1-[(2,4-dichlorophenoxy)acetyl]-2-(2-hydroxybenzylidene)hydrazine | 54918-94-4

• 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: 1-[(2,4-dichlorophenoxy)acetyl]-2-(2-hydroxybenzylidene)hydrazine
• 英文别名: 2-(2,4-dichlorophenoxy)-N'-(2-hydroxybenzylidene)acetohydrazide；salicylidenehydrazone of 2,4-dichlorophenoxyacetic acid；(2,4-dichloro-phenoxy)-acetic acid salicylidenehydrazide；(2,4-Dichlor-phenoxy)-essigsaeure-salicylidenhydrazid；2-(2,4-dichlorophenoxy)-N-[(2-hydroxyphenyl)methylideneamino]acetamide
• CAS: 54918-94-4
• 化学式: C₁₅H₁₂Cl₂N₂O₃
• mdl: MFCD00410481
• 分子量: 339.178
• InChiKey: ZPCHVLOAXWMZPG-UHFFFAOYSA-N

物化性质

• 熔点：
  202-204 °C(Solv: ethanol (64-17-5))
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  70.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[(2,4-dichlorophenoxy)acetyl]-2-(2-hydroxybenzylidene)hydrazine 、 cobalt(II) diacetate tetrahydrate 以97%的产率得到
  参考文献：
  名称：

  Facile solid state ball milling as a green strategy to prepare 2-(2,4-dichlorophenoxy)-N′-(2-hydroxybenzylidene)acetohydrazide complexes

  摘要：

  2-(2,4-Dichlorophenoxy)-N'-(2-hydroxybenzylidene)acetohydrazide (H2L) complexes were prepared by ball milling involving the reaction of ligand with Ni(II), Co(II), Cu(II) and VO(II) salts (mechanochemical syntheses). The compounds were elucidated by elemental analysis, spectroscopy (1H NMR, IR, UV-visible, MS spectra), and physical measurements (magnetic susceptibility and molar conductance). IR spectra suggested that the H2L behaved as a monodentate and/or bidentate ligand coordinating via azomethine nitrogen and/or deprotonated enolized carbonyl oxygen. The electronic spectra of the complexes and their magnetic moments provided information about geometries. The antimicrobial activities of the ligand and its complexes were studied against gram positive bacteria; Staphylococcus aureus, gram-negative bacteria; Escherichia coli and pathogenic fungi; Candida albicans by using minimum inhibition concentrations method (MIC). Also, the antioxidant (ABTS-derived free radical method) and cytotoxic (in vitro Ehrlich Ascites) activities of the isolated compounds were evaluated.

  DOI：

  10.1016/j.saa.2014.05.062
• 作为产物：
  描述：

  2,4-二氯苯氧乙酸 在 一水合肼 作用下， 反应 4.03h， 生成 1-[(2,4-dichlorophenoxy)acetyl]-2-(2-hydroxybenzylidene)hydrazine
  参考文献：
  名称：

  Li, Jian-Ping; Zheng, Peng-Zhi; Zhu, Jun-Ge, South African Journal of Chemistry, 2006, vol. 59, p. 90 - 92

  摘要：

  DOI：

文献信息

• Synthesis of 5-membered heterocycles and related compounds.
  作者：VISHNUJI RAM、HRIDVANAND PANDEY

  DOI：10.1248/cpb.22.2778

  日期：——

  Some 1-(2, 4-dichlorophenoxy and 2, 4, 5-trichlorophenoxy) acetyl-4-arylthiosemicarbazides were prepared from corresponding chlorophenoxyacetohydrazide. The resulting thiosemicarbazides were cyclised into 1, 3, 4-thiadiazoles and 5-mercapto-1, 2, 4-triazoles under different reaction conditions. The mercapto compounds were converted into sulphides and sulphones. N'-arylidene (2, 4-dichlorophenoxy) acetohydrazides and 5-substituted-1, 3, 4-oxadiazole-2-thiones were also prepared from (2, 4-dichlorophenoxy and 2, 4, 5-trichlorophenoxy) acetohydrazides separately and were subjected to Mannich reaction. Some of these compounds were evaluated as fungicides against Aspergillus niger.

  以相应的氯苯氧乙酰肼为原料，制备了一些 1-（2，4-二氯苯氧基和 2，4，5-三氯苯氧基）乙酰基-4-芳基硫代氨基甲酰肼。在不同的反应条件下，生成的硫代氨基甲酰肼被环化成 1，3，4-噻二唑和 5-巯基-1，2，4-三唑。巯基化合物被转化为硫化物和砜。此外，还分别从（2，4-二氯苯氧基和 2，4，5-三氯苯氧基）乙酰肼制备了 N'-芳基（2，4-二氯苯氧基）乙酰肼和 5-取代的-1，3，4-噁二唑-2-硫酮，并进行了曼尼希反应。其中一些化合物被评估为针对黑曲霉的杀真菌剂。
• Discovering phenoxy acetohydrazide derivatives as urease inhibitors and molecular docking studies
  作者：Muhammad Taha、Fazal Rahim、Imad Uddin、Mohd Amir、Naveed Iqbal、Abdul Wadood、Khalid Mohammed Khan、Nizam Uddin、Ashfaq Ur Rehman、Rai Khalid Farooq

  DOI：10.1080/07391102.2023.2212794

  日期：2024.4.12

  Helicobacter pylori causes severe stomach disorders and the use of enzyme inhibitors for treatment is one of the possible therapies. The great biological potential of imine analogs as urease inhibi...

  幽门螺杆菌会引起严重的胃部疾病，使用酶抑制剂进行治疗是可能的疗法之一。亚胺类似物作为脲酶抑制剂的巨大生物潜力...
• Chao; Sah; Oneto, Recueil des Travaux Chimiques des Pays-Bas
  作者：Chao、Sah、Oneto

  DOI：——

  日期：——
• Identification of a selective small molecule inhibitor of breast cancer stem cells
  作者：Andrew R. Germain、Leigh C. Carmody、Barbara Morgan、Cristina Fernandez、Erin Forbeck、Timothy A. Lewis、Partha P. Nag、Amal Ting、Lynn VerPlank、Yuxiong Feng、Jose R. Perez、Sivaraman Dandapani、Michelle Palmer、Eric S. Lander、Piyush B. Gupta、Stuart L. Schreiber、Benito Munoz

  DOI：10.1016/j.bmcl.2012.01.035

  日期：2012.5

  A high-throughput screen (HTS) with the National Institute of Health-Molecular Libraries Small Molecule Repository (NIH-MLSMR) compound collection identified a class of acyl hydrazones to be selectively lethal to breast cancer stem cell (CSC) enriched populations. Medicinal chemistry efforts were undertaken to optimize potency and selectivity of this class of compounds. The optimized compound was declared as a probe (ML239) with the NIH Molecular Libraries Program and displayed greater than 20-fold selective inhibition of the breast CSC-like cell line (HMLE_sh_Ecad) over the isogenic control line (HMLE_sh_GFP). (C) 2012 Elsevier Ltd. All rights reserved.
• Shulgin, V. F.; Konnik, O. V.; Rabotyagov, K. V., Russian Journal of Inorganic Chemistry, 1994, vol. 39, p. 1607 - 1610
  作者：Shulgin, V. F.、Konnik, O. V.、Rabotyagov, K. V.、Ellert, O. G.、Shcherbakov, V. M.、et al.

  DOI：——

  日期：——