3-安替比林基-1-苯基硫脲 | 51641-29-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3-安替比林基-1-苯基硫脲
• 英文名称: 4-anilino(thioxo)methylamino-1,5-dimethyl-2-phenyl-2,3-dihydro-1H-3-pyrazolone
• 英文别名: 1-(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)-3-phenyl-thiourea；N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-N'-phenylthiourea；N-(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)-N'-phenylthiourea；N-(antipyrin-4-yl)-N'-phenylthiourea；1-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-3-phenyl-thiourea；N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-N'-phenyl-thiourea；3-(4-Antipyrinyl)-1-phenyl-2-thiourea；1-(1,5-dimethyl-3-oxo-2-phenylpyrazol-4-yl)-3-phenylthiourea
• CAS: 51641-29-3
• 化学式: C₁₈H₁₈N₄OS
• mdl: MFCD00219275
• 分子量: 338.433
• InChiKey: YGXLLLUEADCXET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  79.7
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933199090

反应信息

• 作为反应物：
  描述：

  3-安替比林基-1-苯基硫脲 在 一水合肼 作用下， 以 异丙醇 为溶剂， 反应 2.0h， 以76%的产率得到N'-(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)-N-phenyl-hydrazinecarboximidamide
  参考文献：
  名称：

  Moustafa, Ahmed H.; Saad, Hosam A., Journal of Chemical Research, 2005, # 5, p. 328 - 331

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氨基安替比林 、 硫代异氰酸苯酯 以 甲醇 为溶剂， 以76 %的产率得到3-安替比林基-1-苯基硫脲
  参考文献：
  名称：

  用于治疗白色念珠菌感染的新型甾醇 24-C-甲基转移酶抑制剂的基于结构的优化

  摘要：

  干扰甾醇生物合成是开发安全有效的抗真菌药物的重要策略。我们之前发现化合物H55是真菌特异性 C-24 甾醇甲基转移酶 Erg6 的变构抑制剂，用于治疗白色念珠菌感染。在此，基于靶标-配体相互作用，设计并合成了 62 种H55衍生物，以识别更活跃的候选物。其中， d28通过靶向Erg6表现出最有效的抗毒能力（MHIC 50 = 0.25 μg/mL），与H55相比，效力提高了8倍。此外， d28在抑制细胞粘附和生物膜形成方面显着优于H55 ，并且表现出最小的细胞毒性和可忽略不计的诱导耐药性的潜力。值得注意的是， d28和其他甾醇生物合成抑制剂（例如十三吗啡或特比萘芬）的共同给药在小鼠皮肤感染模型中在体外和体内表现出强大的协同抗真菌作用。这些结果支持d28在治疗白色念珠菌感染中的潜在应用。

  DOI：

  10.1021/acs.jmedchem.4c00470

文献信息

• Mohamed; Hassan; Ibrahim, Pharmazie, 1992, vol. 47, # 8, p. 592 - 595
  作者：Mohamed、Hassan、Ibrahim、Semida、Mourad

  DOI：——

  日期：——
• Antimicrobial Activity and Structural Study of Disubstituted Thiourea Derivatives
  作者：Silvio Cunha、Fernando C. Macedo、Giselle A. N. Costa、Manoel T. Rodrigues、Rosival B. V. Verde、Lourdes C. de Souza Neta、Ivo Vencato、Carlito Lariucci、Fernando P. Sá

  DOI：10.1007/s00706-007-0600-y

  日期：2007.5

  The antimicrobial activity of six N-phenyl- and fourteen N-benzoylthiourea derivatives were evaluated from their Minimal Inhibitory Concentration (MIC) values using the microdilution procedure against ten microorganisms. Most of the compounds exhibited selective activity against fungi and Gram-positive bacteria, which were very effectively inhibited by some of the tested thioureas. Additionally, SAR considerations and four novel X-ray diffraction structures of N-benzoylthioureas are included.
• Mayekar, Amita V.; Bobade, Anil S.; Patil, Indian Journal of Heterocyclic Chemistry, 2010, vol. 19, # 3, p. 297 - 298
  作者：Mayekar, Amita V.、Bobade, Anil S.、Patil、Athlekar、Chowdhary, Abhay S.

  DOI：——

  日期：——
• Takahashi; Kanematsu, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1959, vol. 79, p. 172,175
  作者：Takahashi、Kanematsu

  DOI：——

  日期：——
• ——
  作者：Ayman K. El-Sawaf

  DOI：10.1023/a:1023218724180

  日期：——

  Reaction of 4-formylantipyrine with N(4)-dimethylthiosemicarbazide and 3-piperidylthiosemicarbazide produces the N(4)-dimethylthiosemicarbazone (1), and the 3-piperidylthiosemicarbazone (2), respectively. Compound 1 is triclinic, space group P-1 with a = 6.329(1) Angstrom, b = 11.699(1) Angstrom, c = 11.943(1) Angstrom, alpha = 65.83(1)degrees, = 80.83(1)degrees, gamma = 84.90(1)degrees, and V = 796.1(1) Angstrom(3) with Z = 2, for D-calc = 1.324 g/cm(3). Compound 2 is triclinic, space group P-1 with a = 6.784(1) Angstrom, b = 10.485(2) Angstrom, c = 13.462(3) Angstrom, alpha = 102.05(2)degrees, = 98.61(2)degrees, gamma = 101.32(2)degrees, and V = 899.8(5) Angstrom(3) with Z = 2, for D-calc = 1.319 g/cm(3). Reaction of 4-aminoantipyrine with phenyl isothiocyanate produced N-antipyrine-N'-phenylthiourea (3). Compound 3 is monoclinic, space group P2(1)/n with a = 6.863(7) Angstrom, b = 15.361(3) Angstrom, c = 16.332(5) Angstrom, = 90.35(6)degrees, and V = 1720.7(18) Angstrom(3) with Z = 4, for D-calc = 1.306 g/cm(3). Compounds 1 and 2 have intermolecular hydrogen bonding between the carbonyl oxygen of the antipyrine moiety and the NH hydrogen of the thiosemicarbazone moiety. In 3 the two unique molecules are held together as a dimer by interactions of the two thiourea NH's and the antipyrine moiety's oxygen.