N-(4-nitrophenyl)acetohydrazonoyl bromide | 38562-65-1

• 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: N-(4-nitrophenyl)acetohydrazonoyl bromide
• 英文别名: N-(4-Nitrophenyl)ethanehydrazonoyl bromide；N-(4-nitrophenyl)ethanehydrazonoyl bromide
• CAS: 38562-65-1
• 化学式: C₈H₈BrN₃O₂
• 分子量: 258.074
• InChiKey: YLJLGXZPXFDLTF-UHFFFAOYSA-N

物化性质

• 熔点：
  125-126 °C(Solv: acetic acid (64-19-7))
• 沸点：
  349.5±44.0 °C(Predicted)
• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-nitrophenyl)acetohydrazonoyl bromide 在 palladium on activated charcoal 一水合肼 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 10.33h， 生成 1-(4-Amino-phenyl)-3,5,7-trimethyl-1H,7H-1,2,3a,5,7,8-hexaaza-cyclopenta[a]indene-4,6-dione
  参考文献：
  名称：

  Synthesis, biological studies and molecular modeling investigation of 1,3-dimethyl-2,4-dioxo-6-methyl-8-(substituted) 1,2,3,4-tetrahydro [1,2,4]-triazolo [3,4-f]-purines as potential adenosine receptor antagonists

  摘要：

  A new series of potential adenosine receptor antagonists with a [1,2,4]-triazolo-[3,4-f]-purine structure have been synthesized, and their affinities at the four adenosine receptor subtypes (A1, A2A, A2B and A3) have been evaluated. The design was based on the demonstrated approach to novel A3 adenosine receptor antagonists of adding a third ring to the xanthine structure. Unfortunately, all the synthesized compounds were completely inactive at all four adenosine receptor subtypes independently of their substitutions. Preliminary molecular modeling investigation has demonstrated that only a low degree of steric and electrostatic complementarity has been observed for all the new synthesized triazolo-purines with respect to other structurally related A3 receptor antagonists. This analysis yielded valuable information about structure-activity relationships and further design of potential adenosine receptor antagonists.

  DOI：

  10.1016/j.farmac.2005.01.008
• 作为产物：
  描述：

  acetaldehyde p-nitrophenylhydrazone 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 为溶剂， 生成 N-(4-nitrophenyl)acetohydrazonoyl bromide
  参考文献：
  名称：

  Nitration of Fullerene Derivatives under Mild Conditions

  摘要：

  一种新的N-(2,4-二硝基苯基)-2-吡唑啉[60]富勒烯衍生物已通过使用三氟甲苯基氮离子进行电亲核硝化合成。CV和OSWV实验表明，与C60相比，这些物质显示出增强的电子受体特性（高达90 mV）。

  DOI：

  10.1055/s-2007-977425

文献信息

• Structure-based design of novel pyrazolyl–chalcones as anti-cancer and antimicrobial agents: synthesis and in vitro studies
  作者：Monica G. Kamel、Farid M. Sroor、Abdelmageed M. Othman、Karima F. Mahrous、Fatma M. Saleh、Hamdi M. Hassaneen、Tayseer A. Abdallah、Ismail A. Abdelhamid、Mohamed A. Mohamed Teleb

  DOI：10.1007/s00706-021-02886-5

  日期：2022.2

  highest antibacterial activity (20 mm) against B. mycoides, whereas 3-(4-chlorophenyl)-1-[3,5-dimethyl-1-(4-nitrophenyl)-1H-pyrazol-4-yl]prop-2-en-1-one and 1-[3,5-dimethyl-1-(4-nitrophenyl)-1H-pyrazol-4-yl]-3-(p-tolyl)prop-2-en-1-one had equivalent antibacterial activity (17 mm) against E. coli. The 4-chlorophenyl derivative exhibited the most potent antifungal activity against C. albicans (17 mm).

  通过 4-乙酰基吡唑衍生物与相应醛的 Claisen-Schmidt 缩合反应，以中等收率制备了一系列新的吡唑基-查尔酮衍生物。新合成的化合物已通过1 H NMR、13 C NMR、IR、质谱和元素分析进行了充分表征。评价了新化合物的体外抗微生物和抗癌活性。根据分子的结构，不同类型的化合物对微生物生长效率有不同的影响。3-(2,4-二甲氧基苯基)-1-[3,5-二甲基-1-(4-硝基苯基)-1 H-吡唑-4-基]prop-2-en-1-one的抗菌活性最高(20 mm) 对抗蕈状芽孢杆菌, 而 3-(4-氯苯基)-1-[3,5-二甲基-1-(4-硝基苯基)-1 H-吡唑-4-基]prop-2-en-1-one 和 1-[3 ,5-二甲基-1-(4-硝基苯基)-1 H-吡唑-4-基]-3-( p -tolyl)prop-2-en-1-one 对大肠杆菌具有同等的抗菌活性 (17 mm) 。大
• A convenient one-pot synthesis and antimicrobial activity of pyrimido[1,2-<i>b</i>][1,2,4,5]tetrazines
  作者：Ahmad S. Shawali、Magda A. Abdallah、Mohie M. Zayed

  DOI：10.1002/jhet.5570390105

  日期：2002.1

  The synthesis of the hitherto unreported 3-amino-2,3-dihydro-6-phenyl-2-thioxo-4(1H)-pyrimidine 2 and 3-amino-2-methylthio-6-phenyl-4(3H)-pyrimidinone 3 is described. Reactions of hydrazonoyl halides 1 with either 2 or 3 afforded 6H-pyrimido[1,2-b][1,2,4,5]tetrazin-6-ones 6. The latter products were screened for their antifungal and antibacterial properties. The mechanism of the studied reactions is

  迄今为止未报道的3-氨基-2,3-二氢-6-苯基-2-硫代氧杂4（1 H）-嘧啶2和3-氨基-2-甲硫基-6-苯基-4（3 H）的合成描述了-嘧啶酮3。酰肼基卤化物1与2或3的反应得到6 H-嘧啶基[1,2- b ] [1,2,4,5]四嗪-6-酮6。筛选了后者的产物的抗真菌和抗菌性能。讨论了所研究反应的机理。
• Preparation of Aryl Hydrazonates and 1,2-Diacylhydrazines by Phase Transfer Catalysis
  作者：Ahmad Sami Shawali、Hamdi Mahmoud Hassaneen、Richard Pagni、Mourad Sherif Sherif

  DOI：10.1246/bcsj.54.2545

  日期：1981.8

  A series of aryl hydrazonates has been prepared in excellent yield (>90%) by phase-transfercatalysis technique from the corresponding phenol and hydrazonoyl bromides in dichloromethane in the presence of tetrabutylammonium iodide. 1,2-Diacyl derivatives of arylhydrazines were also prepared by the same technique using carboxylic acids in place of phenols.

  在四丁基碘化铵的存在下，通过相转移催化技术从相应的苯酚和腙酰溴化物在二氯甲烷中制备了一系列芳基腙酯，收率极好（>90%）。芳基肼的 1,2-二酰基衍生物也通过相同的技术使用羧酸代替苯酚制备。
• Hassaneen, Hamdi M.; Hilal, Rifaat H.; Elwan, Nehal M., Journal of Heterocyclic Chemistry, 1984, vol. 21, p. 1013 - 1016
  作者：Hassaneen, Hamdi M.、Hilal, Rifaat H.、Elwan, Nehal M.、Harhash, Abdelhamid、Shawali, Ahmad S.

  DOI：——

  日期：——
• Synthesis, biological and modeling studies of 1,3-di-n-propyl-2,4-dioxo-6-methyl-8-(substituted) 1,2,3,4-tetrahydro [1,2,4]-triazolo [3,4-f]-purines as adenosine receptor antagonists
  作者：G. Pastorin、C. Bolcato、B. Cacciari、S. Kachler、K.-N. Klotz、C. Montopoli、S. Moro、G. Spalluto

  DOI：10.1016/j.farmac.2005.04.012

  日期：2005.8

  A new series of potential adenosine receptor antagonists with a [1,2,4]-triazolo-[3,4-f]-purine structure bearing at the 1 and 3 position n-propyl groups have been synthesized, and their affinities at the four human adenosine receptor subtypes (A(1), A(2A), A(2B) and A(3)) have been evaluated. In this case the presence of n-propyl groups seems to induce potency at the A(2A) and A(3) adenosine receptor subtypes as opposed to our previously reported series bearing methyl substituents at the 1 and 3 positions. In particular the non-acylated derivative 17 showed affinity at these two receptor subtypes in the micromolar range. Indeed, preliminary molecular modeling investigations according to the experimental binding data indicate a modest steric and electrostatic antagonist-receptor complementarity.