سنتز تک مرحله‌ای هتروسیکل‌های نوین دی‌هیدروکینولون-کومارین در حضور کاتالیست ZnBr2

نوع مقاله : علمی-پژوهشی

نویسندگان

1 گروه شیمی، دانشکده علوم پایه، دانشگاه قم، قم، ایران

2 انستیتو شیمی، دانشگاه روستوک، روستوک، آلمان

چکیده

ترکیب­ های دارای بخش کومارینی و 4،3-دی­هیدروکینولونی، ویژگی­ های زیستی و دارویی متنوعی دارند.  از جمله ویژگی ­های ضد سرطان، ضد بسته شدن رگ­ های خونی و ضد HIV برای آن­ ها گزارش شده است. تهیه مولکول­ های هیبریدی با ترکیب کردن فارماکوفورهای شناخته شده برای توسعه طیف گسترده ای از اسکلت های دارویی نوین که به صورت بالقوه می­ توانند داروهای با ویژگی­ های بهتری باشند، از اهمیت بالایی برخوردار است.در این پژوهش تعدادی از هتروسیکل ­های نوین چهار و پنج حلقه­ ای 4،3-دی هیدروکینولون­ های متصل به تتراهیدروپیرانوکومارین و تتراهیدرو پیرانوآلفا ـ پیرون با واکنش پیاپی ناوناگل هترو دیلز ـ آلدر مشتق­ های N-آکریل آنترانیل آلدهید با 4-هیدروکسی کومارین و آلفا-پیرون (4-هیدروکسی-6-متیل-2H -پیران-2-اون) در حضور 50 درصد مولی ZnBr2 به ­عنوان کاتالیستی ارزان و ملایم در دمای بازروانی حلال استیک اسید در یک مرحله سنتز شدند.همه فراورده­ ها با بازده بسیار خوب و همچنین ناحیه ­گزینی و فضاگزینی درخشان به­ دست آمدند.

کلیدواژه‌ها

موضوعات

مراجع

[1] Murray R.D.H., "Naturally Occurring Plant Coumarins, In Fortschritte der Chemie Organischer Naturstoffe, Progress in the Chemistry of Organic Natural Products", (pp. 83-316), Springer Vienna (1991).
[2] Thornes R.D., O’Kennedy R., Thornes R.D., "Coumarins: Biology, Applications and Mode of Action", Jone Wiley and Sons, Inc., (1997).
[3] Shaabani A., Ghadari R., Rezayan A.H., Synthesis of Functionalized Coumarins, Iran. J. Chem. Chem. Eng. (IJCCE), 30(4): 19-22 (2011).
[4] Maeda M., "Laser Dyes: Properties of Organic Compounds for Dye Lasers", Academic Press (1982).
[5] Kotharkar S.A., Bahekar S.S., Shinde D.B., Chlorosulfonic Acid-Catalysed One-Pot Synthesis of Coumarin, Mendeleev Commun., 16: 241-242 (2006).
[6] Lanoot B., Vancanneyt M., Cleenwerck I., Wang L., Li W., Liu Z., Swings J., The Search for Synonyms Among Streptomycetes by Using SDS-PAGE of Whole-Cell Proteins. Emendation of the Species Streptomyces aurantiacus, Streptomyces Cacaoi Subsp. Cacao, Streptomyces Caeruleus And Streptomyces Violaceus, Int. J. Syst. Evol. Microbial., 52: 823-829 (2002).
[7] Chaturvedula V.S.P., Schilling J.K., Kingston D.G.I., New Cytotoxic Coumarins and Prenylated Benzophenone Derivatives from the Bark of Ochrocarpos Punctatus from the Madagascar Rainforest, J. Nat. Prod. 65: 965-972 (2002).
[8] Flavin M.T., Rizzo J.D., Khilevich A., Kucherenko A., Sheinkman A.K., Vilaychack V., Lin L., Chen W., Greenwood E.M., Pengsuparp T., Pezzuto J.M., Synthesis, Chromatographic Resolution, and Anti-Human Immunodeficiency Virus Activity of (±)-Calanolide A and Its Enantiomers, J. Med. Chem., 39: 1303-1313 (1996). 
[9] Seitz W., Geneste H., Backfisch G., Delzer J., Graef C., Hornberger W., Kling A., Subkowski T., Zimmermann N., Design and Synthesis of Novel Potent and Selective Integrin α v β 3 Antagonists—Novel Synthetic Routes to Isoquinolinone, Benzoxazinone, and Quinazolinone Acetates, Bioorg. Med. Chem. Lett., 18: 527-531 (2008).
[10] Guthrie D.B., Geib S.J., Curran D.P., Synthesis of Highly Enantioenriched 3, 4-dihydroquinolin-2-ones by 6-exo-trig Radical Cyclizations of Axially Chiral α-halo-ortho-alkenyl Anilides, J. Am. Chem. Soc., 131: 15492-15500 (2009).
[11] Wang H., Sun B., Yang J., Wang J., Mao P., Yang L., Mai W., The synthesis of 3, 4-disubstituted Dihydroquinolin-2 (1H)-one under Metal-Free Conditions in Aqueous Solution, J. Chem. Res., 38: 542-545 (2014).
[12] Morita S., Irie Y., Saitoh Y., Kohri H., Evaluation of a New Beta-Adrenergic Blocking Agent, Carteolol, Based on Metabolic Responses in rats—I: Blockade in vivo of Epinephrine- and Isoproterenol-Induced Alterations of Blood Concentrations of Carbohydrate and Lipid Intermediary Metabolites, Biochem. Pharmacol., 25: 1837-1842 (1976).
[13] Nishi T., Tabusa F., Tanaka T., Shimizu T., Kanbe T., Kimura Y., Nakagava K., Studies on 2-Oxoquinoline Derivatives as Blood Platelet Aggregation Inhibitors. II. 6-[3-(1-cyclohexyl- 5-tetrazolyl) propoxy]-1, 2-dihydro-2-oxoquinoline and Related Compounds, Chem. Pharm. Bull., 31: 1151-1157 (1983).
[14] Semba J., Watanabe A., Kito S., Toru M., Behavioural and Neurochemical Effects of OPC-14597, A Novel Antipsychotic Drug, on Dopaminergic Mechanisms in Rat Brain, Neuropharmacology, 34: 785-791 (1995).
[15] Joseph B., Darro F., Béhard A., Lesur B., Collignon F., Decaestecker C., Frydman A., Guillaumet G., Kiss R., 3-Aryl-2-Quinolone Derivatives: Synthesis and Characterization of in Vitro and in Vivo Antitumor Effects with Emphasis on a New Therapeutical Target Connected with Cell Migration, J. Med. Chem., 45: 2543-2555 (2002).
[16] Nishi T., Tabusa F., Tanaka T., Shimizu T., Nakagawa K., Studies on 2-Oxoquinoline Derivatives as Blood Platelet Aggregation Inhibitors. IV. Synthesis and Biological Activity of the Metabolites of 6-[4-(1-cyclohexyl-1H-5-tetrazolyl) butoxy]-2-oxo-1, 2, 3, 4-tetrahydroquinoline (OPC-13013), Chem. Pharm. Bull., 33: 1140-1147 (1985).
[17] Huang L.J., Hsieh M.C., Teng C.M., Lee K.H., Kuo S.C., Synthesis and antiplatelet activity of phenyl quinolones, Biorg. Med. Chem., 6: 1657-1662 (1998).
[18] Suzuki M., Ohuchi Y., Asanuma H., Kaneko T., Yokomori S., Ito C., Isobe Y., Muramatsu M., Synthesis and Evaluation of Novel 2-oxo-1, 2-dihydro-3-quinolinecarboxamide Derivatives as Serotonin 5-HT4 Receptor Agonists, Chem. Pharm. Bull., 48: 2003-2008 (2000).
[19] Li K., Foresee L.N., Tunge J.A., Trifluoroacetic Acid-Mediated Hydroarylation: Synthesis of Dihydrocoumarins and Dihydroquinolones, J. Org. Chem., 70: 2881-2883 (2005).
[20] Denmark S.E., Venkatraman S., On the Mechanism of the Skraup− Doebner− Von Miller Quinoline Synthesis, J. Org. Chem., 71: 1668-1676 (2006).
[21] Fujita K.I., Takahashi Y., Owaki M., Yamamoto K., Yamaguchi R., Synthesis of Five-, Six-, and Seven-Membered Ring Lactams by Cp* Rh Complex-Catalyzed Oxidative N-heterocyclization of Amino Alcohols, Org. lett., 6: 2785-2788 (2004).
[22] Binot G., Zard S.Z., Access to 4-substituted 3, 4-dihydroquinolin-2 (1H)-ones by an Unusual Radical Cyclisation of a Secondary Amide, Tetrahedron Lett., 46: 7503-7506 (2005).
[23] Akritopoulou-Zanze I., Whitehead A., Waters J.E., Henry R.F., Djuric S.W., Synthesis of Substituted 3, 4-dihydroquinolin-2 (1H)-one Derivatives by Sequential Ugi/acrylanilide [6π]-Photocyclizations, Tetrahedron Lett., 48: 3549-3552 (2007).
[24] Horn J., Li H.Y., Marsden S.P., Nelson A., Shearer R.J., Campbell A.J., House D., Weingarten G.G., Convergent Synthesis of Dihydroquinolones from o-aminoarylboronates, Tetrahedron, 65: 9002-9007 (2009).
[25] Mishra S., Singh P., Hybrid Molecules: The Privileged Scaffolds for Various Pharmaceuticals, Eur. J. Med. Chem., 124: 500-536 (2016).
[26] Sangani C.B., Makawana J.A., Zhang X., Teraiya S.B., Lin L., Zhu H.L., Design, Synthesis and Molecular Modeling of Pyrazole–Quinoline–Pyridine Hybrids as a New Class of Antimicrobial and Anticancer Agents, Eur. J. Med. Chem., 76: 549-557 (2014).
[27] Wang H.K., Bastow K.F., Cosentino L.M., Lee K.H., Antitumor Agents. 166. Synthesis and Biological Evaluation of 5, 6, 7, 8-substituted-2-phenylthiochromen-4-ones, J. Med. Chem., 39: 1975-1980 (1996).
[28] Ho T.L., Kung L.R., Chein R.J., Total Synthesis of (±)-2-Isocyanoallopupukeanane, J. Org. Chem., 65: 5774-5779 (2000).
[29] Amos D.T., Renslo A.R., Danheiser R.L., Intramolecular [4+ 2] Cycloadditions of Iminoacetonitriles: A New Class of Azadienophiles for Hetero Diels− Alder Reactions, J. Am. Chem. Soc., 125: 4970-4971 (2003).
[30] Tanaka N., Suzuki T., Hosoya Y., Nakada M., Synthetic Studies on (−)-FR182877: Construction of the ABCD Ring System via the Intramolecular Cycloadditions (2), Tetrahedron Lett., 48: 6488-6492 (2007).
[31] Majumdar K.C., Taher A., Ray K., Domino-Knoevenagel-hetero-Diels–Alder Reactions: An Efficient One-Step Synthesis of Indole-Annulated Thiopyranobenzopyran Derivatives, Tetrahedron Lett., 50: 3889-3891 (2009).
[32] Devi I., Bhuyan P.J., Stereoselective Intramolecular Hetero Diels–Alder reactions of 1-oxa-1, 3-Butadienes: A Novel Approach for the Synthesis of Complex Annulated Uracils, Tetrahedron Lett., 45: 7727-7728 (2004).
[33] Snider B.B., Lu Q., Total Synthesis of (±)-leporin A, J. Org. Chem., 61: 2839-2844 (1996).
[34] Tietze L.F., Rackelmann N., Domino Reactions in the Synthesis of Heterocyclic Natural Products and Analogs, Pure Appl. Chem., 76: 1967-1983 (2004).
[35] Tietze L.F., Modi A., Multicomponent Domino Reactions for the Synthesis of Biologically Active Natural Products and Drugs, Med. Res. Rev., 20: 304-322 (2000).
[36] Tietze L.F., Ott C., Gerke K., Buback M., The First Example of an Increase in the Enantioselectivity of a Chemical Reaction in the Presence of a Chiral Lewis Acid Under High Pressure, Angew. Chem. Int. Ed. Engl., 32: 1485-1486 (1993).
[37] Khoshkholgh M.J., Balalaie S., Gleiter R., Rominger F., Intramolecular Hetero-Diels–Alder Reaction of 1-oxa-1, 3-butadienes with Terminal Acetylenes in Aqueous Media Using CuI, Tetrahedron, 64: 10924-10929 (2008).
[38] Khoshkholgh M.J., Balalaie S., Bijanzadeh H.R., Gross J.H., Copper (I) Iodide Catalyzed Domino Knoevenagel Hetero-Diels-Alder Reaction of Terminal Acetylenes: Synthesis of Pyrano [2, 3-c] pyrazoles, Synlett, 55-58 (2009).
[39] Khoshkholgh M.J., Lotfi M., Balalaie S., Rominger F., Efficient Synthesis of Pyrano [2, 3-c] Coumarins Via Intramolecular Domino Knoevenagel Hetero-Diels–Alder Reactions, Tetrahedron, 65: 4228-4234 (2009).
[40] Moghaddam F.M., Kiamehr M., Khodabakhshi M.R., Mirjafary Z., Fathi S., Saeidian H., A New Domino Knoevenagel-hetero-Diels–Alder Reaction: An Efficient Catalyst-Free Synthesis of Novel Thiochromone-Annulated Thiopyranocoumarin Derivatives in Aqueous Medium, Tetrahedron, 66: 8615-8622 (2010).
[41] Moghaddam F.M., Kiamehr M., Taheri S., Mirjafary Z., Synthesis of Novel Polycyclic Indole‐Annulated Thiopyranocoumarin Derivatives via Domino Knoevenagel–Hetero‐Diels–Alder Reaction in Aqueous Media, Helv. Chim. Acta., 93: 964-973 (2010).
[42] Ghandi M., Mohammadimehr E., Sadeghzadeh M., Bozcheloei A.H., Efficient Access to Novel Hexahydro-chromene and Tetrahydro-pyrano [2, 3-d] Pyrimidine-annulated Benzo-δ-sultones Via a Domino Knöevenagel-hetero-Diels–Alder Reaction in Water, Tetrahedron, 67: 8484-8491 (2011).
[43] Ghandi M., Nazeri M.T., Kubicki M., An Efficient One-Pot, Regio-and Stereoselective Synthesis of Novel Pentacyclic-Fused Pyrano [3, 2, c] Chromenone or Quinolinone Benzosultone Derivatives in Water, Tetrahedron, 69: 4979-4989 (2013).
[44] Ghandi M., Sheibani S., Sadeghzadeh M., Daha F.J., Kubicki M., Synthesis of Novel Tetra-and Pentacyclic Benzosultam Scaffolds Via Domino Knoevenagel hetero-Diels–Alder Reactions in Water, J. Iran. Chem. Soc., 10: 1057-1065 (2013).
[45] Kiamehr M., Alipour B., Mohammadkhani L., Jafari B., Langer P., ZnBr2 Catalyzed Domino Knoevenagel-hetero-Diels–Alder reaction: An Efficient Route to Polycyclic Thiopyranoindol Annulated [3, 4-c] quinolone derivatives, Tetrahedron, 73: 3040-3047 (2017).
[46] Apple I.A., Meth-Cohn O., 2-Aminobenzaldehydes from Quinolinium Salts and Alkaline Hydrogen Peroxide, Arkivoc, 6: 4-14 (2002).

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