2-trifluoromethanesulfonyloxy-8-acetylaminonaphthalene | 168901-50-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-trifluoromethanesulfonyloxy-8-acetylaminonaphthalene
• 英文别名: (8-acetamidonaphthalen-2-yl) trifluoromethanesulfonate
• CAS: 168901-50-6
• 化学式: C₁₃H₁₀F₃NO₄S
• 分子量: 333.288
• InChiKey: XRLNBOXYPCFVLW-UHFFFAOYSA-N

物化性质

• 沸点：
  504.1±50.0 °C(Predicted)
• 密度：
  1.528±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-trifluoromethanesulfonyloxy-8-acetylaminonaphthalene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  Design and synthesis of potent substrate-based inhibitors of the Trypanosoma cruzi dihydroorotate dehydrogenase

  摘要：

  Chagas disease, caused by the parasitic protozoan Trypanosoma cruzi, is the leading cause of heart disease in Latin America. T. cruzi dihydroorotate dehydrogenase (DHODH), which catalyzes the production of orotate, was demonstrated to be essential for T. cruzi survival, and thus has been considered as a potential drug target to combat Chagas disease. Here we report the design and synthesis of 75 compounds based on the orotate structure. A comprehensive structure-activity relationship (SAR) study revealed two 5-substituted orotate analogues (5u and 5v) that exhibit nPP values of several ten nanomolar level and a selectivity of more than 30,000-fold over human DHODH. The information presented here will be invaluable in the search for next-generation drug leads for Chagas disease. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.01.009
• 作为产物：
  描述：

  三氟甲磺酸酐 、 1-乙酰氨基-7-萘酚 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-trifluoromethanesulfonyloxy-8-acetylaminonaphthalene
  参考文献：
  名称：

  Design and synthesis of potent substrate-based inhibitors of the Trypanosoma cruzi dihydroorotate dehydrogenase

  摘要：

  Chagas disease, caused by the parasitic protozoan Trypanosoma cruzi, is the leading cause of heart disease in Latin America. T. cruzi dihydroorotate dehydrogenase (DHODH), which catalyzes the production of orotate, was demonstrated to be essential for T. cruzi survival, and thus has been considered as a potential drug target to combat Chagas disease. Here we report the design and synthesis of 75 compounds based on the orotate structure. A comprehensive structure-activity relationship (SAR) study revealed two 5-substituted orotate analogues (5u and 5v) that exhibit nPP values of several ten nanomolar level and a selectivity of more than 30,000-fold over human DHODH. The information presented here will be invaluable in the search for next-generation drug leads for Chagas disease. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.01.009

文献信息

• Retinoid-like compounds
  申请人：Bristol-Myers Squibb Company

  公开号：US05523457A1

  公开（公告）日：1996-06-04

  This invention relates to a retinoid mpound of formula I ##STR1## in which Y is --CO--NH--, --CR.sup.2 .dbd.CR.sup.3 --, --CO--O--, --O--CO--, --C(.dbd.S)--NH--, --C.tbd.C--, --O--CH.sub.2 --, --CH.sub.2 --O--, or --CH.sub.2 --CH.sub.2 --; A is --(CH.sub.2).sub.t -- or a bond; Q is phenyl optionally substituted with one to three same or different C.sub.1-6 alkyl, C.sub.1-6 alkoxy, halogen, or --CO.sub.2 R.sup.4 ; R.sup.1 is --CO.sub.2 Z, --CONHR.sup.5, C.sub.1-6 alkyl, --CH.sub.2 OH, or --CHO; R.sup.2, R.sup.3, R.sup.4, R.sup.5, and Z are independently hydrogen or C.sub.1-6 alkyl; t is one to six.

  这项发明涉及一种化合物I的视黄醇类化合物##STR1##，其中Y为--CO--NH--, --CR.sup.2 .dbd.CR.sup.3 --, --CO--O--, --O--CO--, --C(.dbd.S)--NH--, --C.tbd.C--, --O--CH.sub.2 --, --CH.sub.2 --O--, 或--CH.sub.2 --CH.sub.2 --；A为--(CH.sub.2).sub.t --或一个键；Q为苯，可选地取代一个至三个相同或不同的C.sub.1-6烷基，C.sub.1-6烷氧基，卤素，或--CO.sub.2 R.sup.4；R.sup.1为--CO.sub.2 Z，--CONHR.sup.5，C.sub.1-6烷基，--CH.sub.2 OH，或--CHO；R.sup.2，R.sup.3，R.sup.4，R.sup.5，和Z独立地为氢或C.sub.1-6烷基；t为一至六。
• Phenyl or phenylalkyl substituted naphtalene derivatives having retinoid-like activity as well as anti-tumor activities
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：EP0661261B1

  公开（公告）日：1997-05-07
• Design and synthesis of potent substrate-based inhibitors of the Trypanosoma cruzi dihydroorotate dehydrogenase
  作者：Daniel Ken Inaoka、Maiko Iida、Satoshi Hashimoto、Toshiyuki Tabuchi、Takefumi Kuranaga、Emmanuel Oluwadare Balogun、Teruki Honma、Akiko Tanaka、Shigeharu Harada、Takeshi Nara、Kiyoshi Kita、Masayuki Inoue

  DOI：10.1016/j.bmc.2017.01.009

  日期：2017.2

  Chagas disease, caused by the parasitic protozoan Trypanosoma cruzi, is the leading cause of heart disease in Latin America. T. cruzi dihydroorotate dehydrogenase (DHODH), which catalyzes the production of orotate, was demonstrated to be essential for T. cruzi survival, and thus has been considered as a potential drug target to combat Chagas disease. Here we report the design and synthesis of 75 compounds based on the orotate structure. A comprehensive structure-activity relationship (SAR) study revealed two 5-substituted orotate analogues (5u and 5v) that exhibit nPP values of several ten nanomolar level and a selectivity of more than 30,000-fold over human DHODH. The information presented here will be invaluable in the search for next-generation drug leads for Chagas disease. (C) 2017 Elsevier Ltd. All rights reserved.