4-氯-3-硝基苯肼 | 77938-04-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-氯-3-硝基苯肼
• 英文名称: 4-Chloro-3-nitrobenzohydrazide
• CAS: 77938-04-6
• 化学式: C₇H₆ClN₃O₃
• mdl: MFCD00017072
• 分子量: 215.596
• InChiKey: LAOXKJJONRHSDD-UHFFFAOYSA-N

物化性质

• 熔点：
  152-154 °C(Solv: ethanol (64-17-5))
• 密度：
  1.531±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 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：
  101
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  4-氯-3-硝基苯肼 在 potassium hydroxide 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 2-(4-chloro-3-nitrophenyl)-5-(methylthio)-1,3,4-oxadiazole
  参考文献：
  名称：

  Inhibition of Tobacco Bacterial Wilt with Sulfone Derivatives Containing an 1,3,4-Oxadiazole Moiety

  摘要：

  A series of new sulfone compounds containing the 1,3,4-oxadiazole moiety were designed and synthesized. Their structures were identified by H-1 and C-13 nuclear magnetic resonance and elemental analyses. Antibacterial bioassays indicated that most compounds exhibited promising in vitro antibacterial bioactivities against tobacco bacterial wilt at 200 mu g/mL. The relationship between structure and antibacterial activity was also discussed. Among the title compounds, 5'c:, 5'h, 5'i, and 5, could inhibit mycelia growth of Ralstonia solanacearum in vitro by approximately 50% (EC50) at 39.8, 60.3, 47.9, and 32.1 mu g/mL, respectively. Among them, compound 5) was identified as the most promising candidate due to its stronger effect than that of Kocide 3000 [Cu(OH)(2)] within the same concentration range. Field trials demonstrated that the control effect of compound 55 against tobacco bacterial wilt was better than that of the commercial bactericide Saisentong. For the first time, the present work demonstrated that sulfone derivatives containing 1,3,4-oxadiazole can be used to develop potential bactericides for plants.

  DOI：

  10.1021/jf203772d
• 作为产物：
  描述：

  4-氯-3-硝基苯甲酸 在 hydrazine hydrate 、 硫酸 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 4-氯-3-硝基苯肼
  参考文献：
  名称：

  Hasan, Aurangzeb; Gapil, Shelly; Khan, Izzat, Asian Journal of Chemistry, 2011, vol. 23, # 5, p. 2007 - 2010

  摘要：

  DOI：

文献信息

• Structure based discovery of novel hexokinase 2 inhibitors
  作者：Yang Liu、Mingxue Li、Yujie Zhang、Canrong Wu、Kaiyin Yang、Suyu Gao、Mengzhu Zheng、Xingzhou Li、Hua Li、Lixia Chen

  DOI：10.1016/j.bioorg.2020.103609

  日期：2020.3

  Hexokinase 2 (HK2) is over-expressed in most of human cancers and has been proved to be a promising target for cancer therapy. In this study, based on the structure of HK2, we screened over 6 millions of compounds to obtain the lead. A total of 26 (E)-N'-(2,3,4-trihydroxybenzylidene) arylhydrazide derivatives were then designed, synthesized, and evaluated for their HK2 enzyme activity and IC50 values

  Hexokinase 2（HK2）在大多数人类癌症中均过表达，并且已被证明是癌症治疗的有希望的靶标。在这项研究中，基于HK2的结构，我们筛选了超过600万种化合物以获得铅。然后设计，合成总共26种（E）-N'-（2,3,4-三羟基亚苄基）芳基酰肼衍生物，并评估其针对两种癌细胞系的HK2酶活性和IC50值。26种目标化合物中的大多数都具有出色的体外活性。其中，化合物3j对HK2酶活性的抑制作用最强，IC50为0.53±0.13μM，对SW480细胞的生长抑制作用最强，IC50为7.13±1.12μM，值得进一步研究。
• Kinetic Study on Nucleophilic Displacement Reactions of 2-Chloro-4-Nitrophenyl X-Substituted-Benzoates with Primary Amines: Reaction Mechanism and Origin of the α-Effect
  作者：Tae-Il Um、Min-Young Kim、Tae-Eun Kim、Ik-Hwan Um

  DOI：10.5012/bkcs.2014.35.2.436

  日期：2014.2.20

  8.31 13.96 hydrazine 8.20 6627 glycine ethyl ester 7.68 7.068 1,2-diaminopropane-H + 7.13 4.459 trifluoroethylamine 5.68 0.124 Figure 1. Bronsted-type plot for the reactions of 2-chloro-4-nitro-phenyl benzoate ( 1d ) with primary amines in 80 mol % of H 2 O/20mol % DMSO at 25.0 ± 0.1 o C. The identity of points is given inTable 1, and hydrazine is excluded in the correlation. Table 2. Summary of Second-Order

  在 80 mol % $H_2O/20$ mol % DMSO 溶液中，于 $25.0^\circ}C$.2-chloro-4-nitrophenyl benzoate (1d) 与一系列伯胺反应的 Br$emptyset}$nsted-type plot 曲线向下，这被认为是速率决定级（RDS）发生变化的阶梯机理的证据。1a-h 与肼和甘氨酰甘氨酸反应的 Hammett 图是非线性的，而 Yukawa-Tsuno 图则表现出很好的线性关系，$\yrho}_X=1.22-1.35$ 和 $\gamma}= 0.57-0.59$，这表明非线性哈米特图不是由于 RDS 的变化造成的，而是通过 EDG 与基质的 C=O 键之间的共振相互作用，使具有电子供体基团 (EDG) 的基质稳定下来造成的。随着取代基 X 从强 EDG 转变为强电子抽离基 (EWG)，肼表现出的 $\alpha}$ 效应也随之增加。研究得出的结论是，通过相邻非键电子之间的电子斥力使肼失稳并不是取代基依赖性 $\alpha}$ 效应的唯一原因，过渡态的稳定也是 $\alpha}$ 效应的一个合理来源。
• Design, Synthesis, and Biological Evaluation of Piperazine and <i>N</i>-Benzylpiperidine Hybrids of 5-Phenyl-1,3,4-oxadiazol-2-thiol as Potential Multitargeted Ligands for Alzheimer’s Disease Therapy
  作者：Digambar Kumar Waiker、Akash Verma、Akhilesh、Gajendra T. A、Namrata Singh、Anima Roy、Hagera Dilnashin、Vinod Tiwari、Surendra Kumar Trigun、Surya P. Singh、Sairam Krishnamurthy、Prem Lama、Vincent Jo Davisson、Sushant Kumar Shrivastava

  DOI：10.1021/acschemneuro.3c00245

  日期：2023.6.7

  Our present work demonstrates the successful design and synthesis of a new class of compounds based upon a multitargeted directed ligand design approach to discover new agents for use in Alzheimer’s disease (AD). All the compounds were tested for their in vitro inhibitory potential against human acetylcholinesterase (hAChE), human butylcholinesterase (hBChE), β-secretase-1 (hBACE-1), and amyloid β

  我们目前的工作展示了基于多目标定向配体设计方法成功设计和合成一类新化合物，以发现用于阿尔茨海默氏病 (AD) 的新药物。测试了所有化合物对人乙酰胆碱酯酶 (hAChE)、人丁基胆碱酯酶 (hBChE)、β-分泌酶-1 (hBACE-1) 和淀粉样蛋白 β (Aβ) 聚集的体外抑制潜力。化合物5d和5f显示出与多奈哌齐相当的 hAChE 和 hBACE-1 抑制作用，而 hBChE 抑制作用与卡巴拉汀相当。化合物5d和5f还证明通过硫黄素 T 测定和共聚焦、原子力和扫描电子显微镜研究显着减少了 Aβ 聚集体的形成，并显着取代了总碘化丙啶，即在 50 μM 浓度下分别为 54% 和 51%。化合物5d和5f在 10–80 μM 浓度下对 RA/BDNF（RA = 视黄酸；BDNF = 脑源性神经营养因子）分化的 SH-SY5Y 神经母细胞瘤细胞系没有神经毒性。在东莨菪碱和 Aβ 诱导的 AD
• An unusual ground-state stabilization effect and origins of the alpha-effect in aminolyses of Y-substituted phenyl X-substituted benzoates
  作者：Ik-Hwan Um、Eun-Kyung Chung、So-Mi Lee

  DOI：10.1139/cjc-76-6-729

  日期：——

  Second-order rate constants have been measured spectrophotometrically for the reactions of X-C6H4CO2C6H4-Y with a series of primary amines in H2O containing 20 mol% DMSO at 25.0 +/- 0.1 degrees C. The reactivity increases as the substituent (X and Y) becomes a stronger electron-withdrawing group. The sigma(+) constants give better Hammett correlation than sigma constants for the reactions of 4-nitrophenyl X-substituted benzoates with glycylglycine (glygly) and hydrazine (NH2NH3, indicating that the ground-state stabilization effect is unusually significant on the reaction rates. The reactions of X-C6H4CO2C6H4-Y with glygly and NH2NH2 appear to proceed through the same mechanism, but the degree of leaving-group departure and the negative charge developed in the acyl moiety at the rate-determining TS is considered to be more significant for the glygly system than the NH2NH2 system based on beta(1g) and rho(x) values. The magnitude of the alpha-effect is observed to be not always dependent on the beta(nuc) value but dependent on the electronic nature of the substituent X and Y, i.e., an electron-donating substituent increases the alpha-effect, while an electron-withdrawing one decreases the alpha-effect. The present study has led to the conclusion that the ground-state effect is important for the reaction rates but it is not solely responsible for the alpha-effect, and the intramolecular H-bonding interactions (4) are proposed for the cause of the increasing or decreasing a-effect trends observed in the present system.
• Antileishmanial activity screening of 5-nitro-2-heterocyclic benzylidene hydrazides
  作者：Daniela G. Rando、Mitchell A. Avery、Babu L. Tekwani、Shabana I. Khan、Elizabeth I. Ferreira

  DOI：10.1016/j.bmc.2008.05.076

  日期：2008.7

  A series of 53 nitro derivatives rationally designed were obtained by parallel synthesis and screened against Leishmania donovani. Six compounds exhibited IC50 values lower than standard drugs. Brief SAR analysis revealed that substitution is important to the activity. Nitrothiophene analogues were more potent than the nitrofuran ones. This was attributed to the ability of sulfur atoms in accommodating electrons from nitro group, which facilitate its reduction and therefore the formation of free radicals lethal to parasites. (c) 2008 Elsevier Ltd. All rights reserved.