(E)-4-((5-chloropyridin-3-yl)diazenyl)-5-hydroxy-3-(4-nitrophenyl)-1H-pyrazole-1-carbothioamide | 1596216-36-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (E)-4-((5-chloropyridin-3-yl)diazenyl)-5-hydroxy-3-(4-nitrophenyl)-1H-pyrazole-1-carbothioamide
• CAS: 1596216-36-2
• 化学式: C₁₅H₁₀ClN₇O₃S
• 分子量: 403.808
• InChiKey: NXPXKHAPCXLXCI-FMQUCBEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  144.82
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  3-氨基-5-氯吡啶 在 盐酸 、 sodium nitrite 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 22.75h， 生成 (E)-4-((5-chloropyridin-3-yl)diazenyl)-5-hydroxy-3-(4-nitrophenyl)-1H-pyrazole-1-carbothioamide
  参考文献：
  名称：

  Synthesis and structure–activity analysis of diphenylpyrazolodiazene inhibitors of the HIV-1 Nef virulence factor

  摘要：

  HIV-1 Nef is a critical AIDS progression factor yet underexplored target for antiretroviral drug discovery. A recent high-throughput screen for pharmacological inhibitors of Nef-dependent Src-family kinase activation identified a diphenylpyrazolodiazene hit compound with submicromolar potency in HIV-1 replication assays against a broad range of primary Nef variants. This compound, known as 'B9', binds directly to Nef and inhibits its dimerization in cells as a possible mechanism of action. Here were synthesized a diverse set of B9 analogs and identified structural features essential to antiretroviral activity. Chemical modifications to each of the three rings present in the parent compound were identified that did not compromise antiviral action. These analogs will guide the development of next-generation compounds with appropriate pharmacological profiles for assessment of antiretroviral activity in vivo. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.02.045

文献信息

• COMPOUNDS FOR TREATING HIV AND METHODS FOR USING THE COMPOUNDS
  申请人：UNIVERSITY OF PITTSBURGH-OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCATION

  公开号：US20150291534A1

  公开（公告）日：2015-10-15

  Disclosed herein are embodiments of a compound capable of treating HIV. In particular disclosed embodiments, the compound is capable of inhibiting Nef, such as by acting as antagonists of HIV Nef function. Also disclosed are embodiments of a method of making the compound, embodiments of a method of using the compound, and embodiments of a method of identifying HIV Nef antagonists. The disclosed compound may be used alone or in combination with other pharmacologically active agents in order to promote reducing drug resistance and/or cumulative toxicity.
• US9695127B2
  申请人：——

  公开号：US9695127B2

  公开（公告）日：2017-07-04
• [EN] COMPOUNDS FOR TREATING HIV AND METHODS FOR USING THE COMPOUNDS<br/>[FR] COMPOSÉS POUR LE TRAITEMENT DU VIH ET PROCÉDÉS D'UTILISATION DES COMPOSÉS
  申请人：UNIV PITTSBURGH

  公开号：WO2014074628A1

  公开（公告）日：2014-05-15

  Disclosed herein are embodiments of a compound capable of treating HIV. In particular disclosed embodiments, the compound is capable of inhibiting Nef, such as by acting as antagonists of HIV Nef function. Also disclosed are embodiments of a method of making the compound, embodiments of a method of using the compound, and embodiments of a method of identifying HIV Nef antagonists. The disclosed compound may be used alone or in combination with other pharmacologically active agents in order to promote reducing drug resistance and/or cumulative toxicity.
• Synthesis and structure–activity analysis of diphenylpyrazolodiazene inhibitors of the HIV-1 Nef virulence factor
  作者：Prema C. Iyer、Jielu Zhao、Lori A. Emert-Sedlak、Kerry K. Moore、Thomas E. Smithgall、Billy W. Day

  DOI：10.1016/j.bmcl.2014.02.045

  日期：2014.4

  HIV-1 Nef is a critical AIDS progression factor yet underexplored target for antiretroviral drug discovery. A recent high-throughput screen for pharmacological inhibitors of Nef-dependent Src-family kinase activation identified a diphenylpyrazolodiazene hit compound with submicromolar potency in HIV-1 replication assays against a broad range of primary Nef variants. This compound, known as 'B9', binds directly to Nef and inhibits its dimerization in cells as a possible mechanism of action. Here were synthesized a diverse set of B9 analogs and identified structural features essential to antiretroviral activity. Chemical modifications to each of the three rings present in the parent compound were identified that did not compromise antiviral action. These analogs will guide the development of next-generation compounds with appropriate pharmacological profiles for assessment of antiretroviral activity in vivo. (C) 2014 Elsevier Ltd. All rights reserved.