N-[(4-nitrophenyl)methylidene]-N-(4-phenyl-1,3-thiazol-2-yl)amine | 19959-15-0

• 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: N-[(4-nitrophenyl)methylidene]-N-(4-phenyl-1,3-thiazol-2-yl)amine
• 英文别名: (4-nitrobenzylidene)(4-phenylthiazol-2-yl)amine；N-(4-nitrobenzylidene)4-phenylthiazol-2-amine；2-(4-nitrobenzylideneamino)-4-phenylthiazole；(4-nitro-benzylidene)-(4-phenyl-thiazol-2-yl)-amine；(4-Nitro-benzyliden)-(4-phenyl-thiazol-2-yl)-amin；2-(p-Nitro-benzylidenamino)-4-phenyl-thiazol；1-(4-nitrophenyl)-N-(4-phenyl-1,3-thiazol-2-yl)methanimine
• CAS: 19959-15-0
• 化学式: C₁₆H₁₁N₃O₂S
• 分子量: 309.348
• InChiKey: AJZXGODXWJLZFQ-UHFFFAOYSA-N

物化性质

• 熔点：
  156.8 °C
• 沸点：
  523.8±52.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  99.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4-硝基苯氧基)乙酰氯 、 N-[(4-nitrophenyl)methylidene]-N-(4-phenyl-1,3-thiazol-2-yl)amine 在 三乙胺 作用下， 以 苯 为溶剂， 生成 3-(4-nitro-phenoxy)-4-(4-nitro-phenyl)-1-(4-phenyl-thiazol-2-yl)-azetidin-2-one
  参考文献：
  名称：

  Osman; Hassan Kh.; El-Kashef, Journal of the Indian Chemical Society, 1979, vol. 56, # 5, p. 521 - 524

  摘要：

  DOI：
• 作为产物：
  描述：

  苯乙酮 在 哌啶 、 碘 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 N-[(4-nitrophenyl)methylidene]-N-(4-phenyl-1,3-thiazol-2-yl)amine
  参考文献：
  名称：

  4-苯基-2-氨基噻唑的席夫碱作为新型抗血吸虫药的命中点：体外，体内和计算机研究的合成。

  摘要：

  血吸虫病的治疗基于单一药物吡喹酮（PZQ），这是一种口服生物利用度高，有效的药物，其副作用极小。但是，这种方法的主要问题在于，仅依靠一种药物来治疗蠕虫病是一种危险的策略，因为历史表明病原体很容易演变成耐药性。实际上，有关PZQ敏感性低的实验菌株的报道可在文献中找到。因此，寻找新的抗血吸虫病是紧迫的。在这里，我们报告了4-（4-取代的苯基）-N-（4-取代的亚苄基）噻唑-2-胺的十七种席夫碱的合成，这些席夫碱已在体外和体内针对曼氏血吸虫成虫进行了测试。此外，在计算机研究中，还提出了潜在的大分子靶标并预测了口服生物利用度。类似物GPQF-108表现出最佳的体外性能（IC50：29.4 µM，SI：6.1），与有希望的体内活性有关，并且成年型和产卵期明显减少。口服生物利用度可能因GPQF-108的低水溶性而受损，尽管它也表现出良好的膜渗透性。但是，可以通过减小粒径来改善水溶性。丝氨酸/苏氨酸和酪

  DOI：

  10.1016/j.ejps.2020.105371

文献信息

• Insecticidal Evaluation and [4+2] Aza-Diels-Alder Synthesis of 3,7-Diaryl-6,7-dihydro-5<i>H</i>-6-substituted Thiazolo[3,2-a]pyrimidin-5-ones Under Coupled Ultrasonic Irradiation and PTC
  作者：Ragini Gupta、Deepti Sharma、P. S. Verma、Anshu Jain

  DOI：10.1002/jhet.776

  日期：2016.1

  A series of 3,7‐diaryl‐6,7‐dihydro‐5H‐6‐substituted‐thiazolo[3,2‐a]pyrimidin‐5‐ones (3a, 3b, 3c, 3d, 3e, 3f, 3g, 3h, 3i, 3j) were synthesized by the [4+2] cycloaddition reaction of 2‐arylideneamino‐4‐arylthiazoles (2a–j) with in situ generated monosubstituted ketenes under PTC conditions coupled with ultrasonication in good to excellent yields. All the synthesized compounds were characterized on the

  一系列3,7-二芳基-6,7-二氢-5 H -6-取代的噻唑并[3,2-a]嘧啶-5-酮（3a，3b，3c，3d，3e，3f，3g，3h，3i，3j）是通过2-芳基亚氨基-4-芳基噻唑（2a–j）与原位的[4 + 2]环加成反应合成的在PTC条件下生成的单取代乙烯酮，再加上超声处理，收率良好。所有合成的化合物均根据其光谱（IR，PMR和质量）和分析数据进行表征。还筛选了合成的化合物对棉铃虫的杀虫活性，其中一些化合物显示出有希望的活性。
• [4+2] Diels–Alder Cycloaddition Reaction of 2-benylidineamino-4-phenyl-1,3-thiazoles with Sulfene and their Antifungal Activities
  作者：Susanta Kr. Borthakur、Paran Boruah、Birendra N. Goswami

  DOI：10.3184/030823407x191877

  日期：2007.2

  2-Benzylidineamino-4-phenyl-1,3-thiazole undergoes [4+2] Diels–Alder cycloaddition reaction with sulfene resulting in good yield of a mixture of isomeric 2,6-diphenyl-2H,4H-[1,3]thiazolo[3,2-c][1,3,5]thiadiazine 3,3-dioxides and 3, 7-diphenyl[1,3]thiazolo[3,2-b] [1,2,4]thiadiazine 5,5-dioxides derivatives are reported.

  2-Benzylidineamino-4-phenyl-1,3-thiazole 与亚砜发生 [4+2] Diels-Alder 环加成反应，得到良好的异构体 2,6-diphenyl-2H,4H-[1,3] 混合物噻唑并[3,2-c][1,3,5]噻二嗪3,3-二氧化物和3,7-二苯基[1,3]噻唑并[3,2-b][1,2,4]噻二嗪5，报道了 5-二氧化物衍生物。
• Formation of Azomethines from 2-Aminothiazoles and (Heterocyclic) Aromatic Aldehydes
  作者：Christopher Hopkinson、George Denis Meakins、Roberts James Purcell

  DOI：10.1055/s-1991-26528

  日期：——

  Reexamination of previous work and new studies show that the reactions of 2-aminothiazoles with (heterocyclic) aromatic aldehydes are not straightforward; there are wide divergencies in behaviour between the various amine-aldehyde pairs. Simple efficient procedures for preparing 2-(alkylideneamino)thiazole derivatives and [bis(thiazol-2-ylamino)methyl]arenes have been developed.

  对先前工作和新研究的重新审视表明，2-氨基噻唑与（杂环）芳香醛的反应并不简单； 各种胺-醛对之间的行为存在很大差异。已经开发出用于制备2-(亚烷基氨基)噻唑衍生物和[双(噻唑-2-基氨基)甲基]芳烃的简单有效的程序。
• Design of New Cognition Enhancers:  From Computer Prediction to Synthesis and Biological Evaluation
  作者：Athina A. Geronikaki、John C. Dearden、Dmitrii Filimonov、Irina Galaeva、Taissia L. Garibova、Tatiana Gloriozova、Valentina Krajneva、Alexey Lagunin、Fliur Z. Macaev、Guenadij Molodavkin、Vladimir V. Poroikov、Serghei I. Pogrebnoi、Felix Shepeli、Tatiana A. Voronina、Maria Tsitlakidou、Liudmila Vlad

  DOI：10.1021/jm031086k

  日期：2004.5.1

  To discover new cognition enhancers, a set of virtually designed synthesizable compounds from different chemical series was investigated using two computer-aided approaches. One of the approaches is prediction of biological activity spectra for substances (PASS) and the second is prediction of toxicity, mutagenicity, and carcinogenicity (DEREK). To increase the probability of finding new chemical entities, we investigated a heterogeneous set of highly diverse chemicals including different types of heterocycles: five-membered (thiophenes, thiazoles, imidazoles, oxazoles, pyrroles), six-membered (pyridines, pyrimidines), seven-membered (diazepines, triazepines), fused five+six-membered heterocycles (indoles, benzothiazoles, purines, indolizines, neutral, mesoionic, and cationic azolopyridines). A database including 5494 structures of compounds was created. On the basis of the PASS and DEREK prediction results, eight compounds with the highest probability of cognition-enhancing effect were selected. The cognition-enhancing activity testing showed that all of the selected compounds had a pronounced antiamnesic effect and were found to reduce significantly scopolamine-induced amnesia of passive avoidance reflex (PAR). The action of compounds at doses of 1 and 10 mg/kg caused a statistically significant increase in latent time of reflex and in the number of animals, which did not enter the dark chamber when testing the PAR. Therefore, on the basis of computer prediction, new cognition-enhancing agents were discovered within the chemical series, in which this activity was not known previously.
• Bhosale; Chavan; Bhosale, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2012, vol. 51, # 11, p. 1649 - 1654
  作者：Bhosale、Chavan、Bhosale

  DOI：——

  日期：——