N'-(3,5-di-tert-butyl-2-hydroxy-benzylidene)isonicotinohydrazide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N'-(3,5-di-tert-butyl-2-hydroxy-benzylidene)isonicotinohydrazide
• 英文别名: N'-(3,5-di-tert-butyl-2-hydroxybenzylidene)isoniazide
• 化学式: C₂₁H₂₇N₃O₂
• 分子量: 353.464
• InChiKey: DCPYAQNIQIDDNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.15
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  74.58
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3,5-二-叔-丁基-4-羟基苄基乙酸酯 、 N'-(3,5-di-tert-butyl-2-hydroxy-benzylidene)isonicotinohydrazide 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以78%的产率得到(E)-N'-(3,5-di-tert-butyl-2-hydroxybenzylidene)-N-(3,5-ditert-butyl-4-hydroxybenzyl)isonicotinohydrazide
  参考文献：
  名称：

  通过酰基腙与 3,5-二叔丁基-4-羟基苄基乙酸酯的苄基化合成杂化化合物

  摘要：

  Ñ与二- 3,5-羟基苯甲醛一系列酰腙的-Benzylation叔丁基-4-羟基苄基酯在室温下在不存在酸或碱催化剂来进行。在类似条件下，羧酰胺不与 3,5-二叔丁基-4-羟基苄基乙酸酯反应。异烟肼和（二苯基磷酰基）乙酸腙的 N-苄基化被证明是合成含有生物活性酰腙和位阻酚部分的新型杂化化合物的有效方法。Ñ异烟肼和（二苯基磷）含有羟基的乙酸腙衍生物苄邻芳香环的位置被形成为单独的ë CN双键的异构体。

  DOI：

  10.1007/s11172-021-3304-2
• 作为产物：
  描述：

  异烟肼 、 3,5-二叔丁基水杨醛 以 甲醇 为溶剂， 生成 N'-(3,5-di-tert-butyl-2-hydroxy-benzylidene)isonicotinohydrazide
  参考文献：
  名称：

  N'-(3-叔丁基-5-硝基-2-羟基苯亚甲基)-异烟肼配位化合物的合成与结构

  摘要：

  摘要 在 Et 3 N存在下，在 MeOH 中合成铜 (II) 与N '-(3 -叔丁基- 5-硝基-2-羟基亚苯亚基) 异烟酰肼 (H 2 L) 的两种配位化合物，并添加 1 ,10-菲咯啉（phen）。结果表明，这些化合物的形成伴随着起始N '-(3,5-二叔丁基-2-羟基亚苄基)异烟酰肼酰腙(H 2 L')转化为N '-(3-叔丁基) -丁基-5-硝基-2-羟基亚苄基)异烟酰肼(H 2 L)形成[Cu(L)(MeOH)] n( 1 )一维配位聚合物和[Cu(L)(phen)]( 2 )分子复合物。

  DOI：

  10.1134/s002247662308019x

文献信息

• Benzaldehyde Schiff bases regulation to the metabolism, hemolysis, and virulence genes expression in vitro and their structure–microbicidal activity relationship
  作者：Lei Xia、Yu-Fen Xia、Li-Rong Huang、Xiao Xiao、Hua-Yong Lou、Tang-Jingjun Liu、Wei-Dong Pan、Heng Luo

  DOI：10.1016/j.ejmech.2015.04.042

  日期：2015.6

  There is an urgent need to develop new antibacterial agents because of multidrug resistance by bacteria and fungi. Schiff bases (aldehyde or ketone-like compounds) exhibit intense antibacterial characteristics, and are therefore, promising candidates as antibacterial agents. To investigate the mechanism of action of newly designed benzaldehyde Schiff bases, a series of high-yielding benzaldehyde Schiff bases were synthesized, and their structures were determined by NMR and MS spectra data. The structure microbicidal activity relationship of derivatives was investigated, and the antibacterial mechanisms were investigated by gene assays for the expression of functional genes in vitro using Escherichia coli, Staphylococcus aureus, and Bacillus subtilis. The active compounds were selective for certain active groups. The polar substitution of the R-2 group of the amino acids in the Schiff bases, affected the antibacterial activity against E. coli and S. aureus; specific active group at the R-3 or R-4 groups of the acylhydrazone Schiff bases could improve their inhibitory activity against these three tested organisms. The antibacterial mechanism of the active benzaldehyde Schiff bases appeared to regulate the expression of metabolism-associated genes in E. coli, hemolysis-associated genes in B. subtilis, and key virulence genes in S. aureus. Some benzaldehyde Schiff bases were bactericidal to all the three strains and appeared to regulate gene expression associated with metabolism, hemolysis, and virulence, in vitro. The newly designed benzaldehyde Schiff bases possessed unique antibacterial activity and might be potentially useful for prophylactic or therapeutic intervention of bacterial infections. (C) 2015 Published by Elsevier Masson SAS.
• 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.
• A novel colorimetric probe derived from isonicotic acid hydrazide for copper (II) determination based on internal charge transfer (ICT)
  作者：Qing Liu、Qiang Fei、Yanqun Fei、Qian Fan、Hongyan Shan、Guodong Feng、Yanfu Huan

  DOI：10.1016/j.saa.2015.07.043

  日期：2015.12

  A novel isonicotic acid hydrazide Schiff base derivative N'-(3,5-di-tert-butyl-2-hydroxy-benzylidene) isonicotinohydrazide (DHIH) has been synthesized and developed as a high selective and sensitive colorimetric probe for Cu(2+) determination. Addition of Cu(2+) to the solution of DHIH resulted in a rapid color change from colorless to yellow together with an obvious new absorption band appeared at the range of 400-440 nm by forming a 1:1 complex. Experimental results indicated that the DHIH could provide absorption response to Cu(2+) with a linear dynamic range from 1.0×10(-5) to 1.0×10(-4)mol/L. The detection limit of Cu(2+) was 5.24×10(-7)mol/L with good tolerance of other metal ions.
• Synthesis of hybrid compounds by benzylation of acylhydrazones with 3,5-di-tert-butyl-4-hydroxybenzyl acetate
  作者：S. V. Bukharov、D. F. Bakhdyrova、R. G. Tagasheva、A. R. Burilov、I. A. Litvinov、D. V. Chachkov、Ya. A. Vereshchagina

  DOI：10.1007/s11172-021-3304-2

  日期：2021.10

  series with 3,5-di-tert-butyl-4-hydroxybenzyl acetate was performed at room temperature in the absence of acid or base catalysts. Carboxamides do not react with 3,5-di-tert-butyl-4-hydroxybenzyl acetate under similar conditions. N-Benzylation of isoniazid and (diphenylphosphoryl)acetic acid hydrazones was shown to be an efficient method for the synthesis of new hybrid compounds containing moieties of

  Ñ与二- 3,5-羟基苯甲醛一系列酰腙的-Benzylation叔丁基-4-羟基苄基酯在室温下在不存在酸或碱催化剂来进行。在类似条件下，羧酰胺不与 3,5-二叔丁基-4-羟基苄基乙酸酯反应。异烟肼和（二苯基磷酰基）乙酸腙的 N-苄基化被证明是合成含有生物活性酰腙和位阻酚部分的新型杂化化合物的有效方法。Ñ异烟肼和（二苯基磷）含有羟基的乙酸腙衍生物苄邻芳香环的位置被形成为单独的ë CN双键的异构体。
• Synthesis and Structure of Cu(II) Coordination Compounds with N′-(3-Tert-Butyl-5-Nitro-2-Hydroxybenzylidene)-Isonicotinohydrazide
  作者：A. K. Matyukhina、E. N. Zorina-Tikhonova、V. A. Novikova、I. V. Skabitsky、M. A. Kiskin、I. L. Eremenko

  DOI：10.1134/s002247662308019x

  日期：2023.8

  Abstract Two coordination compounds of copper(II) with N′-(3-tert-butyl-5-nitro-2-hydroxybenzylidene) isonicotinohydrazide (H2L) are synthesized in MeOH in the presence of Et3N and with the addition of 1,10-phenanthroline (phen). It is shown the formation of these compounds is accompanied by the transformation of the starting N′-(3,5-di-tert-butyl-2-hydroxybenzylidene)isonicotinohydrazide acylhydrazone

  摘要 在 Et 3 N存在下，在 MeOH 中合成铜 (II) 与N '-(3 -叔丁基- 5-硝基-2-羟基亚苯亚基) 异烟酰肼 (H 2 L) 的两种配位化合物，并添加 1 ,10-菲咯啉（phen）。结果表明，这些化合物的形成伴随着起始N '-(3,5-二叔丁基-2-羟基亚苄基)异烟酰肼酰腙(H 2 L')转化为N '-(3-叔丁基) -丁基-5-硝基-2-羟基亚苄基)异烟酰肼(H 2 L)形成[Cu(L)(MeOH)] n( 1 )一维配位聚合物和[Cu(L)(phen)]( 2 )分子复合物。