3-硝基噻吩-2-羧酰胺 | 391680-93-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 3-硝基噻吩-2-羧酰胺
• 中文别名: 3-硝基噻吩-2-甲酰胺
• 英文名称: 3-nitrothiophene-2-carboxamide
• CAS: 391680-93-6
• 化学式: C₅H₄N₂O₃S
• 分子量: 172.164
• InChiKey: ZLQCTRAVERGIJA-UHFFFAOYSA-N

物化性质

• 沸点：
  353.8±22.0 °C(Predicted)
• 密度：
  1.572±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-硝基噻吩-2-羧酰胺 在 三乙胺 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 生成 3-硝基噻吩-2-甲腈
  参考文献：
  名称：

  Dihydroxypyrimidine carboxylic acids as viral polymerase inhibitors

  摘要：

  2-芳基-4,5-二羟基-6-羧基嘧啶的一类化合物的化学式(I)：其中Ar是一个可选择地取代的芳基或杂环基；以及在4-羟基、5-羟基或6-羧基中的一个或多个位置衍生的化合物的化学式(I)；以及它们的互变异构体，以及它们的药用盐或酯；以及病毒聚合酶抑制剂，特别是乙型肝炎病毒（HCV）聚合酶酶。

  公开号：

  US20040106627A1
• 作为产物：
  描述：

  3-硝基噻吩-2-羧酸甲酯 在 氨 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以74%的产率得到3-硝基噻吩-2-羧酰胺
  参考文献：
  名称：

  2-(2-Thienyl)-5,6-dihydroxy-4-carboxypyrimidines as Inhibitors of the Hepatitis C Virus NS5B Polymerase:  Discovery, SAR, Modeling, and Mutagenesis

  摘要：

  Infections caused by hepatitis C virus (HCV) are a significant world health problem for which novel therapies are in urgent demand. The polymerase of HCV is responsible for the replication of viral RNA. We recently disclosed dihydroxypyrimidine carboxylates 2 as novel, reversible inhibitors of the HCV NS5B polymerase. This series was further developed into 5,6-dihydroxy-2-(2-thienyl)pyrimidine-4-carboxylic acids such as 34 (EC50 9.3 mu M), which now show activity in the cell-based HCV replication assay. The structure-activity relationship of these inhibitors is discussed in the context of their physicochemical properties and of the polymerase crystal structure. We also report the results of mutagenesis experiments which support the proposed binding model, which involves pyrophosphate-like chelation of the active site Mg ions.

  DOI：

  10.1021/jm051064t

文献信息

• Dihydroxypyrimidine carboxylic acids as viral polymerase inhibitors
  申请人：——

  公开号：US20040106627A1

  公开（公告）日：2004-06-03

  A class of 2-aryl-4,5-dihydroxy-6-carboxypyrimidines of formula (I): wherein Ar is an optionally substituted aryl or heterocyclic group; as well as compounds of formula (I) which are derivatised at one or more of the 4-hydroxy, 5-hydroxy or 6-carboxy groups; and tautomers thereof, and pharmaceutically acceptable salts or esters thereof; and inhibitors of viral polymerases, especially the hepatitis C virus (HCV) polymerase enzyme. 1

  2-芳基-4,5-二羟基-6-羧基嘧啶的一类化合物的化学式(I)：其中Ar是一个可选择地取代的芳基或杂环基；以及在4-羟基、5-羟基或6-羧基中的一个或多个位置衍生的化合物的化学式(I)；以及它们的互变异构体，以及它们的药用盐或酯；以及病毒聚合酶抑制剂，特别是乙型肝炎病毒（HCV）聚合酶酶。
• Pyrimidinone viral polymerase inhibitors
  申请人：Avolio Salvatore

  公开号：US20050130997A1

  公开（公告）日：2005-06-16

  A class of pyrimidinone derivatives of formula (I): wherein Z, R 1 , R 2 and R 3 are as defined herein; and pharmaceutically acceptable salts thereof; are inhibitors of viral polymerases, especially (the hepatitis C virus (HCV) polymerase enzyme.

  一类嘧啶酮衍生物，其化学式为(I)：其中Z，R1，R2和R3如下定义；以及其药学上可接受的盐；是病毒聚合酶的抑制剂，特别是丙型肝炎病毒（HCV）聚合酶酶。
• Dihydroxypyridmidine carboxylic acids as viral polymerase inhibitors
  申请人：Merck & Co., Inc.

  公开号：US07091209B2

  公开（公告）日：2006-08-15

  A class of 2-aryl-4,5-dihydroxy-6-carboxypyrimidines of formula (I): wherein Ar is an optionally substituted aryl or heterocyclicgroup; as well as compounds of formula (I) which are derivatized at one or more of the 4-hydroxy, 5-hydroxy or 6-carboxy groups; and tautomers thereof, and pharmaceutically acceptable salts or esters thereof; and inhibitors of viral polymerases, especially the hepatitis C virus (HCV) polymerase enzyme

  一类化合物的化学式为(I)的2-芳基-4,5-二羟基-6-羧基嘧啶，其中Ar是可选取代的芳基或杂环基；以及在4-羟基，5-羟基或6-羧基中的一个或多个位置上衍生的化合物的化学式(I)；它们的互变异构体和其药学上可接受的盐或酯；以及用于抑制病毒聚合酶，特别是丙型肝炎病毒（HCV）聚合酶酶的抑制剂。
• 2-(2-Thienyl)-5,6-dihydroxy-4-carboxypyrimidines as Inhibitors of the Hepatitis C Virus NS5B Polymerase:  Discovery, SAR, Modeling, and Mutagenesis
  作者：Uwe Koch、Barbara Attenni、Savina Malancona、Stefania Colarusso、Immacolata Conte、Marcello Di Filippo、Steven Harper、Barbara Pacini、Claudia Giomini、Steven Thomas、Ilario Incitti、Licia Tomei、Raffaele De Francesco、Sergio Altamura、Victor G. Matassa、Frank Narjes

  DOI：10.1021/jm051064t

  日期：2006.3.1

  Infections caused by hepatitis C virus (HCV) are a significant world health problem for which novel therapies are in urgent demand. The polymerase of HCV is responsible for the replication of viral RNA. We recently disclosed dihydroxypyrimidine carboxylates 2 as novel, reversible inhibitors of the HCV NS5B polymerase. This series was further developed into 5,6-dihydroxy-2-(2-thienyl)pyrimidine-4-carboxylic acids such as 34 (EC50 9.3 mu M), which now show activity in the cell-based HCV replication assay. The structure-activity relationship of these inhibitors is discussed in the context of their physicochemical properties and of the polymerase crystal structure. We also report the results of mutagenesis experiments which support the proposed binding model, which involves pyrophosphate-like chelation of the active site Mg ions.