746
Views
8
CrossRef citations to date
0
Altmetric
Research Article

Three-component synthesis and carbonic anhydrase inhibitory properties of novel octahydroacridines incorporating sulfaguanidine scaffold

, , , &
Pages 63-69 | Received 15 Mar 2016, Accepted 05 May 2016, Published online: 30 May 2016

References

  • Albert A. The acridines. London: Edward Arnold Publication Ltd.; 1996:13–18.
  • Grove WR, Fortner CI, Wiernik PH. Review of amsacrine, an investigational antineoplastic agent. Clin Pharm 1982;1:320–6.
  • Yeşildağ İ, Ulus R, Başer E, et al. Facile, highly efficient and clean one-pot synthesis of acridine sulfonamide derivatives at room temperature and their inhibition of human carbonic anhydrase isoenzymes. Mon Chem 2014;145:1027–37.
  • Esirden İ, Ulus R, Aday B, et al. Synthesis of novel acridine bis-sulfonamides with effective inhibitory activity against the carbonic anhydrase isoforms I, II, IX and XII. Bioorg Med Chem 2015;23:6573–80.
  • Kaya M, Yildirir Y, Çelik GY. Synthesis, characterization, in vitro antimicrobial and antifungal activity of novel acridines. Pharm Chem J 2015;48:769–73.
  • Di Stilo A, Visentin S, Cena C, et al. New 1,4-dihydropyridines conjugated to furoxanyl moieties, endowed with both nitric oxide-like and calcium channel antagonist vasodilator activities. J Med Chem 1998;41:5393–401.
  • Li JH, Yasay GD, Kau ST, et al. Studies of the k(ATP), channel opening activity of the new dihydropyridine compound 9-(3-cyanophenyl)-3,4,6,7,9,10-hexahydro-1,8-(2H,5H)-acridinedione in bladder detrusor in vitro. Arzneimittelforschung 1996;46:525–30.
  • Supuran CT. How many carbonic anhydrase inhibition mechanisms exist? J Enzyme Inhib Med Chem 2016;31:345–60.
  • Capasso C, Supuran CT. An overview of the alpha-, beta- and gamma-carbonic anhydrases from bacteria: can bacterial carbonic anhydrases shed new light on evolution of bacteria? J Enzyme Inhib Med Chem 2015;30:325–32.
  • Supuran CT. Structure-based drug discovery of carbonic anhydrase inhibitors. J Enzyme Inhib Med Chem 2012;27:759–72.
  • Supuran CT, Conroy CW, Maren TH. Carbonic anhydrase inhibitors: synthesis and inhibitory properties of 1,3,4-thiadiazole-2,5-bissulfonamide. Eur J Med Chem 1996;31:843–6.
  • Supuran CT. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discov 2008;7:168–81.
  • Hewett-Emmett D, Tashian RE. Functional diversity, conservation, and convergence in the evolution of the alpha-, beta-, and gammacarbonic anhydrase gene families. Mol Phylogenet Evol 1996;5:50–77.
  • Briganti F, Mangani S, Orioli P, et al. Carbonic anhydrase activators: X-ray crystallographic and spectroscopic investigations for the interaction of isozymes I and II with histamine. Biochemistry 1997;36:10384–92.
  • Supuran CT, Scozzafava A. Applications of carbonic anhydrase inhibitors and activators in therapy. Exp Opin Ther Pat 2002;12:217–42.
  • Sugrue MF. Pharmacological and ocular hypotensive properties of topical carbonic anhydrase inhibitors. Prog Retin Eye Res 2000;19:87–112.
  • Masini E, Carta F, Scozzafava A, Supuran CT. Antiglaucoma carbonic anhydrase: a patent review. Expert Opin Ther Pat 2013;23:705–16.
  • Almasieh M, Wilson MA, Morquette B, et al. The molecular basis of retinal ganglion cell death in glaucoma. Prog Retin Eye Res 2012;31:152–81.
  • Maren TH. The development of topical carbonic anhydrase inhibitors. J Glaucoma 1995;4:49–62.
  • Reiss WG, Oles KS. Acetazolamide in the treatment of seizures. Ann Pharmacother 1996;30:514–19.
  • Becker B. The mechanism of the fall in intraocular pressure induced by the carbonic anhydrase inhibitor, diamox. Am J Ophthalmol 1955;39:177–84.
  • Lou Y, McDonald PC, Oloumi A, et al. Targeting tumor hypoxia: suppression of breast tumor growth and metastasis by novel carbonic anhydrase IX inhibitors. Cancer Res 2011;71:3364–76.
  • Pacchiano F, Carta F, McDonald PC, et al. Ureido-substituted benzenesulfonamides potently inhibit carbonic anhydrase IX and show antimetastatic activity in a model of breast cancer metastasis. J Med Chem 2011;54:1896–902.
  • Mincione F, Starnotti M, Menabuoni L, et al. Carbonic anhydrase inhibitors: 4-sulfamoyl-benzenecarboxamides and 4-chloro-3-sulfamoylbenzenecarboxamides with strong topical antiglaucoma properties. Bioorg Med Chem Lett 2001;11:1787–91.
  • Silver LH. Dose-response evaluation of the ocular hypotensive effect of brinzolamide ophthalmic suspension (Azopt (R)). Surv Ophthalmol 2000;44:147–53.
  • Ulus R, Yeşildağ İ, Tanç M, et al. Synthesis of novel acridine and bis acridine sulfonamides with effective inhibitory activity against the cytosolic carbonic anhydrase isoforms II and VII. Bioorg Med Chem 2013;21:5799–805.
  • Kaya M, Basar E, Cakir E, et al. Synthesis and characterization of novel dioxoacridine sulfonamide derivatives as new carbonic anhydrase inhibitors. J Enzyme Inhib Med Chem 2012;27:509–14.
  • Chohan ZH, Shaikh AU, Rauf A, Supuran CT. Antibacterial, antifungal and cytotoxic properties of novel N-substituted sulfonamides from 4-hydroxycoumarin. J Enzyme Inhib Med Chem 2006;21:741–8.
  • Chohan ZH, Rauf A, Naseer MM, et al. Antibacterial, antifungal and cytotoxic properties of some sulfonamide-derived chromones. J Enzyme Inhib Med Chem 2006;21:173–7.
  • Rickli EE, Ghazanfar SA, Gibbons BH, Edsall JT. Carbonic anhydrases from human erythrocytes. Preparation and properties of two enzymes. J Biol Chem 1964;239:1065–78.
  • Bradford MM. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein dye binding. Anal Biochem 1976;72:248–54.
  • Laemmli UK. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 1970;227:680–5.
  • Wilbur KM, Anderson NG. Electrometric and colorimetric determination of carbonic anhydrase. J Biol Chem 1948;176:147–54.
  • Verpoorte JA, Mehta S, Edsall JT. Esterase activities of human carbonic anhydrases B and C. J Biol Chem 1967;242:4221–2229.
  • Yamali C, Tugrak M, Gul HI, et al. The inhibitory effects of phenolic Mannich bases on carbonic anhydrase I and II isoenzymes. J Enzyme Inhib Med Chem 2016. [Epub ahead of print]. doi:10.3109/14756366.2015.1126715.
  • Akbaba Y, Bastem E, Topal F, et al. Synthesis and carbonic anhydrase inhibitory effects of novel sulfamides derived from 1-aminoindanes and anilines. Arch Pharm (Weinheim) 2014;347:950–7.
  • Akbaba Y, Balaydin HT, Menzek A, et al. Synthesis and biological evaluation of novel bromophenol derivatives as carbonic anhydrase inhibitors. Arch Pharm (Weinheim) 2013;346:447–54.
  • Akincioglu A, Göçer A, Gülçin İ, et al. Discovery of potent carbonic anhydrase and acetylcholine esterase inhibitors: novel sulfamoylcarbamates and sulfamides derived from acetophenones. Bioorg Med Chem 2015;23:3592–602.
  • Kaya M, Basar E, Colak F. Synthesis and antimicrobial activity of some bisoctahydroxanthene-1,8-dione derivatives. Med Chem Res 2011;20:1214–19.
  • Başar E, Tunca E, Bülbül M, Kaya M. Synthesis of novel sulfonamides under mild conditions with effective inhibitory activity against the carbonic anhydrase isoforms I and II. J Enzym Inhib Med Chem 2016. [Epub ahead of print]. doi:10.3109/14756366.2015.1134524.
  • Aday B, Sola P, Colak F, Kaya M. Synthesis of novel sulfonamide analogs containing sulfamerazine/sulfaguanidine and their biological activities. J Enzym Inhib Med Chem 2015. [Epub ahead of print]. doi:10.3109/14756366.2015.1079183.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.