N-((4-trifluoromethoxy)phenyl)ethane-1,2-diamine | 913180-86-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-((4-trifluoromethoxy)phenyl)ethane-1,2-diamine
• 英文别名: N'-[4-(trifluoromethoxy)phenyl]ethane-1,2-diamine
• CAS: 913180-86-6
• 化学式: C₉H₁₁F₃N₂O
• 分子量: 220.194
• InChiKey: GEKCWQCHNDIFMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  47.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-((4-trifluoromethoxy)phenyl)ethane-1,2-diamine 在 1H-咪唑-1-磺酰叠氮盐酸盐 、 copper(ll) sulfate pentahydrate 、 溴 、 potassium carbonate 、 copper(II) sulfate 、 溶剂黄146 、 sodium ascorbate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 6.0h， 生成 3-(2-(4-(2,4-difluorophenyl)-1,2,3-triazol-1-yl)ethyl)-6-trifluoromethoxybenzothiazol-2-imine
  参考文献：
  名称：

  Riluzole–Triazole Hybrids as Novel Chemical Probes for Neuroprotection in Amyotrophic Lateral Sclerosis

  摘要：

  Despite intense attention from biomedical and chemical researchers, there are few approved treatments for amyotrophic lateral sclerosis (ALS), with only riluzole (Rilutek) and edaravone (Radicava) currently available to patients. Moreover, the mechanistic basis of the activity of these drugs is currently not well-defined, limiting the ability to design new medicines for ALS. This Letter describes the synthesis of triazole-containing riluzole analogues, and their testing in a novel neuroprotective assay. Seven compounds were identified as having neuroprotective activity, with two compounds having similar activity to riluzole.

  DOI：

  10.1021/acsmedchemlett.8b00103
• 作为产物：
  描述：

  [2-(4-trifluoromethoxy-phenylamino)-ethyl]-carbamic acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 N-((4-trifluoromethoxy)phenyl)ethane-1,2-diamine
  参考文献：
  名称：

  Synthesis and SAR of arylaminoethyl amides as noncovalent inhibitors of cathepsin S: P3 cyclic ethers

  摘要：

  The synthesis and structure-activity relationship of a series of arylaminoethyl amide cathepsin S inhibitors are reported. Optimization of P3 and P2 groups to improve overall physicochemical properties resulted in significant improvements in oral bioavailability over early lead compounds. An X-ray structure of compound 37 bound to the active site of cathepsin S is also reported.

  DOI：

  10.1016/j.bmcl.2006.07.033

文献信息

• [EN] METHYL 2-ALLYL-1 -METHYL-3-OXOINDOLINE-2-CARBOXYLATE AND 9A-ALLYL-1,2,3,9A-TETRAHYDRO-9H-PYRROLO[1,2-A]INDOL-9-ONE DERIVATIVES AND RELATED COMPOUNDS FOR USE AS FLUORESCENT MARKERS FOR LABELLING OF DRUGS, AMINO ACIDS AN PROTEINS<br/>[FR] DÉRIVÉS DE MÉTHYL 2-ALLYL-1 -MÉTHYL-3-OXOINDOLINE-2-CARBOXYLATE AND 9A-ALLYL-1,2,3,9A-TÉTRAHYDRO-9H-PYRROLO[1,2-A]INDOL-9-ONE ET COMPOSÉS ASSOCIÉS DESTINÉS À ÊTRE UTILISÉS COMME MARQUEURS FLUORESCENTS POUR LE MARQUAGE DE MÉDICAMENTS, D'ACIDES AMINÉS ET DE PROTÉINES
  申请人：UNIV OF LANCASTER

  公开号：WO2021116686A1

  公开（公告）日：2021-06-17

  Compounds of formulae (3) and (I) for use as fluorescent markers for labelling an amine containing target drug, an amino acid or a protein. (3) (I) Exemplary compounds are e.g. (II) (III) (IV).

  用作标记含有胺基的靶药物、氨基酸或蛋白质的荧光标记物的化合物的化学式（3）和（I）。 （3）（I）示例化合物例如（II）（III）（IV）。
• Synthesis and SAR of succinamide peptidomimetic inhibitors of cathepsin S
  作者：Arnab K. Chatterjee、Hong Liu、David C. Tully、Jianhua Guo、Robert Epple、Ross Russo、Jennifer Williams、Michael Roberts、Tove Tuntland、Jonathan Chang、Perry Gordon、Thomas Hollenbeck、Christine Tumanut、Jun Li、Jennifer L. Harris

  DOI：10.1016/j.bmcl.2007.02.049

  日期：2007.5

  Peptidic, non-covalent inhibitors of lysosomal cysteine protease cathepsin S (1 and 2) were investigated due to low oral bioavailability, leading to an improved series of peptidomimetic inhibitors. Utilizing phenyl succinamides as the P2 residue increased the oral exposure of this lead series of compounds, while retaining selective inhibition of the cathepsin S isoform. Concurrent investigation of

  由于口服生物利用度低，研究了溶酶体半胱氨酸蛋白酶组织蛋白酶S（1和2）的肽类非共价抑制剂，从而产生了一系列拟肽抑制剂。使用苯基琥珀酰亚胺作为P2残基可增加该先导系列化合物的口腔暴露，同时保留对组织蛋白酶S亚型的选择性抑制作用。对P1和P2亚位点的同时研究导致发现了几种有效的和选择性的组织蛋白酶S抑制剂，这些酶由于消除了饱和脂肪族P2残基而具有良好的药代动力学特性。
• Discovery of novel selective phosphodiesterase‑1 inhibitors for the treatment of acute myelogenous leukemia
  作者：Mei-Ling Le、Yi-Yi Yang、Mei-Yan Jiang、Chuan Han、Zhi-Rong Guo、Run-Duo Liu、Zheng-Jiong Zhao、Qian Zhou、Shijun Wen、Yinuo Wu

  DOI：10.1016/j.bioorg.2024.107114

  日期：2024.3

  Acute myelogenous leukemia (AML) is the most common form of acute leukemia in adults. PDE1 (Phosphodiesterase 1) is a subfamily of the PDE super-enzyme families that can hydrolyze the second messengers cAMP and cGMP simultaneously. Previous research has shown that suppressing the gene expression of PDE1 can trigger apoptosis of human leukemia cells. However, no selective PDE1 inhibitors have been used

  急性髓性白血病（AML）是成人中最常见的急性白血病。 PDE1（磷酸二酯酶1）是PDE超级酶家族的一个亚家族，可以同时水解第二信使cAMP和cGMP。此前的研究表明，抑制PDE1基因表达可以引发人类白血病细胞凋亡。然而，尚未使用选择性 PDE1 抑制剂来探索 PDE1 是否是治疗 AML 的潜在靶点。基于我们之前报道的PDE9/PDE1双重抑制剂11a，本研究设计了一系列新型吡唑并嘧啶酮衍生物。先导化合物6c对 PDE1 的 IC 50为 7.5 nM，比其他 PDE 具有优异的选择性和良好的代谢稳定性。在AML细胞中，化合物6c显着抑制增殖并诱导细胞凋亡。进一步的实验表明， 6c诱导的细胞凋亡是通过线粒体依赖性途径，通过降低 Bcl-2/Bax 的比率并增加 caspase-3、7、9 和 PARP 的裂解来实现的。所有这些结果表明 PDE1 可能是 AML 的新靶点。
• Substituted 4-hetarylpyrazolines
  申请人：Maurer Fritz

  公开号：US20080064732A1

  公开（公告）日：2008-03-13

  The present invention relates to novel substituted pyrazolines of the formula (I) in which R 1 , R 2 , R 3 and R 4 are as defined in the disclosure, to a plurality of processes for preparing these substances and their use for controlling pests, and to novel intermediates and processes for their preparation.
• Pyrazoline Derivatives and Their Use As Pesticides
  申请人：Maurer Fritz

  公开号：US20090143454A1

  公开（公告）日：2009-06-04

  The present invention relates to novel pyrazoline derivatives of the formula (I) in which R 1 , R 2 , R 3 and R 4 are as defined in the disclosure, to a plurality of processes for preparing these substances, and to their use for controlling pests, and further relates to novel intermediates and processes for their preparation.