4-((4-bromo-3-hydroxybenzyl)(4H-1,2,4-triazol-4-yl)amino)-benzonitrile | 870779-67-2

• 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: 4-((4-bromo-3-hydroxybenzyl)(4H-1,2,4-triazol-4-yl)amino)-benzonitrile
• 英文别名: 4-[(4-bromo-3-hydroxybenzyl)(4-cyanophenyl)amino]-4H-[1,2,4]triazole；4-[(4-bromo-3-hydroxyphenyl)methyl-(1,2,4-triazol-4-yl)amino]benzonitrile
• CAS: 870779-67-2
• 化学式: C₁₆H₁₂BrN₅O
• 分子量: 370.208
• InChiKey: WKQPRXJLBFKRFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  78
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-((4-bromo-3-hydroxybenzyl)(4H-1,2,4-triazol-4-yl)amino)-benzonitrile 在 氨基磺酰氯 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 以64%的产率得到(2-bromo-5-{[(4-cyanophenyl)(4H-1,2,4-triazol-4-yl)amino]methyl}phenyl) sulfamate
  参考文献：
  名称：

  Dual Aromatase−Steroid Sulfatase Inhibitors

  摘要：

  By introducting the steroid sulfatase inhibitory pharmacophore into aromatase inhibitor 1 (YM511), two series of single agent dual aromatase-sulfatase inhibitors (DASIs) were generated. The best DASIs in vitro (JEG-3 cells) are 5, (IC50(aromatase) = 0.82 nM; IC50(sulfatase) = 39 nM), and 14, (IC50(aromatase) = 0.77 nM; IC50(sulfatase) = 590 nM). X-ray crystallography of 5, and docking studies of selected compounds into an aromatase homology model and the steroid sulfatase crystal structure are presented. Both 5 and 14 inhibit aromatase and sulfatase in PMSG pretreated adult female Wistar rats potently 3 h after a single oral 10 mg/kg dose. Almost complete dual inhibition is observed for 5 but the levels were reduced to 85% (aromatase) and 72% (sulfatase) after 24 h. DASI 5 did not inhibit aldosterone synthesis. The development of a potent and selective DASI should allow the therapeutic potential of dual aromatase-sulfatase inhibition in hormone-dependent breast cancer to be assessed.

  DOI：

  10.1021/jm061462b
• 作为产物：
  描述：

  间羟基苯甲酸 在 吡啶 、 lithium aluminium tetrahydride 、 四溴化碳 、 硫酸 、 溴 、 sodium hydride 、 对甲苯磺酸 、 溶剂黄146 、 三苯基膦 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 4-((4-bromo-3-hydroxybenzyl)(4H-1,2,4-triazol-4-yl)amino)-benzonitrile
  参考文献：
  名称：

  Dual Aromatase−Steroid Sulfatase Inhibitors

  摘要：

  By introducting the steroid sulfatase inhibitory pharmacophore into aromatase inhibitor 1 (YM511), two series of single agent dual aromatase-sulfatase inhibitors (DASIs) were generated. The best DASIs in vitro (JEG-3 cells) are 5, (IC50(aromatase) = 0.82 nM; IC50(sulfatase) = 39 nM), and 14, (IC50(aromatase) = 0.77 nM; IC50(sulfatase) = 590 nM). X-ray crystallography of 5, and docking studies of selected compounds into an aromatase homology model and the steroid sulfatase crystal structure are presented. Both 5 and 14 inhibit aromatase and sulfatase in PMSG pretreated adult female Wistar rats potently 3 h after a single oral 10 mg/kg dose. Almost complete dual inhibition is observed for 5 but the levels were reduced to 85% (aromatase) and 72% (sulfatase) after 24 h. DASI 5 did not inhibit aldosterone synthesis. The development of a potent and selective DASI should allow the therapeutic potential of dual aromatase-sulfatase inhibition in hormone-dependent breast cancer to be assessed.

  DOI：

  10.1021/jm061462b

文献信息

• [EN] SULFAMIC ACID ESTER COMPOUNDS USEFUL IN THE INHIBITION OF SEROID SULPHATASE ACTIVITY AND AROMATASE ACTIVITY<br/>[FR] COMPOSES D'ESTER D'ACIDE SULFAMIQUE UTILISES POUR INHIBER L'ACTIVITE DE LA STEROIDE SULFATASE ET L'ACTIVITE DE L'AROMATASE
  申请人：STERIX LTD

  公开号：WO2005115996A1

  公开（公告）日：2005-12-08

  There is provided a compound of Formula (III) or Formula (IV), wherein A is selected from H, OH, halogen and hydrocarbyl D, E and F are each independently of each other an optional linker group; P, Q and R are independently of each other a ring system, wherein R4 and R5 are independently selected from H, alkyl, cycloalkyl, alkenyl, acyl and aryl, or combinations thereof, or together represent alkylene, wherein the or each alkyl or cycloalkyl or alkenyl or optionally contain one or more hetero atoms or groups.

  提供一种化合物，其化学式为（III）或（IV），其中A从H、OH、卤素和烃基中选择，D、E和F分别是可选的连接基团；P、Q和R分别是独立的环系统，其中R4和R5从H、烷基、环烷基、烯烃基、酰基和芳基中独立选择，或者它们的组合，或者一起代表烷基，其中每个烷基或环烷基或烯烃基或可选地含有一个或多个杂原子或基团。
• Sulfamic acid ester compounds useful in the inhibition of steroid sulphatase activity and aromatase activity
  申请人：Potter Victor Lloyd Barry

  公开号：US20070213383A1

  公开（公告）日：2007-09-13

  There is provided a compound of Formula III or Formula IV wherein A is selected from H, OH, halogen and hydrocarbyl D, E and F are each independently of each other an optional linker group; P, Q and R are independently of each other a ring system, wherein R 4 and R 5 are independently selected from H, alkyl, cycloalkyl, alkenyl, acyl and aryl, or combinations thereof, or together represent alkylene, wherein the or each alkyl or cycloalkyl or alkenyl or optionally contain one or more hetero atoms or groups.

  提供一种化合物，其化学式为III或IV，其中A从H、OH、卤素和烃基中选择，D、E和F各自独立地是可选的连接基团；P、Q和R各自独立地是环系统，其中R4和R5各自独立地从H、烷基、环烷基、烯烃基、酰基和芳基或其组合中选择，或者一起表示烷基，其中每个烷基、环烷基或烯烃基或可选地包含一个或多个杂原子或基团。
• Compound
  申请人：Reed John Michael

  公开号：US20060241173A1

  公开（公告）日：2006-10-26

  The present invention relates to sulphamate compounds that are an inhibitor of both oestrone sulphatase activity and aromatase activity.

  本发明涉及一种硫酰胺化合物，它是雌酮硫酸酯酶活性和芳香化酶活性的抑制剂。
• Novel ¹⁸F-Labeled PET Tracers Specific to Aromatase: Design, Synthesis, and Biological Evaluation
  作者：Wei Zheng、Xuebo Cheng、Hualong Chen、Zeng Jiang、Yuli Sun、Ziyue Yu、Tingyu Yang、Lu Zhang、Yajing Liu、Xunming Ji、Zehui Wu

  DOI：10.1021/acs.molpharmaceut.2c00176

  日期：2022.7.4
• US8148415B2
  申请人：——

  公开号：US8148415B2

  公开（公告）日：2012-04-03