4-(3,5-difluoro-phenyl)thiosemicarbazide | 1038978-61-8

• 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: 4-(3,5-difluoro-phenyl)thiosemicarbazide
• 英文别名: 1-Amino-3-(3,5-difluorophenyl)thiourea
• CAS: 1038978-61-8
• 化学式: C₇H₇F₂N₃S
• 分子量: 203.215
• InChiKey: URRWDFPCVGKGHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.2
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-氟靛红 、 4-(3,5-difluoro-phenyl)thiosemicarbazide 在 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以77%的产率得到N-(3,5-difluorophenyl)-2-(5-fluoro-2-oxo-1,2-dihydro-3Hindol-3-ylidene)-1-hydrazinecarbothioamide
  参考文献：
  名称：

  Synthesis and biological evaluation of some N 4-aryl-substituted 5-fluoroisatin-3-thiosemicarbazones

  摘要：

  A series of N (4)-aryl-substituted 5-fluoroisatin-3-thiosemicarbazones 3a-3l was synthesized and evaluated for selected biological activities. The brine shrimp lethality bioassay was carried out to study their in vitro cytotoxicity potential and besides, their antifungal, phytotoxic and urease inhibitory effects were also investigated. Seven compounds i.e. 3a, 3d, 3f, 3g, 3h, 3j and 3k proved to be active in the brine shrimp assay, displaying promising cytotoxicity (LD50 = 6.89 x 10(-5)-2.79 x 10(-4) M). Amongst these, 3a and 3h were found to be the most active ones (LD50 = 6.89 x 10(-5) and 9.79 x 10(-5) M, respectively). Compounds 3i, 3j and 3 k displayed moderate (40 %) antifungal activity against one or two fungal strains i.e. A. flavus and/or M. canis. In phytotoxicity assay, all the synthesized compounds, including the reference point 2m showed weak-to-moderate (15-70 %) activity at the highest tested concentration (500 mu g/mL). In urease inhibition assay, compounds 3f, 3g and 3j proved to be the most potent inhibitors, demonstrating relatively a higher degree of enzymatic inhibition with IC50 values ranging from 37.7 to 47.3 mu M.

  DOI：

  10.1007/s00044-013-0575-7
• 作为产物：
  描述：

  3,5-二氟苯基异氰酸酯 在 一水合肼 作用下， 生成 4-(3,5-difluoro-phenyl)thiosemicarbazide
  参考文献：
  名称：

  新型螺（吲哚酮-3,2'-[1,3,4]噻二唑）-2-酮的合成及其抗抑郁和抗惊厥活性的评价

  摘要：

  的3-反应（二氰基亚）-2-吲哚酮在乙醇/哌啶与4-取代的氨基硫脲溶液形成5的衍生物' - （取代的氨基）-3' ħ -螺（二氢吲哚-3,2' - [ 1,3,4]噻二唑-2-酮。这些转化涉及在二氰基亚甲基碳原子上进行亲核加成反应的原理，并通过尾部悬浮行为绝望测试评估了所制备的化合物的抗抑郁活性以及对戊四氮诱发癫痫发作的抗惊厥活性。 J. Heterocyclic Chem。，（2011）。

  DOI：

  10.1002/jhet.687

文献信息

• Synthesis and Toxicity Evaluation of Some N4-Aryl Substituted 5-Trifluoromethoxyisatin-3-thiosemicarbazones
  作者：Humayun Pervez、Naveeda Saira、Mohammad Saeed Iqbal、Muhammad Yaqub、Khalid Mohammed Khan

  DOI：10.3390/molecules16086408

  日期：——

  A series of twenty one N4-aryl substituted 5-trifluoromethoxyisatin-3-thiosemicarbazones 3a-3u was synthesized by the reaction of trifluoromethoxyisatin 1 with different arylthiosemicarbazides 2 in aqueous ethanol (50%), containing a few drops of acetic acid. Their structures were established on the basis of analytical (CHN) and spectral (IR, 1H-NMR, EIMS) data. All the synthesized compounds were evaluated for their toxicity potential by a brine shrimp lethality bioassay. Ten compounds i.e., 3a, 3e, 3i-3l and 3n-3q proved to be active in this assay, displaying promising toxicity (LD50 = 1.11 × 10−5 M − 1.80 × 10−4 M). Amongst these, 3k, 3n and 3o were found to be the most active ones (LD50 = 1.11 × 10−5 M − 1.43 × 10−5 M). Compound 3k showed the highest activity with a LD50 value of 1.11 × 10−5 M and can, therefore, be used as a lead for further studies. Structure-activity relationship (SAR) studies revealed that the presence of strong inductively electron-attracting trifluoromethoxy substituent at position-5 of the isatin moiety played an important role in inducing or enhancing toxic potentiality of some of the synthesized compounds.

  通过三氟甲氧基异吲哚1与不同芳基缩氨基脲2在含有几滴醋酸的50%乙醇水溶液中的反应，合成了一系列21种N4-芳基取代的5-三氟甲氧基异吲哚-3-缩氨基脲3a-3u。它们的结构是基于分析（CHN）和光谱（IR，1H-NMR，EIMS）数据确定的。所有合成的化合物都通过卤虫致死生物测定法评估了它们的毒性潜力。其中10种化合物，即3a，3e，3i-3l和3n-3q在此测定中表现活跃，显示出有前景的毒性（LD50 = 1.11 × 10−5 M − 1.80 × 10−4 M）。在这些化合物中，3k，3n和3o被发现是最活跃的（LD50 = 1.11 × 10−5 M − 1.43 × 10−5 M）。化合物3k显示出最高的活性，其LD50值为1.11 × 10−5 M，因此可以作为进一步研究的先导化合物。构效关系（SAR）研究表明，在异吲哚部分的5位上存在强诱导电子吸引的三氟甲氧基取代基，在诱导或增强某些合成化合物的毒性潜力方面发挥了重要作用。
• Synthesis of Spiro(indenepyrazole) and Indenotriazinone Derivatives from 4-substituted Thiosemicarbazides and (1,3-dioxo-2,3-dihydro-1<i>H</i>-Inden-2-Ylidene)Propanedinitrile
  作者：Alaa A. Hassan、Ahmed M. Nour El. Din、Fathy F. Abdel Latif、Sara M. Mostafa、Stefan Bräse

  DOI：10.3184/030823410x12810986062376

  日期：2010.10

  ano-1,3-dioxo-1,3-dihydro-spiro[indene-2,3′-pyrazole]-2′(1H) carbothioamides (63–71 %) and 4-substituted-3-thioxo-3H-indeno[1,2-e][1,2,4] triazin-9(4H)-ones (17–26 %) have been formed, from a series of 4-substituted thiosemicarbazides 1a–f with (1,3-dioxo-2,3-dihydro-1H-inden-2-ylidene)propanedinitrile 3 in aerated ethyl acetate. Rationales of these conversions involving the nucleophilic reactions

  在多步反应中，N-取代的-5'-氨基-4'-氰基-1,3-二氧代-1,3-二氢-螺[茚-2,3'-吡唑]-2'(1H)碳硫酰胺（ 63–71 %) 和 4-取代-3-硫代-3H-茚[1,2-e][1,2,4] 三嗪-9(4H)-酮 (17–26 %) 已形成，来自一系列 4-取代氨基硫脲 1a–f 与（1,3-dioxo-2,3-dihydro-1H-inden-2-ylidene）丙二腈 3 在充气乙酸乙酯中。介绍了涉及亲核反应和缩合的这些转化的基本原理。
• Synthesis and biological evaluation of some N 4-aryl-substituted 5-fluoroisatin-3-thiosemicarbazones
  作者：Humayun Pervez、Naveeda Saira、Mohammad Saeed Iqbal、Muhammad Yaqub、Khalid Mohammed Khan

  DOI：10.1007/s00044-013-0575-7

  日期：2013.12

  A series of N (4)-aryl-substituted 5-fluoroisatin-3-thiosemicarbazones 3a-3l was synthesized and evaluated for selected biological activities. The brine shrimp lethality bioassay was carried out to study their in vitro cytotoxicity potential and besides, their antifungal, phytotoxic and urease inhibitory effects were also investigated. Seven compounds i.e. 3a, 3d, 3f, 3g, 3h, 3j and 3k proved to be active in the brine shrimp assay, displaying promising cytotoxicity (LD50 = 6.89 x 10(-5)-2.79 x 10(-4) M). Amongst these, 3a and 3h were found to be the most active ones (LD50 = 6.89 x 10(-5) and 9.79 x 10(-5) M, respectively). Compounds 3i, 3j and 3 k displayed moderate (40 %) antifungal activity against one or two fungal strains i.e. A. flavus and/or M. canis. In phytotoxicity assay, all the synthesized compounds, including the reference point 2m showed weak-to-moderate (15-70 %) activity at the highest tested concentration (500 mu g/mL). In urease inhibition assay, compounds 3f, 3g and 3j proved to be the most potent inhibitors, demonstrating relatively a higher degree of enzymatic inhibition with IC50 values ranging from 37.7 to 47.3 mu M.
• Synthesis of novel spiro(indolone-3,2′-[1,3,4]thiadiazol)-2-ones and evaluation of their antidepressant and anticonvulsant activities
  作者：Alaa A. Hassan、Fathy F. Abdel-Latif、Ahmed M. Nour El-Din、Mohamed Abdel-Aziz、Sara M. Mostafa、Stefan Bräse

  DOI：10.1002/jhet.687

  日期：2011.9

  derivatives of 5′‐(substituted amino)‐3′H–spiro(indoline‐3,2′‐[1,3,4]thiadiazol‐2‐one. Rationales for these conversions involving the nucleophilic addition on the dicyanomethylene carbon atom are presented. The prepared compounds were evaluated each for antidepressant activity using tail suspension behavioral despair test and anticonvulsant activity against pentylenetetrazol induced seizures in mice. J. Heterocyclic

  的3-反应（二氰基亚）-2-吲哚酮在乙醇/哌啶与4-取代的氨基硫脲溶液形成5的衍生物' - （取代的氨基）-3' ħ -螺（二氢吲哚-3,2' - [ 1,3,4]噻二唑-2-酮。这些转化涉及在二氰基亚甲基碳原子上进行亲核加成反应的原理，并通过尾部悬浮行为绝望测试评估了所制备的化合物的抗抑郁活性以及对戊四氮诱发癫痫发作的抗惊厥活性。 J. Heterocyclic Chem。，（2011）。