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In today’s data-driven world, we are constantly exposed to a vast amount of information. This information is stored in various information systems and is used for analysis and management purposes. One important approach to handle these data is through the process of clustering or categorization. Clustering algorithms are powerful tools used in data analysis and machine learning to group similar data points together based on their inherent characteristics. These algorithms aim to identify patterns and structures within a dataset, allowing for the discovery of hidden relationships and insights. By partitioning data into distinct clusters, clustering algorithms enable efficient data exploration, classification, and anomaly detection. In this study, we propose a novel centroid-based clustering algorithm, namely, the morphological accuracy clustering algorithm (MAC algorithm). The proposed algorithm uses a morphological accuracy measure to define the centroid of the cluster. The empirical results demonstrate that the proposed algorithm achieves a stable clustering outcome in fewer iterations compared to several existing centroid-based clustering algorithms. Additionally, the clusters generated by these existing algorithms are highly susceptible to the initial centroid selection made by the user.

3-(4-Bromophenyl)-2-cyanoprop-2-enethioamide (1) reacted with ethyl 3-oxo-3-phenylpropanoate (2) to give ethyl 4-(4-bromophenyl)-5-cyano-2-phenyl-6-thioxo-1,6-dihydropyridine-3-carboxylate (3). Compound 3 was taken as a starting material for the synthesis of thio-substituted ethyl nicotinate derivatives 5a-d, which underwent cyclization to the corresponding thieno[2,3-b]pyridines 6a-d. Also 3 reacted with hydrazine hydrate to give the pyrazolo[3,4-b]pyridine derivative 7, which upon diazotization gave the diazonium derivative 8. Compound 6a condensed with dimethylformamide-dimethylacetal to afford thieno[2,3-b]pyridine derivative 9, which reacted with different amines 10a-e to afford the pyridothienopyrimidine derivatives 12a-e through the Dimroth rearrangement. Moreover, compound 6a reacted with different reagents to give pyridothienopyrimidine derivatives 14a and b, 17 and pyrazolothienopyridine derivative 18. In addition, acetylating compound 6c with chloroacetylchloride afforded the 3-[(2)-chloroacetylamino]thieno[2,3-b]pyridine derivative 20, which upon cyclization yielded the corresponding 2-chloromethylpyrido[3',2':4,5]thieno[3,2-d]pyrimidine derivative 21. Some of the newly synthesized compounds were screened in vitro for their antimicrobial activities. [image omitted] [ABSTRACT FROM AUTHOR]