What question did this study set out to answer?

To develop an automated computational method that systematically extracts and quantifies the frequency of one-to-one chemical group replacements between molecules sharing biological activity.

January 1, 2002Journal of Chemical Information and Computer Sciences

The Most Common Chemical Replacements in Drug-Like Compounds

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Authors

RSRobert P. SheridanMerck & Co., Inc., Rahway, NJ, USA (United States)

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Implication

Computational analysis reveals frequent one-to-one chemical group replacements in paired drug-like compounds, highlighting an automated strategy to systematically identify candidate bioisosteres.

Key Points

To develop an automated computational method that systematically extracts and quantifies the frequency of one-to-one chemical group replacements between molecules sharing biological activity.
Designed an algorithm with two variations (differing in ring-replacement handling) to extract one-to-one chemical group substitutions between biologically matched compound pairs.
Applied the extraction and counting method across the MDDR database covering diverse drug-like structures across multiple therapeutic areas.
Identified recurring chemical group replacements that align consistently with established medicinal chemistry intuition regarding functional equivalence.
Observed that the most frequent replacements reflect functional groups commonly interchanged through standard synthetic reactions or known metabolic pathways.

Cite This Study

Robert P. Sheridan (2002) studied this question.

synapsesocial.com/papers/6a8fc33c794117ff9ac8be77 https://doi.org/10.1021/ci0100806

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Implication

Computational analysis reveals frequent one-to-one chemical group replacements in paired drug-like compounds, highlighting an automated strategy to systematically identify candidate bioisosteres.

The Most Common Chemical Replacements in Drug-Like Compounds

Discussion

Member takes

Implication

Key Points

Cite This Study

The Most Common Chemical Replacements in Drug-Like Compounds

Discussion

Member takes

Implication

Key Points

Cite This Study

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