5-硝基呋喃-2-甲酰肼 | 5469-78-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 中文名称: 5-硝基呋喃-2-甲酰肼
• 英文名称: 5-nitrofuran-2-carbohydrazide
• 英文别名: 5‐nitrofuran‐2‐carboxylic acid hydrazide；5-nitro-2-furancarbohydrazide；5-nitro-furan-2-carboxylic acid hydrazide；5-Nitro-furan-2-carbonsaeure-hydrazid；5-nitrofurane-2-carboxylic acid hydrazide；5-nitro-furoyl-hydrazide
• CAS: 5469-78-3
• 化学式: C₅H₅N₃O₄
• mdl: MFCD00179297
• 分子量: 171.112
• InChiKey: HRYYAHKXNSUDFH-UHFFFAOYSA-N

物化性质

• 熔点：
  173-174 °C(Solv: methanol (67-56-1))
• 密度：
  1.533±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  12
• 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：
  114
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-硝基呋喃-2-甲酰肼 在 盐酸 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 32.0h， 生成 N'-[(2R)-2-amino-2-phenylacetyl]-5-nitrofuran-2-carbohydrazide;hydrochloride
  参考文献：
  名称：

  Antitrypanosomal activities and cytotoxicity of 5-nitro-2-furancarbohydrazides

  摘要：

  A series of 5-nitro-2-furancarbohydrazides were synthesized. In vitro antitrypanosomal activities of these compounds were determined against the closely related protozoa Trypanosoma cruzi Trypanosoma brucei and discussed in relation to potential targets. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00788-6
• 作为产物：
  描述：

  5-硝基-2-糠酸 在 三乙胺 、 三氟乙酸 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 5-硝基呋喃-2-甲酰肼
  参考文献：
  名称：

  硝基呋喃-1,3,4-恶二唑杂化物作为新型抗结核药物的设计、合成和生物学评价

  摘要：

  设计并合成了三个系列的新型硝基呋喃-1,3,4-恶二唑杂化物作为新型抗结核药物。构效关系研究表明，恶二唑部分的连接基和取代基对活性影响很大，取代的苯比环烷基或杂环基更受青睐。此外，系列 2 中的最佳化合物对 MTB H 37 Rv 菌株和 MDR-MTB 16883 临床分离株均具有活性，并且还显示出低细胞毒性、低 hERG 抑制和良好的口服 PK，表明其有望成为进一步结构的领先者。修改。

  DOI：

  10.1016/j.bmc.2021.116529

文献信息

• Synthesis, <i>in Vitro</i> and <i>in Silico</i> Studies of Some Novel 5-Nitrofuran-2-yl Hydrazones as Antimicrobial and Antitubercular Agents
  作者：Hatem Abdel-Kader Abdel-Aziz、Wagdy Mohamed Eldehna、Mohamed Fares、Tilal Elsaman、Marwa Mostafa Abdel-Aziz、Dalia Hussein Soliman

  DOI：10.1248/bpb.b15-00439

  日期：——

  In this study, we synthesized two series of novel 5-nitrofuran-2-carbohydrazides 21a–h and 22a–e in addition to a third series of thiophene-2-carbohydrazides 23a–g to develop potent antimicrobial and/or antitubercular agents. The newly synthesized compounds were evaluated in vitro for their antimicrobial and antimycobacterial activities. Most of the 5-nitrofuran-2-carbohydrazides 21a–h and 22a–e displayed variable activity against Aspergillus fumigates, Staphylococcus aureus, Streptococcus pneumonia, Bacillis subtilis, Salmonella typhimurium, Klebsiella pneumonia, Escherichia coli and Mycobacterium tuberculosis. The sulfonamide derivative 21f exhibited superior potency and broad-spectrum antimicrobial activity with minimum inhibitory concentration (MIC)=0.06–0.98 µg/mL and antimycobacterial activity with MIC=3.9 µg/mL. The 5-nitrofuran-2-carbohydrazides 21a, b, g, h and 22a–c exhibited significant antibacterial activity with MIC values in the range of 0.12–7.81 µg/mL. The significances of the 5-nitrofuran moiety and sulfonamide function were explored via the structure–activity relationship (SAR) study. In addition, docking studies revealed that the p-amino benzoic acid (PABA) and binding pockets of the dihydropteroate synthase (DHPS) were successfully occupied by compound 21f. Furthermore, two quantitative structure–activity relationship (QSAR) models were built to explore the structural requirements which controlled the activity.

  在本研究中，我们合成了两系列新型5-硝基呋喃-2-甲酰肼21a–h和22a–e，以及第三系列噻吩-2-甲酰肼23a–g，旨在开发强效抗菌和/或抗结核剂。新合成的化合物在体外进行了抗菌和抗分枝杆菌活性评估。大多数5-硝基呋喃-2-甲酰肼21a–h和22a–e对烟曲霉、金黄色葡萄球菌、肺炎链球菌、枯草芽孢杆菌、鼠伤寒沙门氏菌、肺炎克雷伯菌、大肠埃希菌和结核分枝杆菌显示出不同程度的活性。磺胺衍生物21f表现出优越的广谱抗菌活性，最小抑制浓度（MIC）=0.06–0.98 µg/mL，以及抗分枝杆菌活性，MIC=3.9 µg/mL。5-硝基呋喃-2-甲酰肼21a、b、g、h和22a–c显示出显著的抗菌活性，MIC值在0.12–7.81 µg/mL范围内。通过结构-活性关系（SAR）研究探讨了5-硝基呋喃部分和磺胺功能的重要性。此外，对接研究揭示了化合物21f成功占据了对氨基苯甲酸（PABA）和二氢蝶酸合酶（DHPS）的结合口袋。进一步地，构建了两个定量结构-活性关系（QSAR）模型，以探索控制活性的结构要求。
• Synthesis and biological testing of 4-carboxyquinolyl-2-aldehyde derivatives
  作者：N. M. Sukhova、I. K. Shprunka、M. Yu. Lidak、A. A. Zidermane

  DOI：10.1007/bf00762028

  日期：1982.2

  Compounds (l-V), (VII), (IX-XIII), and (XVIII) (see Table i), were isolated as monohydrates; they are crystalline substances ranging in color from colorless to orange, and, with the exception of VIII and XVII, which are water-soluble, they are soluble with difficulty in water and common organic solvents. The composition and structures of the compounds were confirmed by elemental analysis and IR spectral

  化合物(IV)、(VII)、(IX-XIII)和(XVIII)(见表i)以一水合物形式分离；它们是结晶物质，颜色从无色到橙色，除VIII和XVII是水溶性的外，它们很难溶于水和普通有机溶剂。通过元素分析和红外光谱数据确定了化合物的组成和结构；光谱显示在 1653-1698 cm -~ 处有吸收，这是~键的特征，在 2950-3430 cm -~ 处来自羟基和氨基。V、Vl 和 VII 的 IR 光谱在 2650-1500 cm - 处没有吸收带：对应于 SH 组 [3]，但在 1104-1068 cm -I 处存在强吸收带，这是 ~ 组的特征 [4 ]。定性分析表明存在偶氮甲炔键 [5]。
• Design, synthesis, topoisomerase I & II inhibitory activity, antiproliferative activity, and structure–activity relationship study of pyrazoline derivatives: An ATP-competitive human topoisomerase IIα catalytic inhibitor
  作者：Pervez Ahmad、Hyunjung Woo、Kyu-Yeon Jun、Adnan A. Kadi、Hatem A. Abdel-Aziz、Youngjoo Kwon、A.F.M. Motiur Rahman

  DOI：10.1016/j.bmc.2016.03.017

  日期：2016.4

  A series of pyrazoline derivatives (5) were synthesized in 92–96% yields from chalcones (3) and hydrazides (4). Subsequently, topo-I and IIα-mediated relaxation and antiproliferative activity assays were evaluated for 5. Among the tested compounds, 5h had a very strong topo-I activity of 97% (Camptothecin, 74%) at concentration of 100 μM. Nevertheless, all the compounds 5a–5i showed significant topo

  从查耳酮（3）和酰肼（4）合成了一系列吡唑啉衍生物（5），产率为92–96％。随后，对topo-I和IIα介导的舒张和抗增殖活性测定进行了评估5。在测试的化合物中，浓度为100μM的5h的topo-I活性非常强，为97％（喜树碱，74％）。尽管如此，所有化合物5a – 5i在相同浓度下显示出显着的topo II抑制活性，范围为90-94％（依托泊苷，96％）。在一组三种人类肿瘤细胞系HCT15，BT474和T47D中测试了这些化合物的细胞毒性潜力。所有化合物均在1.9-10.4μM的范围内显示出对HCT15细胞系的强活性，IC 50为（阿霉素23.0；依托泊苷6.9；喜树碱7.1μM）。此外，观察到化合物5c，5f和5i对BT474细胞系具有强的抗增殖活性。由于化合物5d在非常低的IC 50下显示出抗增殖活性，因此5d然后选择了ATP，通过多种ATP竞争测定，ATPase测定和DNA-to
• 신규한 피라졸린 유도체 및 이의 용도
  申请人：Ewha University - Industry Collaboration Foundation 이화여자대학교 산학협력단(220040083301) BRN ▼110-82-10456

  公开号：KR101655697B1

  公开（公告）日：2016-09-08

  본 발명은 신규한 피라졸린 유도체 화합물, 이의 약학적으로 허용가능한 염, 및 상기 피라졸린 유도체 화합물 또는 이의 약학적으로 허용가능한 염을 유효성분으로 포함하는, 암의 예방 또는 치료용 약학적 조성물 및 암의 예방 또는 개선용 식품 조성물에 관한 것이다. 본 발명의 화학식 1로 표시되는 피라졸린 유도체 화합물 또는 이의 약학적으로 허용가능한 염은 토포이소머라제 II, HER2 또는 둘 다의 활성을 억제함으로써 암의 예방 또는 치료에 유용하게 사용될 수 있으며, 또한 HER2 양성 암의 치료제인 허셉틴(Herceptin)에 내성을 나타내는 암의 치료에 적용할 수 있다.

  本发明涉及新的吡拉졸林衍生物化合物，其药学上可接受的盐，以及包含上述吡拉졸林衍生物化合物或其药学上可接受的盐作为有效成分的用于预防或治疗癌症的药学组合物和用于预防或改善癌症的食品组合物。化学式1所示的吡拉졸林衍生物化合物或其药学上可接受的盐可通过抑制Topoisomerase II、HER2或两者的活性来在癌症的预防或治疗中发挥作用，并且可应用于对HERceptin（一种HER2阳性癌症治疗药物）表现出耐药性的癌症的治疗。
• Schiff Bases of Indoline-2,3-dione: Potential Novel Inhibitors of Mycobacterium Tuberculosis (Mtb) DNA Gyrase
  作者：Tarek Aboul-Fadl、Hatem A. Abdel-Aziz、Mohammed K. Abdel-Hamid、Tilal Elsaman、Jane Thanassi、Michael J. Pucci

  DOI：10.3390/molecules16097864

  日期：——

  In the present study a series of Schiff bases of indoline-2,3-dione were synthesized and investigated for their Mtb gyrase inhibitory activity. Promising inhibitory activity was demonstrated with some of these derivatives, which exhibited IC50 values ranging from 50–157 mM. The orientation and the ligand-receptor interactions of such molecules within the Mtb DNA gyrase A subunit active site were investigated applying a multi-step docking protocol using Molecular Operating Environment (MOE) and Autodock4 docking software. The results revealed the importance of the isatin moiety and the connecting side chain for strong interactions with the enzyme active site. Among the tested compounds the terminal aromatic ring benzofuran showed the best activity. Promising new leads for developing a novel class of Mtb gyrase inhibitors were obtained from Schiff bases of indoline-2,3-dione.

  在本研究中，合成了一系列吲哚啉-2,3-二酮的施夫碱，并研究了它们对结核分枝杆菌（Mtb）拓扑异构酶抑制活性。其中一些衍生物显示出良好的抑制活性，IC50值范围为50–157 mM。通过采用多步骤的对接方案，利用分子操作环境（MOE）和Autodock4对接软件，研究了这些分子在Mtb DNA拓扑异构酶A亚基活性位点内的取向和配体-受体相互作用。结果揭示了异羧酸基团及连接侧链在与酶活性位点强相互作用中的重要性。在测试的化合物中，末端芳香环苯并呋喃表现出最佳活性。从吲哚啉-2,3-二酮的施夫碱中获得了开发新型Mtb拓扑异构酶抑制剂的有希望的新线索。