[(4-methylphenyl)sulfonyl]-3-thienylmethanisocyanide | 263389-44-2

• 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-methylphenyl)sulfonyl]-3-thienylmethanisocyanide
• 英文别名: 3-(isocyano(tosyl)methyl)thiophene；(3-thienyl)tosylmethyl isonitrile；α-(p-toluenesulfonyl)-α-(thien-3-yl)methylisocyanide；3-[1-isocyano-1-(toluene-4-sulfonyl)-methyl]-thiophene；3-[isocyano[(4-methylphenyl)sulfonyl]methyl]Thiophene；3-[isocyano-(4-methylphenyl)sulfonylmethyl]thiophene
• CAS: 263389-44-2
• 化学式: C₁₃H₁₁NO₂S₂
• 分子量: 277.368
• InChiKey: GAHAOIVMWHDBMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  75.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  丙醛 、 [(4-methylphenyl)sulfonyl]-3-thienylmethanisocyanide 在 ammonium hydroxide 、 哌嗪 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 26.0h， 以78%的产率得到3-(5-ethylimidazol-4-yl)thiophene
  参考文献：
  名称：

  An Investigation of Imidazole and Oxazole Syntheses Using Aryl-Substituted TosMIC Reagents¹

  摘要：

  This article describes efficient and mild protocols for preparing polysubstituted imidazoles in a single pot fi om aryl-substituted tosylmethyl isocyanide (TosMIC) reagents and imines generated in situ. Traditional imine-forming reactions employing virtually any aldehyde and amine followed by addition of the TosMIC reagent delivers 1,4,5-trisubstituted imidazoles with predictable regiochemistry. Employing chiral amines and aldehydes, particularly those derived from or-amino acids, affords imidazoles with asymmetric centers appended to N-1 or C-5 with excellent retention of chiral purity. 1,4-Disubstituted imidazoles are also readily prepared by a simple variant of the above procedure. Selecting glyoxylic acid as the aldehyde component of this procedure leads to intermediates such as 48, which readily undergo decarboxylation and elimination oft;he tosyl moiety to deliver 1,4-disubstituted imidazoles in high yields. Alternatively, using NH4OH as the amine component in conjunction with a variety of aldehydes delivers 4,5-disubstituted imidazoles in moderate to good yields in a single pot while avoiding the need for protecting groups. Finally, the facile preparation of mono- and disubstituted oxazoles from these TosMIC reagents and aldehydes is described.

  DOI：

  10.1021/jo991782l
• 作为产物：
  描述：

  3-噻吩甲醛 在 三甲基氯硅烷 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲苯 、 乙腈 为溶剂， 反应 5.0h， 生成 [(4-methylphenyl)sulfonyl]-3-thienylmethanisocyanide
  参考文献：
  名称：

  合成取代的TosMIC前体的有效方法

  摘要：

  取代的甲苯磺酰基甲基异氰化物（TosMICs）是有用的试剂，没有通用的制备方法。我们在这里描述了一种高产率的方法，用于合成取代的甲苯磺酰基甲基甲酰胺，该酰胺很容易转化为相应的异氰化物。

  DOI：

  10.1016/0040-4039(96)01886-2

文献信息

• [EN] 4—(1H— IMIDAZOL— 5— YL) -1H-PYRROLO [2, 3-B] PYRIDINES FOR USE IN THE TREATMENT OF LEUKAEMIAS, LYMPHOMAS AND SOLID TUMORS<br/>[FR] 4-(1H-IMIDAZOL-5-YL)-1H-PYRROLO [2,3-B] PYRIDINES DESTINÉES À ÊTRE UTILISÉES DANS LE TRAITEMENT DE LEUCÉMIES, DE LYMPHOMES ET DE TUMEURS SOLIDES
  申请人：UNIV MASARYKOVA

  公开号：WO2019185631A1

  公开（公告）日：2019-10-03

  The present invention relates to novel 4-(1H-imidazol-5-yl)-1H-pyrrolo[2,3-b]pyridine compounds which are useful in the treatment of lymphomas, leukaemias, and solid tumors.

  本发明涉及一种新型的4-(1H-咪唑-5-基)-1H-吡咯[2,3-b]吡啶化合物，可用于治疗淋巴瘤、白血病和实体肿瘤。
• <i>In silico</i>-driven multicomponent synthesis of 4,5- and 1,5-disubstituted imidazoles as indoleamine 2,3-dioxygenase inhibitors
  作者：S. Fallarini、A. Massarotti、A. Gesù、S. Giovarruscio、G. Coda Zabetta、R. Bergo、B. Giannelli、A. Brunco、G. Lombardi、G. Sorba、T. Pirali

  DOI：10.1039/c5md00317b

  日期：——

  starting point for the development of IDO1 inhibitors. With the aim of discovering more potent ligands, a virtual library of imidazoles synthesizable via the van Leusen multicomponent reaction was created and filtered to afford a set of 4,5- and 1,5-disubstituted imidazoles as virtual lead candidates. The compounds were selected according to their docking score and to their synthetic feasibility, synthesized

  吲哚胺2，3-二加氧酶参与病理性免疫逃逸，最近已成为抗癌治疗的有吸引力的靶标。4-苯基咪唑（4-PI）为IDO1抑制剂的开发提供了一个有希望的起点。为了发现更有效的配体，可通过以下方法合成一个虚拟的咪唑文库产生van Leusen多组分反应并过滤，得到一组4,5-和1,5-二取代的咪唑作为潜在的潜在候选铅。根据化合物的对接分数和合成可行性选择化合物，进行合成和生物学评估。与4-PI相比，这种实验方法产生的IDO1抑制剂具有增强的效力。活性最高的化合物在酶和细胞分析中均显示出较低的微摩尔效价，而无可检测的细胞毒性。观察到基于静电和空间配体-蛋白质相互作用的3D定量结构-活性关系。
• Antibacterial compounds
  申请人：SmithKline Beecham Corporation

  公开号：US20030149089A1

  公开（公告）日：2003-08-07

  Compounds of formula (I) and formula (II) are disclosed which are useful in the treatment bacterial infections: 1 wherein: R 1 is C 1-4 alkyl, Ar or 2-thienyl or 3-thienyl; R 2 is C 1-4 alkyl or Ar; and n is 0-3; or a pharmaceutically acceptable salt thereof.

  公开了式(I)和式(II)的化合物，它们在治疗细菌感染方面有用：1其中：R1是C1-4烷基，Ar或2-噻吩基或3-噻吩基；R2是C1-4烷基或Ar；n为0-3；或其药学上可接受的盐。
• Disubstituted imidazoles useful in the treatment of bacterial infections
  申请人：Affinium Pharmaceuticals, Inc.

  公开号：US06673941B2

  公开（公告）日：2004-01-06

  Compounds of formula (I) and formula (II) are disclosed which are useful in the treatment bacterial infections: wherein: R1 is C1-4alkyl, Ar or 2-thienyl or 3-thienyl; R2 is C1-4alkyl or Ar; and n is 0-3; or a pharmaceutically acceptable salt thereof.

  公开了化学式（I）和化学式（II）的化合物，其对治疗细菌感染有用：其中：R1是C1-4烷基，芳基或2-噻吩基或3-噻吩基；R2是C1-4烷基或芳基；n为0-3；或其药学上可接受的盐。
• Discovery of Potent and Exquisitely Selective Inhibitors of Kinase CK1 with Tunable Isoform Selectivity
  作者：Václav Němec、Prashant Khirsariya、Pavlína Janovská、Paula Martín Moyano、Lukáš Maier、Petra Procházková、Pavlína Kebková、Tomáš Gybel'、Benedict‐Tilman Berger、Apirat Chaikuad、Maria Reinecke、Bernhard Kuster、Stefan Knapp、Vítězslav Bryja、Kamil Paruch

  DOI：10.1002/anie.202217532

  日期：2023.3.6

  and CK1ϵ in cells as well as in vivo. Our observations suggest that the central scaffold can be used more broadly in compounds targeting other protein kinases, as evidenced by the highly selective p38α inhibitor MU1299.

  新发现的化学生物学探针MU1250、MU1500和MU1742，基于 1 H-吡咯并[2,3- b ]吡啶-咪唑支架，允许高度特异性靶向细胞中的亚型 CK1α、CK1δ 和 CK1ε体内。我们的观察表明，中央支架可以更广泛地用于靶向其他蛋白激酶的化合物，高选择性 p38α 抑制剂MU1299证明了这一点。