2-hydrazino-5-methyl-1,3-benzoxazole | 933945-38-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: 2-hydrazino-5-methyl-1,3-benzoxazole
• 英文别名: (5-Methyl-1,3-benzoxazol-2-yl)hydrazine
• CAS: 933945-38-1
• 化学式: C₈H₉N₃O
• 分子量: 163.179
• InChiKey: NOPLRCBLGNBVRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  64.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-hydrazino-5-methyl-1,3-benzoxazole 在 sodium hydroxide 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 0.5h， 生成 N-[2-cyanoethyl-(5-methyl-1,3-benzoxazol-2-yl)amino]formamide
  参考文献：
  名称：

  3-[1-(2-Benzoxazolyl)hydrazino]propanenitrile derivatives: inhibitors of immune complex induced inflammation

  摘要：

  3-[1-(2-Benzoxazolyl)hydrazino]propanenitrile derivatives were evaluated in the dermal and pleural reverse passive Arthus reactions in the rat. In the pleural test these compounds were effective in reducing exudate volume and accumulation of white blood cells. This pattern of activity was similar to that of hydrocortisone and different from that of indomethacin. The structural requirements for inhibiting the Arthus reactions were studied by systematic chemical modification of 1. These structure-activity relationship studies revealed that nitrogen 1' of the hydrazino group is essential for activity and must be electron rich, whereas chemical modifications of other sites of 1 had only a modest effect on activity.

  DOI：

  10.1021/jm00117a010
• 作为产物：
  描述：

  邻氨基对甲苯酚 在 hydrazine hydrate 、 potassium carbonate 、 potassium hydroxide 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 14.0h， 生成 2-hydrazino-5-methyl-1,3-benzoxazole
  参考文献：
  名称：

  苯并恶唑相关苯并噻嗪-4-酮的合成及其体外和计算机抗菌、抗氧化活性

  摘要：

  在本研究中，一系列3-[(5-甲基-1,3-苯并恶唑-2-基)氨基]-2-苯基-2,3-二氢-4H-1,3-苯并噻嗪-4-酮( 6a-n) 是通过元素、FT-IR、1H 和 13C NMR 以及 LC-MS 研究合成和阐明的。以四环素为参考标准，对枯草芽孢杆菌、金黄色葡萄球菌、表皮葡萄球菌等革兰氏阳性菌和大肠杆菌、铜绿假单胞菌等革兰氏阴性菌进行体外抗菌筛选。通过与氟康唑作为参考标准进行比较，评估了对不同真菌菌株（即米曲霉、黑曲霉、黄曲霉、白色念珠菌和酿酒酵母）的抗真菌活性。化合物 6b、6c、6e、6j、6m 和 6n 成为高效抗菌剂。合成部分的 DPPH 自由基清除测定显示出与标准抗坏血酸相当的良好抗氧化效力。所有活性构象类似物的标题化合物与目标蛋白（PDB ID 2XCT-抗菌、PDB ID 1IYL-抗真菌、PDB ID 2HCK-抗氧化剂）的分子对接模拟研究在得分最高的姿势中表现出

  DOI：

  10.14233/ajchem.2021.22964

文献信息

• Synthesis of Benzoxazole Associated Benzothiazine-4-ones and their in vitro and in silico Antimicrobial, Antioxidant Activities
  作者：T.R. Padmini、H.M. Vagdevi、Usha Jinendra

  DOI：10.14233/ajchem.2021.22964

  日期：——

  of the synthesized moieties showed good antioxidant potency comparable to standard ascorbic acid. The molecular docking simulation studies of all the title compounds in their active conformation analogues with target proteins (PDB ID 2XCT-antibacterial, PDB ID 1IYL-antifungal, PDB ID 2HCK- antioxidant) exhibited good binding interactions in top scoring poses. The pharmacokinetic properties prediction

  在本研究中，一系列3-[(5-甲基-1,3-苯并恶唑-2-基)氨基]-2-苯基-2,3-二氢-4H-1,3-苯并噻嗪-4-酮( 6a-n) 是通过元素、FT-IR、1H 和 13C NMR 以及 LC-MS 研究合成和阐明的。以四环素为参考标准，对枯草芽孢杆菌、金黄色葡萄球菌、表皮葡萄球菌等革兰氏阳性菌和大肠杆菌、铜绿假单胞菌等革兰氏阴性菌进行体外抗菌筛选。通过与氟康唑作为参考标准进行比较，评估了对不同真菌菌株（即米曲霉、黑曲霉、黄曲霉、白色念珠菌和酿酒酵母）的抗真菌活性。化合物 6b、6c、6e、6j、6m 和 6n 成为高效抗菌剂。合成部分的 DPPH 自由基清除测定显示出与标准抗坏血酸相当的良好抗氧化效力。所有活性构象类似物的标题化合物与目标蛋白（PDB ID 2XCT-抗菌、PDB ID 1IYL-抗真菌、PDB ID 2HCK-抗氧化剂）的分子对接模拟研究在得分最高的姿势中表现出
• N1-Hetaryl Substituted Pyridine- and Pyrazinecarboxamidrazones with Antimycobacterial Activity
  作者：Donald Ranft、Gudrun Lehwark-Yvetot、Klaus-Jürgen Schaper、Axel Büge

  DOI：10.1002/ardp.19973300603

  日期：——

  A series of amidrazones was prepared and characterized by 1H NMR and mass spectroscopy. The substances were tested against M. tuberculosis, M. avium, M. intracellulare, and M. lufu. Compounds 11–13 exhibit a satisfactory inhibition of mycobacteria.

  制备了一系列脒腙并通过 1 H NMR 和质谱进行表征。这些物质针对结核分枝杆菌、鸟分枝杆菌、胞内分枝杆菌和鲁弗分枝杆菌进行了测试。化合物11-13表现出令人满意的分枝杆菌抑制作用。
• HAVIV, FORTUNA;RATAJCZYK, JAMES D.;DENET, ROBERT W.;KERDESKY, FRANCIS A.;+, J. MED. CHEM., 31,(1988) N 9, C. 1719-1728
  作者：HAVIV, FORTUNA、RATAJCZYK, JAMES D.、DENET, ROBERT W.、KERDESKY, FRANCIS A.、+

  DOI：——

  日期：——
• 3-[1-(2-Benzoxazolyl)hydrazino]propanenitrile derivatives: inhibitors of immune complex induced inflammation
  作者：Fortuna Haviv、James D. Ratajczyk、Robert W. DeNet、Francis A. Kerdesky、Roland L. Walters、Steven P. Schmidt、James H. Holms、Patrick R. Young、George W. Carter

  DOI：10.1021/jm00117a010

  日期：1988.9

  3-[1-(2-Benzoxazolyl)hydrazino]propanenitrile derivatives were evaluated in the dermal and pleural reverse passive Arthus reactions in the rat. In the pleural test these compounds were effective in reducing exudate volume and accumulation of white blood cells. This pattern of activity was similar to that of hydrocortisone and different from that of indomethacin. The structural requirements for inhibiting the Arthus reactions were studied by systematic chemical modification of 1. These structure-activity relationship studies revealed that nitrogen 1' of the hydrazino group is essential for activity and must be electron rich, whereas chemical modifications of other sites of 1 had only a modest effect on activity.
• Novel promising benzoxazole/benzothiazole‐derived immunomodulatory agents: Design, synthesis, anticancer evaluation, and in silico ADMET analysis
  作者：Hazem Elkady、Khaled El‐Adl、Helmy Sakr、Adel S. Abdelraheem、Sally I. Eissa、Mohamed Ayman El‐Zahabi

  DOI：10.1002/ardp.202300097

  日期：2023.9

  synthesized to obtain new effective antitumor immunomodulatory agents. The synthesized compounds were evaluated for their cytotoxic activities against HepG-2, HCT-116, PC3, and MCF-7 cells. Generally, the open analogs with semicarbazide and thiosemicarbazide moieties (10, 13a–c, 14, and 17a,b) exhibited higher cytotoxic activities than derivatives with closed glutarimide moiety (8a–d). In particular, compound

  设计并合成了11种新型苯并恶唑/苯并噻唑基沙利度胺类似物，以获得新的有效抗肿瘤免疫调节剂。评估了合成化合物对 HepG-2、HCT-116、PC3 和 MCF-7 细胞的细胞毒活性。一般来说，具有氨基脲和氨基硫脲部分的开放类似物（10、13a -c、14和17a,b ）比具有封闭戊二酰亚胺部分的衍生物（8a-d）表现出更高的细胞毒性活性。特别是，化合物13a（针对 HepG-2、HCT-116、PC3 和 MCF-7 的 IC 50 分别为 6.14、5.79、10.26 和 4.71 µM）和 14（IC 50 =  7.93、8.23、12.37 和 5.43） µM）对四种测试细胞系表现出最高的抗癌活性。进一步评估了最具活性的化合物13a和14对肿瘤坏死因子-α (TNF-α)、caspase-8 (CASP8)、血管内皮生长因子 (VEGF) 和核因子 kappa-B p65 的体外免疫调节活性HCT-116