2-fluoro-N-(2-(2-phenylthiazol-4-yl)ethyl)benzamide | 863512-79-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-fluoro-N-(2-(2-phenylthiazol-4-yl)ethyl)benzamide
• 英文别名: 2-fluoro-N-[2-(2-phenyl-1,3-thiazol-4-yl)ethyl]benzamide
• CAS: 863512-79-2
• 化学式: C₁₈H₁₅FN₂OS
• mdl: MFCD05906918
• 分子量: 326.394
• InChiKey: NQUCRBBKCZQARP-UHFFFAOYSA-N

物化性质

• 密度：
  1.259±0.06 g/cm3(Predicted)
• 溶解度：
  40.2 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2-苯基-1,3-噻唑-4-基)乙腈 在 盐酸 、 sodium tetrahydroborate 、 nickel(II) chloride hexahydrate 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.5h， 生成 2-fluoro-N-(2-(2-phenylthiazol-4-yl)ethyl)benzamide
  参考文献：
  名称：

  Hit-to-Lead Optimization of a Novel Class of Potent, Broad-Spectrum Trypanosomacides

  摘要：

  The parasitic trypanosomes Trypanosoma brucei and T. cruzi are responsible for significant human suffering in the form of human African trypanosomiasis (HAT) and Chagas disease. Drugs currently available to treat these neglected diseases leave much to be desired. Herein we report optimization of a novel class of N-(2-(2-phenylthiazol-4-yl)ethyl)amides, carbamates, and ureas, which rapidly, selectively, and potently kill both species of trypanosome. The mode of action of these compounds is unknown but does not involve CYP51 inhibition. They do, however, exhibit clear structure activity relationships, consistent across both trypanosome species. Favorable physicochemical parameters place the best compounds in CNS drug-like chemical space but, as a class, they exhibit poor metabolic stability. One of the best compounds (64a) cleared all signs of T. cruzi infection in mice when CYP metabolism was inhibited, with sterile cure achieved in one mouse. This family of compounds thus shows significant promise for trypanosomiasis drug discovery.

  DOI：

  10.1021/acs.jmedchem.6b00442

文献信息

• NEW HETEROCYCLYLETHYLBENZAMIDE DERIVATIVES
  申请人：BAYER CROPSCIENCE SA

  公开号：EP1871744A1

  公开（公告）日：2008-01-02
• Heterocyclylethylbenzamide Derivatives
  申请人：Mansfield Darren

  公开号：US20090156651A1

  公开（公告）日：2009-06-18

  A compound of general formula (I): A process for preparing this compound. A fungicide composition comprising a compound of general formula (I). A method for treating plants by applying a compound of general formula (I) or a composition comprising it.
• US7888289B2
  申请人：——

  公开号：US7888289B2

  公开（公告）日：2011-02-15
• [EN] NEW HETEROCYCLYLETHYLBENZAMIDE DERIVATIVES<br/>[FR] NOUVEAUX DERIVES HETEROCYCLYLETHYLBENZAMIDE
  申请人：BAYER CROPSCIENCE SA

  公开号：WO2006108792A1

  公开（公告）日：2006-10-19

  [EN] A compound of general formula (I). A process for preparing this compound. A iungicide composition comprising a compound of general formula (I). A method for treating plants by applying a compound of general formula (I) or a composition comprising it.
  [FR] La présente invention se rapporte à un composé représenté par la formule (I), à un procédé de préparation de ce composé, à une composition fongicide comprenant un composé représenté par la formule (I) et à un procédé de traitement de végétaux qui consiste à appliquer un composé représenté par la formule (I) ou une composition contenant ledit composé. Formule (I)
• Hit-to-Lead Optimization of a Novel Class of Potent, Broad-Spectrum Trypanosomacides
  作者：Stephanie Russell、Raphaël Rahmani、Amy J. Jones、Harriet L. Newson、Kevin Neilde、Ignacio Cotillo、Marzieh Rahmani Khajouei、Lori Ferrins、Sana Qureishi、Nghi Nguyen、Maria S. Martinez-Martinez、Donald F. Weaver、Marcel Kaiser、Jennifer Riley、John Thomas、Manu De Rycker、Kevin D. Read、Gavin R. Flematti、Eileen Ryan、Scott Tanghe、Ana Rodriguez、Susan A. Charman、Albane Kessler、Vicky M. Avery、Jonathan B. Baell、Matthew J. Piggott

  DOI：10.1021/acs.jmedchem.6b00442

  日期：2016.11.10

  The parasitic trypanosomes Trypanosoma brucei and T. cruzi are responsible for significant human suffering in the form of human African trypanosomiasis (HAT) and Chagas disease. Drugs currently available to treat these neglected diseases leave much to be desired. Herein we report optimization of a novel class of N-(2-(2-phenylthiazol-4-yl)ethyl)amides, carbamates, and ureas, which rapidly, selectively, and potently kill both species of trypanosome. The mode of action of these compounds is unknown but does not involve CYP51 inhibition. They do, however, exhibit clear structure activity relationships, consistent across both trypanosome species. Favorable physicochemical parameters place the best compounds in CNS drug-like chemical space but, as a class, they exhibit poor metabolic stability. One of the best compounds (64a) cleared all signs of T. cruzi infection in mice when CYP metabolism was inhibited, with sterile cure achieved in one mouse. This family of compounds thus shows significant promise for trypanosomiasis drug discovery.