A series of new triazole fused imidazo[2,1-b]thiazole hybrids (9a-u) were designed, synthesized and evaluated as antimicrobial agents. Compounds 9c, 9d, 9e, 9j and 9l showed promising broad spectrum antimicrobial activity. Further, compound 9c exhibited significant anti-biofilm activity with single and mixed biofilm disruption demonstrated by Field Emission Scanning Electron Microscope (FE-SEM). Furthermore, molecular docking studies revealed that they interact with the virulence factor, Staphylococcus aureus dehydrosqualene synthase (CrtM) (PDB ID: 2ZCS). Overall, the findings suggest compound 9c as potential lead for further development of novel antibacterial and anti-biofilm agents.
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http://dx.doi.org/10.1016/j.bmcl.2019.08.025 | DOI Listing |
J Org Chem
January 2025
College of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, People's Republic of China.
A copper-catalyzed domino addition/cyclization reaction was developed to synthesize novel benzoselenazole-linked 1,2,3-triazole and tetracyclic fused 12-benzo[4,5]selenazole[2,3-]quinazolin-12-one derivatives from isoselenocyanates. This domino reaction efficiently constructed multiple new chemical bonds in a single step, forming either four (one C-Se and three C-) or three (one C-Se and two C-) bonds. The reaction offers several key advantages, including mild conditions, broad substrate compatibility, and straightforward and safe operation.
View Article and Find Full Text PDFArch Pharm (Weinheim)
January 2025
School of Chemistry and Pharmaceutical Engineering, Huanghuai University, Zhumadian, Henan, China.
Cancer, characterized by uncontrolled growth and spread of abnormal cells potentially influencing almost all tissues in the body, is one of the most devastating and lethal diseases throughout the world. Chemotherapy is one of the principal approaches for cancer treatment, but multidrug resistance and severe side effects represent the main barriers to the success of therapy, creating a vital need to develop novel chemotherapeutic agents. The 1,2,3-triazole moiety can be conveniently constructed by "click chemistry" and could exert diverse noncovalent interactions with various enzymes in cancer cells.
View Article and Find Full Text PDFJ Org Chem
January 2025
Department of Chemistry, 107 Physical Sciences, Oklahoma State University, Stillwater, Oklahoma 74078, United States.
Fused heterocyclic scaffolds, such as benzimidazoles or larger ring systems containing a benzimidazole fragment, are frequently encountered in pharmaceutical compounds and other biologically active molecules. While there are many examples of N9- and/or C3-substituted 9-benzo[4,5]imidazo[2,1-][1,2,4]triazoles, current examples of the regioselective preparation of N1-substituted 1-benzo[4,5]imidazo[2,1-][1,2,4]triazoles are limited to N1-aryl substituted compounds, which also contain a C3-substituent. Here, we report an iodine-promoted C-H bond amination reaction that allows the selective preparation of 1-benzo[4,5]imidazo[2,1-][1,2,4]triazoles with a variety of aryl and alkyl N1-substituents.
View Article and Find Full Text PDFJ Org Chem
December 2024
Pfizer Oncology Medicinal Chemistry, San Diego, California 92121, United States.
A 3-step modular procedure combining carboxylic acids with acyl hydrazines provides access to medicinally relevant [1,2,4]-fused triazoles. Good to excellent yields are achieved with tolerance of aliphatic and aryl substituents as well as 5-, 6-, and 7-membered rings for the fused ring. Conditions that can avoid column chromatography and be applicable for both small scale discovery efforts as well as large scale development processes are demonstrated within.
View Article and Find Full Text PDFOrg Lett
December 2024
Energetic Materials Laboratory, Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur 208016, Uttar Pradesh, India.
In this study, we synthesized trifluoromethyl-substituted bis-triazole nitrogen-rich compounds (-) using a simple, cost-effective method. The newly made compounds were characterized using NMR, IR, elemental analysis, TGA-DSC, and single-crystal X-ray diffraction (for compounds and ). They demonstrated high density (1.
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