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Design, synthesis, and biological evaluation of potent quinoline and pyrroloquinoline ammosamide analogues as inhibitors of quinone reductase 2.

Reddy PV, Jensen KC, Mesecar AD, Fanwick PE, Cushman M
J Med Chem 55 367-77 (2012)
Cited: 14 times
EuropePMC logo PMID: 22206487

Abstract

A variety of ammosamide B analogues have been synthesized and evaluated as inhibitors of quinone reductase 2 (QR2). The potencies of the resulting series of QR2 inhibitors range from 4.1 to 25,200 nM. The data provide insight into the structural parameters necessary for QR2 inhibitory activity. The natural product ammosamide B proved to be a potent QR2 inhibitor, and the potencies of the analogues generally decreased as their structures became more distinct from that of ammosamide B. Methylation of the 8-amino group of ammosamide B was an exception, resulting in an increase in quinone reductase 2 inhibitory activity from an IC(50) of 61 nM to IC(50) 4.1 nM.

Reviews citing this publication (4)

  1. Recent advances in deep-sea natural products. Skropeta D, Wei L. Nat Prod Rep 31 999-1025 (2014)
  2. Quinone reductase 2 as a promising target of melatonin therapeutic actions. Boutin JA. Expert Opin Ther Targets 20 303-317 (2016)
  3. Mechanism of Action of Ribosomally Synthesized and Post-Translationally Modified Peptides. Ongpipattanakul C, Desormeaux EK, DiCaprio A, van der Donk WA, Mitchell DA, Nair SK. Chem Rev 122 14722-14814 (2022)
  4. A look around the West Indies: The spices of life are secondary metabolites. Demeritte A, Wuest WM. Bioorg Med Chem 28 115792 (2020)

Articles citing this publication (10)

  1. Identification and Optimization of the First Highly Selective GLUT1 Inhibitor BAY-876. Siebeneicher H, Cleve A, Rehwinkel H, Neuhaus R, Heisler I, Müller T, Bauser M, Buchmann B. ChemMedChem 11 2261-2271 (2016)
  2. Precursor-Directed Generation of Amidine Containing Ammosamide Analogs: Ammosamides E-P. Pan E, Oswald NW, Legako AG, Life JM, Posner BA, Macmillan JB. Chem Sci 4 482-488 (2013)
  3. A tandem Friedel-Crafts based method for the construction of a tricyclic pyrroloquinoline skeleton and its application in the synthesis of ammosamide B. Takayama Y, Yamada T, Tatekabe S, Nagasawa K. Chem Commun (Camb) 49 6519-6521 (2013)
  4. The melatonin analog 5-MCA-NAT increases endogenous dopamine levels by binding NRH:quinone reductase enzyme in the developing chick retina. Sampaio Lde F, Mesquita FP, de Sousa PR, Silva JL, Alves CN. Int J Dev Neurosci 38 119-126 (2014)
  5. S29434, a Quinone Reductase 2 Inhibitor: Main Biochemical and Cellular Characterization. Boutin JA, Bouillaud F, Janda E, Gacsalyi I, Guillaumet G, Hirsch EC, Kane DA, Nepveu F, Reybier K, Dupuis P, Bertrand M, Chhour M, Le Diguarher T, Antoine M, Brebner K, Da Costa H, Ducrot P, Giganti A, Goswami V, Guedouari H, Michel PP, Patel A, Paysant J, Stojko J, Viaud-Massuard MC, Ferry G. Mol Pharmacol 95 269-285 (2019)
  6. Role of Quinone Reductase 2 in the Antimalarial Properties of Indolone-Type Derivatives. Cassagnes LE, Rakotoarivelo N, Sirigu S, Pério P, Najahi E, Chavas LM, Thompson A, Gayon R, Ferry G, Boutin JA, Valentin A, Reybier K, Nepveu F. Molecules 22 E210 (2017)
  7. Discovery of ammosesters by mining the Streptomyces uncialis DCA2648 genome revealing new insight into ammosamide biosynthesis. Luo J, Yang D, Hindra, Adhikari A, Dong LB, Ye F, Yan X, Rader C, Shen B. J Ind Microbiol Biotechnol 48 kuab027 (2021)
  8. Synthesis of novel МТ3 receptor ligands via an unusual Knoevenagel condensation. Volkova MS, Jensen KC, Lozinskaya NA, Sosonyuk SE, Proskurnina MV, Mesecar AD, Zefirov NS. Bioorg Med Chem Lett 22 7578-7581 (2012)
  9. 3-Arylidene-2-oxindoles as Potent NRH:Quinone Oxidoreductase 2 Inhibitors. Lozinskaya NA, Bezsonova EN, Dubar M, Melekhina DD, Bazanov DR, Bunev AS, Grigor'eva OB, Klochkov VG, Sokolova EV, Babkov DA, Spasov AA, Sosonyuk SE. Molecules 28 1174 (2023)
  10. Practical, scalable, and transition metal-free visible light-induced heteroarylation route to substituted oxindoles. Majhi J, Granados A, Matsuo B, Ciccone V, Dhungana RK, Sharique M, Molander GA. Chem Sci 14 897-902 (2023)


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