5-(3-溴苯基)-4H-1,2,4-三唑-3-胺 | 383130-99-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-(3-溴苯基)-4H-1,2,4-三唑-3-胺
• 英文名称: 3-(3-bromophenyl)-1H-1,2,4-triazol-5-amine
• 英文别名: 5-(3-bromophenyl)-4H-1,2,4-triazol-3-amine；5-(3-bromophenyl)-1H-1,2,4-triazol-3-amine
• CAS: 383130-99-2
• 化学式: C₈H₇BrN₄
• mdl: MFCD05182411
• 分子量: 239.074
• InChiKey: KGXKHNJAQOISSJ-UHFFFAOYSA-N

物化性质

• 沸点：
  468.7±47.0 °C(Predicted)
• 密度：
  1.732

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.6
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  5-(3-溴苯基)-4H-1,2,4-三唑-3-胺 在 sodium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 生成 2-(3-bromophenyl)-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：

  Synthesis andin vitroEvaluation of 1,2,4-Triazolo[1,5-a][1,3,5]triazine Derivatives as Thymidine Phosphorylase Inhibitors

  摘要：

  In our lead finding program, a series of 1,2,4‐triazolo[1,5‐a][1,3,5]triazine derivatives were synthesized, and their in vitro thymidine phosphorylase inhibitory potential was explored. Among the different derivatives, compounds having keto group (C = O) at C7 and thioketo group (C = S) at C5 positions showed varying degrees of TP inhibitory activity comparable with positive control, 7‐deazaxanthine (7‐DX, 2) (IC50 value = 42.63 μm). Enzyme inhibition kinetics study suggested that compound IVn behaved as a mixed‐type inhibitor of the enzyme with respect to thymidine (dThd) as a variable substrate. Compound IVn was also found to inhibit PMA‐induced MMP‐9 expression in MDA‐MB‐231 cells at sublethal concentrations. Computational docking study was performed to illustrate the enzyme inhibition kinetics and to explore the ligand–enzyme interactions.

  DOI：

  10.1111/cbdd.12171
• 作为产物：
  描述：

  3-溴苯甲酰氯 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.33h， 生成 5-(3-溴苯基)-4H-1,2,4-三唑-3-胺
  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

• A green one-pot synthesis of 3(5)-substituted 1,2,4-triazol-5(3)-amines as potential antimicrobial agents
  作者：Hamid Beyzaei、Zahra Khosravi、Reza Aryan、Behzad Ghasemi

  DOI：10.1007/s13738-019-01714-2

  日期：2019.12

  The best antibacterial effects were observed with 3(5)-phenyl-1H-1,2,4-triazol-5(3)-amine according to its MIC values (4–8 μg mL−1). All compounds were successful in blocking the growth of fungi. Acceptable antioxidant properties were observed only with 3(5)-(4-nitrophenyl)-1H-1,2,4-triazol-5(3)-amine. Graphic abstract3(5)-Substituted 1,2,4-triazol-5(3)-amines were efficiently prepared via a one-pot

  摘要提出了一种通过硫脲，硫酸二甲酯和各种酰肼的一锅反应合成3（5）-取代的1,2,4-三唑-5（3）-胺的有效方法。1,2,4-三唑衍生物是在温和的条件下在水性介质中制备的，同时遵守一些绿色化学原理。无需任何进一步纯化即可轻松分离出产物，产率为83–95％。评估了所有合成化合物对各种革兰氏阳性和革兰氏阴性病原菌以及一些真菌病原体的抑制活性。根据其MIC值（4–8μgmL -1，使用3（5）-苯基-1 H -1,2,4-三唑-5（3）-胺观察到了最佳的抗菌作用）。所有化合物均能成功阻止真菌生长。仅使用3（5）-（4-硝基苯基）-1 H -1,2,4-三唑-5（3）-胺观察到可接受的抗氧化剂性能。 图形摘要通过硫脲，硫酸二甲酯和各种酰肼在水中作为溶剂的一锅反应，可有效地制备3（5）-取代的1,2,4-三唑-5（3）-胺。根据它们的MIC，MBC和MFC值证明了所有合成衍生物的抑制活性。发现它们是潜在的抗真菌剂。
• Metallo-beta-lactamase inhibitors
  申请人：Merck Sharp & Dohme Corp.

  公开号：US10221163B2

  公开（公告）日：2019-03-05

  The present invention relates to metallo-beta-lactamase inhibitor compounds of Formula I: and pharmaceutically acceptable salts thereof, wherein Z, RA, X1, X2 and R1 are as defined herein. The present invention also relates to compositions which comprise a metallo-beta-lactamase inhibitor compound of the invention or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier, optionally in combination with a beta-lactam antibiotic and/or a beta-lactamase inhibitor. The invention further relates to methods for treating a bacterial infection comprising administering to a patient a therapeutically effective amount of a compound of the invention, in combination with a therapeutically effective amount of one or more β-lactam antibiotics and optionally in combination with one or more beta-lactamase inhibitor compounds. The compounds of the invention are useful in the methods described herein for overcoming antibiotic resistance.

  本发明涉及式 I 的金属-β-内酰胺酶抑制剂化合物：及其药学上可接受的盐，其中 Z、RA、X1、X2 和 R1 如本文所定义。本发明还涉及组合物，其包含本发明的金属-β-内酰胺酶抑制剂化合物或其药学上可接受的盐，以及药学上可接受的载体，可选择与β-内酰胺抗生素和/或β-内酰胺酶抑制剂结合使用。本发明进一步涉及治疗细菌感染的方法，包括向患者施用治疗有效量的本发明化合物，与治疗有效量的一种或多种β-内酰胺类抗生素联合使用，也可选择与一种或多种β-内酰胺酶抑制剂化合物联合使用。本发明的化合物在本文所述的克服抗生素耐药性的方法中是有用的。
• 3-TETRAZOLYL-BENZENE-1,2-DISULFONAMIDE DERIVATIVES AS METALLO-BETA-LACTAMASE INHIBITORS
  申请人：Merck Sharp & Dohme Corp.

  公开号：EP3313832A1

  公开（公告）日：2018-05-02
• Non-crystallizable Pi-conjugated Molecular Glass Mixtures, Charge Transporting Molecular Glass Mixtures, Luminescent Molecular Glass Mixtures, or Combinations Thereof for Organic Light Emitting Diodes and other Organic Electronics and Photonics Applications
  申请人：Molaire Consulting

  公开号：US20150275076A1

  公开（公告）日：2015-10-01

  The present invention provides charge transporting molecular glass mixtures, luminescent molecular glass mixtures, or combinations thereof comprising at least two nonpolymeric compounds each independently corresponding to the structure (R 1 Y 1 ) p [(Z 1 Y 2 ) m R 2 Y 3 ] n Z 2 Y 4 R 3 wherein m is zero or one; n is zero up to an integer at which said compound starts to become a polymer; p is an integer of from one to eight; each R 1 and R 3 is independently a monovalent aliphatic or cycloaliphatic hydrocarbon group having 1 to 20 carbon atoms, an aromatic group or a multicyclic aromatic nucleus; R 2 , Z 1 , and Z 2 each independently represent multivalent aliphatic or cycloaliphatic hydrocarbon groups having 1 to 20 carbon atoms or an aromatic group; and Y 1 , Y 2 , Y 3 and Y 4 each independently represent a triple bond, a double bond, or a single bond link.
• METALLO-BETA-LACTAMASE INHIBITORS
  申请人：Merck Sharp & Dohme Corp.

  公开号：US20180244656A1

  公开（公告）日：2018-08-30

  The present invention relates to metallo-beta-lactamase inhibitor compounds of Formula I: and pharmaceutically acceptable salts thereof, wherein Z, R A , X 1 , X 2 and R 1 are as defined herein. The present invention also relates to compositions which comprise a metallo-beta-lactamase inhibitor compound of the invention or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier, optionally in combination with a beta-lactam antibiotic and/or a beta-lactamase inhibitor. The invention further relates to methods for treating a bacterial infection comprising administering to a patient a therapeutically effective amount of a compound of the invention, in combination with a therapeutically effective amount of one or more β-lactam antibiotics and optionally in combination with one or more beta-lactamase inhibitor compounds. The compounds of the invention are useful in the methods described herein for overcoming antibiotic resistance.