m-Hydroxy-benzaldehyd-hydrazon | 52211-81-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: m-Hydroxy-benzaldehyd-hydrazon
• 英文别名: 3-methanehydrazonoylphenol
• CAS: 52211-81-1
• 化学式: C₇H₈N₂O
• 分子量: 136.153
• InChiKey: VYUATCMAQLIAIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  m-Hydroxy-benzaldehyd-hydrazon 在 氢氧化钾 作用下， 以 二乙二醇 为溶剂， 反应 0.2h， 生成 间甲酚
  参考文献：
  名称：

  Chattopadhyay, Sarmishtha; Banerjee, Sajal Kumar; Mitra, Alok Kumar, Journal of the Indian Chemical Society, 2002, vol. 79, # 11, p. 906 - 907

  摘要：

  DOI：
• 作为产物：
  描述：

  间羟基苯甲醛 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成 m-Hydroxy-benzaldehyd-hydrazon
  参考文献：
  名称：

  带有双-席夫碱的三嗪基吲哚作为β-葡萄糖醛酸酶抑制剂的合成、体外和计算机研究

  摘要：

  通过三嗪基吲哚-硫酮环形成、三嗪基吲哚-硫醇-苯乙酮，然后是三嗪基吲哚双-席夫碱形成来合成带有双-希夫碱类似物的三嗪基吲哚(1-20) 。与标准 D-糖精酸 1,4-内酯 (IC 50  = 48.10 ± 1.2 µ M)相比，合成的类似物显示出β-葡萄糖醛酸酶潜力，IC 50值范围为 2.60 ± 0.10 至 55.40 ± 1.60 µ M。模拟 20 是最有效的一种，IC 50值为 2.60 ± 0.10 µ M。类似物 17、4 的 IC 50值分别为 5.20 ± 0.20 和 5.70 ± 0.20 µ M，可承受 2次和3次排名合成类似物之间的支架。所有其他 16 种类似物的 IC 50值范围为 7.9 ± 0.2 至 48.1 ± 1.2 µ M，均显示出多倍的效力。通过分子对接研究建立了结构-活性关系并确认了结合相互作用。

  DOI：

  10.1016/j.molstruc.2021.131003

文献信息

• Arylidene semicarbazones and their utility as herbicides
  申请人：STAUFFER CHEMICAL COMPANY

  公开号：US03753680A1

  公开（公告）日：1973-08-21

  Substituted-arylidene semicarbazone having the formula:

  取代芳基亚胺脲酮的化学式为：
• Retroviral protease inhibiting compounds
  申请人：Abbott Laboratories

  公开号：US05461067A1

  公开（公告）日：1995-10-24

  A retroviral protease inhibiting compound of the formula: ##STR1## is disclosed wherein R.sub.1, R.sub.2, R.sub.5, R.sub.6, Y.sub.m and Y'.sub.n are herein defined.

  公开了一种化学式为##STR1##的逆转录病毒蛋白酶抑制化合物，其中R.sub.1、R.sub.2、R.sub.5、R.sub.6、Y.sub.m和Y'.sub.n在此有定义。
• Discovery of 5-aryl-3-thiophen-2-yl-1H-pyrazoles as a new class of Hsp90 inhibitors in hepatocellular carcinoma
  作者：Samy Mohamady、Muhammad I. Ismail、Samar M. Mogheith、Yasmeen M. Attia、Scott D. Taylor

  DOI：10.1016/j.bioorg.2019.103433

  日期：2020.1

  Although hepatocellular carcinoma (HCC)-related mortality has increased over the past decades, treatment options are still very limited, underlining the need for developing new therapeutic strategies. The molecular chaperone heat shock protein 90 (Hsp90) plays a key role in post-translational maturation of many oncogenic client proteins that are important for survival and proliferation of cancer cells. Thus, inhibitors of Hsp90 are promising targets for many cancer types. In this study, 15 diarylpyrazole compounds were screened against MCF7 and HepG2 cell lines. Compound 8, which contained a thiophene group, demonstrated the highest antiproliferative activity against HepG2 cells having an IC50, of 0.083 mu M. Four additional diarylpyrazoles, each containing a thiophene group, were prepared and screened for antiproliferative activity. None of these four compounds exhibited superior activity to compound 8 on HepG2 cells. Therefore, compound 8 was selected for further in vitro assays. Cell cycle arrest was observed at the G2 phase in compound 8-treated cells. Compound 8 also caused a 7.7-fold increase in caspase-3. These results confirm the apoptotic effect of compound 8 on HepG2 cells. Moreover, compound 8 inhibited Hsp90 (IC50, = 2.67 +/- 0.18 mu M) in an in vitro assay and caused a 70.8% reduction in Hsp90 levels in a HepG2 cell-based assay. Additionally, compound 8 caused significant reduction in the levels of Hsp90 client proteins (Akt, c-Met, c-Raf, and EGFR) and a 1.57-fold increase in Hsp70. Molecular docking studies were also performed to predict the binding mode of compound 8 and followed by molecular dynamics simulations to give further insights into the binding mode of 8.
• Facile synthesis of (E)-β-(trifluoromethyl)styrenes from halothane (HCFC-123B1)
  作者：Kensuke Hirotaki、Genyu Kawazoe、Takeshi Hanamoto

  DOI：10.1016/j.jfluchem.2014.07.018

  日期：2015.3

  A practical and convenient synthesis of (E)-beta-(trifluoromethyl)styrenes has been achieved by the reaction of commercially available halothane (HCFC-123B1) and hydrazones prepared in advance in situ, in the presence of 1,2-ethylenediamine and a catalytic amount of CuCl2.2H(2)O at room temperature. The products showed acceptable to high yields and high to excellent stereoselectivity. This handy synthetic method provided easy access to a variety of (E)-beta-(trifluoromethyl)styrenes. (C) 2014 Elsevier B.V. All rights reserved.
• Novel pyranopyrazole derivatives comprising a benzoxazole core as antimicrobial inhibitors: Design, synthesis, microbial resistance and machine aided results
  作者：Guda Mallikarjuna Reddy、Avula Krishna Kumari、Vemulapati Hanuman Reddy、Jarem Raul Garcia

  DOI：10.1016/j.bioorg.2020.103908

  日期：2020.7

  From a medical point of view lot of existing antibiotics became unusable because microbial gained strong antibiotic resistance. The combination of two compounds in one core may lead to kill such type of pathogens. Herein, we developed pyranopyrazole derivatives comprising benzoxazole moiety by green approach strategy and studied their antimicrobial performance on four bacteria and two fungi. As a result, most of the compounds delivered reliable toxicity to kill the pathogens. In those,6aexhibited considerable activity against the microbial pathogens. Moreover,compounds 6d, 6l,and6nshowed prominent antibacterial activity. In addition, molecular docking studies of docked compounds revealed the strong bonding interaction with DNA-Gyrase and were docked into the intercalation location of DNA of the DNA-gyrase complex. The molecule bounded to the DNA stabilized by the H bonds, hydrophobic interactions, and π-π interaction. In addition, the linked 5-chlorobenazoxazole structure stabilized by the DT-8 and DG2009 of the F chain with pi-pi interactions. From the computer-aided results, it was observed that compound6a demonstrated maximum docking score -10.0 kcal/mole towards DNA-gyrase. Overall, this investigation suggested that these biologically active compounds can be utilized as leads for preclinical studies with the goal of developing newer antimicrobial drugs.