3-(4-methoxyphenyl)-1-tosyl-1H-pyrazole | 1416587-64-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4-methoxyphenyl)-1-tosyl-1H-pyrazole
• 英文别名: 3-(4-Methoxyphenyl)-1-(4-methylphenyl)sulfonylpyrazole；3-(4-methoxyphenyl)-1-(4-methylphenyl)sulfonylpyrazole
• CAS: 1416587-64-8
• 化学式: C₁₇H₁₆N₂O₃S
• 分子量: 328.392
• InChiKey: NBIFPZFKEGGZOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  69.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-(dimethylamino)-1-(4-methoxyphenyl)prop-2-en-1-one 在 吡啶 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 1.75h， 生成 3-(4-methoxyphenyl)-1-tosyl-1H-pyrazole
  参考文献：
  名称：

  Identification of anticancer agents based on the thieno[2,3-b]pyridine and 1H-pyrazole molecular scaffolds

  摘要：

  Structural similarity search of commercially available analogues of thieno[2,3-b]pyridine and 1H-pyrazole derivatives, known anticancer agents, resulted in 717 hits. These were docked into the phosphoinositide specific-phospholipase C (PLC) binding pocket, the putative target of the compounds, to further focus the selection. Thirteen derivatives of the thieno[2,3-b]pyridines were identified and tested against the NCI60 panel of human tumour cell lines. The most active derivative 1 was most potent against the MDA-MB-435 melanoma cell line with GI(50) at 30 nM. Also, it was found that a piperidine moiety is tolerated on the thieno[2,3-b]pyridine scaffold with GI(50) = 296 nM (MDA-MB-435) for derivative 10 considerably expanding the structure activity relationship for the series. For the 1H-pyrazoles four derivatives were identified using the in silico approach and additionally ten were synthesised with various sub-stituents on the phenyl moiety to extend the structural activity relationship but only modest anticancer activity was found. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.05.061

文献信息

• Zinc-promoted cyclization of tosylhydrazones and 2-(dimethylamino)malononitrile: an efficient strategy for the synthesis of substituted 1-tosyl-1H-pyrazoles
  作者：Bang-Hong Zhang、Lin-Sheng Lei、Si-Zhan Liu、Xue-Qing Mou、Wei-Ting Liu、Shao-Hua Wang、Jie Wang、Wen Bao、Kun Zhang

  DOI：10.1039/c7cc04610c

  日期：——

  A Zn(OTf)2-promoted cyclization reaction of tosylhydrazones with 2-(dimethylamino)malononitrile has been successfully developed providing an efficient strategy for the synthesis of substituted 1-tosyl-1H-pyrazoles.

  已成功开发了甲苯磺酰肼与2-（二甲氨基）丙二腈的Zn（OTf）2促进的环化反应，为合成取代的1-tosyl-1 H-吡唑提供了有效的策略。
• Chemoselective synthesis of substituted pyrazoles through AgOTf-catalyzed cascade propargylic substitution–cyclization–aromatization
  作者：Su-Xia Xu、Lu Hao、Tao Wang、Zong-Cang Ding、Zhuang-Ping Zhan

  DOI：10.1039/c2ob27016a

  日期：——

  A cascade AgOTf-catalyzed chemoselective approach to 3,5/1,3-disubstitued pyrazoles from propargylic alcohols and para-tolylsulfonohydrazide has been developed. Good chemoselectivity is observed depending on the different substituents in the alkyne moiety of the propargylic alcohols, generating two different kinds of products through different aromatization mechanisms. The pyrazolo[5,1-a]isoquinoline skeleton can also be effectively constructed by this method through a cascade bicyclization process.

  开发了一种瀑布式AgOTf催化的化学选择性方法，能够从丙炔醇和对甲苯磺酰肼得到3,5/1,3二取代的吡唑。根据丙炔醇中炔烃部分的不同取代基，观察到良好的化学选择性，通过不同的芳构化机制生成两种不同类型的产物。该方法还可以通过级联双环化过程有效构建吡唑[5,1-a]异喹啉骨架。
• Synthesis of <i>N</i> -Sulfonyl Pyrazoles Through Cyclization Reactions of Sulfonyl Hydrazines with Enaminones Promoted by <i>p</i> -TSA
  作者：Qiaohe Zhang、Biao Hu、Yuxuan Zhao、Siyun Zhao、Yanqin Wang、Biao Zhang、Shengjiao Yan、Fuchao Yu

  DOI：10.1002/ejoc.201901886

  日期：2020.3.8

  An efficient protocol for the synthesis of 3‐substituted N‐sulfonyl pyrazoles through p‐TSA‐promoted cyclization reactions of N,N‐dimethyl enaminones with sulfonyl hydrazines is described.

  描述了一种通过p -TSA促进N，N-二甲基烯胺酮与磺酰基肼的环化反应合成3-取代的N-磺酰基吡唑的有效方案。
• 一种合成取代的1-磺酰基-1H-吡唑的方法
  申请人：五邑大学

  公开号：CN107162976A

  公开（公告）日：2017-09-15

  本发明公开一种合成取代的1‑磺酰基‑1H‑吡唑的方法，旨在提供一种起始原料简单易得，收率高，操作方便的1‑磺酰基‑1H‑吡唑合成方法，其技术要点是将磺酰腙、N,N‑二甲基丙二腈和路易斯酸催化剂，依次加入到有机溶剂中，加热回流条件下反应得到取代的1‑磺酰基‑1H‑吡唑；属于有机合成技术领域。