4-Nitroimidazole-1-acetic acid hydrazide | 93637-75-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-Nitroimidazole-1-acetic acid hydrazide
• 英文别名: 2-(4-nitro-1H-imidazol-1-yl)acetohydrazide；(4-nitroimidazol-1-yl)acetic acid hydrazide；2-(4-Nitroimidazol-1-yl)acetohydrazide
• CAS: 93637-75-3
• 化学式: C₅H₇N₅O₃
• 分子量: 185.142
• InChiKey: NLAQCYRYFPZSRB-UHFFFAOYSA-N

物化性质

• 熔点：
  122-123 °C(Solv: methanol (67-56-1))
• 沸点：
  590.4±30.0 °C(Predicted)
• 密度：
  1.77±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-Nitroimidazole-1-acetic acid hydrazide 在 硫酸 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Synthesis and anti-Helicobacter pylori activity of (4-nitro-1-imidazolylmethyl)-1,2,4-triazoles, 1,3,4-thiadiazoles, and 1,3,4-oxadiazoles

  摘要：

  制备了一系列[(4-硝基-1H-咪唑-1-基)甲基]-1,2,4-三唑和 1,3,4-噻二唑，并评估了它们对敏感和耐药幽门螺杆菌菌株的活性。 对这些系列化合物结构-活性关系的研究表明，硝基咪唑分子的类型和杂芳基类似物上的悬垂基团对抗幽门螺杆菌活性有显著影响。 在三唑系列中，三唑环上含有 4-甲基苯基的化合物 5d 是对甲硝唑敏感菌株和耐药菌株抗性最强的化合物，浓度为 8 \mu g。

  DOI：

  10.3906/kim-1004-522
• 作为产物：
  描述：

  2-(4-硝基咪唑-1-基)乙酸乙酯 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以83%的产率得到4-Nitroimidazole-1-acetic acid hydrazide
  参考文献：
  名称：

  Synthesis and anti-Helicobacter pylori activity of (4-nitro-1-imidazolylmethyl)-1,2,4-triazoles, 1,3,4-thiadiazoles, and 1,3,4-oxadiazoles

  摘要：

  制备了一系列[(4-硝基-1H-咪唑-1-基)甲基]-1,2,4-三唑和 1,3,4-噻二唑，并评估了它们对敏感和耐药幽门螺杆菌菌株的活性。 对这些系列化合物结构-活性关系的研究表明，硝基咪唑分子的类型和杂芳基类似物上的悬垂基团对抗幽门螺杆菌活性有显著影响。 在三唑系列中，三唑环上含有 4-甲基苯基的化合物 5d 是对甲硝唑敏感菌株和耐药菌株抗性最强的化合物，浓度为 8 \mu g。

  DOI：

  10.3906/kim-1004-522

文献信息

• Imidazole derivatives XVIII. Synthesis and antitumor activity of some bis[2-chloroethyl]amino imidazole derivatives
  作者：M. A. Iradyan、N. S. Iradyan、A. A. Ovagimyan、G. M. Stepanyan、F. G. Arsenyan、B. T. Garibdzhanyan

  DOI：10.1007/bf00769799

  日期：1984.7

  T h e 1 b e n z y l s u b s t i t u t e d i m i d a z o l e s ( I V g a n d h ) w e r e o b t a i n e d b y t h e a l k y l a t i o n o f t h e i s o d i u m s a l t o f 4 ( 5 ) ( 4 a c e t y l a m i n o p h e n y l ) i m i d a z o l e w i t h b e n z y l c h l o r i d e w i t h s u b s e q u e n t d e a c e t y l a t i o n o f t h e 1 b e n z y l 4 ( 4 a c e t y l a m i n o p h e n y l ) i m i d a

  1 苄基取代咪唑 (IV gandh) 是通过 4 ( 5 ) ( 4 乙酰氨基苯基) 咪唑与苄基氯醚钠的烷基化反应以及随后 1 苄基 4 ( 4 乙酰氨基苯基) 咪唑的脱乙酰化得到的。
• Investigation of the antitrypanosomal effects of 2-formyl-8-hydroxyquinoline-derived hydrazones and their antimony(<scp>iii</scp>) and bismuth(<scp>iii</scp>) complexes
  作者：Ana Paula A. Oliveira、Angel A. Recio-Despaigne、Isabella P. Ferreira、Renata Diniz、Karoline A. F. Sousa、Tanira M. Bastos、Milena B. Pereira Soares、Diogo Rodrigo M. Moreira、Heloisa Beraldo

  DOI：10.1039/c9nj02676b

  日期：——

  values ranging from 0.06 to 30.05 μM. Complex 3 proved to be as potent as the reference drug benznidazole whereas complexes 4–6 were more potent than benznidazole as antiparasitic agents. The antimony(III) (4, EC50 = 0.33 μM) and bismuth(III) (6, EC50 = 0.06 μM) complexes presented the highest activities against the extracellular parasites. As expected, complexes 4 and 6 also exhibited the highest anti-T

  在本工作中，获得了8-羟基喹啉衍生的hydr，即2-甲酰基-8-羟基喹啉-4-硝基咪唑hydr（H2Q4NO 2 Im）（H 2 La，1）和2-甲酰基-8-羟基喹啉-4-硝基苯hydr （ H2Q4NO 2 Ph·H 2 O）（H 2 Lb，2）及其锑（III）[Sb（L）Cl 2 ]（3，4）和铋（III）[Bi（L）Cl 2 ] （5、6）复合体。首先在未感染的人和小鼠细胞中确定化合物的细胞毒性浓度范围。此外，评估了它们对南美锥虫病致病性克鲁氏锥虫的抗寄生虫活性。当H 2 Lb（2）失活时，H 2 La（1）和配合物3-6抑制了克鲁氏锥虫的拟鞭毛虫的EC 50值在0.06至30.05μM之间。复合物3被证明与参考药物苯硝唑一样有效，而复合物4–6比苯硝唑作为抗寄生虫药更有效。锑（III）（4，EC 50 = 0.33μM）和铋（III）（6，EC 50 = 0.06μM）复合物对细胞
• New Derivatives of Thiosemicarbazide and 1,2,4-Triazoline-5-thione with Potential Antimicrobial Activity
  作者：Monika Wujec、Urszula Kosikowska、Agata Siwek、Anna Malm

  DOI：10.1080/10426500802208490

  日期：2009.3.10

  In the reaction of the hydrazide of (4-nitroimidazol-1-yl)acetic acid 1 with isothiocyanates, the respective thiosemicarbazide derivatives 2-6 were obtained. Further cyclization with 2% NaOH led to the formation of 3-[(4-nitroimidazol-1-yl)-methyl]-4-substituted-1,2,4-triazoline-5-thiones 7-11. The structures of all new products were confirmed by analytical and spectroscopic methods. Six compounds 2-5, 8, and 10 were screened for their in vitro activity against some species of aerobic bacteria and fungi. Compound 3 appears to be a promising precursor of agents with antibacterial activity against Micrococcus luteus.
• Unique Azolyl Acylhydrazonyl Hybridization of Aloe Emodins to Access Potential Antibacterial Agents
  作者：Yi‐Xin Wang、Zhao Deng、Aisha Bibi、Bo Fang、Cheng‐He Zhou

  DOI：10.1002/cjoc.202400160

  日期：——

  A type of unique azole‐hybridized acylhydrazonyl aloe emodins (AAEs) were developed as new antibacterial agents for combating bacterial infections. Some target AAEs showed strong antibacterial activities, especially, tetrazolylthioether AAE 27a exhibited broad antibacterial spectrum with 16—256 folds and 8—64 folds more active antibacterial efficacy than the reference drugs aloe emodin and norfloxacin, respectively. Tetrazolylthioether AAE 27a also gave low hemolysis and cytotoxicity, as well as favorable bioavailability. Preliminary mechanism explorations revealed that tetrazolylthioether AAE 27a could cause bacterial membrane depolarization and damage the cell membrane, resulting in nucleic acid leakage. Moreover, compound 27a could intercalate into DNA to impede its replication and form supramolecular 27a‐DNA gyrase complex to disturb the function of DNA gyrase. These findings would provide valuable insights for the further exploration of azolyl acylhydrazonyl aloe emodins as new potential antibacterial candidates.
• Synthesis and anti-Helicobacter pylori activity of (4-nitro-1-imidazolylmethyl)-1,2,4-triazoles, 1,3,4-thiadiazoles, and 1,3,4-oxadiazoles
  作者：ASAL FALLAH-TAFTI、TAHMINEH AKBARZADEH、PARASTOO SANIEE、FARIDEH SIAVOSHI、ABBAS SHAFIEE、ALIREZA FOROUMADI

  DOI：10.3906/kim-1004-522

  日期：——

  A series of [(4-nitro-1H-imidazol-1-yl)methyl]-1,2,4- triazoles and 1,3,4-thiadiazoles were prepared and evaluated for their activity against sensitive and resistant H. pylori strains. Study of the structure-activity relationship of these series of compounds indicated that the type of nitroimidazole moiety and the pendent group on the heteroaryl analog dramatically impact the anti-H. pylori activity. In triazole series, compound 5d, containing a 4-methyl phenyl group on the triazole ring, was the most potent compound tested against both metronidazole-sensitive and -resistant strains at a concentration of 8 \mu g.

  制备了一系列[(4-硝基-1H-咪唑-1-基)甲基]-1,2,4-三唑和 1,3,4-噻二唑，并评估了它们对敏感和耐药幽门螺杆菌菌株的活性。 对这些系列化合物结构-活性关系的研究表明，硝基咪唑分子的类型和杂芳基类似物上的悬垂基团对抗幽门螺杆菌活性有显著影响。 在三唑系列中，三唑环上含有 4-甲基苯基的化合物 5d 是对甲硝唑敏感菌株和耐药菌株抗性最强的化合物，浓度为 8 \mu g。