1-[(phenyl)carbonyl] 4-(naphthyl)semicarbazide | 18248-54-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-[(phenyl)carbonyl] 4-(naphthyl)semicarbazide
• 英文别名: 4-Naphthyl-(1)-1-benzoyl-semicarbazid；1-Benzoyl-4-(α-naphthyl)semicarbazid；1-Benzamido-3-naphthalen-1-ylurea
• CAS: 18248-54-9
• 化学式: C₁₈H₁₅N₃O₂
• 分子量: 305.336
• InChiKey: FUHJLAWHPUFWTE-UHFFFAOYSA-N

物化性质

• 熔点：
  214-216 °C(Solvent: Diethyl ether)
• 密度：
  1.306±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[(phenyl)carbonyl] 4-(naphthyl)semicarbazide 在 copper(l) chloride 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 4.08h， 生成 4-(1-naphthyl)-5-phenyl-2-[4-(2,6-dimethylpiperidino)-2-butynyl]-2,4-dihydro-3H-1,2,4-triazol-3-one
  参考文献：
  名称：

  Synthesis and antimicrobial evaluation of 4,5-diaryl-2-[4-(t-amino)-2-butynyl]-2,4-dihydro-3H-1,2,4-triazol-3-ones

  摘要：

  A series of 4,5-diaryl-2-[4-(t-amino)-2-butynyl]-2,4-dihydro-3H-1,2,4-triazol-3-ones were synthesized and characterized by infrared spectrum (IR), H-1-NMR spectra and elemental analyses. Investigation of their antimicrobial activity was performed. Antimicrobial activity profile of the title compounds were evaluated against Gram- positive bacteria, Gram-negative bacteria and fungi. The synthesized compounds displayed different degrees of antimicrobial activities as shown in Table 3. Compound 12 was the most active one. This may be attributed to 4,5-diphenylsubstituent on the triazoline-3-one ring and the nature of the amino groups at terminal acetylenic moiety.

  DOI：

  10.1007/s00044-011-9840-9
• 作为产物：
  描述：

  苯甲酰肼 、 1-Alapha-萘异氰酸酯 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 以60%的产率得到1-[(phenyl)carbonyl] 4-(naphthyl)semicarbazide
  参考文献：
  名称：

  Alam, Faima; Ali, Basharat; Ali, Mahboob, Journal of the Chemical Society of Pakistan, 2021, vol. 43, # 4, p. 475 - 483

  摘要：

  DOI：

文献信息

• Mazurkiewicz; Grymel, Polish Journal of Chemistry, 1997, vol. 71, # 1, p. 77 - 82
  作者：Mazurkiewicz、Grymel

  DOI：——

  日期：——
• Discovery and SAR of a Series of Agonists at Orphan G Protein-Coupled Receptor 139
  作者：Feng Shi、Jing Kang Shen、Danqi Chen、Karina Fog、Kenneth Thirstrup、Morten Hentzer、Jens-Jakob Karlsson、Veena Menon、Kenneth A. Jones、Kelli E. Smith、Garrick Smith

  DOI：10.1021/ml100293q

  日期：2011.4.14

  GPR139 is an orphan G-protein coupled receptor (GPCR) Which is primarily expressed in the central nervous system (CNS). In order to explore the biological function of this receptor, selective tool compounds are required. A screening campaign identified compound 1a as a high potency PR139 agonist with an EC(50) = 39 nM in a calcium mobilization assay in CHO-K1 cells stably expressing the GPR139 receptor. In the absence of a known endogenous ligand, the maximum effect was set as 100% for 1a. Screening against 90 diverse targets revealed no cross-reactivity issues. Assessment of the pharmacokinetic properties showed limited utility,as in vivo tool compound in rat with a poor whole brain exposure of 61 ng/g and a brain/plasma (b/p) ratio of 0.03. Attempts to identify a more suitable analogue identified the des-nitrogen analogue is with a reduced polar surface area of 76.7 angstrom(2) and an improved b/p ratio of 2.8. The whole brain exposure remained low at 95 ng/g due to a low plasma exposure.
• Alam, Faima; Ali, Basharat; Ali, Mahboob, Journal of the Chemical Society of Pakistan, 2021, vol. 43, # 4, p. 475 - 483
  作者：Alam, Faima、Ali, Basharat、Ali, Mahboob、Khan, Khalid Mohammed、Khan, Momin、Manaf, Abdul、Zaman, Khair

  DOI：——

  日期：——
• Synthesis and antimicrobial evaluation of 4,5-diaryl-2-[4-(t-amino)-2-butynyl]-2,4-dihydro-3H-1,2,4-triazol-3-ones
  作者：E. N. Al-kaissi、N. F. Al-Ghrary、N. K. Al-Kaisi、A. Al-Shamma、Z. Muhi-eldeen

  DOI：10.1007/s00044-011-9840-9

  日期：2012.11

  A series of 4,5-diaryl-2-[4-(t-amino)-2-butynyl]-2,4-dihydro-3H-1,2,4-triazol-3-ones were synthesized and characterized by infrared spectrum (IR), H-1-NMR spectra and elemental analyses. Investigation of their antimicrobial activity was performed. Antimicrobial activity profile of the title compounds were evaluated against Gram- positive bacteria, Gram-negative bacteria and fungi. The synthesized compounds displayed different degrees of antimicrobial activities as shown in Table 3. Compound 12 was the most active one. This may be attributed to 4,5-diphenylsubstituent on the triazoline-3-one ring and the nature of the amino groups at terminal acetylenic moiety.