3-(2-thienyl)-5-(p-nitrophenyl)-2-pyrazoline | 136786-73-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(2-thienyl)-5-(p-nitrophenyl)-2-pyrazoline
• 英文别名: 5-(4-nitro-phenyl)-3-thiophen-2-yl-4,5-dihydro-1H-pyrazole；5-(4-nitrophenyl)-3-thiophen-2-yl-4,5-dihydro-pyrazole；5-(4-nitrophenyl)-3-thiophen-2-yl-4,5-dihydro-1H-pyrazole
• CAS: 136786-73-7
• 化学式: C₁₃H₁₁N₃O₂S
• 分子量: 273.315
• InChiKey: SZLPEAVYYHGTOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  98.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(2-thienyl)-5-(p-nitrophenyl)-2-pyrazoline 在 盐酸 、 sodium nitrite 作用下， 生成 3-(4-nitrophenyl)-2-nitroso-5-thiophen-2-yl-3,4-dihydropyrazole
  参考文献：
  名称：

  Khalaf, Ali A.; Kabli, Reda A.; Zimaity, M. T., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 11, p. 1125 - 1129

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(4-nitrophenyl)-1-(thiophen-2-yl)prop-2-en-1-one 在 肼 作用下， 以 乙醇 为溶剂， 生成 3-(2-thienyl)-5-(p-nitrophenyl)-2-pyrazoline
  参考文献：
  名称：

  WO2007/38425

  摘要：

  公开号：

文献信息

• Kabli; Khalaf; Zimaity, Journal of the Indian Chemical Society, 1991, vol. 68, # 1, p. 47 - 51
  作者：Kabli、Khalaf、Zimaity、Khalil、Kaddah、Al-Rifaie

  DOI：——

  日期：——
• Weber,F.G.; Brosche,K., Zeitschrift fur Chemie, 1972, vol. 12, p. 132 - 133
  作者：Weber,F.G.、Brosche,K.

  DOI：——

  日期：——
• WO2007/38425
  申请人：——

  公开号：——

  公开（公告）日：——
• [EN] ANTI-VIRAL COMPOUINDS<br/>[FR] COMPOSES ANTIVIRAUX
  申请人：UNIV MINNESOTA

  公开号：WO2007038425A2

  公开（公告）日：2007-04-05

  [EN] The invention provides anti-viral compounds of formula (I) wherein R₁-R₃ and A have any of the values defined herein. The invention also provides pharmaceutical compositions comprising such compounds as well as methods for treating viral infections by administering such compounds to an animal.
  [FR] L'invention concerne des composés antiviraux de formule (I), dans laquelle R₁ à R₃ et A sont tels que définis dans la description. L'invention concerne également des compositions pharmaceutiques comprenant ces composés, ainsi que des méthodes de traitement d'infections virales par administration desdits composés à un animal.
• Identification of Compounds with Anti-West Nile Virus Activity
  作者：John R. Goodell、Francesc Puig-Basagoiti、Brett M. Forshey、Pei-Yong Shi、David M. Ferguson

  DOI：10.1021/jm051229y

  日期：2006.3.1

  The lack of antiviral compounds targeting flaviviruses represents a significant problem in the development of strategies for treating West Nile Virus (WNV), Dengue, and Yellow Fever infections. Using WNV high-throughput screening techniques developed in Our laboratories, we report the identification of several small molecule anti-WNV compounds belonging to four different structural classes including pyrazolines, xanthanes, acridines, and quinolines. The initial set of "hits" was further refined using cell viability-cytotoxicity assays to two 1,3,5-triaryl pyrazoline compounds: 1-(4-chlorophenylacetyl)-5-(4-nitrophenyl)-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazole and 1-benzoyl-5-(4-chlorophenyl)-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazole. On the basis of their activity and favorable therapeutic indexes, these compounds were identified as viable leads and subjected to additional evaluation using an authentic viral titer reduction assay employing an epidemic strain of WNV. The compounds were further evaluated in a transient replicon reporting system to gain insight into the mechanism of action by identifying the step at which inhibition takes place during viral replication. The results indicate the pyrazolines inhibit RNA synthesis, pointing to viral RNA polymerase, RNA helicase, or other viral replication enzymes as potential targets. Progress was also made in understanding the structural requirements for activity by synthesizing a focused chemical library of substituted pyrazolines. Preliminary SAR data are presented that show the aryl-rings are required for activity against WNV. More importantly, the results indicate WNV activity is tolerant to aryl-substitutions paving the way for the design and development of much larger combinatorial libraries with varied physicochemical properties.