1-azido-4-(methylsulfonyl)benzene | 85862-86-8

• 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: 1-azido-4-(methylsulfonyl)benzene
• 英文别名: 1-Azido-4-(methanesulfonyl)benzene；1-azido-4-methylsulfonylbenzene
• CAS: 85862-86-8
• 化学式: C₇H₇N₃O₂S
• 分子量: 197.217
• InChiKey: HZFMOHIBTBOZRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  56.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-azido-4-(methylsulfonyl)benzene 、 4-二甲基氨基苯乙炔 在 copper(l) iodide 、 三乙胺 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 以80%的产率得到{4-[1-(4-methanesulfonylphenyl)-1H-[1,2,3]triazol-4-yl]-phenyl}-dimethylamine
  参考文献：
  名称：

  Synthesis and cyclooxygenase inhibition of various (aryl-1,2,3-triazole-1-yl)-methanesulfonylphenyl derivatives

  摘要：

  A series of 1,4- and 1,5-diaryl substituted 1,2,3-triazoles was synthesized by either Cu( I)-catalyzed or Ru( II)-catalyzed 1,3-dipolar cycloaddition reactions between 1-azido-4-methane-sulfonylbenzene 9 and a panel of various para-substituted phenyl acetylenes ( 4- H, 4- Me, 4- OMe, 4- NMe2, 4- Cl, 4- F). All compounds were used in in vitro cyclooxygenase ( COX) assays to determine the combined electronic and steric effects upon COX-1 and COX-2 inhibitory potency and selectivity. Structure-activity relationship studies showed that compounds having a vicinal diaryl substitution pattern showed more potent COX-2 inhibition (IC50 = 0.03-0.36 mu M) compared to their corresponding 1,3-diaryl-substituted counterparts (IC50 = 0.15 to > 10.0 mu M). In both series, compounds possessing an electron-withdrawing group ( Cl and F) at the para-position of one of the aryl rings displayed higher COX-2 inhibition potency and selectivity as determined for compounds containing electron-donating groups ( Me, OMe, NMe2). The obtained data show, that the central carbocyclic or heterocyclic ring system as found in many COX-2 inhibitors can be replaced by a central 1,2,3-triazole unit without losing COX-2 inhibition potency and selectivity. The high COX-2 inhibition potency of some 1,2,3-triazoles having a vicinal diaryl substitution pattern along with their ease in synthesis through versatile Ru( II)-catalyzed click chemistry make this class of compounds interesting candidates for further design and synthesis of highly selective and potent COX-2 inhibitors. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.12.032
• 作为产物：
  描述：

  4-（甲磺酰基）苯硼酸 在 sodium azide 、 copper diacetate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以84%的产率得到1-azido-4-(methylsulfonyl)benzene
  参考文献：
  名称：

  铜 (II) 催化芳基/杂芳基硼酸、硼酸盐和三氟硼酸盐转化为相应的叠氮化物：底物范围和限制

  摘要：

  我们报告了铜 (II) 催化的有机硼化合物转化为相应的叠氮化物衍生物。评估了一系列系统的苯基硼酸衍生物，以检查取代基的空间和电子效应对反应产率以及官能团兼容性的重要性。杂环底物也被证明参与了这种温和的反应，而结合了 BC( sp³) 键在反应条件下不反应。铜 (II) 催化的硼酸-叠氮化物偶联反应进一步扩展到硼酸酯和有机三氟硼酸钾盐。本文描述的方法补充了从各自的氨基、三氮烯和卤化物衍生物制备芳基叠氮化物的现有程序，我们预计它将极大地促进铜和钌催化的叠氮化物-炔环加成反应，以制备多种功能化的 1-芳基-或1-杂芳基-1,2,3-三唑衍生物。 叠氮化物 - 有机硼化合物 - 铜催化 - 1,2,3-三唑

  DOI：

  10.1055/s-0029-1218683

文献信息

• Iridium(III)-Catalyzed Direct C-7 Amination of Indolines with Organic Azides
  作者：Kwangmin Shin、Sukbok Chang

  DOI：10.1021/jo5018475

  日期：2014.12.19

  Iridium-catalyzed regioselective C-7 amination of indolines has been achieved with organic azides as a facile nitrogen source. The developed procedure is convenient to perform even at room temperature and applicable to a wide range of substrates with high catalytic activity. Various types of organic azides (sulfonyl, aryl, and alkyl derivatives) were all successfully reacted under the present conditions

  用有机叠氮化物作为方便的氮源，已经完成了铱催化的吲哚的区域选择性C-7胺化反应。所开发的程序即使在室温下也很方便执行，并且适用于具有高催化活性的各种底物。在当前条件下，各种类型的有机叠氮化物（磺酰基，芳基和烷基衍生物）都作为可行的反应物成功地反应了。此外，轴承容易去除二氢吲哚基片Ñ保护基团如ñ -Boc或ñ -Cbz可容易地被采用，突出这种方法的合成的效用。
• Synthesis, Biological Activity, and Molecular Modeling Studies of Pyrazole and Triazole Derivatives as Selective COX-2 Inhibitors
  作者：Mohyeddin Assali、Murad Abualhasan、Hadeel Sawaftah、Mohammed Hawash、Ahmed Mousa

  DOI：10.1155/2020/6393428

  日期：2020.3.24

  derivatives were designed and synthesized in a facile synthetic approach in order to produce selective COX-2 inhibitor. These series of derivatives were synthesized by different reactions like Vilsmeier–Haack reaction and click reaction. In vitro COX-1 and COX-2 inhibition studies showed that five compounds were potent and selective inhibitors of the COX-2 isozyme with IC50 values in 0.551–0.002 μM

  以简便的合成方法设计并合成了一系列基于二芳基的吡唑和三唑衍生物，以制备选择性 COX-2 抑制剂。这些系列的衍生物是通过不同的反应合成的，如 Vilsmeier-Haack 反应和点击反应。体外 COX-1 和 COX-2 抑制研究表明，五种化合物是 COX-2 同工酶的有效选择性抑制剂，IC50 值在 0.551–0.002 μM 范围内。在二芳基吡唑衍生物中，化合物4b对COX-2表现出最好的抑制活性，IC50 = 0.017 μM，因为其中一个N-芳环被磺酰胺取代，另一个芳环未被取代。然而，当N-芳环被磺酰胺取代而另一个芳环被砜（化合物4d）取代时，实现了最佳 COX-2 选择性（IC50 = 0.098 μM，SI = 54.847）。在二芳基三唑衍生物中，与包括参考塞来昔布在内的所有合成化合物相比，化合物 15a 显示出最好的抑制活性，IC50 = 0.002 μM 和 SI =
• [EN] INHIBITORS OF CD40-CD154 BINDING<br/>[FR] INHIBITEURS DE LIAISON CD40-CD154
  申请人：TONIX PHARMACEUTICALS HOLDING CORP

  公开号：WO2020210831A1

  公开（公告）日：2020-10-15

  Disclosed herein are compounds including pharmaceutically acceptable salts, esters, prodrugs, hydrates and tautomers thereof which modulate the interactions of CD-40-CD40L. The compounds are useful for treating, ameliorating or preventing an autoimmune disease, inflammatory disease, or other immune-related disease in a patient in need of treatment.

  本文披露了包括药用可接受的盐、酯、前药、水合物和互变异构体在内的化合物，这些化合物调节CD-40-CD40L的相互作用。这些化合物可用于治疗、改善或预防患有自身免疫疾病、炎症性疾病或其他免疫相关疾病的患者。
• Rhodium-Catalyzed Direct CH Amination of Benzamides with Aryl Azides: A Synthetic Route to Diarylamines
  作者：Jaeyune Ryu、Kwangmin Shin、Sae Hume Park、Ji Young Kim、Sukbok Chang

  DOI：10.1002/anie.201205723

  日期：2012.9.24

  No muss, no fuss: A rhodium‐catalyzed direct intermolecular CH amination of benzamides and ketoximes using aryl azides as the amine source has been developed. The reaction exhibits a broad substrate scope with excellent functional‐group tolerance, requires no external oxidants, releases N2 as the only by‐product, and produces diarylamines in high yields.

  勿乱，勿扰：已开发出使用芳基叠氮化物作为胺源的铑催化的苯甲酰胺和酮肟的分子间CH胺化反应。该反应具有广泛的底物范围，具有出色的官能团耐受性，不需要外部氧化剂，释放N 2作为唯一的副产物，并以高收率生产二芳基胺。
• SNAr azidation of phenolic functions utilizing diphenyl phosphorazidate
  作者：Kotaro Ishihara、Takayuki Shioiri、Masato Matsugi

  DOI：10.1016/j.tetlet.2019.151493

  日期：2020.2

  A useful method for the synthesis of aryl azides via SNAr reaction of phenol derivatives using diphenyl phosphorazidate (DPPA) as an azidation reagent was developed. Various phenol derivatives bearing electron-withdrawing groups were converted into the corresponding aryl azides in a single step. This method is easy to perform and enables the preparation of aryl azides without the use of explosive azide

  开发了一种有用的方法，该方法通过使用叠氮磷酸二苯酯（DPPA）作为叠氮化试剂通过苯酚衍生物的SNAr反应进行芳基叠氮化物的合成。带有吸电子基团的各种酚衍生物可在一个步骤中转化为相应的芳基叠氮化物。该方法易于实施，并且能够在不使用爆炸性叠氮化物源的情况下制备芳基叠氮化物。