Isoflavonoids Modified with Azole Heterocycles with Three Heteroatoms

Authors

  • Natalia Gorbulenko
  • Tetyana Shokol
  • Volodymyr Khilya

DOI:

https://doi.org/10.17721/fujcV10I1P101-127

Keywords:

3-oxadiazolylchromones, 3-thiadiazolylchromones, 3-dithiazolylchromones, 3-triazolylchromones

Abstract

Heterocycle modified chromones are attracting increasing attention as novel potential therapeutic agents due to their effective bioactivities and low toxicity. This review describes all strategies and versatile synthons that have been developed for the synthesis of isoflavone heterocyclic analogs containing isolated 5-member heterocyclic rings with three identical or different heteroatoms. Their biological activity is also presented.

References

Keri R, Budagumpi S, Pai R, Balakrishna R. Chromones as a privileged scaffold in drug discovery: A review. European Journal of Medicinal Chemistry 2014;78:340-374. https://doi.org/10.1016/j.ejmech.2014.03.047

Gaspar A, Matos M, Garrido J, Uriarte E, Borges F. Chromone: A Valid Scaffold in Medicinal Chemistry. Chemical Reviews 2014;114(9):4960-4992. https://doi.org/10.1021/cr400265z

Gorbulenko NV, Khilya VP. Synthesis and biological properties of isoflavonoids modified with nitrogen-containing heterocycles. Ukr. Chem. Journal. 1994;60(1):79-91.

Parsons JH, Hunt RG, Leach SE, Perci A, Buss AD, GreenDE, Mellor M, inventor; Waldman RD et al Schering Agrochemicals Limited Industrial Property Department Chesterford Park assignee. Benzoheterocyclic fungicides. EP 0247760 A2. 1987 02.12 (Bulletin 87/49).

Wang W, Zhang S, Wang J, Wu F, Wang T, Xu G. Bioactivity-Guided Synthesis Accelerates the Discovery of 3-(Iso)quinolinyl-4-chromenones as Potent Fungicide Candidates. Journal of Agricultural and Food Chemistry 2020;69(1):491-500. https://doi.org/10.1021/acs.jafc.0c06700

Lohar S, Dhara K, Roy P, Sinha Babu S, Chattopadhyay P. Highly Sensitive Ratiometric Chemosensor and Biomarker for Cyanide Ions in the Aqueous Medium. ACS Omega 2018;3(8):10145-10153. https://doi.org/10.1021/acsomega.8b01035

Gronowitz S, Ekman R. Synthetic estrogenic isoflavonoids. 1. Synthesis of 3-(2’-thienyl)-5,7-dihydroxychromone. Arkiv. Kemi. 1960;17(9):93-96

Nohara A, Kuriki H, Saijo T, Sugihara H, Kanno M, Sanno Y. Studies on antianaphylactic agents. 5. Synthesis of 3-(1H-tetrazol-5-yl)chromones, a new series of antiallergic substances. Journal of Medicinal Chemistry 1977;20(1):141-145. https://doi.org/10.1021/jm00211a030

Tsao L, Van V, Sun G, Lyu Y. . Russian Journal of General Chemistry 2001;71(5):767-769. https://doi.org/10.1023/a:1012369621168

Cao L, Wang W. Synthesis of 3-(5-Aryl-1,3,4-oxadiazol-2-yl)chromones. Chemistry of Heterocyclic Compounds 2003;39(8):1072-1075. https://doi.org/10.1023/b:cohc.0000003526.98678.6e

Ibrahim M, Ali T, El-Kazak A, Mohamed A. Studies on the Chemical Reactivity of 6,8-dibromo-7-hydroxychromone-3-carboxaldehyde Towards Some Nitrogen Nucleophilic Reagents. Journal of Heterocyclic Chemistry 2014;52(3):815-826. https://doi.org/10.1002/jhet.2195

Rachakonda V, Alla M, Kotipalli S, Ummani R. Design, diversity-oriented synthesis and structure activity relationship studies of quinolinyl heterocycles as antimycobacterial agents. European Journal of Medicinal Chemistry 2013;70:536-547. https://doi.org/10.1016/j.ejmech.2013.10.034

Kim B, Ahn S, Koh D, Cho S, Song Y, Sung J, Lim Y. 1H and 13C NMR characterization of 1,3,4-oxadiazole derivatives. Magnetic Resonance in Chemistry 2018;56(8):782-791. https://doi.org/10.1002/mrc.4718

Lim Yong-ho inventor; UNIV KONKUK IND COOP CORP current patent assignee. 1,3,4-Oxadiazole derivative, a method for producing the same, and an anticancer drug containing the same KR 101937587 B1, 2019, 01.10.

Tu Q, Song F, Zhang H, Zhang H, Ye H, Xiong D, Tu Y, Wang G X, Tan S, Miao Z, inventors; JIANGXI SCIENCE & TECHNOLOGY NORMAL UNIVERSITY, assignee. Chromone oxadiazole compound as well as preparation method and application thereof. CN113563321 A, 2021, 10. 29.

Shin S, Yoo M, Koh D. Crystal structure of 6-methoxy-3-(5-(3-methoxyphenyl)-1,3,4-oxadiazol-2-yl)-4H-chromen-4-one-methanol (1/1), C20H18N2O6. Zeitschrift für Kristallographie - New Crystal Structures 2020;235(5):1253-1255. https://doi.org/10.1515/ncrs-2020-0298

Tsao L, Chzhan L, Lyu T. Synthesis of 3-(3′-Acetyl-5′-aroyl-1′,3′,4′-oxadiazolyl-2′)-chromones. Chemistry of Natural Compounds 2001;37(4):311-314. https://doi.org/10.1023/a:1013754030975

Cao L, Zhang L, Liu J. Synthesis of 3-(3-Acetyl-5-aryl-2,3-dihydro-1,3,4-oxadiazol-2-yl)chromones. Chemistry of Heterocyclic Compounds 2004;40(2):214-218. https://doi.org/10.1023/b:cohc.0000027895.56561.7a

Song F, Zhang H, Zhang H, Ye H, Tu Q, Xiong D, Tu Y, Wang X, Tan S, Miao Z, inventors; Jiangxi Science and Technology Normal Universityity, current assignee. Chromone bis-oxadiazoline compound and preparation method and application thereof CN 113416185 A 2021-09-21.

Ling-Hua C, Yu- JL, Huang T, Sun GZ. Microwave irradiation promoted synthesis of 3-(3'-acety-5'-aryl-1', 3', 4'-dihydrooxadiazol-2'-yl)chromones. Jingyong Huaxue. 2001;18(4):312-314.

Kaspentakis G, Tsoleridis C, Stephanidou-Stephanatou J. Reaction of 3-formylchromone-N-benzoylhydrazone with ketenes. Synthesis and structural studies of chromone 1,3,4-oxadiazolines. Journal of Heterocyclic Chemistry 2007;44(2):425-430. https://doi.org/10.1002/jhet.5570440223

Kuram M, Kim W, Myung K, Hong S. Copper-Catalyzed Direct Synthesis of 1,2,4-Oxadiazoles from Amides and Organic Nitriles by Oxidative N-O Bond Formation. European Journal of Organic Chemistry 2015;2016(3):438-442. https://doi.org/10.1002/ejoc.201501502

Baruah A, Prajapati D, Sandhu J. Studies in chromone derivatives: cycloaddition reactions of 4-oxo 4h-1-benzopyran-3-carboxaldehyde imines with benzonitrile oxide and nitrilimine of 4-oxo-4h-1-benzopyran-3-carboxaldehyde with alkenes. Tetrahedron 1988;44(4):1241-1246. https://doi.org/10.1016/s0040-4020(01)85904-4

Anderson ED, Aronow SD, Boyles NA, Dahlgren MK, Feng S, Gerasyuto AI, et all, inventors; PETRA PHARMA CORPORATION, current patent assignee. Allosteric chromenone inhibitors of phosphoinositide 3-kinase (PI3K) for the treatment of diseases associated with P13K modulation. WO2021/202964 A1, 2021 07.10. Patent Family Members: WO2021/202964 A1; TW2022/567 A.

Kaviarasan L, Gowramma B, Kalirajan R, Mevithra M, Chandralekha S. Molecular docking studies and synthesis of a new class of chroman-4-one fused 1,3,4-thiadiazole derivatives and evaluation for their anticancer potential. Journal of the Iranian Chemical Society 2020;17(8):2083-2094. https://doi.org/10.1007/s13738-020-01913-2

Ali T, Abdel-Aziz S, El-Shaaer H, Hanafy F, El-Fauomy A. Synthesis of Bioactive 4-Oxo-4H-Chromenes Bearing Heterocyclic Systems from Hydrazonecarbodithioic Acid and Thiocarbohydrazone. Phosphorus, Sulfur, and Silicon and the Related Elements 2008;183(9):2139-2160. https://doi.org/10.1080/10426500701851291

Bari A. A Facile Route to Synthesize 1,2-Dihydropyridine and 1,6 Pyrimidinone Analogues from 4-Oxo-4H-Chromene-3-Carbaldehyde. Journal of Heterocyclic Chemistry 2015;53(2):461-466. https://doi.org/10.1002/jhet.2311

Myannik K, Yarovenko V, Beloglazkina E, Moiseeva A, Krayushkin M. Novel copper(II), cobalt(II) and nickel(II) complexes with 5-(4-oxo-4H-chromen-3-yl)-4,5-dihydro-1,3,4-thiadiazole-2-carboxamide: Synthesis, structure, spectroscopic studies. Polyhedron 2018;139:208-214. https://doi.org/10.1016/j.poly.2017.10.027

Shokol T, Semenyuchenko V, Khilya V. 2-R-6-ethyl-7-hydroxy-3-(5-phenyl-1,3,4-thiadiazolyl-2)chromones. Chemistry of Heterocyclic Compounds 2004;40(12):1588-1594. https://doi.org/10.1007/s10593-005-0102-y

Pivovarenko V, Khilya V. Acetoformic anhydride in the synthesis of chromones. 1. Synthesis of 3-hetarylchromones. Chemistry of Heterocyclic Compounds 1991;27(5):496-501. https://doi.org/10.1007/bf00473991

Raj T, Ishar M, Gupta V, Pannu A, Kanwal P, Singh G. Unusual conversion of substituted-3-formylchromones to 3-(5-phenyl-3H-[1,2,4]dithiazol-3-yl)chromen-4-ones: a facile and efficient route to novel 1,2,4-dithiazoles. Tetrahedron Letters 2008;49(2):243-246. https://doi.org/10.1016/j.tetlet.2007.11.081

Raj T, Bhatia R, Sharma R, Gupta V, Sharma D, Ishar M. Mechanism of unusual formation of 3-(5-phenyl-3H-[1,2,4]dithiazol-3-yl)chromen-4-ones and 4-oxo-4H-chromene-3-carbothioic acid N-phenylamides and their antimicrobial evaluation. European Journal of Medicinal Chemistry 2009;44(8):3209-3216. https://doi.org/10.1016/j.ejmech.2009.03.030

Raj T, Bhatia R, kapur A, Sharma M, Saxena A, Ishar M. Cytotoxic activity of 3-(5-phenyl-3 H -[1,2,4]dithiazol-3-yl)chromen-4-ones and 4-oxo-4 H -chromene-3-carbothioic acid N -phenylamides. European Journal of Medicinal Chemistry 2010;45(2):790-794. https://doi.org/10.1016/j.ejmech.2009.11.001

Aggarwal N, Sharma V, Kaur H, Ishar M. Synthesis and Evaluation of Some Novel Chromone Based Dithiazoles as Antimicrobial Agents. International Journal of Medicinal Chemistry 2013;2013:1-6. https://doi.org/10.1155/2013/815453

Sharma SK, Kumar S, Chand K, Kathuria A, Gupta A, Jain R. An Update on Natural Occurrence and Biological Activity of Chromones. Current Medicinal Chemistry 2011;18(25):3825-3852. https://doi.org/10.2174/092986711803414359

Baruah A, Prajapati D, Sandhu J. Studies on chromone derivatives. Novel 1,3 dipolar cycloadditions of 4-oxo-1-benzopyran-3-carbaldehyde imines and imine oxides. Journal of the Chemical Society, Perkin Transactions 1 1987;(9):1995-1998. https://doi.org/10.1039/p19870001995

Watanabe K, Saito T, Niimura K, inventor; Kureha Chemical Industry Co., Ltd., assignee. Chromone compounds, pharmaceutical compositions containing the same, and use of the same. United States patent 5698575A. 1997. 16 Dec.

Akram M, Bera S, Patil N. A facile strategy for accessing 3-alkynylchromones through gold-catalyzed alkynylation/cyclization of o-hydroxyarylenaminones. Chemical Communications 2016;52(83):12306-12309. https://doi.org/10.1039/c6cc07119h

Rao B, Rao Y. An Efficient and Facile Synthesis of Novel Triazole C-N Linked Chromone Hybrids. Asian Journal of Chemistry 2020;32(7):1806-1808. https://doi.org/10.14233/ajchem.2020.22734

Cao L, Yan X, Liu Y. Synthesis of 3-heterocycle-substituted chromones. He Cheng Huaxue. 1997;5(3):273-276.

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

Shokol T, Turov V, Turov A, Krivokhizha N, Semenyuchenko V, Khilya V. 3-(4-Phenyl-1,2,4-triazol-3-yl)chromones. Chemistry of Heterocyclic Compounds 2005;41(11):1411-1418. https://doi.org/10.1007/s10593-006-0011-8

Khilya VP, Belashova IG, Golubushina GM. Тriazol analogs of isoflavones. Dokl. AN Ukrainian SSR Ser. B 1978;3:257-261.

Kolb HC, Walsh JC, Liang Q, Duclos BA, Zhang W, Scott PJ.h, Chen K, Gao Z, Zhao T, Mocharla VP, Kasi D, Chen G, Wang E, Sinha A, Xia C, Padgett HC, Karimi F, inventors; Eli Lilly and Company Indianapolis, assignee. Novel imaging agents for detecting neurological dysfunction. EP 2247558 B1. 2022 02. 02 (Bulletin 2022/05).

Kolb HC, Walsh JC, Liang Q, Duclos BA, Zhang W, Scott PJ.h, Chen K, Gao Z, Zhao T, Mocharla VP, Kasi D, Chen G, Wang E, Sinha A, Xia C, Padgett HC, Karimi F, inventors; ELI LILLY & CO, current patent assignee, Novel imaging agents for detecting neurological dysfunction. WO 2009/102498 A 1. 2009 20. 08. Patent Family Members: CA2715390 A1; EP2247558 A1; EP2599763 A1; JP2011/512354 A; KR2010/135235 A.

Shokol T, Semenyuchenko V, Khilya V. 5-Phenyl-2-(pyrazol-4-yl)-1,3,4-thiadiazoles. Chemistry of Heterocyclic Compounds 2005;41(5):673-678. https://doi.org/10.1007/s10593-005-0201-9

Gorbulenko N, Tkachuk T, Shokol T, Semeniuchenko V, Turov A, Khilya V. 2-[6-Alkyl-3-hetaryl-4-oxo-9,10-dihydro-4H,8H-chromeno-[8,7-e][1,3]oxazin-9-yl]acetic acids. Chemistry of Heterocyclic Compounds 2007;43(5):569-575. https://doi.org/10.1007/s10593-007-0091-0

Shokol T, Gorbulenko N, Khilya V. Modifications of 7-hydroxy-3-(5-phenyl-1,3,4-thiadiazol-2-yl)-6-ethylchromone. Taras Shevchenko National University of Kyiv Chem. Bull. 2016;1(52):68-70.

Shokol T, Turov V, Semeniuchenko V, Krivokhizha N, Khilya V. Recyclization of 7-hydroxy-3-(4-phenyl-1,2,4-triazol-3-yl)-chromones using binucleophiles. Chemistry of Heterocyclic Compounds 2006;42(4):500-505. https://doi.org/10.1007/s10593-006-0117-z

Shokol T, Lozinskii O, Turov A, Khilya V. Synthesis of 9-azolyl-3-(4-phenyl-4h-1,2,4-triazol-3-yl)-4h,8h-pyrano-[2,3-f]chromene-4,8-diones. Chemistry of Heterocyclic Compounds 2009;45(9):1089-1094. https://doi.org/10.1007/s10593-009-0402-8

Shokol T, Semenyuchenko V, Shilin S, Turov A, Ogorodniichuk A, Khilya V. Amino-Acid and Dipeptide Derivatives of 2-(6-ethyl-4-oxo-3-(4-phenyl-4H-1,2,4-triazol-3-yl)-4H-chromen-7-yloxy)acetic Acid. Chemistry of Natural Compounds 2005;41(5):533-538. https://doi.org/10.1007/s10600-005-0199-3

Semeniuchenko V, Garazd Y, Garazd M, Shokol T, Groth U, Khilya V. Highly efficient glucosylation of flavonoids. Monatshefte für Chemie - Chemical Monthly 2009;140(12):1503-1512. https://doi.org/10.1007/s00706-009-0207-6

Downloads

Published

2022-07-14

Issue

Section

Review