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Mini-Reviews in Organic Chemistry

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ISSN (Print): 1570-193X
ISSN (Online): 1875-6298

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Review Article

The Synthesis and Use of BMS 204352 (MaxiPostTM)

Author(s): Renato Dalpozzo*

Volume 17, Issue 1, 2020

Page: [67 - 73] Pages: 7

DOI: 10.2174/1570193X16666181228100254

Price: $65

Abstract

MaxiPostTM is an interesting 3-fluorooxindole derivative, discovered in the late nineties of the last century as potassium channel opener. Since then, two different research fields were discovered: the discovery of new synthetic methods, especially asymmetric ones, and the in vitro and in vivo tests for its use as a drug for different diseases. This mini-review aims to summarize the state of art in both fields.

Keywords: Asymmetric synthesis, BMS204352, fluoroindoles, K-channel, MaxiPost, stroke.

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Graphical Abstract

[1]
(a)Hewawasam, P.; Meanwell, N.A.; Gribkoff, V.K. 3-Substituted oxindole derivatives as potassium channel modulators U.S. Patent 5,565,483, October 15, 1996;.
(b)Hewawasam, P.; Meanwell, N. A.; Gribkoff, V.K. 3-Substituted oxindole derivatives as potassium channel modulators. US. Patent 5,602,169A, February 11, 1997.
[2]
Mackay, K.B. BMS-204352 (Bristol Myers Squibb). Curr. Opin. Investig. Drugs, 2001, 2(6), 820-823.
[PMID: 11572663]
[3]
Hewawasam, P.; Gribkoff, V.K.; Dworetzky, S.I.; Ortiz, A.A.; Kinney, G.G.; Boissard, C.G.; Post-Munson, D.J.; Trojnacki, J.T.; Huston, K.; Signor, L.G.; Lombardo, L.A.; Reid, S.A.; Hibbard, J. R.; Myers, R.A.; Moon, S.L.; Wiener, H.L.; Thalody, G.; Yeleswaram, K.; Pajor, L.M.; Knipe, J.O.; Meanwell, N.A.; Johnson, G.; Molinoff, P.B.; Starrett, J.E., Jr; Gao, Q. Discovery of openers of large conductance, calcium activated potassium (maxi-K) channels: A new approach to stroke neuroprotection. Abstr. Pap. Am. Chem. S, 2000, 219, 320-MEDI, Part, 2.
[4]
(a)Nosova, E.V.; Lipunova, G.N.; Charushin, V.N.; Chupakhin, O.N. Fluorine-containing indoles: Synthesis and biological activity. J. Fluor. Chem., 2018, 212, 51-106.
[http://dx.doi.org/10.1016/j.jfluchem.2018.05.012]
(b)Dalpozzo, R. Catalytic asymmetric synthesis of hetero-substituted oxindoles. Org. Chem. Front., 2017, 4, 2063-2078.
(c)Dalpozzo, R.; Bartoli, G.; Bencivenni, G. Recent advances in organocatalytic methods for the synthesis of disubstituted 2-and 3-indolinones. Chem. Soc. Rev., 2012, 41, 7247-7290.
[http://dx.doi.org/10.1039/c2cs35100e] [PMID: 22899437]
[5]
Hewawasam, P.; Gribkoff, V.K.; Pendri, Y.; Dworetzky, S.I.; Meanwell, N.A.; Martinez, E. Boissard, C.G.; Post-Munson, D.J.; Trojnacki, J.T.; Yeleswaram, K.; Pajor, L.M.; Knipe, J.; Gao, Q.; Perrone, R.; Starrett, J.E. Jr. The synthesis and characterization of BMS-204352 (MaxiPosttm) and related 3-fluorooxindoles as openers of Maxi-K Potassium Channels. Bioorg. Med. Chem. Lett., 2002, 12, 1023-1026.
[http://dx.doi.org/10.1016/S0960-894X(02)00101-4] [PMID: 11909708]
[6]
(a)Kiesewetter, D.O.; Jagoda, E.M.; Starrett, J.E., Jr; Gribkoff, V.K.; Hewawasam, P.; Srinivas, N.; Salazar, D.; Eckelman, W.C. Radiochemical synthesis and biodistribution of a novel maxi-K potassium channel opener. Nucl. Med. Biol., 2002, 29(1), 55-59.
[http://dx.doi.org/10.1016/S0969-8051(01)00281-5] [PMID: 11786276]
(b)Dischino, D.D.; Dulac, H.A.; Gillman, K.V.; Keller, L.S.; Kozlowski, E.S.; Marcin, L.R.; Mongillo, J.J.; Starrett, J.E., Jr Microwave-assisted synthesis and chiral HPLC separation of 18F-labeled MaxiPostTM. An agent for post-stroke neuroprotection. J. Labelled Comp. Radiopharm., 2003, 46, 1161-1171.
[http://dx.doi.org/10.1002/jlcr.748]
[7]
Dischino, D.D.; Gribkoff, V.K.; Hewawasam, P.; Luke, G.M.; Rinehart, J.K.; Spears, T.L.; Starrett, J.E., Jr Synthesis of 3H and 14C labeled (S)-3-(5-chloro-2-methoxyphenyl)-1,3-dihydro-3-flu-oro-6-(trifluoromethyl)-2H-indol-2-one, MaxiPosttm. An agent for post-stroke neuroprotection. J. Labelled Comp. Radiopharm., 2003, 46, 139-149.
[http://dx.doi.org/10.1002/jlcr.652]
[8]
Mizuta, S.; Otaki, H.; Kitagawa, A.; Kitamura, K.; Morii, Y.; Ishihara, J.; Nishi, K.; Hashimoto, R.; Usui, T.; Chiba, K. Ionic liquid-mediated hydrofluorination of O-azaxylylenes derived from 3-bromooxindoles. Org. Lett., 2017, 19(10), 2572-2575.
[http://dx.doi.org/10.1021/acs.orglett.7b00887] [PMID: 28453283]
[9]
Shibata, N.; Ishimaru, T.; Suzuki, E.; Kirk, K.L. Enantioselective fluorination mediated by N-fluoroammonium salts of cinchona alkaloids: First enantioselective synthesis of BMS-204352 (MaxiPost). J. Org. Chem., 2003, 68(6), 2494-2497.
[http://dx.doi.org/10.1021/jo026792s] [PMID: 12636425]
[10]
Zoute, L.; Audouard, C.; Plaquevent, J-C.; Cahard, D. Enantioselective synthesis of BMS-204352 (MaxiPost) using N-fluoroammonium salts of cinchona alkaloids (F-CA-BF4). Org. Biomol. Chem., 2003, 1(11), 1833-1834.
[http://dx.doi.org/10.1039/B303113F] [PMID: 12945759]
[11]
Zhu, C-L.; Maeno, M.; Zhang, F-G.; Shigehiro, T.; Kagawa, T.; Kawada, K.; Shibata, N.; Ma, J-A.; Cahard, D. Chiral N-fluorodibenzenesulfonimide analogues for enantioselective electrophilic fluorination and oxidative fluorination. Eur. J. Org. Chem., 2013, 2013(29), 6501-6505.
[http://dx.doi.org/10.1002/ejoc.201300956]
[12]
Shibata, N.; Kohno, J.; Takai, K.; Ishimaru, T.; Nakamura, S.; Toru, T.; Kanemasa, S. Highly enantioselective catalytic fluorination and chlorination reactions of carbonyl compounds capable of two-point binding. Angew. Chem. Int. Ed. Engl., 2005, 44(27), 4204-4207.
[http://dx.doi.org/10.1002/anie.200501041] [PMID: 15942966]
[13]
Deng, Q-H.; Wadepohl, H.; Gade, L.H. The synthesis of a new class of chiral pincer ligands and their applications in enantioselective catalytic fluorinations and the Nozaki-Hiyama-Kishi reaction. Chemistry, 2011, 17(52), 14922-14928.
[http://dx.doi.org/10.1002/chem.201102375] [PMID: 22052847]
[14]
Hamashima, Y.; Suzuki, T.; Takano, H.; Shimura, Y.; Sodeoka, M. Direct generation of nucleophilic chiral palladium enolate from 1,3-dicarbonyl compounds: Catalytic enantioselective michael reaction with enones. J. Am. Chem. Soc., 2005, 127, 10164-10165.
[http://dx.doi.org/10.1021/ja0513077] [PMID: 16028916]
[15]
Hamashima, Y. Acid-base catalysis of chiral Pd complexes: Development of novel catalytic asymmetric reactions and their application to synthesis of drug candidates. Chem. Pharm. Bull. (Tokyo), 2006, 54(10), 1351-1364.
[http://dx.doi.org/10.1248/cpb.54.1351] [PMID: 17015970]
[16]
Hamashima, Y.; Sodeoka, M. Catalytic enantioselective a-fluorination of carbonyl compounds using chiral transition metal complexes. J. Synth. Org. Chem. Jpn., 2007, 65, 1099-1107.
[http://dx.doi.org/10.5059/yukigoseikyokaishi.65.1099]
[17]
Li, J.; Cai, Y.; Chen, W.; Liu, X.; Lin, L.; Feng, X. Highly enantioselective fluorination of unprotected 3-substituted oxindoles: one-step synthesis of BMS 204352 (MaxiPost). J. Org. Chem., 2012, 77(20), 9148-9155.
[http://dx.doi.org/10.1021/jo301705t] [PMID: 23030737]
[18]
Frantz, S.W.; Srinivas, N.; Dominick, M.; Kelly, W.; Sanderson, T.; Schilling, B. Safety assessment of BMS-204352, a novel therapeutic agent for the treatment of stroke. Eur. J. Neurol., 2000, 7(Suppl. 3), 3017.
[19]
Gribkoff, V.K.; Starrett, J.E., Jr; Dworetzky, S.I.; Hewawasam, P.; Boissard, C.G.; Cook, D.A.; Frantz, S.W.; Heman, K.; Hibbard, J.R.; Huston, K.; Johnson, G.; Krishnan, B.S.; Kinney, G.G.; Lombardo, L.A.; Meanwell, N.A.; Molinoff, P.B.; Myers, R.A.; Moon, S.L.; Ortiz, A.; Pajor, L.; Pieschl, R.L.; Post-Munson, D.J.; Signor, L.J.; Srinivas, N.; Taber, M.T.; Thalody, G.; Trojnacki, J.T.; Wiener, H.; Yeleswaram, K.; Yeola, S.W. Targeting acute ischemic stroke with a calcium-sensitive opener of maxi-K potassium channels. Nat. Med., 2001, 7(4), 471-477.
[http://dx.doi.org/10.1038/86546] [PMID: 11283675]
[20]
Krishna, R.; Yao, M.; Kaczor, D.; Vachharajani, N.; Srinivas, N.R. In vitro protein binding studies with BMS-204352: Lack of protein binding displacement interaction in human serum. Biopharm. Drug Dispos., 2001, 22(1), 41-44.
[http://dx.doi.org/10.1002/bdd.269] [PMID: 11745906]
[21]
Krishna, R.; Shah, V.R.; Mantha, S.; Vachharajani, N.N.; Srinivas, N. Pharmacokinetics and dose proportionality of BMS-204352 after intravenous administration to dogs. Biopharm. Drug Dispos., 2002, 23(2), 83-86.
[http://dx.doi.org/10.1002/bdd.294] [PMID: 11932963]
[22]
Krishna, R.; Palme, H.; Zeng, J.; Srinivas, N. Effect of dose and input rate on the brain penetration of BMS-204352 following intravenous administration to rats. Biopharm. Drug Dispos., 2002, 23(6), 227-231.
[http://dx.doi.org/10.1002/bdd.317] [PMID: 12214322]
[23]
Krishna, R.; Shah, V.R.; Srinivas, N. Pharmacokinetics and dose proportionality of BMS-204352 after intraarterial administration to rats. Biopharm. Drug Dispos., 2002, 23(6), 233-237.
[http://dx.doi.org/10.1002/bdd.318] [PMID: 12214323]
[24]
Krishna, R.; Yao, M.; Srinivas, N.R.; Shah, V.; Pursley, J.M.; Arnold, M.; Vachharajani, N.N. Disposition of radiolabeled BMS-204352 in rats and dogs. Biopharm. Drug Dispos., 2002, 23(1), 41-46.
[http://dx.doi.org/10.1002/bdd.292] [PMID: 11891672]
[25]
Zhang, D.; Ogan, M.; Gedamke, R.; Roongta, V.; Dai, R.; Zhu, M.; Rinehart, J.K.; Klunk, L.; Mitroka, J. Protein covalent binding of MaxiPost through a cytochrome P450-mediated ortho-quinone methide intermediate in rats. Drug Metab. Dispos., 2003, 31(7), 837-845.
[http://dx.doi.org/10.1124/dmd.31.7.837] [PMID: 12814959]
[26]
Schrøder, R.L.; Jespersen, T.; Christophersen, P.; Strøbaek, D.; Jensen, B.S.; Olesen, S.P. KCNQ4 channel activation by BMS-204352 and retigabine. Neuropharmacology, 2001, 40(7), 888-898.
[http://dx.doi.org/10.1016/S0028-3908(01)00029-6] [PMID: 11378159]
[27]
Korsgaard, M.P.; Hartz, B.P.; Brown, W.D.; Ahring, P.K.; Strøbaek, D.; Mirza, N.R. Anxiolytic effects of MaxiPost (BMS-204352) and retigabine via activation of neuronal Kv7 channels. J. Pharmacol. Exp. Ther., 2005, 314(1), 282-292.
[http://dx.doi.org/10.1124/jpet.105.083923] [PMID: 15814569]
[28]
Lobarinas, E.; Dalby-Brown, W.; Stolzberg, D.; Mirza, N.R.; Allman, B.L.; Salvi, R. Effects of the potassium ion channel modulators BMS-204352 MaxiPost and its R-enantiomer on salicylate-induced tinnitus in rats. Physiol. Behav., 2011, 104(5), 873-879.
[http://dx.doi.org/10.1016/j.physbeh.2011.05.022] [PMID: 21640740]
[29]
Sheppard, A.M.; Chen, G.D.; Salvi, R. Potassium ion channel openers, MaxiPost and Retigabine, protect against peripheral salicylate ototoxicity in rats. Hear. Res., 2015, 327, 1-8.
[http://dx.doi.org/10.1016/j.heares.2015.04.007] [PMID: 25937133]
[30]
Langguth, B.; Elgoyhen, A.B.; Schlee, W. Potassium channels as promising new targets for pharmacologic treatment of tinnitus: Can Internet-based ‘crowd sensing’ initiated by patients speed up the transition from bench to bedside? Expert Opin. Ther. Targets, 2016, 20(3), 251-254.
[http://dx.doi.org/10.1517/14728222.2016.1125884] [PMID: 26609769]
[31]
Jensen, B.S. BMS-204352: A potassium channel opener developed for the treatment of stroke. CNS Drug Rev., 2002, 8(4), 353-360.
[http://dx.doi.org/10.1111/j.1527-3458.2002.tb00233.x] [PMID: 12481191]

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