression suggests that the present dual inhibitors down-regulate cyclooxygenase and lipoxygenase enzymes through CD44v6. The compounds also exhibited enhanced antiproliferative potency compared to standard dual COX/LOX inhibitor, viz. Licofelone. Importantly, the HA/CD44v6 antagonist CD44v6shRNA in combination with synthetic compounds had a sensitizing effect on the cancer cells which enhanced their antiproliferative potency, a finding which is crucial for the anti-proliferative potency of the novel synthetic di-tert-butyl phenol based dual COX-LOX inhibitors in colon cancer cells. (C) 2013 Elsevier Ltd. All rights reserved.
• Iron(III) Complexes with a Biologically Relevant Aroylhydrazone:  Crystallographic Evidence for Coordination Versatility
  作者：Dariusz Matoga、Janusz Szklarzewicz、Katarzyna Stadnicka、Musa S. Shongwe

  DOI：10.1021/ic701435x

  日期：2007.10.1

  Complexation of iron(III) with the heterodonor chelating agent 3,5di-tert-butylsalicylidene benzoylhydrazine, H-2(3,5-Bu-t(2))salbh, in the absence or presence of a base affords the complex cation [FeH(35-Bu-2)salbh}(2)]+ or the neutral compound [FeH(3,5-Bu-2)salbh}(3,5-tBu(2))salbhJJ, respectively, as revealed by single-crystal X-ray analyses. Such a synthetic and crystallographic demonstration of the coordination versatility of an aroylhydrazone toward iron is uncommon. The oxidation and spin states of the iron have been verified with magnetic and spectroscopic measurements.
• Highly Selective Schiff-Base Fluorescent Probe for Rare Earth Ion Lu3+
  作者：Xiaolei Liu、Xiaohong Peng、Fei Xu、Lina Wang、Manhong Liu

  DOI：10.1134/s1070363221060165

  日期：2021.6
• Role of co-ligand and solvent on properties of V(IV) oxido complexes with ONO Schiff bases
  作者：Janusz Szklarzewicz、Anna Jurowska、Maciej Hodorowicz、Ryszard Gryboś、Dariusz Matoga

  DOI：10.1016/j.molstruc.2018.12.047

  日期：2019.3

  different position of 5- and 6-membered ring of ONO ligand versus V O, excluding 1. The position of the V O band in IR spectra was found to be dependent on the V O and trans located donor atom bond distances. Two complexes, 3 and 3a, were isolated as unsolvated and solvated ones, the coordination of solvent molecule drastically changed the structure parameters. The cyclic voltammetry measurements show

  摘要 描述了四种八面体几何形状的 V(IV/V) 配合物，具有三齿 ONO Schiff 碱配体、氧化和双齿（麦芽酚、1,10-菲咯啉或 2,2'-联吡啶）共配体。席夫碱由 3,5-二-叔丁基-2-羟基苯甲醛和酰肼（苯甲酰肼、2-羟基苯甲酰肼和苯乙酸酰肼）形成。所有配合物的 X 射线单晶结构显示它们是 1:1 异构体的混合物，ONO 配体的 5 和 6 元环与 VO 的位置​​不同，不包括 1。VO 带的位置在发现红外光谱取决于 VO 和易位的供体原子键距离。两种配合物3和3a被分离为非溶剂化和溶剂化复合物，溶剂分子的配位极大地改变了结构参数。循环伏安测量显示钒氧化还原系统的不可逆过程和共配体的可逆过程。讨论了配合物在溶液中的稳定性。