Advancements in tetronic acid chemistry. Part 2: Use as a simple precursor to privileged heterocyclic motifs
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Dabiri M, Tisseh ZN, Bahramnejad M, Bazgir A (2011) Sonochemical multi-component synthesis of spirooxindoles. Ultrason Sonochem 18:1153–1159. doi: 10.1016/j.ultsonch.2010.12.004
Baba A, Oda T, Taketomi S, Notoya K, Nishimura A, Makino H, Sohda T (1999) Studies on disease-modifying antirheumatic drugs. III. Bone resorption inhibitory effects of ethyl 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-(1,2,4-triazol-1-ylmethyl)quinoline-3-carboxylate (TAK-603) and related compounds. Chem Pharm Bull 47:369–374. doi: 10.1248/cpb.47.369
Skrastin’sh IP, Vitolinya RO, Kastron VV, Avakumova GM, Dubur GY (1992) Cardiovascular activity of difuropyridines. Pharm Chem J 26:416–418. http://link.springer.com/article/10.1007%2FBF00772904
Iida A, Kano M, Kubota Y, Koga K, Tomioka K (1997) Targeting DNA topoisomerase II with podophyllotoxin aza-analogue. Bioorg Med Chem Lett 7:2565–2566. doi: 10.1016/S0960-894X(97)10029-4
Hehn JP, Gamba-Sánchez D, Kemmler M, Fleck M, Basler B, Bach T (2010) [2+2]-Photocycloaddition reactions of tetronic acid esters and amides. Synthesis 2308–2312: doi: 10.1055/s-0029-1218793
Bourdreux Y, Bodio E, Willis C, Billaud C, Gall TL, Mioskowski C (2008) Synthesis of vulpinic and pulvinic acids from tetronic acid. Tetrahedron 64:8930–8937. doi: 10.1016/j.tet.2008.06.058
Kozlov NG, Bondarev SL, Kadutskii AP, Basalaeva LI, Pashkovskii FS (2008) Tetronic acid in reaction with aromatic aldehydes and 2-naphthylamine. Investigation of fluorescent and nonlinear-optical characteristics of compounds obtained. Russ J Org Chem 44:1031–1037. doi: 10.1134/S1070428008070142
Kadutskii AP, Kozlov NG, Pashkovskii FS (2009) Synthesis of benzo[ $$f$$ f ]quinoline derivatives by three-component condensation of tetronic acid with naphthalen-2-amine and formaldehyde. Russ J Org Chem 45:399–403. doi: 10.1134/S1070428009030087
Shaabani A, Soleimani E, Sarvary A, Rezayan AH (2008) A simple and efficient approach to the synthesis of 4H-furo[3,4-b]pyrans via a three-component reaction of isocyanides. Bioorg Med Chem Lett 18:3968–3970. doi: 10.1016/j.bmcl.2008.06.014
Shaabani A, Sarvary A, Keshipour S, Rezayan AH, Ghadari R (2010) Unexpected Knoevenagel self-condensation reaction of tetronic acid: synthesis of a new class of organic heterocyclic salts. Tetrahedron 66:1911–1914. doi: 10.1016/j.tet.2010.01.009
Abdou MM, El-Saeed RA, Bondock S (2015) Recent advances in 4-hydroxycoumarin chemistry. Part 1: Synthesis and reactions. Arab J Chem. doi: 10.1016/j.arabjc.2015.06.012
Abdou MM, El-Saeed RA, Bondock S (2015) Recent advances in 4-hydroxycoumarin chemistry. Part 2: Scaffolds for heterocycle molecular diversity. Arab J Chem. doi: 10.1016/j.arabjc.2015.06.029
Abdou MM (2014) 3-Acetyl-4-hydroxycoumarin: Synthesis, reactions and applications. Arab J Chem. doi: 10.1016/j.arabjc.2014.04.005
Abdou MM (2014) Chemistry of 4-Hydroxy-2(1H)-quinolone. Part 1: Synthesis and reactions. Arab J Chem. doi: 10.1016/j.arabjc.2014.01.012
Abdou MM (2014) Chemistry of 4-hydroxy-2(1H)-quinolone. Part 2. As synthons in heterocyclic synthesis. Arab J Chem. doi: 10.1016/j.arabjc.2015.06.012
Abdou MM (2014) Utility of 4-hydroxythiocoumarin in organic synthesis. Arab J Chem. doi: 10.1016/j.arabjc.2014.06.002
Metwally MA, Bondock S, El-Desouky EI, Abdou MM (2013) A facile synthesis, tautomeric structure of novel 4-arylhydrazono-3-(2-hydroxyphenyl)-2-pyrazolin-5-ones and their application as disperse dyes. Color Technol 129:418–424. doi: 10.1111/cote.12052
Metwally MA, Bondock S, El-Desouky EI, Abdou MM (2012) A worthy insight into the dyeing applications of azo pyrazolyl dyes. Int J Modern Org Chem 1:165–192
Metwally MA, Bondock S, El-Desouky EI, Abdou MM (2012) Pyrazol-5-ones: tautomerism, synthesis and reactions. Int J Modern Org Chem 1:19–54
Metwally MA, Bondock S, El-Desouky EI, Abdou MM (2012) Synthesis, structure investigation and dyeing assessment of novel bisazo disperse dyes derived from 3-(2-hydroxyphenyl)-1-phenyl-2-pyrazolin-5-ones for dyeing polyester fabrics. J Korean Chem Soc 56:348–356. doi: 10.5012/jkcs.2012.56.3.348
Metwally MA, Bondock S, El-Desouky EI, Abdou MM (2012) Synthesis, structure elucidation and application of some new azo disperse dyes derived from 4-hydroxycoumarin for dyeing polyester fabrics. Am J Chem 2:347–354. doi: 10.5923/j.chemistry.20120206.09
Metwally MA, Bondock S, El-Desouky EI, Abdou MM (2012) Synthesis, tautomeric structure, dyeing characteristics, and antimicrobial activity of novel 4-(2-arylazophenyl)-3-(2-hydroxyphenyl)-1-phenyl-2-pyrazolin-5-ones. J Korean Chem Soc 56:82–91. doi: 10.5012/jkcs.2012.56.1.082
Metwally MA, Bondock S, El-Desouky EI, Abdou MM (2013) Synthesis, spectroscopic studies and technical evaluation of novel disazo disperse dyes derived from 3-(2-hydroxyphenyl)-2-pyrazolin-5-ones for dyeing polyester fabrics. Am J Chem 3:59–67. doi: 10.5923/j.chemistry.20130303.04
Abdou MM, El-Saeed RA, Abozeid MA, Elattar KM, Zaki EG, Barakat Y, Ibrahim V, Fathy M, Amine M, Bondock S (2015) Advancements in tetronic acid chemistry. Part 1: Synthesis and reactions. Arab J Chem. doi: 10.1016/j.arabjc.2015.11.004
Shaabani A, Amini MM, Ghasemi S, Ghadari R, Rezayan AH, Fazaeli Y, Feizi S (2010) Pyridine-functionalized MCM-41 as an efficient and recoverable catalyst for the synthesis of Pyran annulated heterocyclic systems. Chem Pharm Bull 58:270–272. doi: 10.1248/cpb.58.270
Babakhani N, Keshipoor S (2013) TiO $$_{2}$$ 2 and TiO $$_{2}$$ 2 nanoparticles as efficient and recoverable catalysts for the synthesis of pyran annulated heterocyclic systems. Res Chem Intermed 39:2401–2406. doi: 10.1007/s11164-012-0766-8
Damavandi S, Sandaroos R, Mohammadi A (2013) Ultrasonic-assisted Cu-catalyzed multicomponent synthesis of furo[3,4-b]pyrazolo[4,3-f]quinolinones. Heterocycl Commun 19:105–108. doi: 10.1515/hc-2011-0086
Peng J-H, Jia R-H, Ma N, Zhang G, Wu F-Y, Cheng C, Tu S-J (2013) A facile and expeditious microwave-assisted synthesis of furo[3,4-b]indeno[2,1-f]quinolin-1-one derivatives via multicomponent reaction. J Heterocycl Chem 50:899–902. doi: 10.1002/jhet.965
Shi D-Q, Yao H (2009) Facile and clean synthesis of furopyridine derivatives via three-component reaction in aqueous media without catalyst. Synth Commun 39:2481–2491. doi: 10.1080/00397910802656034
Tu S-J, Zhang Y, Jiang H, Jiang B, Zhang J-Y, Jia R-H, Shi F (2007) A simple synthesis of furo[3 $$\prime $$ ′ ,4 $$\prime $$ ′ :5,6]pyrido[2,3-d]pyrimidine derivatives through multicomponent reactions in water. Eur J Org Chem 9:1522–1528. doi: 10.1002/ejoc.200600913
Wang S-L, Cheng C, Wu F-Y, Jiang B, Shi F, Tu S-J, Rajale T, Li G (2011) Microwave-assisted multi-component reaction in water leading to highly regioselective formation of benzo[f]azulen-1-ones. Tetrahedron 67:4485–4493. doi: 10.1016/j.tet.2011.05.002
Wang SL, Cheng C, Wu F-Y, Li J, Jiang B (2011) An efficient three-component tandem reaction leading to pentacyclic isoindole-fused Benzo[b,e][1,4]diazepines in water. Chem Lett 40:834–836. doi: 10.1246/cl.2011.834
Shaker RM, Mahmoud AF, Abdel-Latif FF (2005) Facile one pot microwave assisted solvent-free synthesis of novel spiro-fused pyran derivatives via the three-component condensation of ninhydrin with malononitrile and active methylene compounds. J Chin Chem Soc 52:563–567. doi: 10.1002/jccs.200500083
Li Y, Chen H, Shi C, Shi D, Ji S (2010) Efficient one-pot synthesis of spirooxindole derivatives catalyzed by l-proline in aqueous medium. J Comb Chem 12:231–237. doi: 10.1021/cc9001185
Wu Q, Feng H, Guo D-D, Yi M-S, Wang X-H, Jiang B, Tu S-J (2013) Microwave-assisted aqueous multicomponent reaction: facile synthesis of polyfunctionalized indoline-spiro fused pyran derivatives. J Heterocycl Chem 50:599–602. doi: 10.1002/jhet.1537
Han C, Zhang T, Zhang A, Wang D, Shi W, Tao J (2014) Efficient catalyst-free one-pot three-component synthesis of novel spirooxindole derivatives, and their cytotoxic activities. Synthesis 1389–1398: doi: 10.1055/s-0033-1341028
Dabiri M, Tisseh ZN, Nobahar M, Bazgir A (2011) Organic reaction in water: a highly efficient and environmentally friendly synthesis of spiro compounds catalyzed by L-proline. Helv Chim Acta 94:824–830. doi: 10.1002/hlca.201000307
Chen H, Shi D (2010) Efficient one-pot synthesis of novel spirooxindole derivatives via three-component reaction in aqueous medium. J Comb Chem 12:571–576. doi: 10.1021/cc100056p
Tratrat C, Giorgi-Renault S, Husson HP (2002) A multicomponent reaction for the one-pot synthesis of 4-Aza-2,3-didehydropodophyllotoxin and derivatives. Org Lett 4:3187–3189. doi: 10.1021/ol0200908
Tu S, Zhang Y, Zhang J, Jiang B, Jia R, Zhang J, Ji S (2006) A Simple procedure for the synthesis of 4-Aza-podophyllotoxin Derivatives in water under microwave irradiation conditions. Synlett 2785–2790: doi: 10.1055/s-2006-950279
Tu S, Zhang Y, Jiang B, Jia R, Zhang J, Zhang J, Ji S (2006) One-pot synthesis of N-substituted azapodophyllotoxin derivatives under microwave irradiation. Synthesis 3874–3882: doi: 10.1055/s-2006-950297
Tu S, Zhang Y, Jia R, Jiang B, Zhang J, Ji S (2006) A multi-component reaction for the synthesis of N-substituted furo[3,4-b]quinoline derivatives under microwave irradiation. Tetrahedron Lett 47:6521–6525. doi: 10.1016/j.tetlet.2006.07.035
Shi C-L, Chen H, Shi D (2012) An efficient one-pot three-component synthesis of tetrahydrofuro[3,4-b]quinoline-1,8(3H,4H)-dione derivatives catalyzed by L-proline. J Heterocycl Chem 49:125–129. doi: 10.1002/jhet.782
Shi F, Ma N, Zhang Y, Zhang G, Jiang B, Tu SJ (2010) Unexpected and green synthesis of azapodophyllotoxin derivatives via microwave-assisted multicomponent reactions in ammonia water. Synth Commun 40:235–241. doi: 10.1080/00397910902964825
Shi F, Zeng X-N, Zhang G, Ma N, Jiang B, Tu S (2011) Facile synthesis of new 4-aza-podophyllotoxin analogs via microwave-assisted multi-component reactions and evaluation of their cytotoxic activity. Bioorg Med Chem Lett 21:7119–7123. doi: 10.1016/j.bmcl.2011.09.082
Kumar A, Alegria AE (2010) Synthesis of novel functionalized 4-aza-2,3-didehydropodophyllotoxin derivatives with potential antitumor activity. J Heterocycl Chem 47:1275–1282. doi: 10.1002/jhet.467
Andreoli M, Persico M, Kumar A, Orteca N, Kumar V, Pepe A, Mahalingam S, Alegria AE, Petrella L, Sevciunaite L, Camperchioli A (2014) Identification of the first inhibitor of the GBP1:PIM1 interaction. implications for the development of a new class of anticancer agents against paclitaxel resistant cancer cells. J Med Chem 57:7916–7932. doi: 10.1021/jm5009902
Magedov IV, Manpadi M, van Slambrouck S, Steelant WFA, Rozhkova E, Przheval’skii NM, Rogelj S, Kornienko A (2007) Discovery and investigation of antiproliferative and apoptosis-inducing properties of new heterocyclic podophyllotoxin analogues accessible by a one-step multicomponent synthesis. J Med Chem 50:5183–5192. doi: 10.1021/jm070528f
Magedov IV, Manpadi M, Rozhkova E, Przheval’skii NM, Rogelj S, Shors ST, Steelant WFA, Van slambrouck S, Kornienko A (2007) Structural simplification of bioactive natural products with multicomponent synthesis: dihydropyridopyrazole analogues of podophyllotoxin. Bioorg Med Chem Lett 17:1381–1385. doi: 10.1016/j.bmcl.2006.11.095
Magedov IV, Frolova L, Manpadi M, Bhoga UD, Tang H, Evdokimov NM, George O, Hadje GK, Renner S, Getlik M, Kinnibrugh TL (2011) Anticancer properties of an important drug lead podophyllotoxin can be efficiently mimicked by diverse heterocyclic scaffolds accessible via one-step synthesis. J Med Chem 54:4234–4246. doi: 10.1021/jm200410r
Semenova MN, Kiselyov AS, Tsyganov DV, Konyushkin LD, Firgang SI, Semenov RV, Malyshev OR, Raihstat MM, Fuchs F (2011) A stielow and m lantow, polyalkoxybenzenes from plants. 5. parsley seed extract in synthesis of azapodophyllotoxins featuring strong tubulin destabilizing activity in the sea urchin embryo and cell culture assays. J Med Chem 54:7138–7149. doi: 10.1021/jm200737s
Shi D-Q, Yang F, Ni S-N (2009) A facile synthesis of furo[3,4-e]pyrazolo[3,4-b]pyridine-5(7H)-one derivatives via three-component reaction in ionic liquid without any catalyst. J Heterocycl Chem 46:469–476. doi: 10.1002/jhet.103
Shi C-L, Shi D-Q, Kim SH, Huang Z-B, Ji S-J, Ji M (2008) A novel and efficient one-pot synthesis of furo[3 $$\prime $$ ′ ,4 $$\prime $$ ′ :5,6]pyrido[2,3-c]pyrazole derivatives using organocatalysts. Tetrahedron 64:2425–2432. doi: 10.1016/j.tet.2007.12.053
Shi D-Q, Yao H (2009) Clean synthesis of furo[3,4-e]pyrazolo[3,4-b]pyridine-5-one derivatives in aqueous media. J Heterocycl Chem 46:1335–1338. doi: 10.1002/jhet.224
Shi F, Wang Q, Tu S, Zhou J, Jiang B, Li C, Zhou D, Shao Q, Cao L (2008) A green and efficient synthesis of furo[3,4-e]pyrazolo[3,4-b]-pyridine derivatives in water under microwave irradiation without catalyst. J Heterocycl Chem 45:1103–1108. doi: 10.1002/jhet.5570450425
Shirvan SA, Khazali F, Dezfuli SH, Borsalani A (2014) An efficient method for the one-pot, four-component benzaldehyde based synthesis of 3-methyl-1,4-diphenyl-7,8-dihydro-1H-furo[3,4-e]pyrazolo[3,4-b]pyridin-5(4H)-ones catalyzed by alum in environment-friendly media. Oriental J Chem 30:279–284
Shi F, Zhou D, Tu S, Shao Q, Li C, Cao L (2008) An efficient microwave-assisted synthesis furo[3,4-b]-[4,7]phenanthroline and indeno[2,1-b][4,7]phenanthroline derivatives in water. J Heterocycl Chem 45:1065–1070. doi: 10.1002/jhet.5570450418
Kamal A, Reddy TS, Polepalli S, Paidakula S, Srinivasulu V, Reddy VG, Jain N, Shankaraiah N (2014) Synthesis and biological evaluation of 4-aza-2,3-dihydropyridophenanthrolines as tubulin polymerization inhibitors. Bioorg Med Chem Lett 24:3356–3360. doi: 10.1016/j.bmcl.2014.05.096
Kamal A, Tamboli JR, Nayak VL, Adil SF, Vishnuvardhan MVPS, Ramakrishna S (2014) Synthesis of a terphenyl substituted 4-aza-2,3-didehydropodophyllotoxin analogues as inhibitors of tubulin polymerization and apoptosis inducers. Bioorg Med Chem 22:2714–2723. doi: 10.1016/j.bmc.2014.03.021
Kamal A, Suresh P, Mallareddy A, Kumar BA, Reddy PV, Raju P, Tamboli JR, Shaik TB, Jain N, Kalivendi SV (2011) Synthesis of a new 4-aza-2,3-didehydropodophyllotoxin analogues as potent cytotoxic and antimitotic agents. Bioorg Med Chem 19:2349–2358. doi: 10.1016/j.bmc.2011.02.020
Wang X-H, Hao W-J, Tu S-J, Zhang X-H, Cao X-D, Yan S, Wu S-S, Han Z-G, Shi F (2009) Microwave-assisted multicomponent reaction for the synthesis of new and significative bisfunctional compounds containing two furo[3,4-b]quinoline and acridinedione skeletons. J Heterocyl Chem 46:742–747. doi: 10.1002/jhet.143
Phuong DT, Ma C-M, Hattori M, Jin JS (2009) Inhibitory effects of antrodins A–E from Antrodia cinnamomea and their metabolites on hepatitis C virus protease. Phytother Res 23:582–584. doi: 10.1002/ptr.2657
Wu M-D, Cheng M-J, Wang B-C, Yech Y-J, Lai J-T, Kuo Y-H, Yuan G-F, Chen I-S (2008) Maleimide and maleic anhydride derivatives from the mycelia of Antrodia cinnamomea and their nitric oxide inhibitory activities in macrophages. J Nat Prod 71:1258–1261. doi: 10.1021/np070634k
Chien S-C, Chen M-L, Kuo H-T, Tsai Y-C, Lin B-F, Kuo Y-H (2008) Anti-inflammatory activities of new succinic and maleic derivatives from the fruiting body of Antrodia camphorata. J Agric Food Chem 56:7017–7022. doi: 10.1021/jf801171x
Wen C-L, Chang C-C, Huang S-S, Kuo C-L, Hsu S-L, Deng J-S, Huang G-J (2011) Anti-inflammatory effects of methanol extract of Antrodia cinnamomea mycelia both in vitro and in vivo. J Ethnopharmacol 137:575–584. doi: 10.1016/j.jep.2011.06.009
Boukouvalas J, Albert V, Loach RP, Lafleur-Lambert R (2012) Unified route to asymmetrically substituted butenolide, maleic anhydride, and maleimide constituents of Antrodia camphorata. Tetrahedron 68:9592–9597. doi: 10.1016/j.tet.2012.09.064
Ortega MJ, Zubıìa E, Ocaña JM, Naranjo S, Salvá J (2000) New Rubrolides from the Ascidian Synoicum blochmanni. Tetrahedron 56:3963–3967. doi: 10.1016/S0040-4020(00)00328-8
Manzanaro S, Salva J, de la Fuente JA (2006) Phenolic marine natural products as aldose reductase inhibitors. J Nat Prod 69:1485–1487. doi: 10.1021/np300580z
Boukouvalas J, McCann LC (2010) Synthesis of the human aldose reductase inhibitor rubrolide L. Tetrahedron Lett 51:4636–4639. doi: 10.1016/j.tetlet.2010.06.129
Kuang H, Yang B, Xia Y, Feng W (2008) Chemical constituents from the flower of datura metel L. Arch Pharm Res 31:1094–1097. doi: 10.1007/s12272-001-1274-6
Kim KH, Noh HJ, Choi SC, Park KM, Seok S-J, Lee KR (2010) Lactarane sesquiterpenoids from Lactarius subvellereus and their cytotoxicity. Bioorg Med Chem Lett 20:5385–5388. doi: 10.1016/j.bmcl.2010.07.119
Hosoe T, Gloer JB, Wicklow DT, Raja HA, Shearer CA (2010) New nonadride analogues from a freshwater isolate of an undescribed fungus belonging to the order pleosporales. Heterocycles 81:2123–2130. doi: 10.3987/COM-10-12009
Lin Y-C, Fazary AE, Shen Y-C (2010) Cespitulins A-D, novel diterpenoids from Taiwanese Cespitularia taeniata. Tetrahedron Lett 51:6654–6657. doi: 10.1016/j.tetlet.2010.10.057
Fujimoto H, Asai T, Kim Y-P, Ishibashi M (2006) Nine constituents including six xanthone-related compounds isolated from two ascomycetes, gelasinospora santi-florii and Emericella quadrilineata, found in a screening study focused on immunomodulatory activity. Chem Pharm Bull 54:550–553. doi: 10.1248/cpb.54.550
Xu Y-J, Tang C-P, Tan M-J, Ke C-Q, Wu T, Ye Y (2010) Sesquiterpenoids and diterpenoids from chloranthus anhuiensis. Chem Biodivers 7:151–157. doi: 10.1002/cbdv.200800300