Synthesis, structure elucidation and plants growth promoting effects of novel quinolinyl chalcones

dc.AffiliationOctober University for modern sciences and Arts (MSA)
dc.contributor.authorHassan, M.M
dc.contributor.authorAlzandi, A.R.A
dc.contributor.authorHassan, M.M
dc.date.accessioned2020-06-24T08:20:48Z
dc.date.available2020-06-24T08:20:48Z
dc.date.issued5/29/2020
dc.descriptionScopusen_US
dc.description.abstractThe readily synthesized 3-(4-Hydroxy-1-methyl-1,2-dihydro-2-oxoquinolin-3-yl)-1-phenyl-1H-pyrazole-4-carbaldehyd (5) and 3-(2-Oxo-2H-chromen-3-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde (6) were utilized as a convenient starting precursor materials for synthesis of novel enone system 4-hydroxy-1-methyl-3-(4-(2H-2-oxo-chromen-3-yl)prop-2-enoyl)-1-phenyl-1H-pyrazol-4-yl)quinolin-2(1H)-one (7) and4-hydroxy-1-methyl-3-(2E)-3-(3-(2-oxo-2H-chromen-3-yl)-1-phenyl-1H-pyrazol-4-yl)acryloyl)quinolin-2(1H)-one (8). Simple homonuclear NOE experiment (NOESY 1D) method was performed for structure elucidation of the novel quinolinyl chalcones. The synthesized compounds have been estimated for their effect of growth on some selective crop of plants (Hibiscus, Mint and Basilen_US
dc.description.sponsorshipAin Shams Universityen_US
dc.description.urihttps://www.scimagojr.com/journalsearch.php?q=19400158709&tip=sid&clean=0
dc.identifier.citationAbdel-Megid, M., Abass, M., Hassan, M. Substituted quinolinones. Part 13 a convenient route to heterocyclization reactions with 3-substituted 4-hydroxyquinolin-2(1H)-one (2007) Journal of Heterocyclic Chemistry, 44 (2), pp. 315-322. Cited 11 times. http://www3.interscience.wiley.com/journal/121521817/home doi: 10.1002/jhet.5570440206 View at Publisher 2 Akbari, M., Ezati, P., Nazari, M., Kor, M. Physiological and pharmaceutical properties of peppermint as a multipurpose and valuable medicinal plant: A Systematic Review (2015) Bangladesh J. Med. Sci., 4, pp. 413-420. 3 Arslan, D., Özcan, M.M., Mengeş, H.O. Evaluation of drying methods with respect to drying parameters, some nutritional and colour characteristics of peppermint (Mentha x piperita L.) (2010) Energy Conversion and Management, 51 (12), pp. 2769-2775. Cited 74 times. doi: 10.1016/j.enconman.2010.06.013 View at Publisher 4 Bag, S., Ramar, S., Degani, M.S. Synthesis and biological evaluation of α, β-unsaturated ketone as potential antifungal agents (2009) Medicinal Chemistry Research, 18 (4), pp. 309-316. Cited 48 times. doi: 10.1007/s00044-008-9128-x View at Publisher 5 Bandgar, B.P., Patil, S.A., Gacche, R.N., Korbad, B.L., Hote, B.S., Kinkar, S.N., Jalde, S.S. Synthesis and biological evaluation of nitrogen-containing chalcones as possible anti-inflammatory and antioxidant agents (2010) Bioorganic and Medicinal Chemistry Letters, 20 (2), pp. 730-733. Cited 82 times. doi: 10.1016/j.bmcl.2009.11.068 View at Publisher 6 Bhattacharjee, T., Sen, S., Chakraborty, R., Maurya, P.K., Chattopadhyay, A. Cultivation of Medicinal Plants: Special Reference to Important Medicinal Plants of India (2020) Herbal Medicine in India S. Sen R. Chakraborty Springer Singapore 7 Chodankar, N.K., Sequeira, S., Seshadri, S. Synthesis of 3-hetarylcoumarins from 3-acetylcoumarins (1986) Dyes and Pigments, 7 (3), pp. 231-236. Cited 11 times. doi: 10.1016/0143-7208(86)85011-2 View at Publisher 8 Dao, T.T.H., Linthorst, H.J.M., Verpoorte, R. Chalcone synthase and its functions in plant resistance (Open Access) (2011) Phytochemistry Reviews, 10 (3), pp. 397-412. Cited 229 times. doi: 10.1007/s11101-011-9211-7 View at Publisher 9 Doan, N., Tran, D. Synthesis, antioxidant and antimicrobial activities of a novel series of chalcones, pyrazolicchalcones, and allylic chalcones (2011) J. Pharm. Pharmacol., 2, pp. 282-288. Cited 54 times. 10 Dorman, H.J.D., Koşar, M., Kahlos, K., Holm, Y., Hiltunen, R. Antioxidant properties and composition of aqueous extracts from Mentha species, hybrids, varieties, and cultivars (2003) Journal of Agricultural and Food Chemistry, 51 (16), pp. 4563-4569. Cited 419 times. doi: 10.1021/jf034108k View at Publisher 11 Echeverria, C., Santibañez, J.F., Donoso-Tauda, O., Escobar, C.A., Ramirez-Tagle, R. Structural antitumoral activity relationships of synthetic chalcones (Open Access) (2009) International Journal of Molecular Sciences, 10 (1), pp. 221-231. Cited 102 times. http://www.mdpi.com/1422-0067/10/1/221/pdf doi: 10.3390/ijms10010221 View at Publisher 12 Figueroa Pérez, M.G., Rocha-Guzmán, N.E., Mercado-Silva, E., Loarca-Piña, G., Reynoso-Camacho, R. Effect of chemical elicitors on peppermint (Mentha piperita) plants and their impact on the metabolite profile and antioxidant capacity of resulting infusions (2014) Food Chemistry, 156, pp. 273-278. Cited 43 times. doi: 10.1016/j.foodchem.2014.01.101 View at Publisher 13 Hans, R.H., Guantai, E.M., Lategan, C., Smith, P.J., Wan, B., Franzblau, S.G., Gut, J., (...), Chibale, K. Synthesis, antimalarial and antitubercular activity of acetylenic chalcones (2010) Bioorganic and Medicinal Chemistry Letters, 20 (3), pp. 942-944. Cited 113 times. http://www.journals.elsevier.com/bioorganic-and-medicinal-chemistry-letters/ doi: 10.1016/j.bmcl.2009.12.062 View at Publisher 14 Huang, C.-C., Chang, N.-C. New approach to 2-quinolinones (2008) Organic Letters, 10 (4), pp. 673-676. Cited 23 times. doi: 10.1021/ol7030312 View at Publisher 15 Kalambe, N., Maldhure, A., Raghuvanshi, P. Synthesis and study of 2-hydroxy substituted Chalcone dibromide effects on different crop plant growth (2015) Der Pharma Chemica., 7, pp. 279-283. 16 Kappe, T., Aigner, R., Jübstl, M., Hohengassner, P., Stadlbauer, W. Reactions of 3-acyl-4-hydroxy-2(1h)-quinolones with nitrogen bases (1995) Heterocyclic Communications, 1 (5-6), pp. 341-352. Cited 27 times. doi: 10.1515/HC.1995.1.5-6.341 View at Publisher 17 Kim, Y.H., Kim, J., Park, H., Kim, H.P. Anti-inflammatory activity of the synthetic chalcone derivatives: Inhibition of inducible nitric oxide synthase-catalyzed nitric oxide production from lipopolysaccharide-treated RAW 264.7 cells (Open Access) (2007) Biological and Pharmaceutical Bulletin, 30 (8), pp. 1450-1455. Cited 63 times. http://www.jstage.jst.go.jp/article/bpb/30/8/1450/_pdf doi: 10.1248/bpb.30.1450 View at Publisher 18 Vijaya Laxmi, S., Suresh Kuarm, B., Rajitha, B. Synthesis and antimicrobial activity of coumarin pyrazole pyrimidine 2,4,6(1H,3H,5H)triones and thioxopyrimidine4,6(1H,5H)diones (2013) Medicinal Chemistry Research, 22 (2), pp. 768-774. Cited 21 times. doi: 10.1007/s00044-012-0078-y View at Publisher 19 Marotti, M., Piccaglia, R., Giovanelli, E. Differences in Essential Oil Composition of Basil (Ocimum basilicum L.) Italian Cultivars Related to Morphological Characteristics (1996) Journal of Agricultural and Food Chemistry, 44 (12), pp. 3926-3929. Cited 192 times. http://pubs.acs.org/journal/jafcau doi: 10.1021/jf9601067 View at Publisher 20 Modzelewska, A., Pettit, C., Achanta, G., Davidson, N.E., Huang, P., Khan, S.R. Anticancer activities of novel chalcone and bis-chalcone derivatives (2006) Bioorganic and Medicinal Chemistry, 14 (10), pp. 3491-3495. Cited 294 times. doi: 10.1016/j.bmc.2006.01.003 View at Publisher 21 Mogilaiah, K., Swamy, T.K., Chandra, A.V., Srivani, N., Vidya, K. Claisen-Schmidt condensation under solventfree conditions (2010) Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 49 (3), pp. 382-385. Cited 8 times. 22 Mohamed, B., Sulaiman, A., Dahab, A. Roselle (Hibiscus sabdariffa L.) in Sudan, cultivation and their uses (2012) Bull. Environ. Pharmacol. Life Sci., 1, pp. 48-54. Cited 20 times. 23 Puro, K., Sunjukta, R., Samir, S., Ghatak, S., Shakuntala, I., Sen, A. Medicinal uses of Roselle plant (Hibiscus sabdariffa L.): A Mini Review (2014) Indian J. Hill Fmg., 27, pp. 81-90. Cited 13 times. 24 Rozmer, Z., Perjési, P. Naturally occurring chalcones and their biological activities (2016) Phytochemistry Reviews, 15 (1), pp. 87-120. Cited 66 times. doi: 10.1007/s11101-014-9387-8 View at Publisher 25 Sahu, S.K., Mishra, A., Behera, R.K. Synthesis of thiazole, benzothiazole, oxadiazole, thiadiazole, triazole and thiazolidinone incorporated coumarins (1996) Indian Journal of Heterocyclic Chemistry, 6 (2), pp. 91-94. Cited 19 times. 26 Salem, M.S., Hussein, R.A., El-Sayed, W.M. Substitution at phenyl rings of chalcone and schiff base moieties accounts for their antiproliferative activity (2019) Anti-Cancer Agents in Medicinal Chemistry, 19 (5), pp. 620-626. Cited 3 times. http://dx.doi.org/10.2174/1871520619666190225122338 doi: 10.2174/1871520619666190225122338 View at Publisher 27 Schuhmacher, A., Reichling, J., Schnitzler, P. Virucidal effect of peppermint oil on the enveloped viruses herpes simplex virus type 1 and type 2 in vitro (2003) Phytomedicine, 10 (6-7), pp. 504-510. Cited 173 times. www.urbanfischer.de/journals/phytomed doi: 10.1078/094471103322331467 View at Publisher 28 Siddiqui, N., Arshad, M.F., Khan, S.A. Synthesis of some new coumarin incorporated thiazolyl semicarbazones as anticonvulsants (2009) Acta Poloniae Pharmaceutica - Drug Research, 66 (2), pp. 161-167. Cited 70 times. http://www.ptfarm.pl/pub/File/acta_pol_2009/2_2009-03-24/161-167.pdf 29 Singh, K., Ralhan, S., Sharma, P.K., Dhawan, S.N. Vilsmeier-Haack reaction on hydrazones: A convenient synthesis of 4-formylpyrazoles (2005) Journal of Chemical Research, (5), pp. 316-318. Cited 15 times. View at Publisher 30 Solankee, A., Kapadia, K., Ana Ćirić, Soković, M., Doytchinova, I., Geronikaki, A. Synthesis of some new S-triazine based chalcones and their derivatives as potent antimicrobial agents (2010) European Journal of Medicinal Chemistry, 45 (2), pp. 510-518. Cited 84 times. doi: 10.1016/j.ejmech.2009.10.037 View at Publisher 31 Spirtovic-Halilovic, S., Salihović, M., Džudžević-Čančar, H., Trifunović, S., Roca, S., Softić, D., Završnik, D. DFT study and microbiology of some coumarin-based compounds containing a chalcone moiety (Open Access) (2014) Journal of the Serbian Chemical Society, 79 (4), pp. 435-443. Cited 16 times. http://www.shd.org.rs/JSCS/Vol79/No4/JSCS_Vol79_No4.pdf doi: 10.2298/JSC130628077S View at Publisher 32 Stadlbauer, W., Hojas, G. Ring closure reactions of 3-arylhydrazonoalkyl-quinolin-2-ones to 1-aryl-pyrazolo[4,3-c]quinolin-2-ones (2004) Journal of Heterocyclic Chemistry, 41 (5), pp. 681-690. Cited 29 times. http://onlinelibrary.wiley.com/journal/10.1002/(ISSN)1943-5193 doi: 10.1002/jhet.5570410505 View at Publisher 33 Telci, I., Bayram, E., Yilmaz, G., Avci, B. Variability in essential oil composition of Turkish basils (Ocimum basilicum L.) (2006) Biochemical Systematics and Ecology, 34 (6), pp. 489-497. Cited 173 times. doi: 10.1016/j.bse.2006.01.009 View at Publisher 34 Tomita, K.J. The antibacterial properties of compounds containing the tricarbonyl-methane Group.V. the synthesis of 3-acyl-2,4-dijhydroxyquinolines and of the related compounds. With respect to their Antibacterial Properties (1951) Pharm. Soc., Jpn, p. 711100. 35 Venkatachalam, H., Nayak, Y., Jayashree, B. Evaluation of the antioxidant activity of novel synthetic chalcones and flavonols (2012) Int. J. Chem. Eng. Appl., 3, pp. 216-219. Cited 12 times. 36 Vogel, S., Barbic, M., Jürgenliemk, G., Heilmann, J. Synthesis, cytotoxicity, anti-oxidative and anti-inflammatory activity of chalcones and influence of A-ring modifications on the pharmacological effect (2010) European Journal of Medicinal Chemistry, 45 (6), pp. 2206-2213. Cited 113 times. doi: 10.1016/j.ejmech.2010.01.060 View at Publisher 37 Vogel, S., Ohmayer, S., Brunner, G., Heilmann, J. Natural and non-natural prenylated chalcones: Synthesis, cytotoxicity and anti-oxidative activity (2008) Bioorganic and Medicinal Chemistry, 16 (8), pp. 4286-4293. Cited 166 times. doi: 10.1016/j.bmc.2008.02.079 View at Publisher 38 Wang, M.L., Morris, B., Tonnis, B., Davis, J., Pederson, G.A. Assessment of oil content and fatty acid composition variability in two economically important Hibiscus species (2012) Journal of Agricultural and Food Chemistry, 60 (26), pp. 6620-6626. Cited 22 times. doi: 10.1021/jf301654yen_US
dc.identifier.doihttps://doi.org/10.1016/j.arabjc.2020.05.024
dc.identifier.issn18785352
dc.identifier.otherhttps://doi.org/10.1016/j.arabjc.2020.05.024
dc.identifier.urihttps://t.ly/awI0
dc.language.isoen_USen_US
dc.publisherElsevier B.V.en_US
dc.relation.ispartofseriesArabian Journal of Chemistry;2020
dc.subjectPyrazolocarbaldehydesen_US
dc.subjectChalconesen_US
dc.subjectHomonuclearen_US
dc.subjectHibiscusen_US
dc.subjectBasilen_US
dc.titleSynthesis, structure elucidation and plants growth promoting effects of novel quinolinyl chalconesen_US
dc.typeArticleen_US

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