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Chemical Compound Review

Azetidin     azetidine

Synonyms: AZETIDINE, Azacyclobutane, Azetidine, L-, PubChem22634, SureCN12502, ...
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Disease relevance of azetidine

  • In cells infected with herpes simplex virus type 1 (HSV-1) in the presence of azetidine, synthesis of cellular proteins, including polypeptide C, was suppressed and infected cell polypeptides ICP 4, 0, 22 and 27 (apparent mol. wt. 170000, 120000, 75000 and 60000, respectively) were made [1].
  • While each of the mutations (located within a conserved 26-amino-acid region of GK) was shown to confer AZ resistance (AZ(r)) on an L. monocytogenes proBA mutant, listerial transformants failed to exhibit the salt-tolerant phenotype observed in E. coli [2].
  • A series of TEPA, Thio-TEPA, Seleno-TEPA, and azetidine analogs, including congeners containing an aminoxyl moiety, were synthesized and evaluated in vivo for anticancer activity against the murine lymphocytic leukemia P388 [3].
  • 3. On the other hand, against five representative gram-positive bacteria, the relative mean antibacterial activity indices, GPM, remained high and rather constant regardless of structural variation in the azetidine moiety [4].
  • Incubation of H35 hepatoma cells with 2.5 mM azetidine before or after treatments with X-rays causes a time- and sequence-dependent enhancement of cell killing [5].

High impact information on azetidine

  • Upon exposure of cells to heat shock, the heavy metal cadmium, or the amino acid analogue azetidine, transcription at the hsp90alpha and hsp70 gene loci is strongly induced, and both hsp transcription sites become associated with speckles in >90% of the cells [6].
  • Above a low basal activity of both HSFs, heat shock preferentially activates HSF1, whereas the amino acid analogue azetidine or the proteasome inhibitor MG132 coactivates both HSFs to different levels and hemin preferentially induces HSF2 [7].
  • In support of this hypothesis, other treatments which act through different mechanisms to interfere with protein processing (i.e., tunicamycin, brefeldin A, and azetidine) were also found to be much more toxic for VHL-deficient cells [8].
  • In cotransfection studies, YY1 specifically enhanced the transcriptional activation of the grp78 promoter under a variety of stress conditions: depletion of the endoplasmic reticulum calcium stores, protein glycosylation block, and formation of aberrant proteins by azetidine treatment [9].
  • HSF activation in response to treatment with sodium arsenite or the proline analog azetidine was also depressed in hsp70-expressing cells relative to that in the nontransfected control cells [10].

Chemical compound and disease context of azetidine


Biological context of azetidine


Anatomical context of azetidine


Associations of azetidine with other chemical compounds


Gene context of azetidine

  • All of the results from the functional studies of azetidine 10f are consistent with a selectivity of action at the NMDA receptor [24].
  • The N-methanesulfonyl piperidine 23 and the N-trifluoroacetyl azetidine 26 were the most potent aggrecanase inhibitors both having an IC(50)=3nM while maintaining >100-fold selectivity over MMP-1, -2, and -9 [25].


  1. Some characteristics of an early protein (ICP 22) synthesized in cells infected with herpes simplex virus. Fenwick, M., Walker, M., Marshall, L. J. Gen. Virol. (1980) [Pubmed]
  2. Mutations in the listerial proB gene leading to proline overproduction: effects on salt tolerance and murine infection. Sleator, R.D., Gahan, C.G., Hill, C. Appl. Environ. Microbiol. (2001) [Pubmed]
  3. In the search for new anticancer drugs. 26. A comparison of anticancer activities of several TEPA, thio-TEPA, Seleno-TEPA, and azetidine analogs, including congeners containing an aminoxyl moiety. Sosnovsky, G., Lukszo, J., Konieczny, M., Purgstaller, K., Laib, F. Journal of pharmaceutical sciences. (1994) [Pubmed]
  4. Quantitative structure-activity relationships of antibacterial agents, 7-heterocyclic amine substituted 1-cyclopropyl-6,8-difluoro-4-oxoquinoline-3-carboxylic acids. Okada, T., Ezumi, K., Yamakawa, M., Sato, H., Tsuji, T., Tsushima, T., Motokawa, K., Komatsu, Y. Chem. Pharm. Bull. (1993) [Pubmed]
  5. Effects of azetidine-2-carboxylic acid on treatments of hepatoma cells with single or fractionated X-ray irradiations and on thermal radiosensitization in normal and thermotolerant cells. van Rijn, J., van den Berg, J., van der Mast, C.A. Radiation oncology investigations. (1999) [Pubmed]
  6. Intron-independent association of splicing factors with active genes. Jolly, C., Vourc'h, C., Robert-Nicoud, M., Morimoto, R.I. J. Cell Biol. (1999) [Pubmed]
  7. Stress-specific activation and repression of heat shock factors 1 and 2. Mathew, A., Mathur, S.K., Jolly, C., Fox, S.G., Kim, S., Morimoto, R.I. Mol. Cell. Biol. (2001) [Pubmed]
  8. Protective function of von Hippel-Lindau protein against impaired protein processing in renal carcinoma cells. Gorospe, M., Egan, J.M., Zbar, B., Lerman, M., Geil, L., Kuzmin, I., Holbrook, N.J. Mol. Cell. Biol. (1999) [Pubmed]
  9. Induction of the mammalian GRP78/BiP gene by Ca2+ depletion and formation of aberrant proteins: activation of the conserved stress-inducible grp core promoter element by the human nuclear factor YY1. Li, W.W., Hsiung, Y., Zhou, Y., Roy, B., Lee, A.S. Mol. Cell. Biol. (1997) [Pubmed]
  10. The DNA-binding activity of the human heat shock transcription factor is regulated in vivo by hsp70. Mosser, D.D., Duchaine, J., Massie, B. Mol. Cell. Biol. (1993) [Pubmed]
  11. On the control of immediate early (alpha) mRNA survival in cells infected with herpes simplex virus. Fenwick, M.L., Owen, S.A. J. Gen. Virol. (1988) [Pubmed]
  12. 7-azetidinylquinolones as antibacterial agents. 2. Synthesis and biological activity of 7-(2,3-disubstituted-1-azetidinyl)-4-oxoquinoline- and -1,8-naphthyridine-3-carboxylic acids. Properties and structure-activity relationships of quinolones with an azetidine moiety. Frigola, J., Torrens, A., Castrillo, J.A., Mas, J., Vañó, D., Berrocal, J.M., Calvet, C., Salgado, L., Redondo, J., García-Granda, S. J. Med. Chem. (1994) [Pubmed]
  13. Requirement of the p38 mitogen-activated protein kinase signalling pathway for the induction of the 78 kDa glucose-regulated protein/immunoglobulin heavy-chain binding protein by azetidine stress: activating transcription factor 6 as a target for stress-induced phosphorylation. Luo, S., Lee, A.S. Biochem. J. (2002) [Pubmed]
  14. Practical asymmetric preparation of azetidine-2-carboxylic acid. Couty, F., Evano, G., Vargas-Sanchez, M., Bouzas, G. J. Org. Chem. (2005) [Pubmed]
  15. Physiological and pharmacological profile of trans-azetidine-2,4-dicarboxylic acid: metabotropic glutamate receptor agonism and effects on long-term potentiation. Manahan-Vaughan, D., Reiser, M., Pin, J.P., Wilsch, V., Bockaert, J., Reymann, K.G., Riedel, G. Neuroscience (1996) [Pubmed]
  16. Evidence contrary to the protein error hypothesis for in vitro senescence. Pendergrass, W.R., Martin, G.M., Bornstein, P. J. Cell. Physiol. (1976) [Pubmed]
  17. Fasciola hepatica: azetidine inhibition of bile duct hyperplasia in the infected rat. Girotra, K.L., Isseroff, H. Exp. Parasitol. (1980) [Pubmed]
  18. Incorporation of L-azetidine-2-carboxylic acid into hemoglobin S in sickle erythrocytes in vitro. Trasko, C.S., Franzblau, C., Troxler, R.F. Biochim. Biophys. Acta (1976) [Pubmed]
  19. Characterization and expression of the mouse Hsc70 gene. Hunt, C.R., Parsian, A.J., Goswami, P.C., Kozak, C.A. Biochim. Biophys. Acta (1999) [Pubmed]
  20. 7-Azetidinylquinolones as antibacterial agents. Synthesis and structure-activity relationships. Frigola, J., Parés, J., Corbera, J., Vañó, D., Mercè, R., Torrens, A., Más, J., Valentí, E. J. Med. Chem. (1993) [Pubmed]
  21. Synthesis and biological activities of angiotensin II, Sarilesin, and Sarmesin analogues containing Aze or Pip at position 7. Matsoukas, J.M., Agelis, G., Hondrelis, J., Yamdagni, R., Wu, Q., Ganter, R., Smith, J.R., Moore, D., Moore, G.J. J. Med. Chem. (1993) [Pubmed]
  22. Structure reinvestigation of gelsemoxonine, a constituent of Gelsemium elegans, reveals a novel, azetidine-containing indole alkaloid. Kitajima, M., Kogure, N., Yamaguchi, K., Takayama, H., Aimi, N. Org. Lett. (2003) [Pubmed]
  23. New fluorinated pyrrolidine and azetidine amides as dipeptidyl peptidase IV inhibitors. Hulin, B., Cabral, S., Lopaze, M.G., Van Volkenburg, M.A., Andrews, K.M., Parker, J.C. Bioorg. Med. Chem. Lett. (2005) [Pubmed]
  24. Synthesis and bioactivity of a new class of rigid glutamate analogues. Modulators of the N-methyl-D-aspartate receptor. Kozikowski, A.P., Tückmantel, W., Reynolds, I.J., Wroblewski, J.T. J. Med. Chem. (1990) [Pubmed]
  25. Potent and selective aggrecanase inhibitors containing cyclic P1 substituents. Cherney, R.J., Mo, R., Meyer, D.T., Wang, L., Yao, W., Wasserman, Z.R., Liu, R.Q., Covington, M.B., Tortorella, M.D., Arner, E.C., Qian, M., Christ, D.D., Trzaskos, J.M., Newton, R.C., Magolda, R.L., Decicco, C.P. Bioorg. Med. Chem. Lett. (2003) [Pubmed]
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