Antiproliferative and antibacterial activity of some glutarimide derivatives

References

• Matsuda F, Terashima S. Total synthesis of natural (+)-sesbanimide A and (−)-sesbanimide B. Tetrahedron 1988;44:4721–36
   Web of Science ®Google Scholar
• Ju J, Rajski SR, Lim SK, et al. Lactimidomycin iso-migrastatin and related glutarimide-containing 12-membered macrolides are extremely potent inhibitors of cell migration. J Am Chem Soc 2009;131:1370–1
   PubMed Web of Science ®Google Scholar
• Schneider-Poetsch T, Ju J, Eyler DE, et al. Inhibition of eukaryotic translation elongation by cycloheximide and lactimidomycin. Nat Chem Biol 2010;6:209–17
   PubMed Web of Science ®Google Scholar
• Sugawara K, Nishiyama Y, Toda S, et al. Lactimidomycin, a new glutarimide group antibiotic. Production, isolation, structure and biological activity. J Antibiot 1992;45:1433–41
   PubMed Web of Science ®Google Scholar
• Machado AL, Lima LM, Araujo Jr JX, et al. Design, synthesis and antiinflammatory activity of novel phthalimide derivatives, structurally related to thalidomide. Bioorg Med Chem Lett 2005;15:1169–72
   PubMed Web of Science ®Google Scholar
• Bartlett JB, Dredge K, Dalgleish AG. The evolution of thalidomide and its IMiD derivatives as anticancer agents. Nat Rev Cancer 2004;4:314–22
   PubMed Web of Science ®Google Scholar
• Wu YH, Rayburn JW, Allen LE, et al. Psychosedative agents. 2. 8-(4-Substituted l-piperazinylalkyl)-8-azaspiro[4.5]decane-7,9-diones. J Med Chem 1972;15:477–9
   PubMed Web of Science ®Google Scholar
• Barrdell LB, Fitton A. Tandospirone. CNS Drugs 1996;5:147–52
   Web of Science ®Google Scholar
• Obrig TG, Culp WJ, Mckeehan WL, Hardesty B. The mechanism by which cycloheximide and related glutarimide antibiotics inhibit peptide synthesis on reticulocyte ribosomes. J Biol Chem 1971;246:174–81
   PubMed Web of Science ®Google Scholar
• Kondo H, Oritani T, Kiyota H. Synthesis and antifungal activity of the four stereoisomers of streptimidone, a glutarimide antibiotic from Streptomyces rimosus forma paromomycinus. Eur J Org Chem 2000;2000:3459–62
   Web of Science ®Google Scholar
• Frohardt RP, Dion HW, Jakubowski ZL, et al. Chemistry of streptimidone, a new antibiotic. J Am Chem Soc 1959;81:5500–6
   Web of Science ®Google Scholar
• Kim BS, Moon SS, Hwang BK. Isolation, antifungal activity, and structure elucidation of the glutarimide antibiotic, streptimidone, produced by Micromonospora coerulea. J Agric Food Chem 1999;47:3372–80
   PubMed Web of Science ®Google Scholar
• Ha DKK, Lau WH. Effect of recombinant human tumor necrosis factor on human nasopharyngeal carcinoma cell line in vitro. Cancer Lett 1988;41:217–24
   PubMed Web of Science ®Google Scholar
• Andres MI, Sanz P, Garfia A, et al. Induction of cell differentiation and other in vitro effects of cycloheximide on neuroblastoma cells. In Vitro Mol Toxicol 1977;10:319–28
   Google Scholar
• Ishikawa Y, Tachibana M, Matsui C, et al. Synthesis and biological evaluation on novel analogs of 9-methylstreptimidone, an inhibitor of NF-κB. Bioorg Med Chem Lett 2009;19:1726–8
   PubMed Web of Science ®Google Scholar
• Powell RG, Smith Jr CR, Weisleder D. Sesbanimide A and related tumor inhibitors from Sesbania drummondii: structure and chemistry. Phytochemistry 1984;23:2789–96
   Web of Science ®Google Scholar
• Powell RG, Smith CR, Weisleder D, et al. Sesbanimide, a potent antitumor substance from Sesbania drummondii seed. J Am Chem Soc 1983;105:3739–41
   Web of Science ®Google Scholar
• Powel RG, Smith Jr CR. An investigation of the antitumor activity of Sesbania drummondii. J Nat Prod 1981;44:86–90
   PubMed Web of Science ®Google Scholar
• Powel RG, Smith Jr CR, Madrigal RV. Antitumor activity of Sesbania vesicaria, S. punicea, and S. drummondii seed extracts. Planta Med 1976;30:1–8
   PubMed Web of Science ®Google Scholar
• Armoiry X, Aulagner G, Facon T. Lenalidomide in the treatment of multiple myeloma: a review. J Clin Pharm Ther 2008;33:219–26
   PubMed Web of Science ®Google Scholar
• Lentzsch S, Rogers MS, LeBlanc R, et al. S-3-Amino-phthalimido-glutarimide inhibits angiogenesis and growth of B-cell neoplasias in mice. Cancer Res 2002;62:2300–5
   PubMed Web of Science ®Google Scholar
• McCarthy PL, Owzar K, Hofmeister CC, et al. Lenalidomide after stem-cell transplantation for multiple myeloma. N Engl J Med 2012;366:1770–81
   PubMed Web of Science ®Google Scholar
• Fischer DS, Woo LW, Mahon MF, et al. D-ring modified estrone derivatives as novel potent inhibitors of steroid sulfatase. Bioorg Med Chem 2003;11:1685–700
   PubMed Web of Science ®Google Scholar
• Brueggemeier RW, Hackett JC, Diaz-Cruz ES. Aromatase inhibitors in the treatment of breast cancer. Endocr Rev 2005;26:331–45
   PubMed Web of Science ®Google Scholar
• Santen RJ, Brodie H, Simpson ER, et al. History of aromatase: saga of an important biological mediator and therapeutic target. Endocr Rev 2009;30:343–75
   PubMed Web of Science ®Google Scholar
• Antonini I, Volpini R, Dal Ben D, et al. Design, synthesis, and biological evaluation of new mitonafide derivatives as potential antitumor drugs. Bioorg Med Chem 2008;16:8440–6
   PubMed Web of Science ®Google Scholar
• Norton JT, Witschi MA, Luong L, et al. Synthesis and anticancer activities of 6-amino amonafide derivatives. Anti-Cancer Drugs 2008;19:23–36
   PubMed Web of Science ®Google Scholar
• Wu A, Xu Y, Qian X, et al. Novel naphthalimide derivatives as potential apoptosis-inducing agents: design, synthesis and biological evaluation. Eur J Med Chem 2009;44:4674–80
   PubMed Web of Science ®Google Scholar
• Machado KE, Navakoski de Oliveira K, Santos-Bubniak L, et al. Evaluation of apoptotic effect of cyclic imide derivatives on murine B16F10 melanoma cells. Bioorg Med Chem 2011;19:6285–91
   PubMed Web of Science ®Google Scholar
• Popović-Đorđević JB, Ivanović MD, Kiricojević VD. A novel tandem process leading to functionalized glutarimides. Tetrahedron Lett 2005;46:2611–14
   Web of Science ®Google Scholar
• Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 1983;65:55–63
   PubMed Web of Science ®Google Scholar
• Ohno M, Abe T. Rapid colorimetric assay for the quantification of leukemia inhibitory factor (LIF) and interleukin-6 (IL-6). J Immunol Methods 1991;145:199–203
   PubMed Web of Science ®Google Scholar
• Tepe B, Daferera D, Sokmen A, et al. Antimicrobial and antioxidant activities of the essential oil and various extracts of Salvia tomentosa Miller (Lamiaceae). Food Chem 2005;90:333–40
   Web of Science ®Google Scholar
• Clinical and Laboratory Standards Institute (CLSI). Performance standards for antimicrobial susceptibility testing: 15th informational supplement 2005. CLSI Document M100-S15. Pennsylvania: CLSI
   Google Scholar
• Klančnik A, Piskernik S, Jeršek B, Smole Možina S. Evaluation of diffusion and dilution methods to determine the antibacterial activity of plant extracts. J Microbiol Methods 2010;81:121–6
   PubMed Web of Science ®Google Scholar
• Sadowski J, Gasteiger J. From atoms and bonds to three-dimensional atomic coordinates: automatic model builders. Chem Rev 1993;93:2567–81
   Web of Science ®Google Scholar
• Sadowski J, Gasteiger J, Klebe G. Comparison of automatic three-dimensional model builders using 639 X-ray structures. J Chem Inform Model 1994;34:1000–8
   Web of Science ®Google Scholar
• Pedretti A, Villa L,Vistoli G. VEGA – an open platform to develop chemo-bio-informatics applications, using plug-in architecture and script programming. J Comput-Aided Mol Des 2004;18:167–73
   PubMed Web of Science ®Google Scholar
• Halgren TA. MMFF VI. MMFF94s option for energy minimization studies. J Comput Chem 1999;20:720–9
   PubMed Web of Science ®Google Scholar
• Harrison RW. Stiffness and energy conservation in molecular dynamics: an improved integrator. J Comput Chem 1993;14:1112–22
   Web of Science ®Google Scholar
• Stewart JJP. Optimization of parameters for semiempirical methods V: modification of NDDO approximations and application to 70 elements. J Mol Model 2007;13:1173–213
   PubMed Web of Science ®Google Scholar
• Stewart JJP. MOPAC: a semiempirical molecular orbital program. J Comput-Aided Mol Des 1990;4:1–103
   PubMed Web of Science ®Google Scholar
• Gaillard P, Carrupt PA, Testa B, Boudon A. Molecular lipophilicity potential, a tool in 3D QSAR: method and applications. J Comput-Aided Mol Des 1994;8:83–96
   PubMed Web of Science ®Google Scholar
• Goodford PJ. A Computational procedure for determining energetically favorable binding sites on biologically important macromolecules. J Med Chem 1985;28:849–57
   PubMed Web of Science ®Google Scholar
• Durán Á, Martínez GC, Pastor M. Development and validation of AMANDA, a new algorithm for selecting highly relevant regions in molecular interaction fields. J Chem Inform Model 2008;48:1813–23 . Pentacle 1.0.6. http://www.moldiscovery.com/software/pentacle/
   PubMed Web of Science ®Google Scholar
• Gokel GW, Cram DJ, Liotta CL, et al. 18-Crown-6 (1,4,7,10,13,16-hexaoxacycloöctadecane). Org Syn 1988;VI:301–2
   Google Scholar
• Cason J. β-Methylglutaric anhydride. Org Syn 1963;IV:630–1
   Google Scholar
• Farmer HH, Rebjohn N. β-Ethyl-β-methylglutaric acid. Org Syn 1963;IV:441–2
   Google Scholar
• Cason J. β-Carbomethoxypropionyl chloride. Org Syn 1955;III:169–70
   Google Scholar
• Vogel AI. Vogel’s text book of practical organic chemistry. 5th ed. Harlow: Longman Group, UK Limited; 1989
   Google Scholar
• Strube RE. Ethyl tert-butyl malonate. Org Syn 1963;IV:417–18
   Google Scholar
• Paquet LA, ed. Encyclopedia of reagents for organic synthesis. Vol. 7. Pennsylvania State University, John-Wiley; 1995. Available from: http://eu.wiley.com/WileyCDA/WileyTitle/productCd-0470017546.html [last accessed 21 Jul 2015]
   Google Scholar
• Krapcho AP, Diamanti J, Cayen C, Bingham R. 2-Carbethoxycyclooctanone. Org Syn 1973;V:198–9
   Google Scholar
• Popović-Djordjević JB, Došen-Mićović LjI, Juranić IO, Drakulić BJ. Antiproliferative activity of NCI-DTP glutarimide derivatives: an alignment independent 3D QSAR study. J Serbian Chem Soc 2010;75:1167–79
   Web of Science ®Google Scholar
• Cruciani G, ed. Methods and principles in medicinal chemistry, molecular interaction fields: applications in drug discovery and ADME prediction. Weinheim: Wiley-VCH; 2006
   Google Scholar