methyl 3-isothiocyanato-5-phenylthiophene-2-carboxylate | 1019164-57-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: methyl 3-isothiocyanato-5-phenylthiophene-2-carboxylate
• CAS: 1019164-57-8
• 化学式: C₁₃H₉NO₂S₂
• mdl: MFCD14728805
• 分子量: 275.352
• InChiKey: QTLQILDACUTMFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  99
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-isothiocyanato-5-phenylthiophene-2-carboxylate 在 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 3-[3-Methoxy-4-(2-pyrrolidin-1-ylethoxy)phenyl]-2-(methylthio)-6 phenylthieno[3,2-d]pyrimidin-4(3h)-one
  参考文献：
  名称：

  Discovery of potent and stable conformationally constrained analogues of the MCH R1 antagonist SB-568849

  摘要：

  A strategy of systematically targeting more rigid analogues of the known MCH R1 receptor antagonist, SB-568849, serendipitously uncovered a binding mode accessible to N-aryl-phthalimide ligands. Optimisation to improve the stability of this compound class led to the discovery of novel N-aryl-quinazolinones, benzotriazinones and thienopyrimidinones as selective ligands with good,affinity for human melanin-concentrating hormone receptor 1. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.06.061
• 作为产物：
  描述：

  3-氨基-5-苯基噻吩-2-甲酸甲酯 在 N,N-二丙基色胺 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 3-isothiocyanato-5-phenylthiophene-2-carboxylate
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Sulfonilamidothienopyrimidinone Derivatives as Novel Anti-inflammatory Agents

  摘要：

  我们合成了八种新的磺胺噻吩嘧啶酮衍生物（1-8），并评估了它们对人类角朊细胞系 NCTC 2544 的抗炎活性。通过 Western 印迹检测环氧化酶（COX）-2、诱导型 NO 合酶（iNOS）、细胞间粘附分子-1（ICAM-1）的表达以及前列腺素（PG）E2 和白细胞介素-8（IL-8）的释放，评估了衍生物（1-8）潜在的抗炎活性。我们的研究结果表明，3、5、6 和 8 号衍生物对 iNOS、COX-2、ICAM-1、MCP-1 和 IL-8 等炎症标志物有很好的抑制作用。这些发现有助于开发治疗各种炎症的新药。

  DOI：

  10.2174/1573406410666140228152807

文献信息

• General Access to <i>N</i> −CF ₃ Secondary Amines and Their Transformation to <i>N</i> −CF ₃ Sulfonamides
  作者：Leibing Wang、Jieping Wang、Sitao Ye、Beihan Jiang、Zihao Guo、Yasir Mumtaz、Wenbin Yi

  DOI：10.1002/anie.202212115

  日期：2022.12.5

  A new and mild method for the generation of HF from triethylsilane and silver fluoride leads to a highly efficient one-pot synthesis of N−CF3 secondary amines. Novel N−CF3 sulfonamides were constructed from these promising amine building blocks and sulfonyl bromides in an unprecedented route.

  一种由三乙基硅烷和氟化银生成 HF 的新型温和方法可实现N -CF 3仲胺的高效一锅法合成。新型N -CF 3磺胺类化合物是通过前所未有的途径由这些有前途的胺结构单元和磺酰溴构建而成的。
• Synthesis of <i>N</i>‐Difluoromethyl Carbonyl Compounds from <i>N</i>‐Difluoromethylcarbamoyl Fluorides
  作者：Chunyang Hu、Lvqi Jiang、Zihao Guo、Yasir Mumtaz、Jie Liu、Jiarong Qin、Yixing Chen、Zhongquan Lin、Wenbin Yi

  DOI：10.1002/anie.202319758

  日期：2024.4.8

  operationally simple and practical protocol to access N-CF2H amides and related carbonyl derivatives was developed. The protocol utilizes a one-pot conversion of thioformamides via desulfurization-fluorination and acylation, providing N-difluoromethylcarbamoyl fluoride that can be further diversified to a diversity of N-CF2H carbonyl compounds including amides, carbamates, ureas, thiocarbamates, and selenocarbamates

  开发了一种操作简单且实用的获取N -CF 2 H 酰胺和相关羰基衍生物的方案。该方案利用硫代甲酰胺通过脱硫氟化和酰化的一锅转化，提供N-二氟甲基氨基甲酰氟，该氟化物可以进一步多样化为多种N -CF 2 H羰基化合物，包括酰胺、氨基甲酸酯、脲、硫代氨基甲酸酯和硒代氨基甲酸酯。丰富的功能。
• Discovery of potent and stable conformationally constrained analogues of the MCH R1 antagonist SB-568849
  作者：David R. Witty、John Bateson、Guillaume J. Hervieu、Kamal Al-Barazanji、Phillip Jeffrey、Dieter Hamprecht、Andrea Haynes、Christopher N. Johnson、Alison I. Muir、Peter J. O’Hanlon、Geoffrey Stemp、Alex J. Stevens、Kevin Thewlis、Kim Y. Winborn

  DOI：10.1016/j.bmcl.2006.06.061

  日期：2006.9

  A strategy of systematically targeting more rigid analogues of the known MCH R1 receptor antagonist, SB-568849, serendipitously uncovered a binding mode accessible to N-aryl-phthalimide ligands. Optimisation to improve the stability of this compound class led to the discovery of novel N-aryl-quinazolinones, benzotriazinones and thienopyrimidinones as selective ligands with good,affinity for human melanin-concentrating hormone receptor 1. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis and Biological Evaluation of Sulfonilamidothienopyrimidinone Derivatives as Novel Anti-inflammatory Agents
  作者：Mariarita Barone、Andrea Santagati、Adriana Graziano、Cosimo Fortuna、Giuseppe Ronsisvalle、Venera Cardile

  DOI：10.2174/1573406410666140228152807

  日期：2014.2.28

  Eight new sulfonilamidothienopyrimidinone derivatives (1-8) were synthesized and evaluated for their antiinflammatory activity on the human keratinocyte line NCTC 2544. The potential anti-inflammatory activity of the derivatives (1-8) was evaluated by determining, through Western blot, the expression of cyclooxygenase (COX)-2, inducible NO synthase (iNOS), intercellular adhesion molecule-1 (ICAM-1), and the release of prostaglandins (PG)E2 and interleukin- 8 (IL-8). Moreover, through ELISA assay, the release of monocyte chemoattractant protein-1 (MCP-1), and interleukin- 8 (IL-8) was analyzed. Our results demonstrated that the derivatives 3, 5, 6 and 8 act as excellent inhibitors of inflammatory markers: iNOS, COX-2, ICAM-1, MCP-1, and IL-8. These findings could be useful for the development of new drugs for the treatment of various inflammatory pathologies.

  我们合成了八种新的磺胺噻吩嘧啶酮衍生物（1-8），并评估了它们对人类角朊细胞系 NCTC 2544 的抗炎活性。通过 Western 印迹检测环氧化酶（COX）-2、诱导型 NO 合酶（iNOS）、细胞间粘附分子-1（ICAM-1）的表达以及前列腺素（PG）E2 和白细胞介素-8（IL-8）的释放，评估了衍生物（1-8）潜在的抗炎活性。我们的研究结果表明，3、5、6 和 8 号衍生物对 iNOS、COX-2、ICAM-1、MCP-1 和 IL-8 等炎症标志物有很好的抑制作用。这些发现有助于开发治疗各种炎症的新药。