Synthesis and In-Vitro Antimycobacterial Evaluation of N-Arylidene-5-Aryl-1,3,4-Oxadiazol-2-Amines Derivatives

被引:0
|
作者
Mazen Almehmadi [1 ]
Osama Abdulaziz [1 ]
Mamdouh Allahyani [1 ]
Abdullah Y. A. Alzahrani [2 ]
Kamal Kant Joshi [3 ]
Mohammad Asif [4 ]
机构
[1] Taif University,Department of Clinical Laboratory Sciences, College of Applied Medical Sciences
[2] King Khalid University,Department of Chemistry, Faculty of Science and Arts
[3] Graphic Era Hill University,Department of Allied Science
[4] Era College of Pharmacy,Department of Pharmaceutical Chemistry
[5] Era University,undefined
关键词
synthesis; 1,3,4-oxadiazole; antimycobacterial activity; heterocyclic; spectra data; MABA method;
D O I
10.1007/s11094-025-03345-9
中图分类号
学科分类号
摘要
A series of N-arylidene-5-aryl-1,3,4-oxadiazol-2-amines (2a-d, 3a-d & 4a-d) were synthesized with the help of aryl acids, semicarbazide, and aryl benzaldehyde. These synthesized compounds were characterized by elemental analysis, FT-IR, 1H NMR, and mass spectral data analysis. The title compounds were evaluated as in-vitro antimycobacterial agents against Mycobacterium tuberculosis H37RV via the Microplate Alamar Blue Dye Assay (MABA) method. The in-vitro antimycobacterial result revealed that the most active compounds (2c, 2d, 3c, 3d, 4d & 4d) showed a minimum inhibitory concentration (MIC) value of 6.25 μg/ml when compared with the standard drugs Ciprofloxacin, Pyrazinamide (3.125 μg/ml), and Streptomycin (6.25 μg/ml). Most of the title compounds exhibited MIC values ranging from 6.25 to 12.5 μg/ml. Compound 3a was found to be the least effective compound. Also, the electron-withdrawing group (Cl & NO2) on the phenyl ring was found to be more effective than the electron-releasing groups (OH). All the synthesized compounds encouraged us to continue to progress and improve other novel compounds with effective antimycobacterial potential.
引用
收藏
页码:1846 / 1850
页数:4
相关论文
共 50 条
  • [21] Synthesis and antimycobacterial activity of 4-(5-substituted-1,3,4-oxadiazol-2-yl)pyridines
    Navarrete-Vazquez, Gabriel
    Molina-Salinas, Gloria Maria
    Duarte-Fajardo, Zetel Vahi
    Vargas-Villarreal, Javier
    Estrada-Soto, Samuel
    Gonzalez-Salazar, Francisco
    Hernandez-Nunez, Emanuel
    Said-Fernandez, Salvador
    BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (16) : 5502 - 5508
  • [22] Synthesis and antimycobacterial activity of 4-(5-substituted-1,3,4-oxadiazol-2-yl)pyridines
    Navarrete-Vazquez, Gabriel
    Molina-Salinas, Gloria
    Duarte-Fajardo, Zetel Vahi
    Vargas-Villarreal, Javier
    Gonzalez-Salazar, Francisco
    Tlahuext, Hugo
    Said-Fernandez, Salvador
    Estrada-Soto, Samuel
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233 : 519 - 519
  • [23] SYNTHESIS AND BIOLOGICAL-ACTIVITY OF 3-AMINOMETHYL DERIVATIVES OF SOME 5-ARYL-1,3,4-OXADIAZOL-2-ONES
    MAZZONE, G
    BONINA, F
    ARRIGOREINA, R
    FARMACO-EDIZIONE SCIENTIFICA, 1980, 35 (01): : 31 - 40
  • [24] SYNTHESIS OF BIS(1,3,4-OXADIAZOL-2-YL)-5-ARYL-HYDRAZONES
    JANI, MK
    UNDAVIA, NK
    TRIVEDI, PB
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 1989, 66 (04) : 281 - 282
  • [25] Synthesis and evaluation of 2-(5-(aryl)-1,3,4-oxadiazol-2-ylthio)-N-(3-(trifluoromethyl)phenyl)acetamides and N-(4-chloro-3-fluorophenyl)-2-(5-(aryl)-1,3,4-oxadiazol-2-ylthio)acetamides as antimicrobial agents
    Parikh, Kalpesh
    Joshi, Deepkumar
    JOURNAL OF CHEMICAL SCIENCES, 2014, 126 (03) : 827 - 835
  • [26] Synthesis and evaluation of 2-(5-(aryl)-1,3,4-oxadiazol-2-ylthio)-N-(3-(trifluoromethyl)phenyl)acetamides and N-(4-chloro-3-fluorophenyl)-2-(5-(aryl)-1,3,4-oxadiazol-2-ylthio)acetamides as antimicrobial agents
    KALPESH PARIKH
    DEEPKUMAR JOSHI
    Journal of Chemical Sciences, 2014, 126 : 827 - 835
  • [27] Synthesis, in vitro anticancer and antimycobacterial evaluation of new 5-(2,5-dimethoxyphenyl)-1,3,4-thiadiazole-2-amino derivatives
    Polkam, Naveen
    Rayam, Parsharamulu
    Anireddy, Jaya Shree
    Yennam, Satyanarayana
    Anantaraju, Hasitha Shilpa
    Dharmarajan, Sriram
    Perumal, Yogeeswari
    Kotapalli, Sudha Sravanti
    Ummanni, Ramesh
    Balasubramanian, Sridhar
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2015, 25 (07) : 1398 - 1402
  • [28] Synthesis and in vitro antifungal activity of 2-aryl-5-phenylsulfonyl-1,3,4-thiadiazole derivatives
    Foroumadi, A
    Daneshtalab, M
    Shafiee, A
    ARZNEIMITTEL-FORSCHUNG-DRUG RESEARCH, 1999, 49 (12): : 1035 - 1038
  • [29] SYNTHESIS OF 3-(5-ARYL-1,3,4-OXADIAZOL-2-YL)QUINAZOLINE-2,4-(1H)-DIONES AND 2-[(5-ARYL-1,3,4-OXADIAZOL-2-YL)AMINO]-3,1-BENZOXAZIN-4-ONES FROM METHYL N-(5-ARYL-1,3,4-OXADIAZOL-2-YL)DITHIOCARBAMATES
    KHAN, RH
    RASTOGI, RC
    JOURNAL OF CHEMICAL RESEARCH-S, 1992, (10): : 342 - 343
  • [30] SYNTHESIS, IN VITRO ANTIMYCOBACTERIAL ACTIVITY OF SOME 2-((5-AMINO-1,3,4-THIADIAZOL-2-YL)METHYL)-6-ARYL-TETRAHYDROPYRIDAZIN-3-ONE DERIVATIVES
    Allahyani, Mamdouh
    Alsharif, Abdulaziz
    Almehmadi, Mazen
    Verma, Shivani
    Asif, Mohammad
    PHARMACEUTICAL CHEMISTRY JOURNAL, 2024, : 753 - 758