tert-butyl [4-(3-{[5-(2-tert-butoxycarbonylaminoethoxy)benzothiazol-2-ylmethyl]amino}[1,2,4]triazin-5-yl)-3,5-dimethylphenyl]carbamate | 1203605-55-3

• 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: tert-butyl [4-(3-{[5-(2-tert-butoxycarbonylaminoethoxy)benzothiazol-2-ylmethyl]amino}[1,2,4]triazin-5-yl)-3,5-dimethylphenyl]carbamate
• 英文别名: tert-butyl N-[3,5-dimethyl-4-[3-[[5-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethoxy]-1,3-benzothiazol-2-yl]methylamino]-1,2,4-triazin-5-yl]phenyl]carbamate
• CAS: 1203605-55-3
• 化学式: C₃₁H₃₉N₇O₅S
• 分子量: 621.761
• InChiKey: QXFVXUAOPCFHFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  44
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  178
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  tert-butyl [4-(3-{[5-(2-tert-butoxycarbonylaminoethoxy)benzothiazol-2-ylmethyl]amino}[1,2,4]triazin-5-yl)-3,5-dimethylphenyl]carbamate 在 盐酸 、 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 生成 tert-butyl [2-(2-{[5-(4-amino-2,6-dimethyl-phenyl)-[1,2,4]triazin-3-ylamino]-methyl}-benzothiazol-5-yloxy)-ethyl]-carbamate
  参考文献：
  名称：

  Vectorization Efforts To Increase Gram-Negative Intracellular Drug Concentration: A Case Study on HldE-K Inhibitors

  摘要：

  In this paper, we present different strategies to vectorize HldE kinase inhibitors with the goal to improve their Gram-negative intracellular concentration. Syntheses and biological effects of siderophoric, aminoglycosidic, amphoteric, and polycationic vectors are discussed. While siderophoric and amphoteric vectorization efforts proved to be disappointing in this series, aminoglycosidic and polycationic vectors were able for the first time to achieve synergistic effects of our inhibitors with erythromycin. Although these effects proved to be nonspecific, this study provides information about the required stereoelectronic arrangement of the polycationic amines and their basicity requirements to fulfill outer membrane destabilization resulting in better erythromycin synergies.

  DOI：

  10.1021/jm400097h
• 作为产物：
  描述：

  tert-butyl 2-{[2-(aminomethyl)-1,3-benzothiazol-5-yl]oxy}ethylcarbamate 、 [4-(3-chloro-[1,2,4]triazin-5-yl)-3,5-dimethylphenyl]carbamic acid tert-butyl ester 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 以58%的产率得到tert-butyl [4-(3-{[5-(2-tert-butoxycarbonylaminoethoxy)benzothiazol-2-ylmethyl]amino}[1,2,4]triazin-5-yl)-3,5-dimethylphenyl]carbamate
  参考文献：
  名称：

  New 1,2,4-triazine derivatives and biological applications thereof

  摘要：

  这项发明涉及公式(I)的新1,2,4-三嗪衍生物： 其中A、B、R2和Y在申请中有定义， 它们的制备和中间体，它们作为药物和药物组合物的用途以及含有它们的关联物。 公式(I)的化合物能够抑制细菌七糖合成。

  公开号：

  EP2141164A1

文献信息

• Vectorization Efforts To Increase Gram-Negative Intracellular Drug Concentration: A Case Study on HldE-K Inhibitors
  作者：Dmytro Atamanyuk、Fabien Faivre、Mayalen Oxoby、Benoit Ledoussal、Elodie Drocourt、François Moreau、Vincent Gerusz

  DOI：10.1021/jm400097h

  日期：2013.3.14

  In this paper, we present different strategies to vectorize HldE kinase inhibitors with the goal to improve their Gram-negative intracellular concentration. Syntheses and biological effects of siderophoric, aminoglycosidic, amphoteric, and polycationic vectors are discussed. While siderophoric and amphoteric vectorization efforts proved to be disappointing in this series, aminoglycosidic and polycationic vectors were able for the first time to achieve synergistic effects of our inhibitors with erythromycin. Although these effects proved to be nonspecific, this study provides information about the required stereoelectronic arrangement of the polycationic amines and their basicity requirements to fulfill outer membrane destabilization resulting in better erythromycin synergies.
• New 1,2,4-triazine derivatives and biological applications thereof
  申请人：Mutabilis

  公开号：EP2141164A1

  公开（公告）日：2010-01-06

  The invention relates to new 1,2,4-triazine derivatives of formula (I): wherein A, B, R2 and Y are defined in the application, their preparation and intermediates, their use as drugs and pharmaceutical compositions and associations containing them. The compounds of formula (I) are capable of inhibiting bacterial heptose synthesis.

  这项发明涉及公式(I)的新1,2,4-三嗪衍生物： 其中A、B、R2和Y在申请中有定义， 它们的制备和中间体，它们作为药物和药物组合物的用途以及含有它们的关联物。 公式(I)的化合物能够抑制细菌七糖合成。