2-(2-hydroxy-1-naphthyl)-4-phenylsulfonylaminophenol | 27827-33-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(2-hydroxy-1-naphthyl)-4-phenylsulfonylaminophenol
• 英文别名: N-[4-hydroxy-3-(2-hydroxynaphthalen-1-yl)phenyl]benzenesulfonamide
• CAS: 27827-33-4
• 化学式: C₂₂H₁₇NO₄S
• 分子量: 391.447
• InChiKey: UUWGREFGSDPMIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  95
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2-hydroxy-1-naphthyl)-4-phenylsulfonylaminophenol 在 盐酸 作用下， 反应 5.0h， 以71.7%的产率得到2-(2-hydroxy-1-naphthyl)-4-aminophenol
  参考文献：
  名称：

  Avdeenko, A. P., Journal of Organic Chemistry USSR (English Translation), 1989, vol. 25, # 11.2, p. 2141 - 2146

  摘要：

  DOI：
• 作为产物：
  描述：

  在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到2-(2-hydroxy-1-naphthyl)-4-phenylsulfonylaminophenol
  参考文献：
  名称：

  Synthesis and SAR study of N-(4-hydroxy-3-(2-hydroxynaphthalene-1-yl)phenyl)-arylsulfonamides: Heat shock protein 90 (Hsp90) inhibitors with submicromolar activity in an in vitro assay

  摘要：

  Heat shock protein 90 is emerging as an important target in cancer chemotherapy. In a program directed toward identifying novel chemical probes for Hsp90, we found N-(4-hydroxy-3-(2-hydroxynaphthalene-1-yl)phenyl)benzene sulfonamide as an Hsp90 inhibitor with very weak activity. In this report, we present a new and general method for the synthesis of a variety of analogs around this scaffold, and discuss their structure-activity relationships. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.08.022

文献信息

• Electrochemical Cross-Coupling between <i>N</i>-(4-Hydroxyphenyl)-sulfonamides and 2-Naphthols: Synthesis of 2,2′-Bis(arenol)s
  作者：Zheng Zhu、Yanan Li、Shitang Ma、Xuan Zhou、Yekai Huang、Jianan Sun、Wei-Yi Ding

  DOI：10.1021/acs.joc.4c00021

  日期：——

  herein present an electrochemical method for the dehydrogenative cross-coupling of N-(4-hydroxyphenyl)-sulfonamides and 2-naphthols. This transformation provides a direct and scalable approach to a wide range of C1-symmetric 2,2′-bis(arenol)s with moderate to high yields under mild conditions. Preliminary attempts with the asymmetric variant of this reaction were also performed with ≤55% ee for the synthesis

  我们在此提出了一种用于 N-（4-羟基苯基）-磺胺类药物和 2-萘酚脱氢交叉偶联的电化学方法。这种转化为在温和条件下以中高产率分析各种 C1 对称 2,2′-双（芳烃醇）提供了一种直接且可扩展的方法。还用 ≤55% ee 对该反应的不对称变体进行了初步尝试，以合成 2,2′-双（芳烃醇）。进行了对照实验以提出一种合理的反应机制。
• Avdeenko, A. P.; Burmistrov, K. S.; Evgrafova, N. I., Journal of Organic Chemistry USSR (English Translation), 1987, vol. 23, # 9, p. 1717 - 1722
  作者：Avdeenko, A. P.、Burmistrov, K. S.、Evgrafova, N. I.

  DOI：——

  日期：——
• AVDEENKO, A. P., ZH. ORGAN. XIMII, 25,(1989) N1, S. 2375-2381
  作者：AVDEENKO, A. P.

  DOI：——

  日期：——
• AVDEENKO, A. P.;BURMISTROV, K. S.;EVGRAFOVA, N. I., ZH. ORGAN. XIMII, 23,(1987) N 9, 1935-1941
  作者：AVDEENKO, A. P.、BURMISTROV, K. S.、EVGRAFOVA, N. I.

  DOI：——

  日期：——
• Synthesis and SAR study of N-(4-hydroxy-3-(2-hydroxynaphthalene-1-yl)phenyl)-arylsulfonamides: Heat shock protein 90 (Hsp90) inhibitors with submicromolar activity in an in vitro assay
  作者：Thota Ganesh、Pahk Thepchatri、Lian Li、Yuhong Du、Haian Fu、James P. Snyder、Aiming Sun

  DOI：10.1016/j.bmcl.2008.08.022

  日期：2008.9

  Heat shock protein 90 is emerging as an important target in cancer chemotherapy. In a program directed toward identifying novel chemical probes for Hsp90, we found N-(4-hydroxy-3-(2-hydroxynaphthalene-1-yl)phenyl)benzene sulfonamide as an Hsp90 inhibitor with very weak activity. In this report, we present a new and general method for the synthesis of a variety of analogs around this scaffold, and discuss their structure-activity relationships. (C) 2008 Elsevier Ltd. All rights reserved.