苯并恶唑-2-羧酸酰肼 | 27507-90-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 中文名称: 苯并恶唑-2-羧酸酰肼
• 中文别名: 2-羧酸酰肼苯并恶唑
• 英文名称: benzoxazole-2-carboxylic acid hydrazide
• 英文别名: Benzo[d]oxazole-2-carbohydrazide；1,3-benzoxazole-2-carbohydrazide
• CAS: 27507-90-0
• 化学式: C₈H₇N₃O₂
• mdl: MFCD09701310
• 分子量: 177.162
• InChiKey: VKHNEIIQEKUELV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  81.2
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P264,P270,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P330,P362,P403+P233,P501
• 危险性描述：
  H302,H312,H332
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  苯并恶唑-2-羧酸酰肼 在 五氯化磷 作用下， 以 氯苯 、 甲苯 为溶剂， 生成 N'-[chloro-(4-methoxy-phenyl)-methylene]-benzooxazole-2-carbohydrazonoyl chloride
  参考文献：
  名称：

  Moeller,H., Justus Liebigs Annalen der Chemie, 1971, vol. 749, p. 1 - 11

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氯苯并恶唑 在 盐酸 、 potassium carbonate 、 一水合肼 作用下， 以 甲醇 、 二甲基亚砜 、 异丙醇 为溶剂， 反应 2.0h， 生成 苯并恶唑-2-羧酸酰肼
  参考文献：
  名称：

  Moeller,H., Justus Liebigs Annalen der Chemie, 1971, vol. 749, p. 1 - 11

  摘要：

  DOI：

文献信息

• Discovery of heterocyclic carbohydrazide derivatives as novel selective fatty acid amide hydrolase inhibitors: design, synthesis and anti-neuroinflammatory evaluation
  作者：Yanguo Shang、Qingjing Hao、Kaixuan Jiang、Mengting He、Jinxin Wang

  DOI：10.1016/j.bmcl.2020.127118

  日期：2020.5

  promising target for the development of drugs to treat pain, inflammation, and other central nervous system disorders. Herein, a series of novel heterocyclic carbohydrazide derivatives were firstly designed by the classic scaffold-hopping strategy. Then, multi-steps synthesis and human FAAH enzyme inhibiting activity assays were conducted. Among them, compound 26 showed strong inhibition against human FAAH

  Fatty acid amide hydrolase (FAAH) is a promising target for the development of drugs to treat pain, inflammation, and other central nervous system disorders. Herein, a series of novel heterocyclic carbohydrazide derivatives were firstly designed by the classic scaffold-hopping strategy. Then, multi-steps synthesis and human FAAH enzyme inhibiting activity assays were conducted. Among them, compound
• Synthesis and Screening of Some Novel 2-[5-(Substituted phenyl)-[1,3,4]oxadiazol-2-yl]-benzoxazoles as Potential Antimicrobial Agents
  作者：Hemalatha Gadegoni、Sarangapani Manda、Shivaprasad Rangu

  DOI：10.5012/jkcs.2013.57.2.221

  日期：2013.4.20

  A series of some novel 2-[5-(substituted phenyl)-[1,3,4]oxadiazol-2-yl]-benzoxazoles were synthesized by using benzoxazole-2-carboxylic acid on reaction with thionyl chloride in presence of ethanol solvent at room temperature gave benzoxazole-2-carbonyl chloride, which is turned into benzoxazole-2-carboxylic acid hydrazide on reaction with hydrazine hydrate in ethanol solvent under reflux. The subsequent treatment of benzoxazole-2-carboxylic acid hydrazide with an appropriate aromatic carboxylic acid in presence of polyphosparic acid under reflux afforded the title compounds. The chemical structures of the newly synthesized compounds were elucidated by their IR, $^1H$ NMR and Mass spectral data analysis. Further the compounds are used to find out their ability towards anti microbial and nematicidal activity.

  在乙醇溶剂中，室温下用苯并恶唑-2-羧酸与亚硫酰氯反应，得到苯并恶唑-2-羧酰氯，再与水合肼在乙醇溶剂中回流反应，得到苯并恶唑-2-羧酸酰肼，从而合成了一系列新型 2-[5-（取代苯基）-[1,3,4]恶二唑-2-基]-苯并恶唑。随后，苯并恶唑-2-羧酸酰肼与适当的芳香族羧酸在聚磷酸存在下进行回流处理，便得到了标题化合物。通过红外光谱、$^1H$ NMR 和质谱数据分析，阐明了新合成化合物的化学结构。此外，这些化合物还具有抗微生物和杀线虫的活性。
• Inhibitory effect of benzyl oxazolecarbamate analogues on aldose reductase.
  作者：TSUYOSHI TANIMOTO、HIDEO FUKUDA、TSUTOMU YAMAHA、YOSHIROU OHMOMO、MASUMI NAKAO、CHIAKI TANAKA

  DOI：10.1248/cpb.34.2501

  日期：——

  Twelve kinds of benzyl oxazolecarbamate analogues were tested in vitro for inhibition of aldose reductases, which play a leading role in the etiology of diabetic complications such as cataract, retinopathy and neuropathy. The comparative study of various analogues substituted with a benzylcarbamate group at C-2, C-4 of C-5 of the oxazole skeleton showed that the benzylcarbamate group at the C-2 position was absolutely necessary for potent aldose reductase inhibitory activity.The group at C-4 of C-5 was ineffective. Introduction of an alkyl group at the C-4 position of benzyl 5-phenyl-2-oxazolecarbamate increased the inhibitory activity, and in particular, the 4-isopropyl analogue was found to be a potent inhibitor. The 50% inhibition concentration of benzyl 4-isopropyl-5-phenyl-2-oxazolecarbamate (IV) for aldose reductases Ia and Ib was about 3.5×10-7M, whereas that of benzyl 5-phenyl-2-oxazolecarbamate (I) was about 1.5×10-5M. Inhibition of rabbit lens aldose reductase by compound IV was of a non-competitive type with DL-glyceraldehyde as a substrate. Compound IV appears to be a specific inhibitor of rabbit lens aldose reductase, because it was found to have little inhibitory effect against several other enzymes.

  我们在体外测试了 12 种噁唑氨基甲酸苄酯类似物对醛糖还原酶的抑制作用，醛糖还原酶是白内障、视网膜病变和神经病变等糖尿病并发症的主要病因。对在恶唑骨架的 C-2、C-4 和 C-5 位上被氨基甲酸苄酯基团取代的各种类似物进行的比较研究表明，C-2 位上的氨基甲酸苄酯基团对于强效醛糖还原酶抑制活性是绝对必要的。在 5-苯基-2-恶唑氨基甲酸苄酯的 C-4 位上引入一个烷基可提高抑制活性，尤其是 4-异丙基类似物被发现是一种强效抑制剂。4-isopropyl-5-phenyl-2-oxazolecarbamate 苯甲酯（IV）对醛糖还原酶 Ia 和 Ib 的 50% 抑制浓度约为 3.5×10-7M，而 5--phenyl-2-oxazolecarbamate 苯甲酯（I）的抑制浓度约为 1.5×10-5M。化合物 IV 对以 DL-甘油醛为底物的兔晶状体醛糖还原酶的抑制作用属于非竞争类型。化合物 IV 似乎是兔晶状体醛糖还原酶的特异性抑制剂，因为它对其他几种酶的抑制作用很小。
• Design, synthesis and screening of some novel benzoxazole based 1,3,4-oxadiazoles as potential antimicrobial agents
  作者：Sunil Vodela、Raghu Vardhan Reddy Mekala、Ravinder Reddy Danda、Venkateshwarlu Kodhati

  DOI：10.1016/j.cclet.2013.04.005

  日期：2013.7

  A series of novel 2-(5-substituted-[1,3,4]oxadiazol-2-yl)-benzoxazoles (7a-h) were synthesized in good yields in two different directions by involving benzoxazole-2-carboxylic acid (1) as raw material and benzoxazole-2-carbonyl chloride (2), benzoxazole-2-carboxylic acid methyl ester (3), benzoxazole-2-carboxylic acid hydrazide (4), benzoxazole-2-carboxylic acid N'-acetyl hydrazide (5a-d) and benzoxazole-2-carboxylic acid-ethylidene-hydrazides (6a-d) as reactive intermediates. The chemical structures of all the synthesized compounds were elucidated by their IR, H-1 NMR and C-13 NMR and mass spectral data. Further, the target compounds were screened for their antimicrobial activity against various Gram-positive and Gram-negative bacteria. (C) 2013 Raghu Vardhan Reddy Mekala. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• US4087409A
  申请人：——

  公开号：US4087409A

  公开（公告）日：1978-05-02