1-(2-Hydroxy-ethyl)-2-nitramino-2-imidazolin | 6266-34-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-(2-Hydroxy-ethyl)-2-nitramino-2-imidazolin
• 英文别名: 2-(2-nitroamino-4,5-dihydro-imidazol-1-yl)-ethanol；2-(2-Nitroamino-4,5-dihydro-imidazol-1-yl)-aethanol；(NZ)-N-[1-(2-hydroxyethyl)imidazolidin-2-ylidene]nitramide
• CAS: 6266-34-8
• 化学式: C₅H₁₀N₄O₃
• 分子量: 174.159
• InChiKey: QDUKYHGZHDVSQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-Hydroxy-ethyl)-2-nitramino-2-imidazolin 在 氯化亚砜 作用下， 生成 1-benzyl-2,3,5,6-tetrahydro-1H-imidazo[1,2-a]imidazole
  参考文献：
  名称：

  A New Molecular Rearrangement Involving Carbonium Ions¹

  摘要：

  DOI：

  10.1021/ja01583a065
• 作为产物：
  描述：

  1-甲基-3-硝基-1-亚硝基胍 、 羟乙基乙二胺 生成 1-(2-Hydroxy-ethyl)-2-nitramino-2-imidazolin
  参考文献：
  名称：

  A New Molecular Rearrangement Involving Carbonium Ions¹

  摘要：

  DOI：

  10.1021/ja01583a065

文献信息

• PREPARATION OF SUBSTITUTED NITROGUANIDINES AND THE CYCLIZATION OF N-γ-NITROXYBUTYL-N′-NITROGUANIDINE
  作者：A. F. Mckay、H. P. Thomas

  DOI：10.1139/v51-047

  日期：1951.5.1

  Several new substituted nitroguanidines were prepared by the reaction of amines with N-methyl-N-nitroso-N′-nitroguanidine. N-γ-Nitroxybutyl-N′-nitroguanidine was cyclized to 1-nitro-2-amino-6-methyl-Δ²-tetrahydropyrimidinium nitrate by refluxing in water.

  通过氨基与N-甲基-N-亚硝基-N'-硝基胍反应制备了几种新的取代硝基胍。N-γ-硝基丁基-N'-硝基胍在水中回流后环化为1-硝基-2-氨基-6-甲基-Δ2-四氢嘧啶钠盐。
• CYCLIC THIOUREAS
  作者：A. F. McKay、G. R. Vavasour

  DOI：10.1139/v54-010

  日期：1954.2.1

  1-β-Hydroxyethylimidazolidine-2-thione was prepared from 1-amino-5-hydroxy-3-azapentane and carbon disulphide. Since its properties differ from those claimed by Sergeyev and Kolychev (7) for this compound prepared from ethylene oxide and thiocyanic acid, its structure was confirmed by conversion to 1-β-hydroxyethyl-2-benzylamino-2-imidazoline. The latter compound was prepared for comparison from the known 1-β-hydroxyethyl-2-nitramino-2-imidazoline.

  1-β-羟乙基咪唑啉-2-硫酮是由1-氨基-5-羟基-3-氮杂戊烷和二硫化碳制备而成的。由于其性质与Sergeyev和Kolychev（7）声称由乙烯氧和硫氰酸制备的该化合物有所不同，因此通过转化为1-β-羟乙基-2-苄基氨基咪唑啉来确认其结构。后一化合物用于与已知的1-β-羟乙基-2-硝基氨基咪唑啉进行比较而制备。
• The activity of 14-hydroxy clarithromycin, alone and in combination with clarithromycin, against penicillin- and erythromycin-resistant Streptococcus pneumoniae
  作者：S. J. Martin、C. G. Garvin、C. R. McBurney、E. G. Sahloff

  DOI：10.1093/jac/47.5.581

  日期：2001.5.1

  There are no data regarding the activity of clarithromycin's active metabolite, 14-hydroxy clarithromycin, against penicillin-intermediate, penicillin-resistant or erythromycin-resistant Streptococcus pneumoniae. Agar dilution MICs were determined for clarithromycin, 14-hydroxy clarithromycin (henceforth called ‘metabolite’), azithromycin, erythromycin and clarithromycin/metabolite (2:1 and 1:1 ratio) against 24 penicillin-intermediate and 14 penicillin-resistant strains, including 13 erythromycin-resistant clinical strains and one ATCC strain of S. pneumoniae. The interaction between clarithromycin and its metabolite was determined using an agar chequerboard assay against all isolates, and time–kill tests were performed against five penicillin-intermediate (macrolide-susceptible) and five penicillin-resistant (two macrolide-resistant) strains of S. pneumoniae using all antibiotics alone at simulated peak serum concentrations, and clarithromycin/metabolite in a 2:1 ratio (physiological). MICs were as follows: clarithromycin, 0.008–>64 mg/L; metabolite, 0.015–>64 mg/L; erythromycin, 0.015–>64 mg/L; azithromycin, 0.125–>64 mg/L; clarithromycin/metabolite (1:1 and 2:1 combinations), 0.001–>64 mg/L. The MIC of the clarithromycin/metabolite combination was one or more tube dilution lower than the MIC of clarithromycin in 28 of the isolates tested. In chequerboard testing, 13 strains (seven erythromycin susceptible and six erythromycin resistant) demonstrated synergy, 18 additivity and seven indifference. In time–kill testing, bacterial eradication below detection limits occurred with clarithromycin and metabolite in seven of 10 organisms. The combination of parent and metabolite was more rapidly bactericidal than clarithromycin alone in six of the seven isolates (P = 0.026). The metabolite has potent activity against S. pneumoniae and enhances the activity of the parent compound against this organism. The metabolite's activity must be considered in evaluating clarithromycin in vitro to avoid underestimation of clarithromycin's activity against the pneumococcus.

  目前还没有关于克拉霉素的活性代谢物 14-羟基克拉霉素对青霉素中度耐药、青霉素耐药或红霉素耐药肺炎链球菌的活性的数据。测定了克拉霉素、14-羟基克拉霉素（以下称为 "代谢物"）、阿奇霉素、红霉素和克拉霉素/代谢物（2:1 和 1:1 比率）对 24 株青霉素中型菌株和 14 株青霉素耐药菌株（包括 13 株红霉素耐药临床菌株和 1 株 ATCC 肺炎链球菌菌株）的琼脂稀释 MIC。使用琼脂棋盘试验测定了克拉霉素及其代谢物与所有分离株之间的相互作用，并对 5 株青霉素中级（对大环内酯类药物敏感）和 5 株青霉素耐药（对两种大环内酯类药物耐药）的肺炎双球菌进行了时间致死试验，在模拟血清峰值浓度下单独使用所有抗生素，克拉霉素/代谢物的比例为 2:1（生理学）。MIC 值如下：克拉霉素，0.008->64 毫克/升；代谢物，0.015->64 毫克/升；红霉素，0.015->64 毫克/升；阿奇霉素，0.125->64 毫克/升；克拉霉素/代谢物（1:1 和 2:1 组合），0.001->64 毫克/升。在测试的 28 个分离株中，克拉霉素/代谢物组合的 MIC 比克拉霉素的 MIC 低一个或多个试管稀释度。在棋盘试验中，13 株菌株（7 株对红霉素敏感，6 株对红霉素耐药）显示出协同作用，18 株显示出相加作用，7 株显示出不相干作用。在时间杀灭试验中，使用克拉霉素和代谢物的 10 种生物中有 7 种的细菌根除率低于检测限。与单用克拉霉素相比，母体和代谢物的组合对七种分离菌中的六种的杀菌速度更快（P = 0.026）。代谢物对肺炎双球菌有很强的活性，并能增强母体化合物对该病菌的活性。在对克拉霉素进行体外评估时，必须考虑代谢物的活性，以避免低估克拉霉素对肺炎球菌的活性。
• A New Molecular Rearrangement. II. Confirmation of Structures and Extension of the Rearrangement Reaction
  作者：A. F. McKay、W. G. Hatton、R. O. Braun

  DOI：10.1021/ja01604a052

  日期：1956.12
• A New Molecular Rearrangement Involving Carbonium Ions¹
  作者：A. F. McKay、J. R. Gilpin

  DOI：10.1021/ja01583a065

  日期：1956.1