4-(tert-butyl)-N-(2-hydroxyphenyl)benzenesulfonamide | 81256-09-9

• 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-(2-hydroxyphenyl)benzenesulfonamide
• 英文别名: 4-tert-butyl-N-(2-hydroxyphenyl)benzenesulfonamide
• CAS: 81256-09-9
• 化学式: C₁₆H₁₉NO₃S
• 分子量: 305.398
• InChiKey: LBLDWCORBVGHIL-UHFFFAOYSA-N

物化性质

• 熔点：
  184.5-185 °C
• 沸点：
  438.4±55.0 °C(Predicted)
• 密度：
  1.253±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 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

• 作为产物：
  描述：

  对叔丁基苯磺酰氯 在 正丁基锂 、 三乙胺 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 4-(tert-butyl)-N-(2-hydroxyphenyl)benzenesulfonamide
  参考文献：
  名称：

  Substitution at tetracoordinate sulfur(VI). Rearrangement of 2-aminoaryl arenesulfonates to N-(2-hydroxyaryl)arenesulfonamides

  摘要：

  DOI：

  10.1021/jo00349a013

文献信息

• Phenylbenzenesulfonates and -sulfonamides as 17β-hydroxysteroid dehydrogenase type 2 inhibitors: Synthesis and SAR-analysis
  作者：Anna Vuorinen、Roger T. Engeli、Susanne Leugger、Christoph R. Kreutz、Daniela Schuster、Alex Odermatt、Barbara Matuszczak

  DOI：10.1016/j.bmcl.2017.05.005

  日期：2017.7

  in multiple studies, synthesis and biological evaluation of promising 17β-HSD2 inhibitors have been reported. Our previous work led to the identification of phenylbenzenesulfonamides and -sulfonates as new 17β-HSD2 inhibitors by ligand-based pharmacophore modeling and virtual screening. In this study, new molecules representing this scaffold were synthesized and tested in vitro for their 17β-HSD2 activity

  2型17β-羟基类固醇脱氢酶（17β-HSD2）将有效的雌激素雌二醇转化为弱活性的酮形式雌酮。由于其在骨中的表达，抑制17β-HSD2为治疗骨质疏松症提供了一种有吸引力的策略，该病症通常是由于活性性类固醇减少而引起的。当前，市场上没有靶向17β-HSD2的药物，但是在多项研究中，已经报道了有前途的17β-HSD2抑制剂的合成和生物学评估。通过基于配体的药效团建模和虚拟筛选，我们以前的工作导致鉴定出新的17β-HSD2抑制剂苯基苯磺酰胺和-磺酸盐。在这项研究中，代表该支架的新分子被合成并在体外测试 为他们的17β-HSD2活性推导更深刻的构效关系规则。
• 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.
• ANDERSEN, K. K.;GOWDA, G.;JEWELL, L.;MCGRAW, P.;PHILLIPS, B. T., J. ORG. CHEM., 1982, 47, N 10, 1884-1889
  作者：ANDERSEN, K. K.、GOWDA, G.、JEWELL, L.、MCGRAW, P.、PHILLIPS, B. T.

  DOI：——

  日期：——
• Substitution at tetracoordinate sulfur(VI). Rearrangement of 2-aminoaryl arenesulfonates to N-(2-hydroxyaryl)arenesulfonamides
  作者：Kenneth K. Andersen、Gopala Gowda、Linda Jewell、Phillip McGraw、Brian T. Phillips

  DOI：10.1021/jo00349a013

  日期：1982.5