3-(1,5-Dimethyl-4-nitroso-1H-pyrazol-3-yl)-5-methyl-isoxazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(1,5-Dimethyl-4-nitroso-1H-pyrazol-3-yl)-5-methyl-isoxazole
• 英文别名: 3-(1,5-dimethyl-4-nitrosopyrazol-3-yl)-5-methyl-1,2-oxazole
• 化学式: C₉H₁₀N₄O₂
• 分子量: 206.204
• InChiKey: BBEZPFHKFNUTIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  73.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  氰胺 、 3-(1,5-Dimethyl-4-nitroso-1H-pyrazol-3-yl)-5-methyl-isoxazole 在 碘苯二乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以90%的产率得到3-[4-(cyano-NNO-azoxy)-1,5-dimethyl-1H-pyrazol-3-yl]-5-methyl-1,2-oxazole
  参考文献：
  名称：

  Synthesis and in vitro antimicrobial activities of new (cyano-NNO-azoxy)pyrazole derivatives

  摘要：

  The antibacterial and antifungal activity of a series of products, in which the 1,5-dimethyl-4-(cyano-NNO-azoxy)pyrazol-3-yl and 1,3-dimethyl-4-(cyano-NNO-azoxy)pyrazol-5-yl moieties were linked to pyridine, pyrazole, isoxazole, thiophene and the furan ring, were examined. No molecule displayed activity against the Gram-negative bacteria tested. Conversely, some compounds displayed activity against two Staphylococcus aureus strains, including the methicillin resistant strain. All compounds displayed interesting antifungal activity, the most active compound of the series being the thiophene derivative 7a. This compound's activity against Candida krusei and Candida glabrata (MIC = 0.25 and 0.5 mu g/mL, respectively), two fungal species resistant to azoles, is noteworthy. The presence of the cyano function appeared essential for activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.101
• 作为产物：
  描述：

  1-(5-methyl-3-isoxazolyl)-2-hydroxyimino-1,3-butanedione 、 甲基肼 以 乙醇 为溶剂， 以30%的产率得到3-(2,5-Dimethyl-4-nitroso-2H-pyrazol-3-yl)-5-methyl-isoxazole
  参考文献：
  名称：

  新型3-（1-R-3（5）-甲基-4-亚硝基-1H-5（3）-吡唑基）-5-甲基异恶唑的合成及抗菌活性。

  摘要：

  合成了许多新的3-（1-R-3（5）-甲基-4-亚硝基-1H-5（3）-吡唑基）-5-甲基异恶唑6a-g（7b-f），并测试了其抗菌和抑菌活性。抗真菌活性。这些化合物中的一些在非细胞毒性浓度下显示出抗真菌活性。衍生物6c在体外的效价比咪康唑高9倍，对新孢梭菌的选择性高20倍。6c的效力分别比两性霉素B和氟康唑高8倍和125倍。没有一种化合物对细菌具有活性。初步的结构-活性关系（SAR）研究表明，吡唑环第4位的NO基对该活性至关重要。吡唑部分的亲脂性，N-烷基链长和两个杂环的平面性似乎在调节细胞毒性和抗真菌活性中起决定性作用。

  DOI：

  10.1016/s0968-0896(00)00211-x

文献信息

• Synthesis and in vitro antimicrobial activities of new (cyano-NNO-azoxy)pyrazole derivatives
  作者：Donatella Boschi、Stefano Guglielmo、Stefania Aiello、Giulia Morace、Elisa Borghi、Roberta Fruttero

  DOI：10.1016/j.bmcl.2011.03.101

  日期：2011.6

  The antibacterial and antifungal activity of a series of products, in which the 1,5-dimethyl-4-(cyano-NNO-azoxy)pyrazol-3-yl and 1,3-dimethyl-4-(cyano-NNO-azoxy)pyrazol-5-yl moieties were linked to pyridine, pyrazole, isoxazole, thiophene and the furan ring, were examined. No molecule displayed activity against the Gram-negative bacteria tested. Conversely, some compounds displayed activity against two Staphylococcus aureus strains, including the methicillin resistant strain. All compounds displayed interesting antifungal activity, the most active compound of the series being the thiophene derivative 7a. This compound's activity against Candida krusei and Candida glabrata (MIC = 0.25 and 0.5 mu g/mL, respectively), two fungal species resistant to azoles, is noteworthy. The presence of the cyano function appeared essential for activity. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis and antimicrobial activity of new 3-(1-R-3(5)-methyl-4-nitroso-1H-5(3)-pyrazolyl)-5-methylisoxazoles
  作者：Enrico Aiello、Stefania Aiello、Francesco Mingoia、Alessia Bacchi、Giancarlo Pelizzi、Chiara Musiu、Maria Giovanna Setzu、Alessandra Pani、Paolo La Colla、Maria Elena Marongiu

  DOI：10.1016/s0968-0896(00)00211-x

  日期：2000.12

  A number of new 3-(1-R-3(5)-methyl-4-nitroso-1H-5(3)-pyrazolyl)-5-methylisoxazoles 6a-g (7b-f) were synthesized and tested for antibacterial and antifungal activity. Some of these compounds displayed antifungal activity at non-cytotoxic concentrations. Derivative 6c was 9 times more potent in vitro than miconazole and 20 times more selective against C. neoformans. 6c was also 8- and 125-fold more potent

  合成了许多新的3-（1-R-3（5）-甲基-4-亚硝基-1H-5（3）-吡唑基）-5-甲基异恶唑6a-g（7b-f），并测试了其抗菌和抑菌活性。抗真菌活性。这些化合物中的一些在非细胞毒性浓度下显示出抗真菌活性。衍生物6c在体外的效价比咪康唑高9倍，对新孢梭菌的选择性高20倍。6c的效力分别比两性霉素B和氟康唑高8倍和125倍。没有一种化合物对细菌具有活性。初步的结构-活性关系（SAR）研究表明，吡唑环第4位的NO基对该活性至关重要。吡唑部分的亲脂性，N-烷基链长和两个杂环的平面性似乎在调节细胞毒性和抗真菌活性中起决定性作用。