4-乙酰基苯甲酸酰肼 | 229315-91-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-乙酰基苯甲酸酰肼
• 英文名称: 4-acetylbenzoic acid hydrazide
• 英文别名: 4-Acetylbenzohydrazide
• CAS: 229315-91-7
• 化学式: C₉H₁₀N₂O₂
• 分子量: 178.191
• InChiKey: DEUYXUFJMAVOFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  72.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-硝基噻吩-2-甲醛 、 4-乙酰基苯甲酸酰肼 在 硫酸 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 生成 4-acetylbenzoic acid [(5-nitrothiophen-2-yl)methylene]hydrazide
  参考文献：
  名称：

  A new class of nifuroxazide analogues: Synthesis of 5-nitrothiophene derivatives with antimicrobial activity against multidrug-resistant Staphylococcus aureus

  摘要：

  Hospital-acquired methicillin-resistant Staphylococcus aureus (MRSA) has been an increasing problem worldwide since the initial reports over 40 years ago. To examine new drug leads with potential antibacterial activities, 14 p-substituted benzoic acid [(5-nitro-thiophen-2-yl)-methylene]-hydrazides were designed, synthesized, and tested against standard and multidrug-resistant S. aureus strains by serial dilution tests. All compounds exhibited significant bacteriostatic activity and some of them also showed bactericidal activity. The results confirmed the potential of this class of compounds as an alternative for the development of selective antimicrobial agents. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.03.068
• 作为产物：
  描述：

  4-乙酰基苯甲酸 在 硫酸 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 14.0h， 生成 4-乙酰基苯甲酸酰肼
  参考文献：
  名称：

  Design, Synthesis, Pharmacological Evaluation and Molecular Docking Studies of Substituted Oxadiazolyl-2-Oxoindolinylidene Propane Hydrazide Derivatives

  摘要：

  The manuscript describes design and synthesis of novel oxadiazolyl-2-oxoindolinylidene propane hydrazides as amide tethered hybrids of indole and oxadiazole and their evaluation for anti-inflammatory and analgesic activity. The compounds were synthesized following five step reaction to yield fifteen derivatives as 3-(5-substituted-1,3,4-oxadiazol-2-yl)-N'-[2-oxo-1,2-dihydro-3H-indol-3-ylidene] propane hydrazides. The final derivatives 3-[5-(4-hydroxyphenyl)-1,3,4-oxadiazol-2-yl]-N'-[2-oxo-1,2-dihydro-3H-indol-3-ylidene] propane hydrazide and 3-[5-(4-methylphenyl)1,3,4-oxadiazol-2-yl]-N'-[2-oxo-1,2-dihydro-3H-indol-3-ylidene] propane hydrazide were found to be highly promising molecules with severity index of 0.35 and 0.56, respectively, which is promising for an analgesic compound. The hydroxy and methyl substitution on phenyl ring system provided with active anti-inflammatory compounds having increase in reaction time of 84.11 and 83.17%, respectively compared to standard drug at 85.84%. Molecular docking studies exhibit comparable interaction with synthesized derivatives and standard drug having a dock score of -4.44 by the K-nearest neighbour genetic algorithm method.

  DOI：

  10.5935/0103-5053.20160090

文献信息

• Design, synthesis and biological evaluation of thieno[3,2-d]pyrimidine derivatives containing aroyl hydrazone or aryl hydrazide moieties for PI3K and mTOR dual inhibition
  作者：Yufei Han、Ye Tian、Ruxin Wang、Siyu Fu、Jia Jiang、Jiawen Dong、Mingze Qin、Yunlei Hou、Yanfang Zhao

  DOI：10.1016/j.bioorg.2020.104197

  日期：2020.11

  position are optimal fragments. Compound 18b showed the most potent in vitro activity (PI3Kα IC50 = 0.46 nM, mTOR IC50 = 12 nM), as well as good inhibition against PC-3 (human prostate cancer), HCT-116 (human colorectal cancer), A549 (human lung adenocarcinoma) and MDA-MB-231 (human breast cancer) cell lines. Furthermore, Annexin-V and propidium iodide (PI) double staining confirmed that 18b induces apoptosis

  最近，PI3K和mTOR被认为是治疗癌症的有希望的靶标。在这里，我们设计和合成了四个系列的新的噻吩并[3,2- d ]嘧啶衍生物，其中含有芳酰基或芳基酰肼部分。这些衍生物充当PI3K / mTOR双重抑制剂，表明它们可用作癌症治疗剂。测试所有化合物对四种癌细胞系的抗增殖活性。通过改变噻吩并[3,2- d ]嘧啶核的C-6和C-2位置的部分进行结构-活性关系（SAR）研究。表明C-6位的芳基酰肼和C-2位的2-氨基嘧啶是最佳片段。化合物18b表现出最强的体外活性（PI3KαIC 50  = 0.46 nM，mTOR IC 50  = 12 nM），并对PC-3（人前列腺癌），HCT-116（人结肠直肠癌），A549（人肺腺癌）和MDA-MB-231（人乳腺癌）细胞系。此外，Annexin-V和碘化丙锭（PI）双重染色证实18b诱导细胞毒性HCT-116细胞凋亡。此外，在HCT-116细胞系上
• Pyridazinone, triazinone and oxapyridazinone lipoxygenase inhibiting compounds
  申请人：ABBOTT LABORATORIES

  公开号：EP0299449A2

  公开（公告）日：1989-01-18

  Pyridazinone, triazinone and oxapyridazinone compounds which are useful in inhibting lipoxygenase enzymes, particularly 5-lipoxygenase.

  可抑制脂氧合酶，特别是 5-脂氧合酶的哒嗪酮、三嗪酮和噁哒嗪酮化合物。
• Srinivas; Subba Reddy; Yadav, Journal of Chemical Research - Part S, 2000, # 8, p. 376 - 377
  作者：Srinivas、Subba Reddy、Yadav、Ramalingam

  DOI：——

  日期：——
• Tavares; Penna; Amaral, Bollettino Chimico Farmaceutico, 1997, vol. 136, # 3, p. 244 - 249
  作者：Tavares、Penna、Amaral

  DOI：——

  日期：——
• Design, synthesis, antimicrobial activity and molecular modeling studies of novel benzofuroxan derivatives against Staphylococcus aureus
  作者：Salomão Dória Jorge、Andrea Masunari、Carlota Oliveira Rangel-Yagui、Kerly Fernanda Mesquita Pasqualoto、Leoberto Costa Tavares

  DOI：10.1016/j.bmc.2009.03.011

  日期：2009.4

  Molecular modi. cation is a quite promising strategy in the design and development of drug analogs with better bioavailability, higher intrinsic activity and less toxicity. In the search of new leads with potential antimicrobial activity, a new series of 14 4-substituted [N'-(benzofuroxan-5-yl) methylene] benzohydrazides, nifuroxazide derivatives, were synthesized and tested against standard and multidrug-resistant Staphylococcus aureus strains. The selection of the substituent groups was based on physicochemical properties, such as hydrophobicity and electronic effect. These properties were also evaluated through the lipophilic and electrostatic potential maps, respectively, considering the compounds with better biological pro. le. Twelve compounds exhibited similar bacteriostatic activity against standard and multidrug-resistant strains. The most active compound was the 4-CF3 substituted derivative, which presented a minimum inhibitory concentration (MIC) value of 14.6-13.1 mu g/mL, and a ClogP value of 1.87. The results highlight the benzofuroxan derivatives as potential leads for designing new future antimicrobial drug candidates. (C) 2009 Elsevier Ltd. All rights reserved.