N-(phenylmethyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide | 625470-37-3

• 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: N-(phenylmethyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide
• 英文别名: N-benzyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide
• CAS: 625470-37-3
• 化学式: C₁₉H₂₄BNO₄S
• 分子量: 373.281
• InChiKey: QJSQMKRQJMMQCG-UHFFFAOYSA-N

物化性质

• 沸点：
  530.9±60.0 °C(predicted)
• 密度：
  1.21±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.46
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  73
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-chloro-3-methyl-[1,2,4]triazolo[3,4-a]phthalazine 、 N-(phenylmethyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以33%的产率得到N-benzyl-3-(3-methyl-[1,2,4]triazolo[3,4-a]phthalazin-6-yl)benzenesulfonamide
  参考文献：
  名称：

  [1,2,4]Triazolo[4,3-a]phthalazines: Inhibitors of Diverse Bromodomains

  摘要：

  Bromodomains are gaining increasing interest as drug targets. Commercially sourced and de novo synthesized substituted [1,2,4]triazolo[4,3-a]phthalazines are potent inhibitors of both the BET bromodomains such as BRD4 as well as bromodomains outside the BET family such as BRD9, CECR2, and CREBBP. This new series of compounds. is the first example of submicromolar inhibitors of bromodomains outside the BET subfamily. Representative compounds are active in cells exhibiting potent cellular inhibition activity in a FRAP model of CREBBP and chromatin association. The compounds described are valuable starting points for discovery of selective bromodomain inhibitors and inhibitors with mixed bromodomain pharmacology.

  DOI：

  10.1021/jm401568s

文献信息

• Protein kinase modulators and methods of use
  申请人：Buhr A. Chris

  公开号：US20060211709A1

  公开（公告）日：2006-09-21

  Substituted aryl 1,4-pyrazine derivatives and their use in treating anxiety disorders, depression and stress related disorders are disclosed.

  本发明揭示了替代芳基1,4-吡嗪衍生物及其在治疗焦虑症、抑郁症和与压力相关的疾病中的应用。
• Identification, Characterization, and Optimization of 2,8-Disubstituted-1,5-naphthyridines as Novel <i>Plasmodium falciparum</i> Phosphatidylinositol-4-kinase Inhibitors with in Vivo Efficacy in a Humanized Mouse Model of Malaria
  作者：Nishanth Kandepedu、Diego Gonzàlez Cabrera、Srinivas Eedubilli、Dale Taylor、Christel Brunschwig、Liezl Gibhard、Mathew Njoroge、Nina Lawrence、Tanya Paquet、Charles J. Eyermann、Thomas Spangenberg、Gregory S. Basarab、Leslie J. Street、Kelly Chibale

  DOI：10.1021/acs.jmedchem.8b00648

  日期：2018.7.12

  A novel 2,8-disubstituted-1,5-naphthyridine hit compound stemming from the open access Medicines for Malaria Venture Pathogen Box formed a basis for a hit-to-lead medicinal chemistry program. Structure-activity relationship investigations resulted in compounds with potent antiplasmodial activity against both chloroquine sensitive (NF54) and multidrug resistant (K1) strains of the human malaria parasite Plasmodium falciparum. In the humanized P. falciparum mouse efficacy model, one of the frontrunner compounds showed in vivo efficacy at an oral dose of 4 X 50 mg.g(-1). In vitro mode-of-action studies revealed Plasmodium falciparum phosphatidylinositol-4-kinase as the target.