Chemical modifications and transformations of 3-azahetarylchroman-4-ones

Natalia Gorbulenko, Tatyana Shokol, Vladimir Khilya

Abstract


Articles reporting on the chemical modifications and transformations of 3-azahetarylchroman-4-ones are rewieved. The following 3-azahetarylchroman-4-ones’ transformation - reduction of 3-azahetarylchromon-4-ones to the corresponding 3-azahetarylchromanols, -chromenes, and -3,4-dihydrochromenes, alkylation of 3-azahetarylchromanols, reconversion into 3-azahetarylchromones, formation of 3-hetarylchroman-4-one oximes and corresponding oxime ethers, recyclization into 3-aryl-4-hetarylpyrazolines are described. The biological activity of 3-azahetarylchroman-4-one modification or transformation products are also adduced.

Keywords


chromones; hydrogenated chromone derivatives; 3-azahetarylchromones; 3-azahetarylchroman-4-ones; chromanone oxime; chromanone oxime ether; chromanone hydrazone; pyrazoline; conformationally constrained analogs of drugs; antifungal activity

Full Text:

PDF

References


Semeniuchenko V, Groth U, Khilya V. Synthesis of chroman-4-ones by Reduction of Chromones. Current Organic Synthesis 2010;7(3):276-309. https://doi.org/10.2174/157017910791163002

Emami S, Ghanbarimasir Z. Recent advances of chroman-4-one derivatives: Synthetic approaches and bioactivities. European Journal of Medicinal Chemistry 2015;93:539-563. https://doi.org/10.1016/j.ejmech.2015.02.048

Gorbulenko NV, Shokol TV, Khilya VP. Fr. Ukr. J. Chem. 2015;3(1):4

Feit P, Forshell G, Jackman L, Sparrow D. 3-Piperidino-Chromanone-(4).. Acta Chem. Scand. 1964;18:2401-2403. https://doi.org/10.3891/acta.chem.scand.18-2401

Cozzi P, Mongelli N, Pillan A. Imidazolyl derivatives of the chroman ring. 1 . Journal of Heterocyclic Chemistry 1984;21(2):311-315. https://doi.org/10.1002/jhet.5570210208

Cozzi P, Branzoli U, Lovisolo P, Orsini G, Carganico G, Pillan A, Chiari A. N-Imidazolyl-4-chromanones, N-imidazolyl-1-tetralones, and their alcohols as hypolipemic agents raising high-density lipoproteins. J. Med. Chem. 1986;29(3):404-410. https://doi.org/10.1021/jm00153a016

Cozzi P, Mongelli N, Pillan A, Bergamachi M, Lovizolo PP. Farmitalia Carle Erba SpA. US Patent 4342775 (1982)

Cozzi P, Carganico G, Pillan A, Branzoli U, Farmitalia Carle Erba SpA. DE Patent 3324069 (1984).

Cozzi P, Carganico G, Severino D, Lovizolo PP, Chiari A, Farmitalia Carlo Erba SRL. WO 8908646 Patent (1989).

Fancelli D, Chiari A, Cozzi P, Lovisolo P, Severino D, Ghiselli G. Imidazolylbenzopyrane Derivatives: A New Class Of Acyl-CoA: Cholesterol Acyltranferase (ACAT) Inhibitors. Journal of Enzyme Inhibition 1994;8(3):159-172. https://doi.org/10.3109/14756369409020198

Chugai Seiyaku Kabashihi Kaisha, US Patent 6645951 (2003).

Relly GE, Heaton A, Faragalla J, Bremner J. Novogen Research PTY LTD. WO Patent 2004/039793 (2004).

Kopczachi P, Wosko M, Walczak J, Walczynski K. Polfarmex SA. WO Patent 2015/047113 (2015).

Lauter JC, Zhihua S, Fiordeliso J. US Patent 2006/40917 (2006).

Byrnes E, Bartlett K, Perfect J, Heitman J. Cryptococcus gattii: an emerging fungal pathogen infecting humans and animals. Microbes and Infection 2011;13(11):895-907. https://doi.org/10.1016/j.micinf.2011.05.009

Ji H, Zhang W, Zhou Y, Zhang M, Zhu J, Song Y, Lü J, Zhu J. A Three-Dimensional Model of Lanosterol 14α-Demethylase of Candida albicans and Its Interaction with Azole Antifungals . J. Med. Chem. 2000;43(13):2493-2505. https://doi.org/10.1021/jm990589g

Rossello A, Bertini S, Lapucci A, Macchia M, Martinelli A, Rapposelli S, Herreros E, Macchia B. Synthesis, Antifungal Activity, and Molecular Modeling Studies of New Inverted Oxime Ethers of Oxiconazole. J. Med. Chem. 2002;45(22):4903-4912. https://doi.org/10.1021/jm020980t

Rossi R, Carpita A, Pazzi P, Mannina L, Valensin D. A novel method for the efficient synthesis of methyl 2-oxo-2-arylacetates and its application to the preparation of fungicidal methyl (E)-O-methyloximino-2-arylacetates and their (Z)-stereoisomers. Tetrahedron 1999;55(37):11343-11364. https://doi.org/10.1016/s0040-4020(99)00632-8

Tuncçbilek M, Bozdagˇ O, Ayhan-Kılcıgil G, Altanlar N, Buyukbingol E, Ertan R. Synthesis and Antimicrobial Activity of Some New Flavonyl Oxime Ether Derivatives. Arzneimittelforschung 2011;49(10):853-857. https://doi.org/10.1055/s-0031-1300514

Rane D, Fishman A, Pike R. A New Application of Mannich Bases. Synthesis 1984;1984(08):694-695. https://doi.org/10.1055/s-1984-30938

Grigg R, Liu A, Shaw D, Suganthan S, Woodall D, Yoganathan G. Synthesis of quinol-4-ones and chroman-4-ones via a palladium-catalysed cascade carbonylation–allene insertion. Tetrahedron Letters 2000;41(36):7125-7128. https://doi.org/10.1016/s0040-4039(00)01176-x

Shafiee A, Emami S. Stereoselective Syntheses of (E)- and (Z)-2,3-Dihydro-3-(1,2,4-triazolyl)-4H-1-benzopyran-4-one Oxime Ethers. HETEROCYCLES 2001;55(11):2059. https://doi.org/10.3987/com-01-9301

Emami S, Falahati M, Banifatemi A, Amanlou M, Shafiee A. (E)- and (Z)-1,2,4-Triazolylchromanone oxime ethers as conformationally constrained antifungals. Bioorganic & Medicinal Chemistry 2004;12(15):3971-3976. https://doi.org/10.1016/j.bmc.2004.06.010

Emami S, Falahati M, Banifatemi A, Moshiri K, Shafiee A. Stereoselective Synthesis and in Vitro Antifungal Evaluation of (E)- and (Z)-Imidazolylchromanone Oxime Ethers. Arch. Pharm. Pharm. Med. Chem. 2002;335(7):318-324. https://doi.org/10.1002/1521-4184(200209)335:7<318::aid-ardp318>3.0.co;2-o

Emami S, Falahati M, Banifatemi A, Shafiee A. Stereoselective synthesis and antifungal activity of (Z)-trans-3-azolyl-2-methylchromanone oxime ethers. Bioorganic & Medicinal Chemistry 2004;12(22):5881-5889. https://doi.org/10.1016/j.bmc.2004.08.030

Emami S, Shafiee A. Synthesis, stereochemical and conformational properties of trans-2,3-dihydro-2-methyl-3-(1,2,4-triazolyl)-4H-1-benzopyran-4-one oxime ethers. Tetrahedron 2005;61(10):2649-2654. https://doi.org/10.1016/j.tet.2005.01.054

Ji H, Zhang W, Zhang M, Kudo M, Aoyama Y, Yoshida Y, Sheng C, Song Y, Yang S, Zhou Y, Lü J, Zhu J. Structure-Based de Novo Design, Synthesis, and Biological Evaluation of Non-Azole Inhibitors Specific for Lanosterol 14α-Demethylase of Fungi. J. Med. Chem. 2003;46(4):474-485. https://doi.org/10.1021/jm020362c

Emami S, Banipoulad T, Irannejad H, Foroumadi A, Falahati M, Ashrafi-Khozani M, Sharifynia S. Imidazolylchromanones containing alkyl side chain as lanosterol 14α-demethylase inhibitors: synthesis, antifungal activity and docking study. Journal of Enzyme Inhibition and Medicinal Chemistry 2013;29(2):263-271. https://doi.org/10.3109/14756366.2013.776554

Parsons JH, Leach SE, Percival AN, Buss AD, Green DE, Uellor M. Schering Agrochemicals Limited, EP Patent 0247760 (1987).

Emami S, Shojapour S, Faramarzi M, Samadi N, Irannejad H. Synthesis, in vitro antifungal activity and in silico study of 3-(1,2,4-triazol-1-yl)flavanones. European Journal of Medicinal Chemistry 2013;66:480-488. https://doi.org/10.1016/j.ejmech.2013.06.008

Emami S, Foroumadi A. 3-Imidazolyl-Substituted Flavans as Potential Antifungal Agents: Synthesis, Stereochemical Properties, and Antifungal Activity. Arch. Pharm. Chem. Life Sci. 2009;342(9):541-545. https://doi.org/10.1002/ardp.200900024

Emami S, Behdad M, Foroumadi A, Falahati M, Lotfali E, Sharifynia S. Design of Conformationally Constrained Azole Antifungals: Efficient Synthesis and Antifungal Activity of trans -3-Imidazolylflavanones . Chemical Biology & Drug Design 2009;73(4):388-395. https://doi.org/10.1111/j.1747-0285.2009.00797.x

Babazadeh-Qazijahani M, Badali H, Irannejad H, Afsarian M, Emami S. Imidazolylchromanones containing non-benzylic oxime ethers: Synthesis and molecular modeling study of new azole antifungals selective against Cryptococcus gattii. European Journal of Medicinal Chemistry 2014;76:264-273. https://doi.org/10.1016/j.ejmech.2014.02.019

Emami S, Kebriaeezadeh A, Zamani M, Shafiee A. Azolylchromans as a novel scaffold for anticonvulsant activity. Bioorganic & Medicinal Chemistry Letters 2006;16(7):1803-1806. https://doi.org/10.1016/j.bmcl.2006.01.004

Kebriaeezadeh A, Emami S, Ebrahimi M, Sharifzadeh M, Khorasani R, Shafiee A. Anticonvulsant and antiepileptogenic effects of azolylchromanones on lithium–pilocarpine induced seizures and pentylenetetrazole-kindling model of epilepsy. Biomedicine & Pharmacotherapy 2008;62(4):208-211. https://doi.org/10.1016/j.biopha.2007.12.003

Emami S, Kebriaeezadeh A, Ahangar N, Khorasani R. Imidazolylchromanone oxime ethers as potential anticonvulsant agents: Anticonvulsive evaluation in PTZ-kindling model of epilepsy and SAR study. Bioorganic & Medicinal Chemistry Letters 2011;21(2):655-659. https://doi.org/10.1016/j.bmcl.2010.12.021

Ayati A, Falahati M, Irannejad H, Emami S. Synthesis, in vitro antifungal evaluation and in silico study of 3-azolyl-4-chromanone phenylhydrazones. DARU Journal of Pharmaceutical Sciences 2012;20(1):46. https://doi.org/10.1186/2008-2231-20-46

Kállay F, Janzsó G, Koczor I. The reactions of flavanone with substituted hydrazines. Tetrahedron 1967;23(11):4317-4321. https://doi.org/10.1016/s0040-4020(01)88830-x

Léavai A. Synthesis of 2-pyrazolines by the reactions of α,β-unsaturated aldehydes, ketones, and esters with diazoalkanes, nitrile imines, and hydrazines. Journal of Heterocyclic Chemistry 2002;39(1):1-13. https://doi.org/10.1002/jhet.5570390101

Foroumadi A, Ghodsi S, Emami S, Najjari S, Samadi N, Faramarzi M, Beikmohammadi L, Shirazi F, Shafiee A. Synthesis and antibacterial activity of new fluoroquinolones containing a substituted N-(phenethyl)piperazine moiety. Bioorganic & Medicinal Chemistry Letters 2006;16(13):3499-3503. https://doi.org/10.1016/j.bmcl.2006.03.103

Foroumadi A, Emami S, Mansouri S, Javidnia A, Saeid-Adeli N, Shirazi F, Shafiee A. Synthesis and antibacterial activity of levofloxacin derivatives with certain bulky residues on piperazine ring. European Journal of Medicinal Chemistry 2007;42(7):985-992. https://doi.org/10.1016/j.ejmech.2006.12.034

Emami S, Foroumadi A, Samadi N, Faramarzi M, Rajabalian S. Conformationally Constrained Analogs of N -Substituted Piperazinylquinolones: Synthesis and Antibacterial Activity of N -(2,3-Dihydro-4-hydroxyimino-4 H -1-benzopyran-3-yl)-piperazinylquinolones . Arch. Pharm. Chem. Life Sci. 2009;342(7):405-411. https://doi.org/10.1002/ardp.200800182

Xie F, Zhao H, Zhao L, Lou L, Hu Y. Synthesis and biological evaluation of novel 2,4,5-substituted pyrimidine derivatives for anticancer activity. Bioorganic & Medicinal Chemistry Letters 2009;19(1):275-278. https://doi.org/10.1016/j.bmcl.2008.09.067

Hoshino Y, Miyaura N, Suzuki A. Novel synthesis of isoflavones by the palladium-catalyzed cross-coupling reaction of 3-bromochromones with arylboronic acids or its esters.. Bulletin of the Chemical Society of Japan 1988;61(8):3008-3010. https://doi.org/10.1246/bcsj.61.3008

Amari G, Armani E, Civeli M, Delcanale M, Galbiati E. CHIESI FARMACEUTICI SpA, EP Patent 1229036 (2002).

Bonfield K, Amato E, Bankemper T, Agard H, Steller J, Keeler J, Roy D, McCallum A, Paula S, Ma L. Development of a new class of aromatase inhibitors: Design, synthesis and inhibitory activity of 3-phenylchroman-4-one (isoflavanone) derivatives. Bioorganic & Medicinal Chemistry 2012;20(8):2603-2613. https://doi.org/10.1016/j.bmc.2012.02.042

Amato E, Bankemper T, Kidney R, Do T, Onate A, Thowfeik F, Merino E, Paula S, Ma L. Investigation of fluorinated and bifunctionalized 3-phenylchroman-4-one (isoflavanone) aromatase inhibitors. Bioorganic & Medicinal Chemistry 2014;22(1):126-134. https://doi.org/10.1016/j.bmc.2013.11.045

Cozzi P, Pillan A. Imidazolyl derivatives of the chroman ring 3. Journal of Heterocyclic Chemistry 2009;23(6):1693-1696. https://doi.org/10.1002/jhet.5570230618




DOI: https://doi.org/10.17721/fujcV4I2P1-27

Refbacks

  • There are currently no refbacks.


Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.

ISSN 2312-3222 (Online)

Creative Commons License
 French-Ukrainian Journal of Chemistry is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.

Copyright (c) 2013 French-Ukrainian Journal of Chemistry