Letter | Published:

A New Class of Antimicrobial Agents

Nature volume 204, page 697 (14 November 1964) | Download Citation

Subjects

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.

Access optionsAccess options

Rent or Buy article

Get time limited or full article access on ReadCube.

from$8.99

All prices are NET prices.

References

  1. 1.

    , Ber., 28, 2635 (1895).

  2. 2.

    , J. Chem. Soc., 824 (1938).

  3. 3.

    , and , Quart. Rev., 11, 15 (1957).

  4. 4.

    , and , J. Pharm. Sci., 51, 1058 (1962).

  5. 5.

    , and , J. Pharm. Sci., 53, 83 (1964).

  6. 6.

    , , and , J. Pharm. Sci., 53, 677 (1964).

  7. 7.

    , , and , Tox. and App. Pharmacol., 6, 529 (1964).

  8. 8.

    , Chem. and Indust., 521 (1955).

Download references

Author information

Affiliations

  1. College of Pharmacy, Ohio State University, Columbus.

    • LEMONT B. KIER
    • , MATTHEW C. DODD
    •  & PAUL SAPKO
  2. College of Pharmacy, University of Florida, Gainesville.

    • THOMAS G. STEWART

Authors

  1. Search for LEMONT B. KIER in:

  2. Search for MATTHEW C. DODD in:

  3. Search for PAUL SAPKO in:

  4. Search for THOMAS G. STEWART in:

About this article

Publication history

Published

DOI

https://doi.org/10.1038/204697a0

Further reading

Comments

By submitting a comment you agree to abide by our Terms and Community Guidelines. If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate.