3-bromo-1-ethyl-5-nitro-2(1H)-pyridinone | 74937-42-1

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 3-bromo-1-ethyl-5-nitro-2(1H)-pyridinone
• 英文别名: 3-bromo-1-ethyl-5-nitropyridin-2(1H)-one；3-bromo-1-ethyl-5-nitropyridin-2-one
• CAS: 74937-42-1
• 化学式: C₇H₇BrN₂O₃
• 分子量: 247.048
• InChiKey: DWIAFJLCBYNTHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  66.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-bromo-1-ethyl-5-nitro-2(1H)-pyridinone 在 palladium on activated charcoal 、 氢气 、 碳酸氢钠 作用下， 以 乙二醇二甲醚 、 乙醇 、 水 为溶剂， 20.0 ℃ 、275.8 kPa 条件下， 生成 5-amino-1-ethyl-[3,3'-bipyridin]-2(1H)-one
  参考文献：
  名称：

  Thiazolopyridone ureas as DNA gyrase B inhibitors: Optimization of antitubercular activity and efficacy

  摘要：

  Scaffold hopping from the thiazolopyridine ureas led to thiazolopyridone ureas with potent antitubercular activity acting through inhibition of DNA GyrB ATPase activity. Structural diversity was introduced, by extension of substituents from the thiazolopyridone N-4 position, to access hydrophobic interactions in the ribose pocket of the ATP binding region of GyrB. Further optimization of hydrogen bond interactions with arginines in site-2 of GyrB active site pocket led to potent inhibition of the enzyme (IC50 2 nM) along with potent cellular activity (MIC = 0.1 mu M) against Mycobacterium tuberculosis (Mtb). Efficacy was demonstrated in an acute mouse model of tuberculosis on oral administration. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.080
• 作为产物：
  描述：

  1-乙基-5-硝基吡啶-2-酮 在 溴 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 生成 3-bromo-1-ethyl-5-nitro-2(1H)-pyridinone
  参考文献：
  名称：

  Haak, H. J. W. van den; Plas, H. C. van der, Recueil des Travaux Chimiques des Pays-Bas, 1980, vol. 99, # 3, p. 83 - 86

  摘要：

  DOI：

文献信息

• HAAK H. J. W. VAN DEN; PLAS H. C. VAN DER, REC. TRAV. CHIM. PAYS-BAS, 1980, 99, NO 3, 83-86
  作者：HAAK H. J. W. VAN DEN、 PLAS H. C. VAN DER

  DOI：——

  日期：——
• Haak, H. J. W. van den; Plas, H. C. van der, Recueil des Travaux Chimiques des Pays-Bas, 1980, vol. 99, # 3, p. 83 - 86
  作者：Haak, H. J. W. van den、Plas, H. C. van der

  DOI：——

  日期：——
• Thiazolopyridone ureas as DNA gyrase B inhibitors: Optimization of antitubercular activity and efficacy
  作者：Ramesh R. Kale、Manoj G. Kale、David Waterson、Anandkumar Raichurkar、Shahul P. Hameed、M.R. Manjunatha、B.K. Kishore Reddy、Krishnan Malolanarasimhan、Vikas Shinde、Krishna Koushik、Lalit Kumar Jena、Sreenivasaiah Menasinakai、Vaishali Humnabadkar、Prashanti Madhavapeddi、Halesha Basavarajappa、Sreevalli Sharma、Radha Nandishaiah、K.N. Mahesh Kumar、Samit Ganguly、Vijaykamal Ahuja、Sheshagiri Gaonkar、C.N. Naveen Kumar、Derek Ogg、P. Ann Boriack-Sjodin、Vasan K. Sambandamurthy、Sunita M. de Sousa、Sandeep R. Ghorpade

  DOI：10.1016/j.bmcl.2013.12.080

  日期：2014.2

  Scaffold hopping from the thiazolopyridine ureas led to thiazolopyridone ureas with potent antitubercular activity acting through inhibition of DNA GyrB ATPase activity. Structural diversity was introduced, by extension of substituents from the thiazolopyridone N-4 position, to access hydrophobic interactions in the ribose pocket of the ATP binding region of GyrB. Further optimization of hydrogen bond interactions with arginines in site-2 of GyrB active site pocket led to potent inhibition of the enzyme (IC50 2 nM) along with potent cellular activity (MIC = 0.1 mu M) against Mycobacterium tuberculosis (Mtb). Efficacy was demonstrated in an acute mouse model of tuberculosis on oral administration. (C) 2014 Elsevier Ltd. All rights reserved.