4-tert-butyl-N-(4-hydroxyphenyl)benzenesulfonamide

• 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-tert-butyl-N-(4-hydroxyphenyl)benzenesulfonamide
• 化学式: C₁₆H₁₉NO₃S
• 分子量: 305.398
• InChiKey: IKOGGLYESDINJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  74.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-tert-butyl-N-(4-hydroxyphenyl)benzenesulfonamide 在 silver(l) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 4-tert-butyl-N-(4-oxocyclohexa-2,5-dien-1-ylidene)benzenesulfonamide
  参考文献：
  名称：

  通过2-吲哚基甲醇与醌亚胺的[3 + 3]环化反应合成吲哚稠合的支架

  摘要：

  实现了2-吲哚基甲醇与醌的正式[3 + 3]环化反应，以中等至优异的产率提供了吲哚融合的支架。该方案在酸性条件下顺利进行，具有高收率和广泛的底物范围。

  DOI：

  10.1016/j.tet.2020.131742
• 作为产物：
  描述：

  bis(4-tert-butylphenyl)disulfide 在 sodium hydrogen sulfate 、 sodium hypochlorite pentahydrate 、 magnesium oxide 作用下， 反应 2.0h， 生成 4-tert-butyl-N-(4-hydroxyphenyl)benzenesulfonamide
  参考文献：
  名称：

  通过可伸缩、环保且经济高效的工艺机械合成磺酰胺

  摘要：

  在此，我们展示了一种无溶剂机械化学方法，涉及由固体次氯酸钠（NaOCl·5H 2 O）介导的一锅双步程序，用于合成磺酰胺。该方案需要在催化固体酸性物质存在下对二硫化物进行串联氧化氯化反应，然后在路易斯酸碱固体无机试剂的促进下进行胺化。该方法适用于芳香族和脂肪族二硫化物和胺。纯化过程充分考虑了环境问题，避免了恶劣的条件，以获得纯净的磺酰胺产品。一些相关的生物活性化合物已经用此过程制备。

  DOI：

  10.1039/d3gc01894f

文献信息

• PHARMACEUTICAL COMPOSITION WITH ENHANCED EFFICACY FOR INHIBITING ANGIOGENESIS
  申请人：Kwon Ho Jeong

  公开号：US20140315947A1

  公开（公告）日：2014-10-23

  The present invention relates to a pharmaceutical composition for inhibiting angiogenesis and a novel sulfonyl amide derivative compound which can be useful for the prevention or treatment of angiogenesis-related diseases or disorders. Since the compound used as an active ingredient in the pharmaceutical composition of the invention is specifically bound to UQCRB and inhibits biological functions thereof, apoptosis is not induced and angiogenic responses are inhibited. Therefore, the compound used as an active ingredient in the pharmaceutical composition of the invention can be useful as an effective and safe angiogenesis inhibitory agent.

  本发明涉及一种用于抑制血管生成的药物组合物以及一种新型磺酰胺衍生物化合物，该化合物可用于预防或治疗与血管生成相关的疾病或疾病。由于本发明药物组合物中所使用的活性成分化合物特异地结合到UQCRB并抑制其生物功能，不会诱导凋亡并抑制血管生成反应。因此，本发明药物组合物中所使用的活性成分化合物可以作为一种有效且安全的抑制血管生成的药剂。
• Development of a Novel Class of Mitochondrial Ubiquinol–Cytochrome <i>c</i> Reductase Binding Protein (UQCRB) Modulators as Promising Antiangiogenic Leads
  作者：Hye Jin Jung、Misun Cho、Yonghyo Kim、Gyoonhee Han、Ho Jeong Kwon

  DOI：10.1021/jm500863j

  日期：2014.10.9

  Recently we identified a novel therapeutic target and small molecule for regulating angiogenesis. Our study showed that ubiquinol-cytochrome c-reductase binding protein (UQCRB) of the mitochondrial complex III plays a crucial role in hypoxia-induced angiogenesis via mitochondrial reactive oxygen species (ROS) mediated signaling. Herein, we developed new synthetic small molecules that specifically bind to UQCRB and regulate its function. To improve the pharmacological properties of 6-((1-hydroxynaphthalen 4-ylamino)dioxysulfone) 2H naphtho[1,8-bc]thiophen-2-one (HDNT), a small molecule that targets UQCRB, a series of HDNT derivatives were designed and synthesied. Several derivatives showed a significant increase in hypoxia inducible factor 1 alpha (HIF-1 alpha) inhibitory potency. compared to HDNT. The compounds bound to UQCRB and suppressed mitochondrial ROS-mediated hypoxic signaling, resulting in potent inhibitor of angiogenesis without inducing cytotoxicity. Notably, one of these new derivatives significantly suppressed tumor growth in a mouse xenograft model. Therefore, these mitochondrial UQCRB modulators could be potential leads for the development of novel antiangiogen agents.
• Novel Arylsulfoanilide−Oxindole Hybrid as an Anticancer Agent That Inhibits Translation Initiation
  作者：Amarnath Natarajan、Yuhong Guo、Frederick Harbinski、Yun-Hua Fan、Han Chen、Lia Luus、Jana Diercks、Huseyin Aktas、Michael Chorev、Jose A. Halperin

  DOI：10.1021/jm0496234

  日期：2004.10.1

  Structure-activity relationship studies of substituted arylsulfoanilides as antiproliferatives, which are mediated by the partial depletion of intracellular Ca2+ stores, resulted in the identification of compounds with micromolar activity against lung cancer cells in a growth inhibition assay. Incorporating the substitution pattern of the best arylsulfoanilides onto the 3-phenyloxindole scaffold resulted in a potent arylsulfoanilide-oxindole hybrid, 27. Compound 27 inhibits cancer cell growth by partial depletion of intracellular Ca2+ stores and phosphorylation of eIF2alpha.
• US9371286B2
  申请人：——

  公开号：US9371286B2

  公开（公告）日：2016-06-21
• Synthesis of indole-fused scaffolds via [3+3] cyclization reaction of 2-indolylmethanols with quinone imines
  作者：Lu-Zhe Qin、Ya-Long Cheng、Xiaoan Wen、Qing-Long Xu、Le Zhen

  DOI：10.1016/j.tet.2020.131742

  日期：2021.1

  A formal [3 + 3] cyclization reaction of 2-indolylmethanols with quinones was realized to furnish indole-fused scaffolds in moderate to excellent yields. This protocol was proceeded smoothly under acid condition, with high high yields and broad substrate scope.

  实现了2-吲哚基甲醇与醌的正式[3 + 3]环化反应，以中等至优异的产率提供了吲哚融合的支架。该方案在酸性条件下顺利进行，具有高收率和广泛的底物范围。