2-Mercapto-N-propylcarbamoylmethyl-benzamide | 824938-56-9

• 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: 2-Mercapto-N-propylcarbamoylmethyl-benzamide
• 英文别名: N-[2-oxo-2-(propylamino)ethyl]-2-sulfanylbenzamide
• CAS: 824938-56-9
• 化学式: C₁₂H₁₆N₂O₂S
• mdl: MFCD30573051
• 分子量: 252.337
• InChiKey: ANVHHCOBEZIPLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  59.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Mercapto-N-propylcarbamoylmethyl-benzamide 、 氯化烟碱盐酸盐 在 三乙胺 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 以32%的产率得到S-[2-[[2-oxo-2-(propylamino)ethyl]carbamoyl]phenyl] pyridine-3-carbothioate
  参考文献：
  名称：

  Optimization of unique, uncharged thioesters as inhibitors of HIV replication

  摘要：

  A combinatorial chemistry approach was employed to prepare a restricted library of N-substituted S-acyl-2-mercapto-benzamide thioesters. It was shown that many members of this chemotype display anti-HIV activity via their ability to interact with HIV-1, HIV-2, SIV-infected cells, cell-free virus, and chronically and latently infected cells in a manner consistent with targeting of the highly conserved HIV-1 NCp7 zinc fingers. Compounds were initially screened using two different in vitro antiviral assays and evaluated for stability in neutral buffer containing 10% pooled human Serum using a spectrophotometric assay. These data revealed that there was no significant correlation between thioester stability and antiviral activity, however, a slight inverse correlation between serum stability and virucidal activity was noted. Based on the virucidal capability and the ability to select lead compounds to inhibit virus expression from latently infected TNFalpha-induced U1 cells, we next determined if these compounds could prevent HIV cell-to-cell transmission. Several thioesters demonstrated potent inhibition of HIV cell-to-cell transmission with EC50 values in the 80-100 nM range. Thus, we have optimized a series of restricted thioesters and provided evidence that serum stability is not required for antiviral activity. Moreover, selected compounds show potential for development as topical microbicides. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.09.032
• 作为产物：
  描述：

  2, 2'-二硫代二苯甲酸 在 三(2-羰基乙基)磷盐酸盐 、 三乙胺 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 4.0h， 生成 2-Mercapto-N-propylcarbamoylmethyl-benzamide
  参考文献：
  名称：

  Optimization of unique, uncharged thioesters as inhibitors of HIV replication

  摘要：

  A combinatorial chemistry approach was employed to prepare a restricted library of N-substituted S-acyl-2-mercapto-benzamide thioesters. It was shown that many members of this chemotype display anti-HIV activity via their ability to interact with HIV-1, HIV-2, SIV-infected cells, cell-free virus, and chronically and latently infected cells in a manner consistent with targeting of the highly conserved HIV-1 NCp7 zinc fingers. Compounds were initially screened using two different in vitro antiviral assays and evaluated for stability in neutral buffer containing 10% pooled human Serum using a spectrophotometric assay. These data revealed that there was no significant correlation between thioester stability and antiviral activity, however, a slight inverse correlation between serum stability and virucidal activity was noted. Based on the virucidal capability and the ability to select lead compounds to inhibit virus expression from latently infected TNFalpha-induced U1 cells, we next determined if these compounds could prevent HIV cell-to-cell transmission. Several thioesters demonstrated potent inhibition of HIV cell-to-cell transmission with EC50 values in the 80-100 nM range. Thus, we have optimized a series of restricted thioesters and provided evidence that serum stability is not required for antiviral activity. Moreover, selected compounds show potential for development as topical microbicides. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.09.032

文献信息

• ACYTHIOLS AND COMPONENT THIOL COMPOSITIONS AS ANTI-HIV AND ANTI-RETROVIRAL AGENTS
  申请人：Inman John K.

  公开号：US20090247473A1

  公开（公告）日：2009-10-01

  Certain thiol and acylthiol compounds inhibit retrovirus growth by attacking the highly conserved zinc finger regions of essential viral proteins. These compounds, compositions containing them, and methods of using them to treat retroviral infections such as HIV are described. These compounds are also useful for preparation of vaccines comprised of inactivated retroviruses such as HIV, prevention of the transmission of such retroviruses, and detection of retroviral proteins.

  某些硫醇和酰硫醇化合物通过攻击必要病毒蛋白质高度保守的锌指区域来抑制逆转录病毒的生长。本文描述了这些化合物、含有它们的组合物以及使用它们治疗逆转录病毒感染（如HIV）的方法。这些化合物还可用于制备由灭活逆转录病毒（如HIV）组成的疫苗，预防这种逆转录病毒的传播以及检测逆转录病毒蛋白质。
• US7528274B2
  申请人：——

  公开号：US7528274B2

  公开（公告）日：2009-05-05
• US8076372B2
  申请人：——

  公开号：US8076372B2

  公开（公告）日：2011-12-13
• Optimization of unique, uncharged thioesters as inhibitors of HIV replication
  作者：Pratibha Srivastava、Marco Schito、Rasem J. Fattah、Toshiaki Hara、Tracy Hartman、Robert W. Buckheit、Jim A. Turpin、John K. Inman、Ettore Appella

  DOI：10.1016/j.bmc.2004.09.032

  日期：2004.12

  A combinatorial chemistry approach was employed to prepare a restricted library of N-substituted S-acyl-2-mercapto-benzamide thioesters. It was shown that many members of this chemotype display anti-HIV activity via their ability to interact with HIV-1, HIV-2, SIV-infected cells, cell-free virus, and chronically and latently infected cells in a manner consistent with targeting of the highly conserved HIV-1 NCp7 zinc fingers. Compounds were initially screened using two different in vitro antiviral assays and evaluated for stability in neutral buffer containing 10% pooled human Serum using a spectrophotometric assay. These data revealed that there was no significant correlation between thioester stability and antiviral activity, however, a slight inverse correlation between serum stability and virucidal activity was noted. Based on the virucidal capability and the ability to select lead compounds to inhibit virus expression from latently infected TNFalpha-induced U1 cells, we next determined if these compounds could prevent HIV cell-to-cell transmission. Several thioesters demonstrated potent inhibition of HIV cell-to-cell transmission with EC50 values in the 80-100 nM range. Thus, we have optimized a series of restricted thioesters and provided evidence that serum stability is not required for antiviral activity. Moreover, selected compounds show potential for development as topical microbicides. (C) 2004 Elsevier Ltd. All rights reserved.