sulphaphenazole | 15520-50-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: sulphaphenazole
• 英文别名: Benzenesulfonamide, 4-amino-N-(1-phenyl-1H-pyrazol-4-yl)-；4-amino-N-(1-phenylpyrazol-4-yl)benzenesulfonamide
• CAS: 15520-50-0
• 化学式: C₁₅H₁₄N₄O₂S
• 分子量: 314.368
• InChiKey: WSAGDYARHNGKFB-UHFFFAOYSA-N

物化性质

• 沸点：
  541.9±56.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  98.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3-二氯-1,4-萘醌 、 sulphaphenazole 以 乙醇 为溶剂， 反应 72.0h， 以24%的产率得到4-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-ylamino)-N-(1-phenyl-1H-pyrazol-4-yl)benzenesulfonamide
  参考文献：
  名称：

  Synthesis and biological evaluation of naphthoquinone analogs as a novel class of proteasome inhibitors

  摘要：

  Screening of the NCI Diversity Set-1 identified PI-083 (NSC-45382) a proteasome inhibitor selective for cancer over normal cells. Focused libraries of novel compounds based on PI-083 chloronaphthoquinone and sulfonamide moieties were synthesized to gain a better understanding of the structure-activity relationship responsible for chymotrypsin-like proteasome inhibitory activity. This led to the demonstration that the chloronaphthoquinone and the sulfonamide moieties are critical for inhibitory activity. The pyridyl group in PI-083 can be replaced with other heterocyclic groups without significant loss of activity. Molecular modeling studies were also performed to explore the detailed interactions of PI-083 and its derivatives with the beta 5 and beta 6 subunits of the 20S proteasome. The refined model showed an H-bond interaction between the Asp-114 and the sulfonamide moiety of the PI-083 in the beta 6 subunit. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.038

文献信息

• Joshi, Sheela; Matkar, Satish; Khosla, Navita, Journal of the Indian Chemical Society, 1997, vol. 74, # 2, p. 156 - 157
  作者：Joshi, Sheela、Matkar, Satish、Khosla, Navita、Bhandari, Vinita

  DOI：——

  日期：——
• Synthesis and biological evaluation of naphthoquinone analogs as a novel class of proteasome inhibitors
  作者：Harshani R. Lawrence、Aslamuzzaman Kazi、Yunting Luo、Robert Kendig、Yiyu Ge、Sanjula Jain、Kenyon Daniel、Daniel Santiago、Wayne C. Guida、Saïd M. Sebti

  DOI：10.1016/j.bmc.2010.06.038

  日期：2010.8

  Screening of the NCI Diversity Set-1 identified PI-083 (NSC-45382) a proteasome inhibitor selective for cancer over normal cells. Focused libraries of novel compounds based on PI-083 chloronaphthoquinone and sulfonamide moieties were synthesized to gain a better understanding of the structure-activity relationship responsible for chymotrypsin-like proteasome inhibitory activity. This led to the demonstration that the chloronaphthoquinone and the sulfonamide moieties are critical for inhibitory activity. The pyridyl group in PI-083 can be replaced with other heterocyclic groups without significant loss of activity. Molecular modeling studies were also performed to explore the detailed interactions of PI-083 and its derivatives with the beta 5 and beta 6 subunits of the 20S proteasome. The refined model showed an H-bond interaction between the Asp-114 and the sulfonamide moiety of the PI-083 in the beta 6 subunit. (C) 2010 Elsevier Ltd. All rights reserved.