3-iodo-N-pentylbut-2-enamide | 1430798-90-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-iodo-N-pentylbut-2-enamide
• CAS: 1430798-90-5
• 化学式: C₉H₁₆INO
• 分子量: 281.137
• InChiKey: YBPQJEBMSVZGDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-iodo-N-pentylbut-2-enamide 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 [N,N'-bis(salicylidene)ethane-1,2-diaminato]cobalt(II) 、 氢溴酸 、 氧气 、 potassium carbonate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 乙二醇二甲醚 、 水 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 生成 4,6-dimethyl-1-pentyl-9H-pyrido[3,2-g]quinoline-2,5,8,10-tetrone
  参考文献：
  名称：

  Efficient NQO1 Substrates are Potent and Selective Anticancer Agents

  摘要：

  A major goal of personalized medicine in oncology is the identification of drugs with predictable efficacy based on a specific trait of the cancer cell, as has been demonstrated with gleevec (presence of Bcr-Abl protein), herceptin (Her2 overexpression), and iressa (presence of a specific EGFR mutation). This is a challenging task, as it requires identifying a cellular component that is altered in cancer, but not normal cells, and discovering a compound that specifically interacts with it. The enzyme NQO1 is a potential target for personalized medicine, as it is overexpressed in many solid tumors. In normal cells NQO1 is inducibly expressed, and its major role is to detoxify quinones via bioreduction; however, certain quinones become more toxic after reduction by NQO1, and these compounds have potential as selective anticancer agents. Several quinones of this type have been reported, including mitomycin C, RH1, EO9, streptonigrin, beta-lapachone, and deoxynyboquinone (DNQ). However, no unified picture has emerged from these studies, and the key question regarding the relationship between NQO1 processing and anticancer activity remains unanswered. Here, we directly compare these quinones as substrates for NQO1 in vitro, and for their ability to kill cancer cells in culture in an NQO1-dependent manner. We show that DNQ is a superior NQO1 substrate, and we use computationally guided design to create DNQ analogues that have a spectrum of activities with NQO1. Assessment of these compounds definitively establishes a strong relationship between in vitro NQO1 processing and induction of cancer cell death and suggests these compounds are outstanding candidates for selective anticancer therapy.

  DOI：

  10.1021/cb4005832

文献信息

• COMPOUNDS FOR TREATMENT OF FLUOROQUINOLONE-RESISTANT BACTERIA
  申请人：The Board of Trustees of the University of IIIinois

  公开号：US20170096436A1

  公开（公告）日：2017-04-06

  Compounds that specifically kill fluoroquinolone (FQ) resistant bacteria have been developed and are described herein. The FQs are the most commonly prescribed antibiotics to adults in the U.S. and thus are extremely important drugs. However, bacterial resistant to these drugs is now ubiquitous in some of the most common and deadly Gram-positive pathogens, including methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant enterococci (VRE). Indeed, FQs are no longer indicated for treatment of MRSA and VRE infections because of such resistance. The compounds have specific and potent activity versus MRSA and VRE.
• US9920069B2
  申请人：——

  公开号：US9920069B2

  公开（公告）日：2018-03-20
• [EN] COMPOUNDS FOR TREATMENT OF FLUORQUINOLONE-RESISTANT BACTERIA<br/>[FR] COMPOSÉS POUR LE TRAITEMENT DE BACTÉRIES RÉSISTANTES À LA FLUORQUINOLONE
  申请人：UNIV ILLINOIS

  公开号：WO2015142952A1

  公开（公告）日：2015-09-24

  Compounds that specifically kill fluoroquinolone (FQ) resistant bacteria have been developed and are described herein. The FQs are the most commonly prescribed antibiotics to adults in the U.S. and thus are extremely important drugs. However, bacterial resistant to these drugs is now ubiquitous in some of the most common and deadly Gram-positive pathogens, including methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant enterococci (VRE). Indeed, FQs are no longer indicated for treatment of MRSA and VRE infections because of such resistance. The compounds have specific and potent activity versus MRSA and VRE.