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4-[3-(5-苯基四唑-2-基)丙基]吗啉 | 3169-54-8

中文名称
4-[3-(5-苯基四唑-2-基)丙基]吗啉
中文别名
——
英文名称
4-[3-(5-phenyl-2H-tetrazol-2-yl)propyl]morpholine
英文别名
4-[3-(5-phenyl-tetrazol-2-yl)-propyl]-morpholine;4-[3-(5-Phenyltetrazol-2-yl)propyl]morpholine
4-[3-(5-苯基四唑-2-基)丙基]吗啉化学式
CAS
3169-54-8
化学式
C14H19N5O
mdl
——
分子量
273.338
InChiKey
ZEIIBTHEFRQZQQ-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    1.7
  • 重原子数:
    20
  • 可旋转键数:
    5
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.5
  • 拓扑面积:
    56.1
  • 氢给体数:
    0
  • 氢受体数:
    5

SDS

SDS:6b77e3294fa6741684763abc0230096f
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上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为产物:
    描述:
    5-苯基四氮唑potassium carbonate 、 potassium hydroxide 作用下, 以 甲醇乙腈 为溶剂, 生成 4-[3-(5-苯基四唑-2-基)丙基]吗啉
    参考文献:
    名称:
    New 1,5 and 2,5-disubstituted tetrazoles-dependent activity towards surface barrier of Candida albicans
    摘要:
    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.
    DOI:
    10.1016/j.ejmech.2017.11.089
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文献信息

  • Alkylation of 5-substituted tetrazoles
    作者:Leland. Huff、Ronald A. Henry
    DOI:10.1021/jm00298a059
    日期:1970.7.1
  • New Antihypertensive Aminoalkyltetrazoles
    作者:Shin. Hayao、Herbert J. Havera、Wallace G. Strycker、T. J. Leipzig、Rodolfo. Rodriguez
    DOI:10.1021/jm00315a025
    日期:1967.5
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