1-benzylimidazole-2-carboxaldehyde oxime | 10045-64-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-benzylimidazole-2-carboxaldehyde oxime
• 英文别名: 1-benzyl-2-imidazolecarbaldehyde oxime；1-benzylimidazole-2-carbaldehyde oxime；1-benzyl-1H-imidazole-2-carbaldehyde oxime；1-benzyl-2-imidazolylcarbaldoxime；1-Benzyl-imidazol-2-carbaldehyd-oxim；N-Benzyl-2-imidazolcarbaldehyd-oxim；1H-Imidazole-2-carboxaldehyde, 1-(phenylmethyl)-, oxime；N-[(1-benzylimidazol-2-yl)methylidene]hydroxylamine
• CAS: 10045-64-4
• 化学式: C₁₁H₁₁N₃O
• 分子量: 201.228
• InChiKey: ZURFKEMTJOYRFN-UHFFFAOYSA-N

物化性质

• 熔点：
  167 °C
• 沸点：
  443.1±38.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933290090

反应信息

• 作为反应物：
  描述：

  1-benzylimidazole-2-carboxaldehyde oxime 在 ammonium chloride 作用下， 以 N-甲基乙酰胺 、 水 为溶剂， 生成 苯替马唑
  参考文献：
  名称：

  Novel derivatives of imidazole, and pharmaceutical compositions

  摘要：

  一种由公式（I）和（II）中的其中一个组成的化合物，其中R.sup.1代表从以下组中选择的基团：氢、含有最多6个碳原子的烷基，未取代或被取代为含有最多4个碳原子的烷氧基和苯基烷氧基中至少一种基团; 芳基或芳基烷基，烷基部分含有1至4个碳原子，未取代或被取代为含有最多4个碳原子的烷基、烷氧基和卤代烷基、卤素和硝基中至少一种取代基; 含有最多2个由O、N和S选择的杂原子的5-或6-成员杂芳环，其中最多一个与氮不同; 含有1至4个碳原子的烷基基团，被这样的杂芳环取代; R.sup.2和R.sup.3，相同或不同，各代表一个氢原子或，含有最多4个碳原子的烷基，未取代或被取代为含有最多4个碳原子的烷基、烷氧基和卤代烷基、卤素和硝基中至少一种取代基; R.sup.2和R.sup.3结合在一起时，或者代表一个未取代或被取代为含有最多4个碳原子的烷基、烷氧基和卤代烷基、卤素和硝基中至少一种取代基的--CH.dbd.CH--CH.dbd.CH--基团; R.sup.4选自氢、烷基、芳基和芳基烷基，每个烷基部分含有最多4个碳原子; A代表单键或含有1至6个碳原子的烷基; 但R.sup.1不是氢原子或甲基基团，当A代表单键且R.sup.2和R.sup.3结合在一起代表一个未取代的--CH.dbd.CH--CH.dbd.CH--基团时; 其生理上可接受的盐，其合成方法以及含有它的药物组合物。

  公开号：

  US04152440A1
• 作为产物：
  描述：

  1-苄基-1H-咪唑-2-甲醛 在 盐酸羟胺 、 sodium acetate 作用下， 以 水 为溶剂， 反应 0.17h， 以75%的产率得到1-benzylimidazole-2-carboxaldehyde oxime
  参考文献：
  名称：

  Some benzyl-substituted imidazoles, triazoles, tetrazoles, pyridinethiones, and structural relatives as multisubstrate inhibitors of dopamine .beta.-hydroxylase. 4. Structure-activity relationships at the copper binding site

  摘要：

  Structure-activity relationships (SAR) were determined for novel multisubstrate inhibitors of dopamine beta-hydroxylase (DBH; EC 1.14.17.1) by examining the effects upon in vitro inhibitory potencies resulting from structural changes at the copper-binding region of inhibitor. Attempts were made to determine replacement groups for the thione sulfur atom of the prototypical inhibitor 1-(4-hydroxybenzyl)imidazole-2-thione described previously. The synthesis and evaluation of oxygen and nitrogen analogues of the soft thione group demonstrated the sulfur atom to be necessary for optimal activity. An additional series of imidazole-2-thione relatives was prepared in an effort to probe the relationship between the pKa of the ligand group and inhibitory potency. In vitro inhibitory potency was shown not to correlate with ligand pKa over a range of approximately 10 pKa units, and a rationale for this is advanced. Additional ligand modifications were prepared in order to explore bulk tolerance at the enzyme oxygen binding site and to determine the effects of substituting a six-membered ligand group for the five-membered imidazole-2-thione ligand.

  DOI：

  10.1021/jm00164a051

文献信息

• Mechanochemical and Conformational Study of N-heterocyclic Carbonyl-Oxime Transformations
  作者：Ines Primožič、Tomica Hrenar、Krešimir Baumann、Lucija Krišto、Ivan Križić、Srđanka Tomić

  DOI：10.5562/cca2476

  日期：——

  New mechanochemical pathways for the transformation of six N-heterocyclic carbonyl compounds into oximes using hydroxylamine hydrochloride were explored. Reactions were performed first without any base since the heterocyclic moieties (imidazole, benzimidazole, pyridine and quinuclidine) have an intrinsic basic nitrogen atom. This green, solvent free method was suitable for all compounds (up to quantitative yields) except for N-benzyl substituted imidazole and bertzimidazole-2-carbaldehyde. For the slower reacting aldehydes, reactions with liquid assisted grinding and addition of sodium hydroxide were performed as well. Conformational analysis and quantum-chemical calculations revealed steric and electronic reasons for the lower reactivity of N-benzyl substituted derivatives.
• Synthesis and antimicrobial profile of N-substituted imidazolium oximes and their monoquaternary salts against multidrug resistant bacteria
  作者：Renata Odžak、Mirjana Skočibušić、Ana Maravić

  DOI：10.1016/j.bmc.2013.09.041

  日期：2013.12

  Two different series of N-substituted imidazolium oximes and their monoquaternary salts were synthesized and biologically tested with respect to their ability to inhibit growth a diverse panel of antibiotic susceptible Gram-positive and antibiotic resistant Gram-negative bacteria as well fungal strains. The newly synthesized compounds were analyzed by spectral studies to confirm their structure. The preliminary results showed that all compounds tested possess promising antimicrobial potential against both susceptible Gram-positive and antibiotic resistant Gram-negative isolates, exhibiting a wide range of MIC values from 0.14 to 100.0 mu g/mL. The structure-activity relationship demonstrates that the p-methylphenyl and p-fluorophenyl groups in monoquaternary salts 6 and 7 attached directly to the imidazolium ring could be essential for observed remarkable inhibitory profiles against clinically important pathogens Pseudomonas aeruginosa (MIC = 0.14 mu g/mL) and Klebsiella pneumoniae (MIC = 1.56 mu g/mL). Furthermore, the broth microdilution assay was then used to investigate the antiresistance efficacy of compound 7 against fourteen extended-spectrum beta-lactamase (ESBL)-producing strains in comparison to eight clinically relevant antibiotics. Compound 7 exhibited a remarkable antiresistance profiles ranging between 0.39 and 12.50 mu g/mL against all of ESBL-producing strains, which leads to the suggestion that may be interesting candidate for development of new antimicrobials to combat multidrug resistant Gram-negative bacteria. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis and Ocular Effects of Imidazole Nitrolic Acids
  作者：Larisa Oresmaa、Hanna Kotikoski、Matti Haukka、Johanna Salminen、Olli Oksala、Esko Pohjala、Eeva Moilanen、Heikki Vapaatalo、Pirjo Vainiotalo、Paula Aulaskari

  DOI：10.1021/jm048949+

  日期：2005.6.1

  Novel 1-R-imidazole-2-nitrolic acids and 1-R-imidazole-5-nitrolic acids (R: H, Me, Bn) were synthesized from oximes by treatment with a mixture of fuming nitric acid and acetic acid. The effects of these potential nitric oxide-donating compounds were tested on ocular variables such as intraocular pressure and formation of cyclic guanosine-3,5 '-monophosphate in the incubation of porcine iris-ciliary body.