Synthesis, Characterization, and Biological Evaluation of 2-(N-((2′-(2H-tetrazole-5-yl)-[1,1′-biphenyl]-4yl)-methyl)-pentanamido)-3-methyl Butanoic Acid Derivatives

被引:7
|
作者
Masood, Anum [1 ]
Khan, Mohsin Abbas [1 ]
Ahmad, Irshad [1 ]
Breena [1 ]
Raza, Asim [1 ]
Ullah, Farhat [1 ]
Shah, Syed Adnan Ali [2 ]
机构
[1] Islamia Univ Bahawalpur, Fac Pharm, Dept Pharmaceut Chem, Bahawalpur 63100, Pakistan
[2] Univ Teknol, Fac Pharm, MARA Cawangan Selangor, Kampus Puncak Alam, Bandar Puncak Alam 42300, Selangor, Malaysia
来源
MOLECULES | 2023年 / 28卷 / 04期
关键词
DPPH; FTIR; NMR; antihypertensive activity; antioxidant activity; valsartan; UREASE INHIBITION; ACCURATE DOCKING; ANTIOXIDANT; ANTIBACTERIAL; VALSARTAN; GLIDE; DRUG;
D O I
10.3390/molecules28041908
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
This study aimed to evaluate 2-(N-((2 '-(2H-tetrazole-5-yl)-[1,1 '-biphenyl]-4yl)-methyl)-pentanamido)-3-methyl butanoic acid-based ester derivatives as a new class of angiotensin-II receptor antagonists. For this purpose, a series of compounds were synthesized using a variety of phenols. Their chemical characterization was established by FTIR, (HNMR)-H-1, and (CNMR)-C-13 techniques. The biological activities including antioxidant potentials using the DPPH assay, the antihypertensive assay, the urease enzyme inhibition assay, and the antibacterial assay using agar well diffusion methods were performed. All the new compounds showed significant free radical scavenging potentials more than the parent drug while retaining antihypertensive potentials along with urease inhibition properties. However, the AV2 test compound was found to be the most potent against hypertension. Most of the synthesized analogs showed urease inhibitory actions. Molecular docking studies were performed for all the active analogs to decode the binding detail of the ligands with receptors of the enzyme's active site.
引用
收藏
页数:15
相关论文
共 50 条
  • [1] EFFICIENT SYNTHESIS OF 5-(4'-METHYL[1,1'-BIPHENYL]-2-YL)-1H-TETRAZOLE
    RUSSELL, RK
    MURRAY, WV
    JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (18): : 5023 - 5024
  • [2] 2-(2-Fluoro-[1,1′-biphenyl]-4-yl)-N-(4-methyl-2-oxo-2H-chromen-7-yl )propanamide
    Manolov, Stanimir
    Ivanov, Iliyan
    Bojilov, Dimitar
    Nedialkov, Paraskev
    MOLBANK, 2023, 2023 (03)
  • [3] Synthesis, reactions and characterization of 2-(2-methyl-5-nitro-1H-benzimidazol-1-yl)-N'-(arylmethylene)acetohydrazide and 2-(2-methyl-5-nitro-1H-benzimidazol-1-yl)-N-(4-oxo-2-aryl-1, 3-thiazolidin-3-yl) acetamide derivatives
    Ramla, Mostafa M.
    El Nazhawy, Ahmed O. H.
    Attaby, Fawzy A.
    AFINIDAD, 2006, 63 (526) : 488 - 494
  • [4] Synthesis and crystal structure of 2-trifluoromethyl-1-[(2′-1H-tetrazole-5-yl-biphenyl-4-yl) methyl]benzimidazole
    Weifa Yu
    Zhiming Zhou
    Xinqi Zhao
    Congxuan Yu
    Journal of Chemical Crystallography, 2004, 34 : 597 - 601
  • [5] Synthesis and crystal structure of 2-trifluoromethyl-1-[(2′-1H-tetrazole-5-yl-biphenyl-4-yl) methyl]benzimidazole
    Yu, WF
    Zhou, ZM
    Zhao, XQ
    Yu, CX
    JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, 2004, 34 (09) : 597 - 601
  • [6] N-(2-(1H-Indol-3-yl)ethyl)-2-(2-fluoro[1,1′-biphenyl]-4-yl)propanamide
    Manolov, Stanimir
    Ivanov, Iliyan
    Bojilov, Dimitar
    MOLBANK, 2021, 2021 (01) : 1 - 4
  • [7] Synthesis, Characterization and in vivo Biological Activity of n-(2-chlorophenyl)-2-(2-methyl-5-nitro-1h-imidazol-1-yl) Acetamide and its Derivatives
    Londhe, Omprakash Arjunrao
    Bhor, Rohit Jaysing
    Ingle, Prashant Suresh
    Shah, Zameer Shah Mahemood
    Gade, Dipali Rajendra
    Ghogare, Rajshree Dadasaheb
    JOURNAL OF YOUNG PHARMACISTS, 2024, 16 (02) : 252 - 260
  • [8] Synthesis of N-substituted derivatives of 2-(4-amino-2-methyl-1H-indol-3-yl)- and 2-(6-amino-2-methyl-1H-indol-3-yl)acetic acids
    Maklakov S.A.
    Smushkevich Yu.I.
    Magedov I.V.
    Chemistry of Heterocyclic Compounds, 2002, 38 (08) : 904 - 907
  • [9] Synthesis of (2-butyl-4-Substitutedthiamidothiocarbamido1-{[2-(1h-tetrazol 5-yl) biphenyl-4-yl] methyl}-1h-imidazol-5-yl) Methanol
    Ande, D. S.
    ORIENTAL JOURNAL OF CHEMISTRY, 2012, 28 (02) : 975 - 978
  • [10] Synthesis of N-substituted derivatives of 2-(5-amino-2-methyl-1H-indol-3-yl)acetic acid
    Maklakov, SA
    Smushkevich, YI
    Magedov, IV
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2002, (05): : 619 - 622