6-methyl-1-(pyridin-2-ylsulfonyl)-1H-indole | 1429474-14-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6-methyl-1-(pyridin-2-ylsulfonyl)-1H-indole
• 英文别名: 6-Methyl-1-(pyridin-2-ylsulfonyl)-1H-indole；6-methyl-1-pyridin-2-ylsulfonylindole
• CAS: 1429474-14-5
• 化学式: C₁₄H₁₂N₂O₂S
• 分子量: 272.327
• InChiKey: UARFMBQBFKWRAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  60.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-methyl-1-(pyridin-2-ylsulfonyl)-1H-indole 、 丙烯酸甲酯（MA） 在 双(乙腈)氯化钯(II) 、 copper(II) acetate monohydrate 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以30%的产率得到methyl 3-(6-methyl-1-(pyridin-2-ylsulfonyl)-1H-indol-2-yl)acrylate
  参考文献：
  名称：

  Design of Potent Poxvirus Inhibitors of the Heterodimeric Processivity Factor Required for Viral Replication

  摘要：

  Smallpox constitutes a major bioterrorism threat, which underscores the need to develop antiviral drugs for rapid response in the event of an attack. Viral processivity factors are attractive drug targets in being both specific and essential for their cognate DNA polymerases to synthesize extended strands of DNA. An in silico model of the vacinnia virus processivity factor, comprised of the A20 and D4 heterocomplex, was constructed and used for lead optimization of an indole-based scaffold identified earlier from a high-throughput screening. On the basis of this model, a new class of potent antivirals against vaccinia virus was designed and synthesized, of which two (24a and 24b) exhibited superior improvement over the parent scaffold (IC50 = 42 and 46 vs 82000 nM, respectively). The ability of 24a to suppress vaccinia DNA synthesis is supported by the inhibition of late viral gene expression, as well as by the diminished incorporation of bromodeoxyuridine into viral replication factories.

  DOI：

  10.1021/jm301735k
• 作为产物：
  描述：

  2-巯基吡啶 在 盐酸 、 水 、 氯 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.25h， 生成 6-methyl-1-(pyridin-2-ylsulfonyl)-1H-indole
  参考文献：
  名称：

  Design of Potent Poxvirus Inhibitors of the Heterodimeric Processivity Factor Required for Viral Replication

  摘要：

  Smallpox constitutes a major bioterrorism threat, which underscores the need to develop antiviral drugs for rapid response in the event of an attack. Viral processivity factors are attractive drug targets in being both specific and essential for their cognate DNA polymerases to synthesize extended strands of DNA. An in silico model of the vacinnia virus processivity factor, comprised of the A20 and D4 heterocomplex, was constructed and used for lead optimization of an indole-based scaffold identified earlier from a high-throughput screening. On the basis of this model, a new class of potent antivirals against vaccinia virus was designed and synthesized, of which two (24a and 24b) exhibited superior improvement over the parent scaffold (IC50 = 42 and 46 vs 82000 nM, respectively). The ability of 24a to suppress vaccinia DNA synthesis is supported by the inhibition of late viral gene expression, as well as by the diminished incorporation of bromodeoxyuridine into viral replication factories.

  DOI：

  10.1021/jm301735k

文献信息

• Potent poxvirus inhibitor
  申请人：The Trustees of the University of Pennsylvania

  公开号：US09233921B2

  公开（公告）日：2016-01-12

  This invention provides compounds of formulas (I), (II), (III), and (IV) as defined in the specification, and pharmaceutical compositions comprising the same, and methods of inhibiting, treating, or abrogating a poxvirus infection in a subject using the compounds or compositions.

  本发明提供了式(I)、(II)、(III)和(IV)的化合物，如规范中所定义，并且包括相同的制药组合物，以及使用这些化合物或组合物抑制、治疗或消除主体中的痘病毒感染的方法。
• Palladium-Catalyzed Intermolecular Dehydrogenative C-2 Pentenylation of Indoles with 2-Methyl-2-butene
  作者：Guo-Qiang Zhang、Xiao-Xuan Wu、Bao-Yin Zhao、Meng-Yue Wang、Hong-Xia Zhang、Yong-Qiang Wang

  DOI：10.1021/acs.orglett.4c00803

  日期：2024.5.3

  natural products. Herein we report an unprecedented unusual C5 functionalization of indole regioselectively at the C-2-position enabled by a (2-pyridyl)sulfonyl-directing palladium-catalyzed dehydrogenative strategy with a bulk chemical 2-methyl-2-butene as a C5 source. Compared to typical C5 functionalization using pentenyl alcohols, carbonates, borates, or halides as the C5 source, the protocol not

  五碳 (C 5 ) 单元是构成多种天然产品的基本构件。在此，我们报道了一种前所未有的不寻常的吲哚在 C-2 位的区域选择性 C 5官能化，这是通过 (2-吡啶基)磺酰基导向的钯催化脱氢策略以大宗化学品 2-甲基-2-丁烯作为 C 5实现的。来源。与典型的使用戊烯醇、碳酸酯、硼酸酯或卤化物作为C 5源的C 5官能化相比，该方案不仅具有低成本优势，而且具有原子和步骤经济性。
• US2014/343114
  申请人：——

  公开号：——

  公开（公告）日：——
• US20140343114A1
  申请人：——

  公开号：——

  公开（公告）日：——
• US9233921B2
  申请人：——

  公开号：US9233921B2

  公开（公告）日：2016-01-12