5-(4-methoxybenzyl)-1H-1,2,4-triazol-3-amine | 502546-43-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(4-methoxybenzyl)-1H-1,2,4-triazol-3-amine
• 英文别名: 5-[(4-methoxyphenyl)methyl]-1H-1,2,4-triazol-3-amine
• CAS: 502546-43-2
• 化学式: C₁₀H₁₂N₄O
• 分子量: 204.231
• InChiKey: MELFSYPVTHGOJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  76.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-methoxybenzyl)-1H-1,2,4-triazol-3-amine 在 sodium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.33h， 生成 2-(4-methoxybenzyl)-5-thioxo-5,6-dihydro-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7(4H)-one
  参考文献：
  名称：

  A structure–activity relationship study of 1,2,4-triazolo[1,5-a][1,3,5]triazin-5,7-dione and its 5-thioxo analogues on anti-thymidine phosphorylase and associated anti-angiogenic activities

  摘要：

  Thirty-three 1,2,4-triazolo[1,5-a][1,3,5]triazin-5,7-dione and its 5-thioxo analogues were designed and synthesized which contained different substituents at meta- and/or para-positions of 2-phenyl or 2-benzyl ring attached to the fused ring structure. The preliminary pharmacological evaluation demonstrated that the 5-thioxo analogues of 1,2,4-triazolo[1,5-a][1,3,5]triazine exhibited a varying degree of inhibitory activity towards thymidine phosphorylase, comparable or better than reference compound, 7-Deazaxanthine (7-DX, 2) (IC50 value = 42.63 mu M). Moreover, compounds 5q and 6i displayed a mixed-type of inhibitory mechanism in the presence of variable concentrations of thymidine (dThd). In addition, selected compounds were found to have a noticeable inhibitory effect on the expression of angiogenesis markers, including VEGF and MMP-9 in MDA-MB-231 breast cancer cells. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.06.051
• 作为产物：
  描述：

  4-甲氧基苯乙酰氯 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.33h， 生成 5-(4-methoxybenzyl)-1H-1,2,4-triazol-3-amine
  参考文献：
  名称：

  A structure–activity relationship study of 1,2,4-triazolo[1,5-a][1,3,5]triazin-5,7-dione and its 5-thioxo analogues on anti-thymidine phosphorylase and associated anti-angiogenic activities

  摘要：

  Thirty-three 1,2,4-triazolo[1,5-a][1,3,5]triazin-5,7-dione and its 5-thioxo analogues were designed and synthesized which contained different substituents at meta- and/or para-positions of 2-phenyl or 2-benzyl ring attached to the fused ring structure. The preliminary pharmacological evaluation demonstrated that the 5-thioxo analogues of 1,2,4-triazolo[1,5-a][1,3,5]triazine exhibited a varying degree of inhibitory activity towards thymidine phosphorylase, comparable or better than reference compound, 7-Deazaxanthine (7-DX, 2) (IC50 value = 42.63 mu M). Moreover, compounds 5q and 6i displayed a mixed-type of inhibitory mechanism in the presence of variable concentrations of thymidine (dThd). In addition, selected compounds were found to have a noticeable inhibitory effect on the expression of angiogenesis markers, including VEGF and MMP-9 in MDA-MB-231 breast cancer cells. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.06.051

文献信息

• Substituted heteroaryl amide modulators of glucocorticoid receptor, AP-1, and/or NF-kB activity and use thereof
  申请人：Sheppeck James

  公开号：US20060154973A1

  公开（公告）日：2006-07-13

  The present invention relates to new class of non-steroidal compounds which are useful in treating diseases associated with modulation of the glucocorticoid receptor, AP-1, and/or NF-κB activity including obesity, diabetes, inflammatory- and immune-associated diseases, and have the structure including all stereoisomers thereof, tautomers thereof, or a prodrug thereof, or a pharmaceutically acceptable salt thereof, wherein X is selected from N, O, and S; Y is N or CR 6 ; Z is a ring; and where R, R a , R b , R c , R d , R 1 , R 2 , R 3 , R 4 , and R 5 are as defined herein. Also provided are pharmaceutical compositions and methods of treating obesity, diabetes and inflammatory or immune associated diseases comprising said compounds.

  本发明涉及一类新的非甾体化合物，用于治疗与糖皮质激素受体、AP-1和/或NF-κB活性调节相关的疾病，包括肥胖、糖尿病、炎症和免疫相关疾病，并具有结构，包括其所有立体异构体、互变异构体或前药，或其药用可接受盐，其中X选自N、O和S；Y为N或CR6；Z为一个环；R、Ra、Rb、Rc、Rd、R1、R2、R3、R4和R5如本文所定义。还提供了包含所述化合物的药物组合物和治疗肥胖、糖尿病以及炎症或免疫相关疾病的方法。
• Substituted heteroaryl amide modulators of glucocorticoid receptor, AP-1, and/or NF-κB activity and use thereof
  申请人：Bristol-Myers Squibb Co.

  公开号：US07361654B2

  公开（公告）日：2008-04-22

  The present invention relates to new class of non-steroidal compounds which are useful in treating diseases associated with modulation of the glucocorticoid receptor, AP-1, and/or NF-κB activity including obesity, diabetes, inflammatory- and immune-associated diseases, and have the structure including all stereoisomers thereof, tautomers thereof, or a prodrug thereof, or a pharmaceutically acceptable salt thereof, wherein X is selected from N, O, and S; Y is N or CR6; Z is a ring; and where R, Ra, Rb, Rc, Rd, R1, R2, R3, R4, and R5 are as defined herein. Also provided are pharmaceutical compositions and methods of treating obesity, diabetes and inflammatory or immune associated diseases comprising such compounds.

  本发明涉及一类新型非甾体化合物，可用于治疗与糖皮质激素受体、AP-1和/或NF-κB活性调节相关的疾病，包括肥胖症、糖尿病、炎症和免疫相关疾病，其结构包括所有立体异构体、互变异构体、前药或其药学上可接受的盐，其中X选择自N、O和S; Y为N或CR6; Z为环; R、Ra、Rb、Rc、Rd、R1、R2、R3、R4和R5的定义如本文所述。还提供了包含这些化合物的药物组合物和治疗肥胖症、糖尿病和炎症或免疫相关疾病的方法。
• SUBSTITUTED HETEROARYL AMIDE MODULATORS OF GLUCOCORTICOID RECEPTOR, AP-1, AND/OR NFkB ACTIVITY AND USE THEREOF
  申请人：Bristol-Myers Squibb Pharma Company

  公开号：EP1896434A1

  公开（公告）日：2008-03-12
• US7361654B2
  申请人：——

  公开号：US7361654B2

  公开（公告）日：2008-04-22
• [EN] SUBSTITUTED HETEROARYL AMIDE MODULATORS OF GLUCOCORTICOID RECEPTOR, AP-1, AND/OR NF?B ACTIVITY AND USE THEREOF<br/>[FR] MODULATEURS HETEROARYL AMIDE SUBSTITUES DE RECEPTEUR GLUCOCORTICOIDE, D'AP-1, ET/OU D'ACTIVITE NF$G(K)B, ET UTILISATION CORRESPONDANTE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2006076632A1

  公开（公告）日：2006-07-20

  [EN] The present invention relates to new class of non-steroidal compounds which are useful in treating diseases associated with modulation of the glucocorticoid receptor, AP-1, and/or NF?B activity including obesity, diabetes, inflammatory- and immune-associated diseases, and have the structure (I) including all stereoisomers thereof, tautomers thereof, or a prodrug thereof, or a pharmaceutically acceptable salt thereof, wherein X is selected from N, O, and S; Y is N or CR⁶; Z is a ring; and where R, R^a, R^b, R^c, R^d, R¹, R², R³, R⁴, and R⁵ are as defined herein. Also provided are pharmaceutical compositions and methods of treating obesity, diabetes and inflammatory or immune associated diseases comprising said compounds.
  [FR] L'invention concerne une classe de composés non stéroïdes utiles dans le traitement de maladies associées à la modulation du récepteur glucocorticoïde, de l'AP-1 et/ou de l'activité NF-?B, y compris l'obésité, le diabète, les maladies inflammatoires et immunes connexes, de structure (I), y compris tous les stéréoisomères correspondants, les tautomères correspondants, ou un promédicament correspondant, ou encore un sel pharmaceutiquement acceptable correspondant, sachant que X peut être N, O, et S; que Y est N ou CR⁶; que Z est une chaîne; et sachant que R, R^a, R^b, R^c, R^d, R¹, R², R³, R⁴, et R⁵ sont tels que définis dans la description. On décrit aussi des compositions pharmaceutiques et des procédés de traitement des maladies susmentionnées faisant appel aux composés en question.