2-amino-5-(4-chlorophenyl)-1-phenyl-1H-pyrrole-3-carbonitrile | 1207645-98-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-amino-5-(4-chlorophenyl)-1-phenyl-1H-pyrrole-3-carbonitrile
• 英文别名: 2-Amino-5-(4-chlorophenyl)-1-phenyl-1h-pyrrole-3-carbonitrile；2-amino-5-(4-chlorophenyl)-1-phenylpyrrole-3-carbonitrile
• CAS: 1207645-98-4
• 化学式: C₁₇H₁₂ClN₃
• 分子量: 293.755
• InChiKey: IDTLSXSFGREKQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 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：
  54.7
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-amino-5-(4-chlorophenyl)-1-phenyl-1H-pyrrole-3-carbonitrile 在 吡啶 、 potassium hydroxide 作用下， 以 水 为溶剂， 反应 5.0h， 生成 6-(4-chlorophenyl)-7-phenyl-1H-pyrrolo[2,3-d]pyrimidine-2,4(3H,7H)-dithione
  参考文献：
  名称：

  Design, synthesis and evaluation of novel diaryl pyrrolopyrimidine and pyrrolothiazine derivatives as inhibitors of tumor necrosis factor stimulated gene-14 (TSG-14) production

  摘要：

  A novel series of pyrrolothiazines 2-4 and pyrrolopyrimidines 5-7 have been synthesized. The structures of these compounds were established by spectroscopic and element microanalytical data. The newly synthesized compounds were evaluated as inhibitors of TSG-14. The most effective results were obtained by the S-sec-butyl derivatives 6e (80%) and the N-ethyl derivatives 4e (70%). (C) 2014 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2014.03.068
• 作为产物：
  描述：

  4-Chlorphenacylmalononetrile 、 苯胺 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 生成 2-amino-5-(4-chlorophenyl)-1-phenyl-1H-pyrrole-3-carbonitrile
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Pyrrolo[2,3-d]pyrimidine Derivatives as Novel Apoptotic Agents for Human Lung Cancer Cells

  摘要：

  DOI：

  10.1134/s1070428023070096

文献信息

• Synthesis of new pyrrolo[2,3-d]pyrimidine derivatives as antibacterial and antifungal agents
  作者：Khalid Mohammed Hassan Hilmy、Maha M.A. Khalifa、Mohammed Abd Allah Hawata、Reda Mohammed AboAlzeen Keshk、Abd Almeneam El-Torgman

  DOI：10.1016/j.ejmech.2010.08.043

  日期：2010.11

  A series of new pyrrole derivatives, pyrrolo[2,3-d]pyrimidine derivatives, pyrrolotriazolopyrimidines and pyrrolotetrazolopyrimidines were synthesized. The evaluation of their antimicrobial activities against Staphylococcus aureus, Escherichia coli, and Candida albicans were carried out. Pyrrolo[2,3-d]pyrimidines 3a–d, 7a,e, 11d exhibited excellent activity against C. albicans with MIC 0.31–0.62 mg/mL

  合成了一系列新的吡咯衍生物，吡咯并[2，3- d ]嘧啶衍生物，吡咯并三唑并嘧啶和吡咯并四唑并嘧啶。评估了它们对金黄色葡萄球菌，大肠杆菌和白色念珠菌的抗菌活性。吡咯并[2,3- d ]嘧啶3a-d，7a，e，11d表现出对白色念珠菌的优异活性，MIC为0.31-0.62 mg / mL。这些化合物显示出比标准药物（氟康唑，MIC 1.5 mg / mL）更好的抗真菌活性。此外，吡咯并[2,3- d ]嘧啶与标准药物（氨苄青霉素，MIC为0.62 mg / mL）相比，图3b，c，7e对MIC为0.31 mg / mL的金黄色葡萄球菌表现出最佳的活性。发现其余化合物对细菌和真菌无活性。
• Synthesis and biological assessment of diversely substituted furo[2,3-b]quinolin-4-amine and pyrrolo[2,3-b]quinolin-4-amine derivatives, as novel tacrine analogues
  作者：Carla Martins、M. Carmo Carreiras、Rafael León、Cristóbal de los Ríos、Manuela Bartolini、Vincenza Andrisano、Isabel Iriepa、Ignacio Moraleda、Enrique Gálvez、Manuela García、Javier Egea、Abdelouhaid Samadi、Mourad Chioua、José Marco-Contelles

  DOI：10.1016/j.ejmech.2011.09.038

  日期：2011.12

  The synthesis and pharmacological analyses of a number of furo[2,3-b]quinolin-4-amine, and pyrrolo[2,3-b]quinolin-4-amine derivatives are reported. Thus, we synthesized diversely substituted tacrine analogues 1–11 and 12–16 by Friedländer-type reaction of readily available o-amino(furano/pyrrolo)nitriles with suitable and selected cycloalkanones. The biological evaluation of furanotacrines 1–11 and

  报道了许多呋喃并[2,3 - b ]喹啉-4-胺和吡咯并[2,3 - b ]喹啉-4-胺衍生物的合成和药理学分析。因此，我们合成了不同地取代的他克林的类似物1 - 11和12 - 16由容易获得的德兰德型反应ø -氨基（呋喃/吡咯）与合适的和选定的环烷酮腈。的生物学评价furanotacrines 1 - 11和pyrrolotacrine 13表明，这些都是很好的，在微摩尔范围内，和丁酰胆碱酯酶的高度选择性抑制剂。在呋喃诺那林中组中，最有趣的抑制剂是2-（对甲苯基）-5,6,7,8-四氢呋喃[2,3- b ]喹啉-4-胺（3）[IC 50（eqBuChE）= 2.9±0.4μM ; IC 50（hBuChE）= 119±15μM]。相反，吡咯烷酮 12和14被证明对两种胆碱酯酶具有中等等价性，分别是1,2-二苯基-5,6,7,8-四氢-1 H-吡咯并[2,3 - b ]喹啉-4-胺（12）。对两种酶的抑制作用最强[IC
• Synthesis and Biological Evaluation of Pyrrolo[2,3-d]pyrimidine Derivatives as a Novel Class of Antimicrobial and Antiviral Agents
  作者：K. Hilmy、M. Tag、E. Aish、M. Elsafty、H. Attia

  DOI：10.1134/s1070428021030155

  日期：2021.3
• Design, synthesis and evaluation of novel diaryl pyrrolopyrimidine and pyrrolothiazine derivatives as inhibitors of tumor necrosis factor stimulated gene-14 (TSG-14) production
  作者：Khalid M.H. Hilmy、Dalia H. Soliman、Esmat B.A. Shahin、Hala S. El-Deeb、Salah M. El-Kousy

  DOI：10.1016/j.ejmech.2014.03.068

  日期：2014.5

  A novel series of pyrrolothiazines 2-4 and pyrrolopyrimidines 5-7 have been synthesized. The structures of these compounds were established by spectroscopic and element microanalytical data. The newly synthesized compounds were evaluated as inhibitors of TSG-14. The most effective results were obtained by the S-sec-butyl derivatives 6e (80%) and the N-ethyl derivatives 4e (70%). (C) 2014 Published by Elsevier Masson SAS.
• Synthesis and Biological Evaluation of Pyrrolo[2,3-d]pyrimidine Derivatives as Novel Apoptotic Agents for Human Lung Cancer Cells
  作者：K. M. H. Hilmy、F. N. M. Kishk、E. B. A. Shahen、M. A. Hawata

  DOI：10.1134/s1070428023070096

  日期：2023.7