2-bromo-N-(4-methanesulfonyl-phenyl)-acetamide | 29182-95-4

• 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-bromo-N-(4-methanesulfonyl-phenyl)-acetamide
• 英文别名: 2-bromo-N-(4-(methylsulfonyl)phenyl)acetamide；2-bromo-N-(4-methylsulfonylphenyl)acetamide
• CAS: 29182-95-4
• 化学式: C₉H₁₀BrNO₃S
• 分子量: 292.153
• InChiKey: MEIZIIQZAAQZPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-bromo-N-(4-methanesulfonyl-phenyl)-acetamide 、 噻菌灵 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 N-(4-methylsulfonylphenyl)-2-(2-thiazol-4-ylbenzimidazol-1-yl)acetamide
  参考文献：
  名称：

  Structure–activity relationship study of selective benzimidazole-based inhibitors of Cryptosporidium parvum IMPDH

  摘要：

  Cryptosporidium parasites are important waterborne pathogens of both humans and animals. The Cryptosporidium parvum and Cryptosporidium hominis genomes indicate that the only route to guanine nucleotides is via inosine 5 '-monophosphate dehydrogenase (IMPDH). Thus the inhibition of the parasite IMPDH presents a potential strategy for treating Cryptosporidium infections. A selective benzimidazole-based inhibitor of C. parvum IMPDH (CpIMPDH) was previously identified in a high throughput screen. Here we report a structure-activity relationship study of benzimidazole-based compounds that resulted in potent and selective inhibitors of CpIMPDH. Several compounds display potent antiparasitic activity in vitro. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.029
• 作为产物：
  描述：

  溴乙酰氯 、 4-甲磺酰基苯胺 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 以84.7%的产率得到2-bromo-N-(4-methanesulfonyl-phenyl)-acetamide
  参考文献：
  名称：

  设计，合成和生物学评估新型乙酰胺取代的doravirine及其前体药物作为有效的HIV-1 NNRTIs。

  摘要：

  通过采用基于结构的药物设计策略，设计并合成了一系列新的乙酰胺取代的衍生物和Doravirine的两种前药，作为有效的HIV-1 NNRTI。在使用MTT方法的基于MT-4细胞的测定中，发现大多数新化合物对野生型（WT）HIV-1菌株均表现出中度至优异的抑制力，最小EC50值为54.8 nM。其中，两种最有效的化合物8i（EC50 = 59.5 nM）和8k（EC50 = 54.8 nM）对野生型HIV-1表现出强大的活性，具有两位数纳摩尔EC50值，优于拉米夫定（3TC，EC50 = 12.8μM ）并与doravirine（EC50 = 13 nM）相当。此外，8i和8k对双RT突变株（K103N + Y181C）HIV-1 RES056株显示中等活性。HIV-1 RT抑制测定进一步验证了结合靶标。通过对代表性化合物的分子模拟，可以深入了解其结构-活性关系（SAR），并指导未来的设计工作

  DOI：

  10.1016/j.bmc.2018.12.039

文献信息

• [EN] PARP INHIBITORS<br/>[FR] INHIBITEURS DE PARP
  申请人：HOFFMANN LA ROCHE

  公开号：WO2013030205A1

  公开（公告）日：2013-03-07

  The present application disclosed compounds of Formula I wherein variables R1 and R2 are defined as described herein, which are inhibitors of PARP and provides compounds and compositions containing the compounds of Formula I. The present application further provides methods of using the disclosed PARP inhibitors for the treatment of PARP-mediated diseases and disorders.

  本申请披露了式I的化合物，其中变量R1和R2如本文所述，这些化合物是PARP的抑制剂，并提供了含有式I化合物的化合物和组合物。本申请还提供了使用披露的PARP抑制剂治疗PARP介导的疾病和疾病的方法。
• PARP INHIBITORS
  申请人：F.Hoffmann-La Roche AG

  公开号：EP2758370A1

  公开（公告）日：2014-07-30
• Structure–activity relationship study of selective benzimidazole-based inhibitors of Cryptosporidium parvum IMPDH
  作者：Sivapriya Kirubakaran、Suresh Kumar Gorla、Lisa Sharling、Minjia Zhang、Xiaoping Liu、Soumya S. Ray、Iain S. MacPherson、Boris Striepen、Lizbeth Hedstrom、Gregory D. Cuny

  DOI：10.1016/j.bmcl.2012.01.029

  日期：2012.3

  Cryptosporidium parasites are important waterborne pathogens of both humans and animals. The Cryptosporidium parvum and Cryptosporidium hominis genomes indicate that the only route to guanine nucleotides is via inosine 5 '-monophosphate dehydrogenase (IMPDH). Thus the inhibition of the parasite IMPDH presents a potential strategy for treating Cryptosporidium infections. A selective benzimidazole-based inhibitor of C. parvum IMPDH (CpIMPDH) was previously identified in a high throughput screen. Here we report a structure-activity relationship study of benzimidazole-based compounds that resulted in potent and selective inhibitors of CpIMPDH. Several compounds display potent antiparasitic activity in vitro. (C) 2012 Elsevier Ltd. All rights reserved.
• Design, synthesis and biological evaluation of novel acetamide-substituted doravirine and its prodrugs as potent HIV-1 NNRTIs
  作者：Zhao Wang、Zhao Yu、Dongwei Kang、Jian Zhang、Ye Tian、Dirk Daelemans、Erik De Clercq、Christophe Pannecouque、Peng Zhan、Xinyong Liu

  DOI：10.1016/j.bmc.2018.12.039

  日期：2019.2

  A novel series of acetamide-substituted derivatives and two prodrugs of doravirine were designed and synthesized as potent HIV-1 NNRTIs by employing the structure-based drug design strategy. In MT-4 cell-based assays using the MTT method, it was found that most of the new compounds exhibited moderate to excellent inhibitory potency against the wild-type (WT) HIV-1 strain with a minimum EC50 value of

  通过采用基于结构的药物设计策略，设计并合成了一系列新的乙酰胺取代的衍生物和Doravirine的两种前药，作为有效的HIV-1 NNRTI。在使用MTT方法的基于MT-4细胞的测定中，发现大多数新化合物对野生型（WT）HIV-1菌株均表现出中度至优异的抑制力，最小EC50值为54.8 nM。其中，两种最有效的化合物8i（EC50 = 59.5 nM）和8k（EC50 = 54.8 nM）对野生型HIV-1表现出强大的活性，具有两位数纳摩尔EC50值，优于拉米夫定（3TC，EC50 = 12.8μM ）并与doravirine（EC50 = 13 nM）相当。此外，8i和8k对双RT突变株（K103N + Y181C）HIV-1 RES056株显示中等活性。HIV-1 RT抑制测定进一步验证了结合靶标。通过对代表性化合物的分子模拟，可以深入了解其结构-活性关系（SAR），并指导未来的设计工作