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Chemical Compound Review

Pyrroline     2,3-dihydro-1H-pyrrole

Synonyms: Dihydropyrrole, SureCN17244, AG-E-90947, CHEBI:32986, CTK1A4482, ...
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Disease relevance of Pyrroline


High impact information on Pyrroline

  • The order of the subsequent steps is (i) aromatization of the dihydropyrrole ring, (ii) ester hydrolysis, and (iii) oxidation of the resulting primary alcohol to the final aldehyde [2].
  • Inosine monophosphate has been considered to be a "mobile pool" of purines, i.e. a reservoir from which peripheral tissues can be supplied; the effect of pyrroline 5-carboxylate on the inosine monophosphate pool may be a mechanism for regulating the function of erythrocytes in purine delivery [3].
  • Analysis of these structures has provided additional support for the presence of the pyrroline ring and, together with previous mass spectroscopy data, has led us to assign the C(4)-substituent to a methyl group [4].
  • Trimetazidine, TMZ-NH (TMZ modified with a pyrroline moiety), or TMZ-PhiNH (TMZ-NH with a phenyl substitute) were infused (50 microM) for 1 min before the onset of ischemia [5].
  • The results are presented of a theoretical study of the nitrosation chemistry of pyrroline 1 (X = CH(2)), imidazoline 2 (X = NH), and 2-oxazoline 3 (X = O) [6].

Biological context of Pyrroline

  • The synthesis was based on a convergent strategy involving a stereocontrolled addition of a beta-phenyl silyl enol ether to a pyrroline N-acyliminium ion followed by an intramolecular palladium-catalyzed aryl triflate amination to afford the (9R*,9aR*)-tetrahydropyrrolo[1,2-a]indole ring system [7].
  • The NMR data indicated that the pyrroline ring and propionic acid parts may be the major binding site for HSA [8].
  • Iteration of organometallic addition to chiral hydroxylated pyrroline N-oxides through an addition-oxidation-addition synthetic sequence allowed highly stereoselective double alkylation of pyrrolidine at C-2 or at C-2 and C-5 depending on the regioselectivity of the oxidation step [9].
  • Palladium-catalyzed cyclization of amino allenes affords either the pyrroline or the pyrrole depending on reaction conditions and provides for introduction of an aryl substituent at the C-3 position of the pyrroline or pyrrole [10].
  • We sought to identify specific inhibitors to probe this unique uptake mechanism, to blockade the metabolic effects of pyrroline 5-carboxylate, and to provide strategies to identify the putative carrier protein [11].

Anatomical context of Pyrroline


Associations of Pyrroline with other chemical compounds


Gene context of Pyrroline

  • Pyrroline 5-carboxylate, an intermediate in this metabolic pathway, has been shown to stimulate PRPP synthesis when added to cultures of resting 3T6 cells [19].
  • Accumulation of pyrroline 5-carboxylic acid in conditioned medium of cultured fibroblast: stimulatory effects of serum, insulin, and IGF-1 [20].


  1. A pyrroline derivative of mexiletine offers marked protection against ischemia/reperfusion-induced myocardial contractile dysfunction. Li, H., Xu, K.Y., Zhou, L., Kalai, T., Zweier, J.L., Hideg, K., Kuppusamy, P. J. Pharmacol. Exp. Ther. (2000) [Pubmed]
  2. Insect pheromone biosynthesis: stereochemical pathway of hydroxydanaidal production from alkaloidal precursors in Creatonotos transiens (Lepidoptera, Arctiidae). Schulz, S., Francke, W., Boppré, M., Eisner, T., Meinwald, J. Proc. Natl. Acad. Sci. U.S.A. (1993) [Pubmed]
  3. Stimulation of phosphoribosyl pyrophosphate and purine nucleotide production by pyrroline 5-carboxylate in human erythrocytes. Yeh, G.C., Phang, J.M. J. Biol. Chem. (1988) [Pubmed]
  4. Reactivity and chemical synthesis of L-pyrrolysine- the 22(nd) genetically encoded amino acid. Hao, B., Zhao, G., Kang, P.T., Soares, J.A., Ferguson, T.K., Gallucci, J., Krzycki, J.A., Chan, M.K. Chem. Biol. (2004) [Pubmed]
  5. Attenuation of myocardial ischemia-reperfusion injury by trimetazidine derivatives functionalized with antioxidant properties. Kutala, V.K., Khan, M., Mandal, R., Ganesan, L.P., Tridandapani, S., Kalai, T., Hideg, K., Kuppusamy, P. J. Pharmacol. Exp. Ther. (2006) [Pubmed]
  6. Nitrosation chemistry of pyrroline, 2-imidazoline, and 2-oxazoline: theoretical Curtin-Hammett analysis of retro-ene and solvent-assisted C-X cleavage reactions of alpha-hydroxy-N-nitrosamines. Wu, H., Loeppky, R.N., Glaser, R. J. Org. Chem. (2005) [Pubmed]
  7. A convergent approach to the mitomycin ring system. Coleman, R.S., Chen, W. Org. Lett. (2001) [Pubmed]
  8. Binding of pirprofen to human serum albumin studied by dialysis and spectroscopy techniques. Otagiri, M., Masuda, K., Imai, T., Imamura, Y., Yamasaki, M. Biochem. Pharmacol. (1989) [Pubmed]
  9. Iterative organometallic addition to chiral hydroxylated cyclic nitrones: highly stereoselective syntheses of alpha,alpha'- and alpha,alpha-substituted hydroxypyrrolidines. Goti, A., Cicchi, S., Mannucci, V., Cardona, F., Guarna, F., Merino, P., Tejero, T. Org. Lett. (2003) [Pubmed]
  10. Synthesis of 3-pyrrolines, annulated 3-pyrrolines, and pyrroles from alpha-amino allenes. Dieter, R.K., Yu, H. Org. Lett. (2001) [Pubmed]
  11. Structural analogues of pyrroline 5-carboxylate specifically inhibit its uptake into cells. Mixson, A.J., Phang, J.M. J. Membr. Biol. (1991) [Pubmed]
  12. Factors influencing pyrroline 5-carboxylate synthesis from glutamate by rat intestinal mucosa mitochondria. Henslee, J.G., Wakabayashi, Y., Small, C., Jones, M.E. Arch. Biochem. Biophys. (1983) [Pubmed]
  13. Potential role of pyrroline 5-carboxylate in regulation of collagen biosynthesis in cultured human skin fibroblasts. Miltyk, W., Palka, J.A. Comp. Biochem. Physiol., Part A Mol. Integr. Physiol. (2000) [Pubmed]
  14. 2,2,5,5-Tetramethylpyrroline-based compounds in prevention of oxyradical-induced myocardial damage. Halmosi, R., Deres, P., Toth, A., Berente, Z., Kalai, T., Sumegi, B., Hideg, K., Toth, K. J. Cardiovasc. Pharmacol. (2002) [Pubmed]
  15. Characterization of human liver cytochrome P450 enzymes involved in the metabolism of a new H+/K+-ATPase inhibitor KR-60436. Ji, H.Y., Lee, H.W., Kim, H.H., Choi, J.K., Lee, H.S. Toxicol. Lett. (2005) [Pubmed]
  16. A pyrroline glucoside ester and steroidal saponins from Lilium martagon. Satou, T., Mimaki, Y., Kuroda, M., Sashida, Y., Hatakeyama, Y. Phytochemistry (1996) [Pubmed]
  17. In the search for new anticancer drugs. 29. A study on the correlation of lipophilicities, ionization constants and anticancer activities of aminoxyl labeled TEPA congeners. Sosnovsky, G., Bell, P. Life Sci. (1998) [Pubmed]
  18. Effects of pyrroline and pyrrolidine nitroxides on lipid peroxidation in heart tissue of rats treated with doxorubicin. Koceva-Chyła, A., Gwoździński, K., Kochman, A., Stolarska, A., Jóźwiak, Z. Cell. Mol. Biol. Lett. (2003) [Pubmed]
  19. Regulation of nucleotide and pentose synthesis in resting and stimulated 3T6 fibroblasts. Buchanan, J.M., Smith, M.L., Smith, R.J. Adv. Enzyme Regul. (1982) [Pubmed]
  20. Accumulation of pyrroline 5-carboxylic acid in conditioned medium of cultured fibroblast: stimulatory effects of serum, insulin, and IGF-1. Semon, B.A., Phang, J.M. In Vitro Cell. Dev. Biol. (1991) [Pubmed]
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