Abstract
THE mesoionic 1,3,4-thiadiazoles, I, were first reported by Busch1, who assigned a bicyclic structure to the compounds. Schoenberg2 later re-examined the structure of Busch and offered a resonance hybrid structure, now accepted as being typical of a large group of heterocycles described as being mesoionic3. We became interested in the mesoionic 1,3,4-thiadiazoles as a natural extension of our interest in the pharmacology and pharmaceutical chemistry of the sydnones II4–7. It occurred to us that since the two ring systems are isoelectronic (that is, being mesoionic they both possess an aromatic, positively charged, 5-membered ring, and a balancing negative charge on an exocyclic atom) the possibility might exist that the two ring systems could also be bioisosteric. That is, the ring itself may behave as a pharmacologically active functional group and that this already expressde similarity between the ring systems may impart similar pharmacological activity. A more conservative speculation would be that perhaps the mesoionic 1,3,4-thiadiazole ring system would have some prominent pharmacological activity.
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References
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KIER, L., DODD, M., SAPKO, P. et al. A New Class of Antimicrobial Agents. Nature 204, 697 (1964). https://doi.org/10.1038/204697a0
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DOI: https://doi.org/10.1038/204697a0
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