A facile one-pot regioselective synthesis of functionalized novel benzo[f]chromeno[4,3-b][1,7]naphthyridines and benzo[f][1,7]naphthyridines via an imino Diels-Alder reaction

[1]  S. Han,et al.  Development of Novel 1,2,3,4-Tetrahydroquinoline Scaffolds as Potent NF-κB Inhibitors and Cytotoxic Agents. , 2016, ACS medicinal chemistry letters.

[2]  S. Han,et al.  Design, synthesis, and biological evaluation of benzofuran- and 2,3-dihydrobenzofuran-2-carboxylic acid N-(substituted)phenylamide derivatives as anticancer agents and inhibitors of NF-κB. , 2015, Bioorganic & medicinal chemistry letters.

[3]  Heesoon Lee,et al.  Novel NF-κB inhibitors: a patent review (2011 – 2014) , 2015, Expert opinion on therapeutic patents.

[4]  L. Fu,et al.  Efficient synthesis and evaluation of antitumor activities of novel functionalized 1,8-naphthyridine derivatives. , 2015, ACS combinatorial science.

[5]  B. Pfeiffer,et al.  Synthesis, antitumor activity, and mechanism of action of benzo[b]chromeno[6,5-g][1,8]naphthyridin-7-one analogs of acronycine. , 2014, Journal of medicinal chemistry.

[6]  M. Lahtela-Kakkonen,et al.  Chroman-4-one- and chromone-based sirtuin 2 inhibitors with antiproliferative properties in cancer cells. , 2014, Journal of medicinal chemistry.

[7]  R. Pratap,et al.  Natural and synthetic chromenes, fused chromenes, and versatility of dihydrobenzo[h]chromenes in organic synthesis. , 2014, Chemical reviews.

[8]  S. Han,et al.  Design and synthesis of 3,4-dihydro-2H-benzo[h]chromene derivatives as potential NF-κB inhibitors. , 2014, Bioorganic & medicinal chemistry letters.

[9]  W. Cho,et al.  Topoisomerase inhibitors as anticancer agents: a patent update , 2013, Expert opinion on therapeutic patents.

[10]  Jun Xu,et al.  First total synthesis and determination of the absolute configuration of 1-N-methyl-3-methylamino-[N-butanoicacid-3-(9-methyl-8-propen-7-one)-amide]-benzo[f][1,7]naphthyridine-2-one, a novel benzonaphthyridine alkaloid , 2012 .

[11]  Y. Pommier,et al.  Dibenzo[c,h][1,5]naphthyridinediones as topoisomerase I inhibitors: design, synthesis, and biological evaluation. , 2012, The Journal of organic chemistry.

[12]  G. Rummel,et al.  2,6-Naphthyridines as potent and selective inhibitors of the novel protein kinase C isozymes. , 2011, Bioorganic & medicinal chemistry letters.

[13]  Zhenyuan Miao,et al.  New strategies in the discovery of novel non-camptothecin topoisomerase I inhibitors. , 2011, Current medicinal chemistry.

[14]  Malgorzata N. Drwal,et al.  Exploring DNA Topoisomerase I Ligand Space in Search of Novel Anticancer Agents , 2011, PloS one.

[15]  Adam Siddiqui-Jain,et al.  Discovery and SAR of 5-(3-chlorophenylamino)benzo[c][2,6]naphthyridine-8-carboxylic acid (CX-4945), the first clinical stage inhibitor of protein kinase CK2 for the treatment of cancer. , 2011, Journal of medicinal chemistry.

[16]  Y. Pommier,et al.  Design, synthesis, and evaluation of dibenzo[c,h][1,6]naphthyridines as topoisomerase I inhibitors and potential anticancer agents. , 2010, Journal of medicinal chemistry.

[17]  J. Hong,et al.  Structure-activity relationship of indoline-2-carboxylic acid N-(substituted)phenylamide derivatives. , 2010, Bioorganic & medicinal chemistry letters.

[18]  R. Nagarajan,et al.  CuI/La(OTf)3 catalyzed, one-pot synthesis of isomeric ellipticine derivatives in ionic liquid , 2010 .

[19]  S. Hotha,et al.  Orthogonal activation of propargyl and n-pentenyl glycosides and 1,2-orthoesters. , 2009, The Journal of organic chemistry.

[20]  T. P. Lebold,et al.  Stereodivergent synthesis of fused bicyclopyrazolidines: access to pyrazolines and pyrrolidines. , 2009, Organic letters.

[21]  S. Desrat,et al.  Intramolecular imino Diels-Alder reaction: progress toward the synthesis of uncialamycin. , 2009, The Journal of organic chemistry.

[22]  S. Matsunaga,et al.  A heterobimetallic Ga/Yb-Schiff base complex for catalytic asymmetric alpha-addition of isocyanides to aldehydes. , 2009, Journal of the American Chemical Society.

[23]  Y. Pommier,et al.  The indenoisoquinoline noncamptothecin topoisomerase I inhibitors: update and perspectives , 2009, Molecular Cancer Therapeutics.

[24]  S. Genovese,et al.  Preparation of Triaryl-and Triheteroarylmethanes under Ytterbium Triflate Catalysis and Solvent-Free Conditions , 2009 .

[25]  Jie Wu,et al.  Tandem cyclization-[3+3] cycloaddition reactions of 2-alkynylbenzaldoxime: synthesis of fused 1,2-dihydroisoquinolines , 2009 .

[26]  Weidong Rao,et al.  Ytterbium(III) triflate-catalyzed amination of 1-cyclopropylprop-2-yn-1-ols as an expedient route to conjugated enynes. , 2009, The Journal of organic chemistry.

[27]  D. Hazuda,et al.  Synthesis of 5-(1-H or 1-alkyl-5-oxopyrrolidin-3-yl)-8-hydroxy-[1,6]-naphthyridine-7-carboxamide inhibitors of HIV-1 integrase. , 2008, Bioorganic & medicinal chemistry letters.

[28]  K. Sharpless,et al.  Mechanistic studies on the Cu-catalyzed three-component reactions of sulfonyl azides, 1-alkynes and amines, alcohols, or water: dichotomy via a common pathway. , 2008, The Journal of organic chemistry.

[29]  Yuehong Wang,et al.  Library synthesis using 5,6,7,8-tetrahydro-1,6-naphthyridines as scaffolds. , 2008, Journal of combinatorial chemistry.

[30]  W. Su,et al.  Yb(OTf)3 catalyzed condensation reaction of β-naphthol and aldehyde in ionic liquids: a green synthesis of aryl-14H-dibenzo[a,j]xanthenes , 2008 .

[31]  Xigeng Zhou,et al.  Direct Substitution of the Hydroxy Group at the Allylic/propargylic Position with Carbon- and Heteroatom- centered Nucleophiles Catalyzed by Yb(OTf)3 , 2008 .

[32]  B. Hwang,et al.  Synthesis of chroman-2-carboxylic acid N-(substituted)phenylamides and their inhibitory effect on nuclear factor-κB (NF-κB) activation , 2008 .

[33]  A. Fürstner,et al.  Two manifolds for metal-catalyzed intramolecular diels-alder reactions of unactivated alkynes. , 2007, Angewandte Chemie.

[34]  Byung Hak Kim,et al.  Structure-activity relationships of 6-hydroxy-7-methoxychroman-2-carboxylic acid N-(substituted)phenylamides as inhibitors of nuclear factor-kB activation , 2007 .

[35]  Y. Pommier,et al.  Nitrated indenoisoquinolines as topoisomerase I inhibitors: a systematic study and optimization. , 2007, Journal of medicinal chemistry.

[36]  Yves Pommier,et al.  Optimization of the indenone ring of indenoisoquinoline topoisomerase I inhibitors. , 2007, Journal of medicinal chemistry.

[37]  Le‐Ping Liu,et al.  Lewis acid-catalyzed reactions of mono-aryl group substituted methylenecyclopropanes with diethyl ketomalonate , 2007 .

[38]  R. Nagarajan,et al.  A new entry to polycyclic indole derivatives via intramolecular imino Diels-Alder reaction: observation of unexpected reaction. , 2007, The Journal of organic chemistry.

[39]  Y. Yun,et al.  Oleanolic acid, a pentacyclic triterpenoid, induces rabbit platelet aggregation through a phospholipase C-calcium dependent signaling pathway , 2007, Archives of pharmacal research.

[40]  Y. Pommier.  Topoisomerase I inhibitors: camptothecins and beyond , 2006, Nature Reviews Cancer.

[41]  B. Harrison,et al.  Synthesis and biological evaluation of novel compounds within a class of 3-aminochroman derivatives with dual 5-HT1A receptor and serotonin transporter affinity. , 2006, Journal of medicinal chemistry.

[42]  W. Su,et al.  A Facile Synthesis of 1-Substituted-1H-1,2,3,4-Tetrazoles Catalyzed by Ytterbium Triflate Hydrate , 2006 .

[43]  Lili Lin,et al.  A mild and efficient aza-Diels–Alder reaction of N-benzhydryl imines with trans-1-methoxy-2-methyl-3-trimethylsiloxybuta-1,3-diene catalyzed by Yb(OTf)3 , 2005 .

[44]  L. Strekowski,,et al.  New triple-helix DNA stabilizing agents. , 2005, Bioorganic & medicinal chemistry letters.

[45]  F. Himo,et al.  Copper(I)-catalyzed synthesis of azoles. DFT study predicts unprecedented reactivity and intermediates. , 2004, Journal of the American Chemical Society.

[46]  H. Tian,et al.  A Convenient Synthesis of α,α′-Bis(substituted benzylidene)cycloalkanones Catalyzed by Yb(OTf)3 Under Solvent-Free Conditions , 2004 .

[47]  M. Crul.  CKD-602. Chong Kun Dang. , 2003, Current opinion in investigational drugs.

[48]  W. Denny,et al.  Synthesis and cytotoxic activity of carboxamide derivatives of benzo[b][1,6]naphthyridines. , 2003, Journal of medicinal chemistry.

[49]  Y. Pommier,et al.  Synthesis of new indeno[1,2-c]isoquinolines: cytotoxic non-camptothecin topoisomerase I inhibitors. , 2000, Journal of medicinal chemistry.

[50]  Yao,et al.  Catalytic enantioselective aza-Diels-alder reactions of imines--an approach to optically active nonproteinogenic alpha-amino acids , 2000, Chemistry.

[51]  S. Mackay,et al.  Synthesis of Dibenzo[c,h][1,6]naphthyridine, [2]Benzopyrano[4,3-c]quinoline and Benzo[i]phenanthridine Analogues of the Quaternary Benzo[c]phenanthridines , 2000 .

[52]  V. D. Dyachenko,et al.  Naphthyridines. Structure, physicochemical properties and general methods of synthesis , 2000 .

[53]  B. Lohray,et al.  Novel antidiabetic and hypolipidemic agents. 5. Hydroxyl versus benzyloxy containing chroman derivatives. , 1999, Journal of medicinal chemistry.

[54]  L. Chan,et al.  Discovery of 1,6-naphthyridines as a novel class of potent and selective human cytomegalovirus inhibitors. , 1999, Journal of medicinal chemistry.

[55]  K. Kusakabe,et al.  A SWITCH OF ENANTIOFACIAL SELECTIVITIES USING DESIGNED SIMILAR CHIRAL LIGANDS IN ZIRCONIUM-CATALYZED ASYMMETRIC AZA DIELS-ALDER REACTIONS , 1999 .

[56]  S. Kobayashi.  Scandium Triflate in Organic Synthesis , 1999 .

[57]  Y. Pommier,et al.  Synthesis of cytotoxic indenoisoquinoline topoisomerase I poisons. , 1999, Journal of medicinal chemistry.

[58]  M. Johannsen,et al.  Catalytic Enantioselective Aza Diels-Alder Reactions of Imino Dienophiles. , 1998, Angewandte Chemie.

[59]  S. Bromidge,et al.  A parallel combinatorial approach to locating homochiral Lewis acid catalysts for the asymmetric aza-Diels-Alder reaction of an imino dienophile , 1998 .

[60]  R. N. Brogden,et al.  Topotecan. A review of its potential in advanced ovarian cancer. , 1998, Drugs.

[61]  H. Audrain,et al.  Catalytic Asymmetric Hetero-Diels−Alder Reactions of Ketones: Chemzymatic Reactions , 1998 .

[62]  H. Ishitani,et al.  The First Enantioselective Aza-Diels-Alder Reactions of Imino Dienophiles on Use of a Chiral Zirconium Catalyst. , 1998, Angewandte Chemie.

[63]  Marvin J. Miller,et al.  DEVELOPMENT AND APPLICATIONS OF AMINO ACID-DERIVED CHIRAL ACYLNITROSO HETERO DIELS-ALDER REACTIONS , 1998 .

[64]  Y. Tsuchida,et al.  Oral versus intraperitoneal administration of irinotecan in the treatment of human neuroblastoma in nude mice. , 1998, Cancer letters.

[65]  P. Zarantonello,et al.  Synthesis and Use of N-(Trimethylsilyl)imines , 1998 .

[66]  Lutz F. Tietze,et al.  HETERO DIELS-ALDER REACTIONS IN ORGANIC CHEMISTRY , 1997 .

[67]  Kiho Lee,et al.  Synthesis and antitumor activity of 7-substituted 20(RS)-camptothecin analogues , 1996 .

[68]  H. Waldmann.  AMINO-ACID ESTERS - VERSATILE CHIRAL AUXILIARY GROUPS FOR THE ASYMMETRIC-SYNTHESIS OF NITROGEN-HETEROCYCLES , 1995 .

[69]  D. Emerson,et al.  In vivo antitumor activity of two new seven-substituted water-soluble camptothecin analogues. , 1995, Cancer research.

[70]  H. Waldmann.  Asymmetric Hetero Diels-Alder Reactions , 1994 .

[71]  D. Boger,et al.  Hetero Diels-Alder methodology in organic synthesis , 1987 .

[72]  S. Weinreb.  Alkaloid total synthesis by intramolecular imino Diels-Alder cycloadditions , 1985 .

[73]  D. Boger.  Diels-Alder reactions of azadienes , 1983 .

[74]  S. Weinreb,et al.  Stereochemistry of the intramolecular imino Diels-Alder reaction , 1980 .

[75]  E. Corey,et al.  Stereo-controlled synthesis of dl-prostaglandins F2.alpha. and E2 , 1969 .

[76]  L. S. Povarov.  αβ-UNSATURATED ETHERS AND THEIR ANALOGUES IN REACTIONS OF DIENE SYNTHESIS , 1967 .

[77]  A. McPhail,et al.  Plant Antitumor Agents. I. The Isolation and Structure of Camptothecin, a Novel Alkaloidal Leukemia and Tumor Inhibitor from Camptotheca acuminata1,2 , 1966 .