ethyl 3-(5-phenyl-1H-tetrazol-1-yl)propanoate | 36855-20-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 3-(5-phenyl-1H-tetrazol-1-yl)propanoate
• 英文别名: 3-(5-phenyl-tetrazol-1-yl)-propionic acid ethyl ester；ethyl 3-(5-phenyltetrazol-1-yl)propionate；Ethyl 3-(5-phenyltetrazol-1-yl)propanoate
• CAS: 36855-20-6
• 化学式: C₁₂H₁₄N₄O₂
• 分子量: 246.269
• InChiKey: CZLFETNYBZNBIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  69.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-phenyltetrazole anion 、 3-氯丙酸乙酯 在 四丁基高氯酸铵 作用下， 以 乙腈 为溶剂， 生成 ethyl 3-(5-phenyl-1H-tetrazol-1-yl)propanoate
  参考文献：
  名称：

  Niyazymbetov, Murat E.; Rongfeng, Zhou; Evans, Dennis H., Journal of the Chemical Society. Perkin transactions II, 1996, # 9, p. 1957 - 1962

  摘要：

  DOI：

文献信息

• New 1,5 and 2,5-disubstituted tetrazoles-dependent activity towards surface barrier of Candida albicans
  作者：Monika Staniszewska、Małgorzata Gizińska、Ewa Mikulak、Klaudia Adamus、Mirosława Koronkiewicz、Edyta Łukowska-Chojnacka

  DOI：10.1016/j.ejmech.2017.11.089

  日期：2018.2

  A series of novel tetrazole derivatives was synthetized using N-alkylation or Michael-type addition reactions, and screened for their fungistatic potential against Candida albicans (the lack of endpoint = 100%). Among them, the selected compounds 2d, 4b, and 6a differing in substituents at the tetrazole ring were non-toxic to Galleria mellonella larvae in vivo and exerted slight toxicity against Caco-2 in vitro (CC50 at 256 mu g/mL). An antagonistic effect of tetrazole derivatives 2d, 4b, and 6a respectively in combination with Fluconazole was shown using the checker board and colorimetric methods (fractional inhibitory concentration indexes FICIs >1). The most active 2d and 6a displayed an inverse relation between MICs in the presence of exogenous ergosterol, the effect was opposite to Itraconazole and Amphotericin B. The differences between 6a's and 2d's action mode were noted. Combining both flow cytometry and fluorescence image analyses respectively showed the complexity of planktonic and biofilm cell demise mode under the tetrazole derivatives tested. The following evidences for 6a's interaction with fungal membrane were noted: necrosis-like programmed cell death (97.03 +/- 0.88), DNA denaturation (no laddering), mitochondrial damage (KIT assay), reduced adhesion to human epithelium (>50% at 0.0313 mu g/mL, p <= .05), irregular deposit of chitin, and attenuated morphogenesis in mature biofilm. The treatment with 6a reduced pathogenicity of C albicans during infection in G. mellonella. Contrariwise, 2d enhancing fungal adhesion displayed mechanism targeted to the cell wall (due to the presence of 3-chloropropyl clubbed with aryltetrazole) in the presence of osmotic protector. Under 2d, the accidental cell death (88.60% +/- 4.81) was observed.In conclusion, all tetrazole derivatives were obtained in satisfactory yields (60-95%) using efficient, simple and not expensive methods. Fungistatic and slightly anticancer tetrazole derivatives with the novel action mode can circumvent an appearance of antifungal-resistant strains. These results indicate that they are worthy of further studies. (C) 2017 Elsevier Masson SAS. All rights reserved.
• Aldose reductase inhibitor
  申请人：Wakamoto Pharmaceutical Co., Ltd.

  公开号：EP0388967B1

  公开（公告）日：1995-06-28
• US5055481A
  申请人：——

  公开号：US5055481A

  公开（公告）日：1991-10-08
• USRE35281E
  申请人：——

  公开号：USRE35281E

  公开（公告）日：1996-06-18