5-(4-fluorophenyl)-3-(2-thienyl)-pyrazoline | 259171-55-6

• 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: 5-(4-fluorophenyl)-3-(2-thienyl)-pyrazoline
• 英文别名: 5-(4-fluorophenyl)-3-thiophen-2-yl-4,5-dihydro-1H-pyrazole
• CAS: 259171-55-6
• 化学式: C₁₃H₁₁FN₂S
• 分子量: 246.308
• InChiKey: KNRQMKGMJCYANQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 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：
  52.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-fluorophenyl)-3-(2-thienyl)-pyrazoline 在 potassium carbonate 、 三乙胺 作用下， 以 丙酮 为溶剂， 反应 5.0h， 生成 2-[(((4-(diethylamino)butyl)amino)methyl)thio]-1-[5-(4-fluorophenyl)-3-(thien-2-yl)-4,5-dihydro-1H-pyrazol-1-yl]ethan-1-one
  参考文献：
  名称：

  对抗阿尔茨海默氏病：合成新的吡唑啉和苯并噻唑衍生物作为新的乙酰胆碱酯酶和MAO抑制剂

  摘要：

  背景：阿尔茨海默氏病（AD）是一种复杂的神经退行性疾病，发病机制多种多样，以逐渐记忆力下降，语言能力下降和其他认知能力下降为特征，已成为人口老龄化的重要风险。这意味着迫切需要找到用于控制和对抗（AD）的新的铅化合物。以此方式，已经合成了新的噻吩-2-吡唑啉衍生物（A1-A5）和苯并噻唑衍生物（A6-A13），以提供有益的化合物来控制和对抗（AD）。 结果：化合物A5和A13表现出最显着的活性，对AChE酶的IC50值为18.53 µM和15.26 µM。同样，化合物A4具有活性，对MAO-A的IC50值为20.34 µM。这些活性化合物实际上是无毒的，因此使其在今后的进一步研究中非常有吸引力。分析了酶的动力学，Lineweaver-Burk图显示化合物A13通常是混合的AChE抑制剂，与多奈哌齐具有显着相似性。此外，通过分析活性最高的化合物A13与峡谷的相容性以及与CAS和PAS的相互作用，可以确定最佳的对接姿势。

  DOI：

  10.2174/1570180814666170704144917
• 作为产物：
  描述：

  3-(4-fluorophenyl)-1-(thiophen-2-yl)prop-2-en-1-one 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 5-(4-fluorophenyl)-3-(2-thienyl)-pyrazoline
  参考文献：
  名称：

  部分1-[(N,N-二取代硫代甲酰氨基甲酰硫基)乙酰基]-3-(2-噻吩基)-5-芳基-2-吡唑啉衍生物的合成及抗菌抗真菌活性研究

  摘要：

  14 种新的 1 - [(N, N - 二取代硫代氨基甲酰硫基) 乙酰基] -3- (2- 噻吩基) -5- 芳基 - 2- 吡唑啉衍生物 (7a - n) 通过与 1- (氯乙酰基) -3- ( 2-噻吩基）-5-芳基-2-吡唑啉（5a-g）和适当的N，N-二取代二硫代氨基甲酸（6a，b）的钠盐。通过元素分析、UV、IR、1H-NMR和FAB+-MS光谱数据确认合成化合物的结构。它们对普通变形杆菌 (NRRL B-123)、大肠杆菌 (NRRL B-3704)、嗜水气单胞菌（安卡拉大学兽医学院）、鼠伤寒沙门氏菌 (NRRL B-4420)、粪链球菌 (NRRL B-1461) 的抗菌活性), 藤黄微球菌 (NRLL B-4375) 进行了调查，在本次调查中，说明了显着的活性水平。发现这些化合物对白色念珠菌和球形念珠菌（从 Osmangazi Uni. Fac. Of Medicine 获

  DOI：

  10.1002/ardp.200400935

文献信息

• Nematicidal pyrazoles
  申请人：Nihon Bayer Agrochem K.K.

  公开号：US06310049B1

  公开（公告）日：2001-10-30

  Novel pyrazoles of formula (1) wherein R1 represents halogen, C1-6 alkyl, C1-5 haloalkyl, C2-6 alkoxy, C1-4 alkylthio, C2-5 alkenyloxy, C3-5 alkynyloxy, C2-6 (total carbon number) alkoxyalkyl, C2-6 (total carbon number) alkylthioalkyl, C1-5 haloalkoxy, C2-6 (total carbon number) alkoxyalkoxy, hydroxy or optionally substituted phenyl, R2 represents hydrogen, halogen, C1-5 alkyl, C2-6 (total carbon number) alkoxyalkyl, C2-6 (total carbon number) alkylthioalkyl, C2-6 (total carbon number) alkylsulfinylalkyl, C2-6 (total carbon number alkylsulfonylalkyl or C1-5 haloalkyl, R3 represents hydrogen, C1-5 alkyl, —COR4, COOR5, CH(OR6)2 or CH2Si(R7)3, R4 represents C1-10 alkyl, C1-6 haloalkyl, C2-6 alkenyl, optionally substituted C3-6 cycloalkyl, C2-6 (total carbon number) alkoxyalkyl, C2-6 (total carbon number alkylthioalkyl, optionally substituted phenyl, C1-6 haloalkyl, alkylamino, di-(C1-6 alkyl)amino or optionally substituted phenylamino, R5 represents C1-7 alkyl, R6 and R7 represent C1-6 alkyl, and n is 1, 2 or 3, and when n is 2 or 3, the corresponding number (n) of R1 radicals may be the same or different, processes for preparing these compounds and their use as nematicides and anthelmintics.

  式（1）中的新型吡唑化合物，其中R1代表卤素、C1-6烷基、C1-5卤代烷基、C2-6烷氧基、C1-4烷基硫基、C2-5烯基氧基、C3-5炔基氧基、C2-6（总碳数）烷氧基烷基、C2-6（总碳数）烷基硫基烷基、C1-5卤代烷氧基、C2-6（总碳数）烷氧基烷氧基、羟基或可选择地取代的苯基；R2代表氢、卤素、C1-5烷基、C2-6（总碳数）烷氧基烷基、C2-6（总碳数）烷基硫基烷基、C2-6（总碳数）烷基磺酰基烷基、C2-6（总碳数）烷基磺基烷基或C1-5卤代烷基；R3代表氢、C1-5烷基、—COR4、COOR5、CH(OR6)2或CH2Si(R7)3；R4代表C1-10烷基、C1-6卤代烷基、C2-6烯基、可选择地取代的C3-6环烷基、C2-6（总碳数）烷氧基烷基、C2-6（总碳数）烷基硫基烷基、可选择地取代的苯基、C1-6卤代烷基、烷基氨基、二（C1-6烷基）氨基或可选择地取代的苯基氨基；R5代表C1-7烷基；R6和R7代表C1-6烷基；n为1、2或3，当n为2或3时，相应数量（n）的R1基团可以相同或不同，以及制备这些化合物的方法以及它们作为线虫杀和驱虫剂的用途。
• Synthesis of Some 1-[(<i>N, N</i>-Disubstituted thiocar bamoylthio)acetyl]-3-(2-thienyl)-5-aryl-2-pyrazoline Derivatives and Investigation of Their Antibacterial and Antifungal Activities
  作者：Gulhan Turan-Zitouni、Ahmet Özdemir、Kiymet Güven

  DOI：10.1002/ardp.200400935

  日期：2005.3

  antibacterial activities against Proteus vulgaris (NRRL B‐123), Escherichia coli (NRRL B‐3704), Aeromonas hydrophila (Ankara University, Faculty of Veterinary Sciences), Salmonella typhimurium (NRRL B‐4420), Streptococcus feacalis (NRRL B‐14617), Micrococcus luteus (NRLL B‐4375) were investigated and in this investigation, a significant level of activity was illustrated. Antifungal activities of the compounds

  14 种新的 1 - [(N, N - 二取代硫代氨基甲酰硫基) 乙酰基] -3- (2- 噻吩基) -5- 芳基 - 2- 吡唑啉衍生物 (7a - n) 通过与 1- (氯乙酰基) -3- ( 2-噻吩基）-5-芳基-2-吡唑啉（5a-g）和适当的N，N-二取代二硫代氨基甲酸（6a，b）的钠盐。通过元素分析、UV、IR、1H-NMR和FAB+-MS光谱数据确认合成化合物的结构。它们对普通变形杆菌 (NRRL B-123)、大肠杆菌 (NRRL B-3704)、嗜水气单胞菌（安卡拉大学兽医学院）、鼠伤寒沙门氏菌 (NRRL B-4420)、粪链球菌 (NRRL B-1461) 的抗菌活性), 藤黄微球菌 (NRLL B-4375) 进行了调查，在本次调查中，说明了显着的活性水平。发现这些化合物对白色念珠菌和球形念珠菌（从 Osmangazi Uni. Fac. Of Medicine 获
• 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.
• New pyrazoline derivatives and their antidepressant activity
  作者：Zafer Asım Kaplancıklı、Ahmet Özdemir、Gülhan Turan-Zitouni、Mehlika Dilek Altıntop、Özgür Devrim Can

  DOI：10.1016/j.ejmech.2010.06.011

  日期：2010.9

  Some triazolo-pyrazoline derivatives were synthesized to investigate their potential antidepressant activities. The chemical structures of the compounds were elucidated by IR, NMR and FAB(+)-MS spectral data and elemental analyses. Antidepressant-like activities of the test compounds (100 mg/kg) were screened using both modified forced swimming and tail suspension tests. Rota-Rod test was performed for the examination of probable neurological deficits due to the test compounds, which may interfere with the test results. The test compounds in the series exhibited different levels of antidepressant activities when compared to reference drug fluoxetine. None of the test compounds changed motor coordination of animals when assessed in the Rota-Rod test. Therefore, experimental results in this study were not interfered with motor abnormalities. (C) 2010 Elsevier Masson SAS. All rights reserved.
• NEMATICIDAL PYRAZOLES
  申请人：NIHON BAYER AGROCHEM K.K.

  公开号：EP1104418A2

  公开（公告）日：2001-06-06