6-phenyl-2,4-dihydro-1H-thieno[3,2-d][1,3]oxazine-2,4-dione | 478028-43-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 6-phenyl-2,4-dihydro-1H-thieno[3,2-d][1,3]oxazine-2,4-dione
• 英文别名: 6-phenyl-2H-thieno[3,2-d][1,3]oxazine-2,4(1H)-dione；6-phenyl-1H-thieno[3,2-d][1,3]oxazine-2,4-dione
• CAS: 478028-43-2
• 化学式: C₁₂H₇NO₃S
• 分子量: 245.258
• InChiKey: ZAFXSUMTLFTRLZ-UHFFFAOYSA-N

物化性质

• 密度：
  1.433±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-乙基苄胺 、 6-phenyl-2,4-dihydro-1H-thieno[3,2-d][1,3]oxazine-2,4-dione 以 水 为溶剂， 生成 5-(phenyl)-3-[(N-ethylbenzylamino)carbonylamino]thiophen-2-carboxylic acid
  参考文献：
  名称：

  Novel small molecule inhibitors targeting the “switch region” of bacterial RNAP: Structure-based optimization of a virtual screening hit

  摘要：

  Rising resistance against current antibiotics necessitates the development of antibacterial agents with alternative targets. The "switch region" of RNA polymerase (RNAP), addressed by the myxopyronins, could be such a novel target site. Based on a hit candidate discovered by virtual screening, a small library of 5-phenyl-3-ureidothiophene-2-carboxylic acids was synthesized resulting in compounds with increased RNAP inhibition. Hansch analysis revealed pi (lipophilicity constant) and sigma (Hammet substituent constant) of the substituents at the 5-phenyl moiety to be crucial for activity. The binding mode was proven by the targeted introduction of a moiety mimicking the enecarbamate side chain of myxopyronin into the hit compound, accompanied by enhanced RNAP inhibitory potency. The new compounds displayed good antibacterial activities against Gram positive bacteria and Gram negative Escherichia coli TolC and a reduced resistance frequency compared to the established antibiotic rifampicin. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.060
• 作为产物：
  描述：

  3-氯-3-苯基丙烯腈 在 甲醇 、 sodium 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 为溶剂， 反应 5.5h， 生成 6-phenyl-2,4-dihydro-1H-thieno[3,2-d][1,3]oxazine-2,4-dione
  参考文献：
  名称：

  Novel small molecule inhibitors targeting the “switch region” of bacterial RNAP: Structure-based optimization of a virtual screening hit

  摘要：

  Rising resistance against current antibiotics necessitates the development of antibacterial agents with alternative targets. The "switch region" of RNA polymerase (RNAP), addressed by the myxopyronins, could be such a novel target site. Based on a hit candidate discovered by virtual screening, a small library of 5-phenyl-3-ureidothiophene-2-carboxylic acids was synthesized resulting in compounds with increased RNAP inhibition. Hansch analysis revealed pi (lipophilicity constant) and sigma (Hammet substituent constant) of the substituents at the 5-phenyl moiety to be crucial for activity. The binding mode was proven by the targeted introduction of a moiety mimicking the enecarbamate side chain of myxopyronin into the hit compound, accompanied by enhanced RNAP inhibitory potency. The new compounds displayed good antibacterial activities against Gram positive bacteria and Gram negative Escherichia coli TolC and a reduced resistance frequency compared to the established antibiotic rifampicin. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.060

文献信息

• Anti-infective agents
  申请人：——

  公开号：US20040087577A1

  公开（公告）日：2004-05-06

  Compounds having the formula 1 are hepatitis C (HCV) polymerase inhibitors. Also disclosed are a composition and method for inhibiting hepatitis C (HCV) polymerase, processes for making the compounds, and synthetic intermediates employed in the processes.

  具有公式1的化合物是丙型肝炎（HCV）聚合酶抑制剂。还公开了一种用于抑制丙型肝炎（HCV）聚合酶的组成和方法，用于制造这些化合物的过程，以及在这些过程中使用的合成中间体。
• Synthesis and combinatorial approach of the reactivity of 6- and 7-arylthieno[3,2-d][1,3]oxazine-2,4-diones
  作者：François-Xavier Le Foulon、Emmanuelle Braud、Frédéric Fabis、Jean-Charles Lancelot、Sylvain Rault

  DOI：10.1016/j.tet.2003.10.028

  日期：2003.12

  This paper describes a general procedure for the synthesis of new substituted thiaisatoic anhydrides or 6- or 7-aryl-1H-thiéno[3,2-d][1,3]oxazine-2,4-diones 3a–j and 4a–f. They were synthesized in large scale under microwave heating conditions with high yields. The reactivity vs nucleophilic reagents of these compounds was studied and permitted to develop a simple combinatorial procedure to synthesize

  本文描述了合成新的取代硫代硫杂酸酐或6-或7-芳基-1 H-噻吩并[3,2- d ] [1,3]恶嗪-2,4-二酮3a – j和4a的一般程序。 – f。它们在微波加热条件下以高收率大规模合成。研究了这些化合物的亲核试剂的反应性与亲核试剂的关系，并允许开发一种简单的组合方法来合成新的噻吩脲酸7a – j和8a – j库。
• Compounds and methods for the treatment or prevention of Flavivirus infections
  申请人：Chan Chun Kong Laval

  公开号：US20060142347A1

  公开（公告）日：2006-06-29

  The present invention provides novel compounds represented by formula I: or pharmaceutically acceptable salts thereof useful for treating flaviviridae viral infection.

  本发明提供了由公式I表示的新化合物：或其药学上可接受的盐，用于治疗黄病毒科病毒感染。
• COMPOUNDS AND METHODS FOR THE TREATMENT OR PREVENTION OF FLAVIVIRUS INFECTIONS
  申请人：Shire BioChem Inc.

  公开号：US20040116509A1

  公开（公告）日：2004-06-17

  The present invention provides novel compounds represented by formula I: 1 or pharmaceutically acceptable salts thereof useful for treating flaviviridae viral infection.

  本发明提供了由公式I表示的新化合物：1或其药学上可接受的盐，用于治疗黄病毒科病毒感染。
• Thiophene derivatives as antiviral agents for flavivirus infection
  申请人：Virochem Pharma Inc.

  公开号：EP2206709A2

  公开（公告）日：2010-07-14

  The present invention provides novel compounds represented by formula I or pharmaceutically acceptable salts thereof useful for treating flaviviridae viral infection.

  本发明提供了由式 I 代表的新型化合物或其药学上可接受的盐类，可用于治疗黄病毒科病毒感染。