N-hydroxybenzo[d]oxazole-2-carbimidoyl cyanide | 75408-39-8

• 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: N-hydroxybenzo[d]oxazole-2-carbimidoyl cyanide
• 英文别名: α-oximino-(2-benzoxazolyl)acetonitrile；2-(hydroximido)-2-benzoxazoleacetonitrile；H(BOCO)；alpha-[Benzoxazol-2-yl]-alpha-oximino-acetonitrile；2-(1,3-benzoxazol-2-yl)-2-hydroxyiminoacetonitrile
• CAS: 75408-39-8
• 化学式: C₉H₅N₃O₂
• 分子量: 187.158
• InChiKey: UWOYEYQTKGFFFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 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：
  82.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-hydroxybenzo[d]oxazole-2-carbimidoyl cyanide 、 potassium carbonate 以 乙醇 、 水 为溶剂， 生成 2-(oximido)-2-benzoxazoleacetonitrile potassium
  参考文献：
  名称：

  Light Insensitive Silver(i) Cyanoximates As Antimicrobial Agents For Indwelling Medical Devices

  摘要：

  本研究合成并使用光谱方法和X射线分析表征了AgL配合物（其中L=NC—C(NO)—R，R为电子吸引基团：—CN，—C（O）NR2，—C（O）R'（烷基），—C（O）OEt，2-杂环芳基片段，如2-吡啶基，2-苯并咪唑基，2-苯并噁唑基，2-苯并噻唑基）。合成的化合物还表现出对可见光和紫外辐射的显著不敏感性。这些化合物的综合特性，如光不敏感性，水溶性差，高热稳定性，有机配体的无毒性和抗微生物活性，使得这些银（I）氰酰肟化合物适用于生物材料和医疗器械。

  公开号：

  US20130096098A1
• 作为产物：
  描述：

  1,3-苯并噁唑-2-乙腈 在 溶剂黄146 、 sodium nitrite 作用下， 反应 12.0h， 以83%的产率得到N-hydroxybenzo[d]oxazole-2-carbimidoyl cyanide
  参考文献：
  名称：

  苯并杂环肟氨基甲酸酯对结核分枝杆菌有活性：合成、结构-活性关系、代谢和生物学分类

  摘要：

  筛选抗结核分枝杆菌( Mtb )的小极性分子文库，鉴定了有效的苯并杂环肟氨基甲酸酯系列。该系列经历了以构效关系研究为基础的药物化学进展，以确定用于概念验证研究的化合物并定义先导优化策略。在肝微粒体中具有良好稳定性且无 hERG 通道抑制倾向的氨基甲酸酯和游离肟领先化合物被鉴定并在体内评估了药代动力学特性。山地车介导的渗透和代谢研究表明氨基甲酸酯充当前药。为了阐明作用机制，在生物学分类试验中测试了选定的化合物，以评估它们对已知混杂靶标的活性。综上所述，这些数据表明这些抗结核药物有一种新颖但未知的作用模式。

  DOI：

  10.1021/acs.jmedchem.1c00707

文献信息

• Benz(2-heteroaryl)cyanoximes and their Tl(i) complexes: new room temperature blue emitters
  作者：Olesya T. Ilkun、Stephen J. Archibald、Charles L. Barnes、Nikolay Gerasimchuk、Richard Biagioni、Svitlana Silchenko、Olga A. Gerasimchuk、Victor N. Nemykin

  DOI：10.1039/b803846e

  日期：——

  A series of five 2-heteroarylcyanoximes such as: α-oximino-(2-benzimidazolyl)acetonitrile (HBIHCO), α-oximino-(N-methy-l-2-benzimidazolyl)acetonitrile (HBIMCO), α-oximino-(2-benzoxazolyl)acetonitrile (HBOCO), α-oximino-(2-benzothiazolyl)acetonitrile (HBTCO) and α-oximino-(2-quinolyl)acetonitrile (HQCO) and their monovalent thallium(I) complexes were synthesized and characterized using spectroscopic methods (1H, 13C NMR, IR, UV-visible, mass-spectrometry) and X-ray analysis. The HBIMCO (as monohydrate) adopts planar trans-anti configuration in the solid state. The crystal structure of “HBOCO” revealed the presence of nitroso anion a, BOCO−, and protonated oxime cation b, H2BOCO+, that form a H-bonded dimer in the unit cell. Both molecules adopt planar structures, but different configurations: cis-anti in the molecule a, and trans-anti for b. This is the first reported case of a zwitterionic pair in oximes and the coexistence of the two geometrical cis/trans isomers in the same crystal. All 2-heteroarylcyanoximes form yellow anions upon deprotonation, which exhibit significant negative solvatochromism in solution. Heterogeneous reactions between hot aqueous solutions of Tl2CO3 and solid protonated 2-heteroarylcyanoximes HL afford yellow TlL. The crystal structure of Tl(BTCO) shows the formation of centrosymmetrical dimers, which connect with each other to form a double-stranded one-dimensional coordination polymer. The oxygen atom of the oxime group acts as a bridge between the three different Tl(I) centers. The anion is non-planar and adopts a trans-anti configuration in the complex. The polymeric motif in the complex represents a ladder-type structure. Staggered π–π interactions between benzothiazolyl groups provide additional stabilization of the structure. Both organic ligands and their Tl(I) complexes exhibit strong room temperature blue emission in the solid state.

  合成了一系列五种2-杂芳腈氧肟酸，包括：α-氧肟基-(2-苯并咪唑基)乙腈（HBIHCO）、α-氧肟基-(N-甲基-2-苯并咪唑基)乙腈（HBIMCO）、α-氧肟基-(2-苯并噻唑基)乙腈（HBTCO）和α-氧肟基-(2-喹啉基)乙腈（HQCO）以及它们的单价铊(I) комплексы。采用光谱方法（1H、13C NMR、红外、紫外可见、质谱）和X射线分析对其进行了表征。HBIMCO（作为单水合物）在固态中采用平面反式反式构型。“HBOCO”的晶体结构揭示了存在亚硝基阴离子a（BOCO−）和质子化的氧肟阳离子b（H2BOCO+），它们在单元胞中形成氢键二聚体。这两种分子均采用平面结构，但配置不同：分子a为顺反构型，而b为反式反式构型。这是首次报告在氧肟中发现了两亲离子对，并且同一晶体中共存的两种几何顺/反异构体。所有2-杂芳腈氧肟酸在去质子化后形成黄色阴离子，在溶液中表现出显著的负溶剂色变效应。在Tl2CO3的热水溶液与固态质子化2-杂芳腈氧肟酸HL之间发生的非均相反应生成黄色的TlL。Tl(BTCO)的晶体结构显示形成了中心对称的二聚体，这些二聚体相互连接形成双链一维配位聚合物。氧肟基团的氧原子在三个不同的铊(I)中心之间起桥接作用。该阴离子在复合物中是非平面的，并采用反式反式构型。复杂中的聚合物结构呈现梯子型结构。苯并噻唑基之间错叠的π–π相互作用为结构提供了额外的稳定性。无论是有机配体还是它们的Tl(I)复合物在固态下均表现出强烈的室温蓝色发光。
• Thiadiazolyl-glyoxylonitrile-2-oxime ether derivatives for protecting
  申请人：Ciba-Geigy Corporation

  公开号：US04715883A1

  公开（公告）日：1987-12-29

  A process for protecting cultivated plants against aggressive agricultural chemicals is described in which oxide derivatives of the formula ##STR1## are used as antidotes. Either the cultivated area for the cultivated plants or the cultivated plants themselves or parts of the plant (seeds, tubers, stem parts, and the like), as desired, can be treated with these oxide derivatives, which are used as a dressing.

  本发明描述了一种保护耕作植物免受侵蚀性农业化学品的过程，其中使用式为##STR1##的氧化物衍生物作为解毒剂。可以将这些氧化物衍生物作为外衣剂处理耕作植物的耕作区域、耕作植物本身或植物的部分（种子、块茎、茎部等），根据需要进行处理。
• Benzoxazolyl-glyoxylonitrile-2-oxime ether derivatives
  申请人：Ciba-Geigy Corporation

  公开号：US04347372A1

  公开（公告）日：1982-08-31

  A process for protecting cultivated plants against aggressive agricultural chemicals is described in which oxime derivatives of the formula ##STR1## are used as antidotes. Either the cultivated area for the cultivated plants or the cultivated plants themselves or parts of the plant (seeds, tubers, stem parts and the like), as desired, can be treated with these oxime derivatives, which are used as a dressing.

  本发明涉及一种保护栽培植物免受侵害性农业化学品的方法，其中使用式为##STR1##的肟衍生物作为解毒剂。可以将栽培区域、栽培植物本身或植物的部分（种子、块茎、茎部等）按需用这些肟衍生物进行处理，作为一种覆盖剂。
• Light Insensitive Silver(I) Cyanoximates As Antimicrobial Agents for Indwelling Medical Devices
  作者：Nikolay Gerasimchuk、Andrzej Gamian、Garrett Glover、Bogumila Szponar

  DOI：10.1021/ic100830x

  日期：2010.11.1

  Ten silver(I) cyanoximates of AgL composition (L = NC-C(NO)-R, where R is electron withdrawing groups: -CN, -C(O)NR2, -C(O)R' (alkyl), -C(O)OEt, 2-heteroaryl fragments such as 2-pyridyl, 2-benzimidazolyl, 2-benzoxazolyl, 2-benzthiazolyl) were synthesized and characterized using spectroscopic methods and X-ray analysis. Crystal structures of four complexes were determined and revealed the formation of two-dimensional (2D) coordination polymers of different complexity in which anions exhibit bridging or combined chelate and bridging binding modes. In these compounds, anions are in the nitroso form. All studied AgL complexes are sparingly soluble in water and are thermally stable to 150 degrees C Synthesized compounds demonstrated remarkable insensitivity toward visible light and UV-radiation, which was explained based on their polymeric structures with multiple covalent bonds between bridging cyanoxime ligands and Ag(I) centers. All 10 silver(I) cyanoximates were tested in vitro on the subject of their antimicrobial activity against both Gram-positive and Gram-negative microorganisms such as Escherichia coli, Klebsiella pneumoniae, Proteus sp., Pseudomonas aeruginosa, Enterococcus hirae, Streptococcus mutans, Staphylococcus aureus, and Mycobacterium fortuitum as well as against Candida albicans in solutions, and in the solid state as pressed pellets and dried filter paper disks presoaked with solutions of AgL in DMF. Results showed pronounced antimicrobial activity for all investigated complexes. A combination of five factors: (1) light insensitivity, (2) poor water solubility, (3) high thermal stability, (4) lack of toxicity of organic ligands, and (5) in vitro antimicrobial activity allows development of silver(I) cyanoximates for medical applications. These include antimicrobial additives to acrylate glue, cured by UV-radiation, used in introduction of prosthetic joints and dental implants, and prevention of biofilm formation on several types of indwelling medical devices.