3-chloro-4-methoxybenzene-1-sulfonamide | 69173-20-2

• 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: 3-chloro-4-methoxybenzene-1-sulfonamide
• 英文别名: 3-chloro-4-methoxy-benzenesulfonic acid amide；3-Chlor-4-methoxy-benzolsulfonsaeure-amid；3-chloro-4-methoxybenzenesulfonamide；3-Chlor-4-methoxy-benzolsulfonamid
• CAS: 69173-20-2
• 化学式: C₇H₈ClNO₃S
• mdl: MFCD03618457
• 分子量: 221.664
• InChiKey: SEBGFUXPGSMUPE-UHFFFAOYSA-N

物化性质

• 沸点：
  387.9±52.0 °C(Predicted)
• 密度：
  1.436±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  77.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2935009090

反应信息

• 作为反应物：
  描述：

  3-chloro-4-methoxybenzene-1-sulfonamide 在 sodium dithionite 、 titanium(IV) chloride tetrahydrofuran 、 水 、 三乙胺 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 生成 3-chloro-N-[4-hydroxy-3-(1H-1,2,4-triazol-5-ylsulfanyl)naphthalen-1-yl]-4-methoxybenzenesulfonamide
  参考文献：
  名称：

  Identification of a Novel Family of BRAF^V600E Inhibitors

  摘要：

  The BRAF oncoprotein is mutated in about half of malignant melanomas and other cancers, and a kinase activating single valine to glutamate substitution at residue 600 (BRAF(V600E)) accounts for over 90% of BRAF-mediated cancers. Several BRAF(V600E) inhibitors have been developed, although they harbor some liabilities, thus motivating the development of other BRAF(V600E) inhibitor options. We report here the use of an ELISA based high-throughput screen to identify a family of related quinolol/naphthol compounds that preferentially inhibit BRAF(V600E) over BRAF(WT) and other kinases. We also report the X-ray crystal structure of a BRAF/quinolol complex revealing the mode of inhibition, employ structure-based medicinal chemistry efforts to prepare naphthol analogues that inhibit BRAF(V600E) in vitro with IC50 values in the 80-200 nM range under saturating ATP concentrations, and demonstrate that these compounds inhibit MAPK signaling in melanoma cells. Prospects for improving the potency and selectivity of these inhibitors are discussed.

  DOI：

  10.1021/jm3004416
• 作为产物：
  描述：

  2-氯苯甲醚 在 chlorosulphuric acid 、 氯仿 作用下， 生成 3-chloro-4-methoxybenzene-1-sulfonamide
  参考文献：
  名称：

  Identification of Organic Compounds. III. Chlorosulfonic Acid as a Reagent for the Characterization of Aromatic Ethers^1,2

  摘要：

  DOI：

  10.1021/ja01860a049

文献信息

• SYNTHESIS OF SUBSTITUTED PYRAZOLINE CARBOXAMIDINE DERIVATIVES
  申请人：van Loevezijn Arnold

  公开号：US20130060041A1

  公开（公告）日：2013-03-07

  This invention relates to organic chemistry, in particular to processes for the preparation of pyrazoline carboxamidine derivatives of formula (I), known as potent 5-HT6 antagonists. The invention also relates to novel intermediates of these compounds. wherein the symbols have the meanings given in the description.

  本发明涉及有机化学，特别是关于制备式(I)的吡唑啉羧酰胺衍生物的过程，这些衍生物被称为有效的5-HT6受体拮抗剂。本发明还涉及这些化合物的新型中间体。其中符号的含义如描述所示。
• Single-Electron-Transfer-Generated Aryl Sulfonyl Ammonium Salt: Metal-Free Photoredox-Catalyzed Modular Construction of Sulfonamides
  作者：Fengying Yan、Qing Li、Shanshan Fu、Yuxing Yang、Duoqi Yang、Shun Yao、Man Song、Hong Deng、Xianwei Sui

  DOI：10.1021/acscatal.4c00816

  日期：2024.4.5

  construction of aryl sulfonamides via an aryl sulfonyl ammonium salt intermediate, which was generated in situ via a SET event, has been established. A variety of structurally diverse primary, secondary, and tertiary aryl sulfonamides were synthesized rapidly from abundant amines or sodium azide under mild conditions. Notably, the primary aliphatic amine, which remains challenging in the Cu-catalyzed protocols

  磺胺类化合物在有机合成和药物化学中具有突出的作用。然而，用于芳基磺酰胺模块化结构的通用合成平台仍然难以捉摸。在此，通过芳基磺酰铵盐中间体建立了无金属光氧化还原催化的芳基磺酰胺三组分结构，该中间体通过SET 事件原位生成。在温和条件下，由丰富的胺或叠氮化钠快速合成了多种结构多样的伯、仲和叔芳基磺酰胺。值得注意的是，脂肪族伯胺在铜催化方案中仍然具有挑战性，但在这种方法中效果良好。此外，以氟化氢钾为亲核试剂，也可以顺利合成芳基磺酰氟。这种转换的潜在效用在三种生物活性药物化合物的简便构建中得到了证明。初步的机理研究表明，芳基磺酰基自由基和芳基磺酰铵盐是这种机械创新方法中的关键中间体。
• Structure-Based Development of a Protein–Protein Interaction Inhibitor Targeting Tumor Necrosis Factor Receptor-Associated Factor 6
  作者：Jun Moriya、Koh Takeuchi、Kenji Tai、Kenzo Arai、Naoki Kobayashi、Naoki Yoneda、Yoshifumi Fukunishi、Atsushi Inoue、Miho Kihara、Takumi Murakami、Kenichi Chiba、Ichio Shimada

  DOI：10.1021/acs.jmedchem.5b00778

  日期：2015.7.23

  The interactions between tumor necrosis factor (TNF) receptor-associated factor 6 (TRAF6) and TNF superfamily receptors (TNFRSFs) are promising targets for rheumatoid arthritis (RA) treatment. However, due to the challenging nature of protein-protein interactions (PPIs), a potent inhibitor that surpasses the affinity of the TRAF6-TNFRSF interactions has not been developed. We developed a small-molecule PPI inhibitor of TRAF6-TNFRSF interactions using NMR and in silico techniques. The most potent compound, TRI4, exhibited an affinity higher than those of TNFRSFs and competitively inhibited a TRAF6-TNFRSF interaction. Structural characterization of the TRAF6-TRI4 complex revealed that TRI4 supplants key interactions in the TRAF6-TNFRSF interfaces. In addition, some TRAF6-TRI4 interactions extend beyond the TRAF6-TNFRSF interfaces and increase the binding affinity. Our successful development of TRI4 provides a new Opportunity for RA treatment and implications fur structure-guided development of PPI inhibitors.
• [EN] SYNTHESIS OF SUBSTITUTED PYRAZOLINE CARBOXAMIDINE DERIVATIVES<br/>[FR] SYNTHÈSE DE DÉRIVÉS DE PYRAZOLINE CARBOXAMIDINE SUBSTITUÉS
  申请人：ABBOTT HEALTHCARE PRODUCTS BV

  公开号：WO2011092226A8

  公开（公告）日：2012-09-07
• Discovery and Optimization of 7-Alkylidenyltetrahydroindazole-Based Acylsulfonamide EP3 Antagonists
  作者：Bin Zhu、Xuqing Zhang、Lili Guo、Matthew Rankin、Ivona Bakaj、George Ho、Seunghun P. Lee、Lisa Norquay、Mark Macielag

  DOI：10.1021/acsmedchemlett.1c00594

  日期：2022.1.13