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Volumn 53, Issue 9, 2010, Pages 3707-3717

Mono-, Di-, and triaryl substituted tetrahydropyrans as cyclooxygenase-2 and tumor growth inhibitors. Synthesis and biological evaluation

Author keywords

[No Author keywords available]

Indexed keywords

2 ((ETHYLTHIO)METHYL) 6 (4 FLUOROPHENYL)TETRAHYDRO 4 PHENYL 2H PYRAN 4 OL; 2 ((ETHYLTHIO)METHYL)TETRAHYDRO 4,6 DIPHENYL 2H PYRAN 4 OL; 2 ((ETHYLTHIO)METHYL)TETRAHYDRO 6 METHYL 4 PHENYL 2H PYRAN 4 OL; 2 (4 BROMOPHENYL) 6 ((ETHYLTHIO)METHYL)TETRAHYDRO 3,4 DIPHENYL 2H PYRAN 4 OL; 2 (4 BROMOPHENYL) 6 ((ETHYLTHIO)METHYL)TETRAHYDRO 4 PHENYL 2H PYRAN 4 OL; 2 (4 BROMOPHENYL)TETRAHYDRO 3,4 DIPHENYL 6 (THIOCYANATOMETHYL) 2H PYRAN 4 OL; 2 (4 BROMOPHENYL)TETRAHYDRO 4 PHENYL 6 (THIOCYANATOMETHYL) 2H PYRAN 4 OL; 2 (4 CHLOROPHENYL) 6 ((ETHYLTHIO)METHYL)TETRAHYDRO 3,4 DIPHENYL 2H PYRAN 4 OL; 2 (4 CHLOROPHENYL) 6 ((ETHYLTHIO)METHYL)TETRAHYDRO 4 PHENYL 2H PYRAN 4 OL; 2 (4 CHLOROPHENYL)TETRAHYDRO 3,4 DIPHENYL 6 (THIOCYANATOMETHYL) 2H PYRAN 4 OL; 2 (4 CHLOROPHENYL)TETRAHYDRO 4 PHENYL 6 (THIOCYANATOMETHYL) 2H PYRAN 4 OL; 2 (4 FLUOROPHENYL)TETRAHYDRO 3,4 DIPHENYL 6 (THIOCYANATOMETHYL) 2H PYRAN 4 OL; 2 (4 FLUOROPHENYL)TETRAHYDRO 4 PHENYL 6 (THIOCYANATOMETHYL) 2H PYRAN 4 OL; 6 ((ETHYLTHIO)METHYL) 2 (4 FLUOROPHENYL)TETRAHYDRO 3,4 DIPHENYL 2H PYRAN 4 OL; 6 ((ETHYLTHIO)METHYL)TETRAHYDRO 2,3,4 TRIPHENYL 2H PYRAN 4 OL; ANTINEOPLASTIC AGENT; CYCLOOXYGENASE 1 INHIBITOR; CYCLOOXYGENASE 2 INHIBITOR; KETONE DERIVATIVE; TETRAHYDRO 2 METHYL 4 PHENYL 6 (THIOCYANATOMETHYL) 2H PYRAN 4 OL; TETRAHYDRO 2,3,4 TRIPHENYL 6 (THIOCYANATOMETHYL) 2H PYRAN 4 OL; TETRAHYDRO 2,4 DIPHENYL 6 (THIOCYANATOMETHYL) 2H PYRAN 4 OL; TETRAHYDROPYRAN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 77952073267     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm1001327     Document Type: Article
Times cited : (46)

References (67)
  • 1
    • 0033709079 scopus 로고    scopus 로고
    • Current problems with non-specific COX inhibitors
    • references therein
    • McGettigan, P.; Henry, D. Current problems with non-specific COX inhibitors Curr. Pharm. Des. 2006, 6, 1693-1724 and references therein
    • (2006) Curr. Pharm. Des. , vol.6 , pp. 1693-1724
    • McGettigan, P.1    Henry, D.2
  • 3
    • 17144393290 scopus 로고    scopus 로고
    • Adverse cardiovascular effects of the coxibs
    • Dogne, J.-M.; Supuran, C. T.; Pratico, D. Adverse cardiovascular effects of the coxibs J. Med. Chem. 2005, 48, 2251-2257
    • (2005) J. Med. Chem. , vol.48 , pp. 2251-2257
    • Dogne, J.-M.1    Supuran, C.T.2    Pratico, D.3
  • 4
    • 27844511950 scopus 로고    scopus 로고
    • Cardiovascular and gastrointestinal effects of COX-2 inhibitors and NSAIDs: Achieving a balance
    • Jeffrey, S. B.; Lee, S. S. Cardiovascular and gastrointestinal effects of COX-2 inhibitors and NSAIDs: achieving a balance Arthritis Res. Ther. 2005, 7, S14-S22
    • (2005) Arthritis Res. Ther. , vol.7
    • Jeffrey, S.B.1    Lee, S.S.2
  • 5
    • 31044441042 scopus 로고    scopus 로고
    • Biological basis for the cardiovascular consequences of COX-2 inhibition: Therapeutic challenges and opportunities
    • Grosser, T.; Fries, S.; FitzGerald., G. A. Biological basis for the cardiovascular consequences of COX-2 inhibition: therapeutic challenges and opportunities J. Clin. Invest. 2006, 116, 4-15
    • (2006) J. Clin. Invest. , vol.116 , pp. 4-15
    • Grosser, T.1    Fries, S.2    Fitzgerald, G.A.3
  • 7
    • 33747883681 scopus 로고    scopus 로고
    • Selective cyclooxygenase inhibition: Its role in pain and anaesthesia
    • Longford, R. M.; Mehta, V. Selective cyclooxygenase inhibition: its role in pain and anaesthesia Biomed. Pharmacother. 2006, 60, 323-328
    • (2006) Biomed. Pharmacother. , vol.60 , pp. 323-328
    • Longford, R.M.1    Mehta, V.2
  • 8
    • 65249118795 scopus 로고    scopus 로고
    • The Coxib experience. A look in the rearview mirror
    • Marnett, L. J. The Coxib experience. A look in the rearview mirror Annu. Rev. Pharmacol. Toxicol. 2009, 49, 265-290
    • (2009) Annu. Rev. Pharmacol. Toxicol. , vol.49 , pp. 265-290
    • Marnett, L.J.1
  • 9
    • 40049087863 scopus 로고    scopus 로고
    • Current status of COX-2 inhibitors
    • references therein
    • Singh, P.; Mittal, A. Current status of COX-2 inhibitors Mini-Rev. Med. Chem. 2008, 8, 73-90 and references therein
    • (2008) Mini-Rev. Med. Chem. , vol.8 , pp. 73-90
    • Singh, P.1    Mittal, A.2
  • 11
    • 0015237292 scopus 로고
    • Inhibition of prostaglandin synthesis as a mechanism of action for aspirin-like drugs
    • Vane, J. R. Inhibition of prostaglandin synthesis as a mechanism of action for aspirin-like drugs Nat. New Biol. 1971, 231, 232-235
    • (1971) Nat. New Biol. , vol.231 , pp. 232-235
    • Vane, J.R.1
  • 12
    • 0030479496 scopus 로고    scopus 로고
    • Prostaglandin endoperoxide H synthases (cyclooxygenases)-1 and -2
    • Smith, W. L.; Garavito, R. M.; DeWitt, D. L. Prostaglandin endoperoxide H synthases (cyclooxygenases)-1 and -2 J. Biol. Chem. 1996, 271, 33157-33160
    • (1996) J. Biol. Chem. , vol.271 , pp. 33157-33160
    • Smith, W.L.1    Garavito, R.M.2    Dewitt, D.L.3
  • 15
    • 0037108979 scopus 로고    scopus 로고
    • COX-3, a cyclooxygenase-1 variant inhibited by acetaminophen and other analgesic/antipyretic drugs: Cloning, structure, and expression
    • Chandersekharan, N. V.; Dai, H.; Roos, K. L. T.; Evanson, N. K.; Tomsik, J.; Elton, T. S.; Simmons, D. L. COX-3, a cyclooxygenase-1 variant inhibited by acetaminophen and other analgesic/antipyretic drugs: cloning, structure, and expression Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 13926-13931
    • (2002) Proc. Natl. Acad. Sci. U.S.A. , vol.99 , pp. 13926-13931
    • Chandersekharan, N.V.1    Dai, H.2    Roos, K.L.T.3    Evanson, N.K.4    Tomsik, J.5    Elton, T.S.6    Simmons, D.L.7
  • 16
    • 25644445318 scopus 로고    scopus 로고
    • Acetaminophen and the cyclooxygenase-3 puzzle. Sorting out facts, fictions and uncertainties
    • Kis, B.; Snipes, J. A.; Busija, D. W. Acetaminophen and the cyclooxygenase-3 puzzle. Sorting out facts, fictions and uncertainties J. Pharmacol. Exp. Ther. 2005, 315, 1-7
    • (2005) J. Pharmacol. Exp. Ther. , vol.315 , pp. 1-7
    • Kis, B.1    Snipes, J.A.2    Busija, D.W.3
  • 19
    • 0037307483 scopus 로고    scopus 로고
    • Cyclooxygenase 2: A molecular target for cancer prevention and treatment
    • Subbaramaiah, K.; Dannenberg, A. J. Cyclooxygenase 2: a molecular target for cancer prevention and treatment Trends Pharmacol. Sci. 2003, 24, 96-102
    • (2003) Trends Pharmacol. Sci. , vol.24 , pp. 96-102
    • Subbaramaiah, K.1    Dannenberg, A.J.2
  • 20
    • 18444408375 scopus 로고    scopus 로고
    • COX-2: A molecular target for colorectal cancer prevention
    • Brown, J. R.; DuBois, R. N. COX-2: a molecular target for colorectal cancer prevention J. Clin. Oncol. 2005, 23, 2840-2855
    • (2005) J. Clin. Oncol. , vol.23 , pp. 2840-2855
    • Brown, J.R.1    Dubois, R.N.2
  • 22
    • 1442301504 scopus 로고    scopus 로고
    • Cyclooxygenase-2: Potential role in regulation of drug efflux and multidrug resistance phenotype
    • SorokA. Cyclooxygenase-2: potential role in regulation of drug efflux and multidrug resistance phenotype Curr. Pharm. Des. 2004, 10, 647-657
    • (2004) Curr. Pharm. Des. , vol.10 , pp. 647-657
    • Sorokin, A.1
  • 23
    • 0036208533 scopus 로고    scopus 로고
    • The MDR phenotype is associated with the expression of COX-2 and iNOS in a human heptacellular carcinama cell line
    • Fantappie, O.; Masini, E.; Sardi, L.; Raimondi, L.; Bani, D.; Solazzo, M.; Vannacci, A.; Mazzanti, R. The MDR phenotype is associated with the expression of COX-2 and iNOS in a human heptacellular carcinama cell line Hepatology 2002, 35, 843-852
    • (2002) Hepatology , vol.35 , pp. 843-852
    • Fantappie, O.1    Masini, E.2    Sardi, L.3    Raimondi, L.4    Bani, D.5    Solazzo, M.6    Vannacci, A.7    Mazzanti, R.8
  • 24
    • 0037138743 scopus 로고    scopus 로고
    • Nonsteroidal anti-inflammatory drugs as anticancer agents: Mechanistic, pharmacologic and clinical issues
    • Thun, M. J.; Henkey, S. J.; Patrono, C. Nonsteroidal anti-inflammatory drugs as anticancer agents: mechanistic, pharmacologic and clinical issues J. Natl. Cancer Inst. 2001, 94, 252-266
    • (2001) J. Natl. Cancer Inst. , vol.94 , pp. 252-266
    • Thun, M.J.1    Henkey, S.J.2    Patrono, C.3
  • 26
    • 8744284312 scopus 로고    scopus 로고
    • Prevention of colorectal cancer through the use of COX-2 selective inhibitors
    • Peek, R. M., Jr. Prevention of colorectal cancer through the use of COX-2 selective inhibitors Cancer Chemother. Pharmacol. 2004, 54 (S1) S50-S56
    • (2004) Cancer Chemother. Pharmacol. , vol.54 , Issue.S1
    • Peek Jr., R.M.1
  • 27
    • 0029117289 scopus 로고
    • Nonsteroidal antiinflammatory drugs cause apoptosis and induce cyclooxygenase in chicken embryo fibroblasts
    • Lu, X.; Xie, W.; Reed, D.; Bradshaw, W. S.; Simmons, D. L. Nonsteroidal antiinflammatory drugs cause apoptosis and induce cyclooxygenase in chicken embryo fibroblasts Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 7961-7965
    • (1995) Proc. Natl. Acad. Sci. U.S.A. , vol.92 , pp. 7961-7965
    • Lu, X.1    Xie, W.2    Reed, D.3    Bradshaw, W.S.4    Simmons, D.L.5
  • 28
    • 0142250380 scopus 로고    scopus 로고
    • A randomized, double-blind, placebo-controlled trial of the effects of rofecoxib, a selective cyclooxygenase-2 inhibitor, on rectal polyps in familial adenomatous polyposis patients
    • references therein
    • Higuchi, T.; Iwama, T.; Yoshinaga, K.; Toyooka, M.; Taketo, M. M.; Sugihara, K. A randomized, double-blind, placebo-controlled trial of the effects of rofecoxib, a selective cyclooxygenase-2 inhibitor, on rectal polyps in familial adenomatous polyposis patients Clin. Cancer Res. 2003, 9, 4756-4760 and references therein
    • (2003) Clin. Cancer Res. , vol.9 , pp. 4756-4760
    • Higuchi, T.1    Iwama, T.2    Yoshinaga, K.3    Toyooka, M.4    Taketo, M.M.5    Sugihara, K.6
  • 29
    • 34147119080 scopus 로고    scopus 로고
    • Structural and functional basis of cyclooxygenase inhibition
    • references therein
    • Blobaum, A. L.; Marnett, L. J. Structural and functional basis of cyclooxygenase inhibition J. Med. Chem. 2007, 50, 1425-1441 and references therein
    • (2007) J. Med. Chem. , vol.50 , pp. 1425-1441
    • Blobaum, A.L.1    Marnett, L.J.2
  • 30
  • 31
    • 60549108357 scopus 로고    scopus 로고
    • Design, synthesis and evaluation of tetrahydropyran based COX-1/2 inhbitors
    • Singh, P.; Bhardwaj, A.; Kaur, S.; Kumar, S. Design, synthesis and evaluation of tetrahydropyran based COX-1/2 inhbitors Eur. J. Med. Chen. 2009, 44, 1278-1287
    • (2009) Eur. J. Med. Chen. , vol.44 , pp. 1278-1287
    • Singh, P.1    Bhardwaj, A.2    Kaur, S.3    Kumar, S.4
  • 32
    • 33750087307 scopus 로고    scopus 로고
    • 5-Substituted-2, 3-diphenyltetrahydrofurans: A new class of moderatelyselective COX-2 inhibitors
    • Singh, P.; Mittal, A.; Kaur, S.; Kumar, S. 5-Substituted-2, 3-diphenyltetrahydrofurans: a new class of moderatelyselective COX-2 inhibitors Bioorg. Med. Chem. 2006, 14, 7910-7916
    • (2006) Bioorg. Med. Chem. , vol.14 , pp. 7910-7916
    • Singh, P.1    Mittal, A.2    Kaur, S.3    Kumar, S.4
  • 33
    • 47849091705 scopus 로고    scopus 로고
    • 2,3-Diaryl-5-ethylsulfanylmethyltetrahydrofurans as a new class of COX-2 inhibitors and cytotoxic agents
    • Singh, P.; Mittal, A.; Kaur, S.; Holzer, W.; Kumar, S. 2,3-Diaryl-5-ethylsulfanylmethyltetrahydrofurans as a new class of COX-2 inhibitors and cytotoxic agents Org. Biomol. Chem. 2008, 6, 2706-2712
    • (2008) Org. Biomol. Chem. , vol.6 , pp. 2706-2712
    • Singh, P.1    Mittal, A.2    Kaur, S.3    Holzer, W.4    Kumar, S.5
  • 34
    • 3242748214 scopus 로고    scopus 로고
    • Design, synthesis and Structure-activity relationship studies of 3,4,5-triphenylpyran-2-ones as selective cyclooxygenase-2 inhibitors
    • Rao, P. N. P.; UddM. J.; Knaus, E. E. Design, synthesis and Structure-activity relationship studies of 3,4,5-triphenylpyran-2-ones as selective cyclooxygenase-2 inhibitors J. Med. Chem. 2004, 47, 3972-3990
    • (2004) J. Med. Chem. , vol.47 , pp. 3972-3990
    • Rao, P.N.P.1    Uddin, M.J.2    Knaus, E.E.3
  • 35
    • 39149102146 scopus 로고    scopus 로고
    • Synthesis of six-membered oxygenated heterocycles through carbon-oxygen bond forming reactions
    • Larrosa, I.; Romea, P.; Urpi, F. Synthesis of six-membered oxygenated heterocycles through carbon-oxygen bond forming reactions Tetrahedron 2008, 64, 2683-2723
    • (2008) Tetrahedron , vol.64 , pp. 2683-2723
    • Larrosa, I.1    Romea, P.2    Urpi, F.3
  • 36
    • 0041808716 scopus 로고    scopus 로고
    • First enantioselective total synthesis of (-)-centrolobine
    • references therein
    • Colobert, F. R.; Mazery, D.; Solladie, G.; Carreno, M. C. First enantioselective total synthesis of (-)-centrolobine Org. Lett. 2002, 4, 1723-1725 and references therein
    • (2002) Org. Lett. , vol.4 , pp. 1723-1725
    • Colobert, F.R.1    Mazery, D.2    Solladie, G.3    Carreno, M.C.4
  • 38
    • 33750531635 scopus 로고    scopus 로고
    • Synthesis and antiproliferative activity of (2 R,3 R)-disubstituted tetrahydropyrans
    • references therein
    • Carrillo, R.; Leon, L. G.; MartT.; MartV. S.; Padron, J. M. Synthesis and antiproliferative activity of (2 R,3 R)-disubstituted tetrahydropyrans Bioorg. Med. Chem. Lett. 2006, 16, 6135-6138 and references therein
    • (2006) Bioorg. Med. Chem. Lett. , vol.16 , pp. 6135-6138
    • Carrillo, R.1    Leon, L.G.2    Martin, T.3    Martin, V.S.4    Padron, J.M.5
  • 39
    • 33749017670 scopus 로고    scopus 로고
    • Efficient oxidative cyclization of 1,6-dienes: A highly diastereoselective entry to substituted tetrahydropyrans
    • Roth, S.; Stark, C. B. W. Efficient oxidative cyclization of 1,6-dienes: a highly diastereoselective entry to substituted tetrahydropyrans Angew. Chem., Int. Ed. 2006, 45, 6218-6221
    • (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 6218-6221
    • Roth, S.1    Stark, C.B.W.2
  • 40
    • 33746303557 scopus 로고    scopus 로고
    • Enantioselective synthesis of cyclic ethers through a vanadium-catalyzed resolution/oxidative cyclization
    • Blanc, A.; Toste, F. D. Enantioselective synthesis of cyclic ethers through a vanadium-catalyzed resolution/oxidative cyclization Angew. Chem., Int. Ed. 2006, 45, 2096-2099
    • (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 2096-2099
    • Blanc, A.1    Toste, F.D.2
  • 41
    • 0141766891 scopus 로고    scopus 로고
    • Reductive cyclizations of hydroxysulfinyl ketones: Enantioselective access to tetrahydropyrans and tetrahydrofuran derivatives
    • Carreno, M. C.; Mazery, R. D.; Urbano, A.; Colobert, F.; Solladie, G. Reductive cyclizations of hydroxysulfinyl ketones: enantioselective access to tetrahydropyrans and tetrahydrofuran derivatives J. Org. Chem. 2003, 68, 7779-7787
    • (2003) J. Org. Chem. , vol.68 , pp. 7779-7787
    • Carreno, M.C.1    Mazery, R.D.2    Urbano, A.3    Colobert, F.4    Solladie, G.5
  • 42
    • 33947166292 scopus 로고    scopus 로고
    • Synthesis of cis -3,4-diarylpiperidines and cis -3,4- diaryltetrahydropyrans
    • Chang, M.-Y.; LC.-Y.; Hung, C.-Y. Synthesis of cis -3,4-diarylpiperidines and cis -3,4-diaryltetrahydropyrans Tetrahedron 2007, 63, 3312-3320
    • (2007) Tetrahedron , vol.63 , pp. 3312-3320
    • Chang, M.-Y.1    Lin, C.-Y.2    Hung, C.-Y.3
  • 43
    • 0032578711 scopus 로고    scopus 로고
    • Synthesis of tetrahydropyrans from sugar lactones
    • Estevez, J. C.; Fairbanks, A. J.; Fleet, G. W. J. Synthesis of tetrahydropyrans from sugar lactones Tetrahedron 1998, 54, 13591-13620
    • (1998) Tetrahedron , vol.54 , pp. 13591-13620
    • Estevez, J.C.1    Fairbanks, A.J.2    Fleet, G.W.J.3
  • 44
    • 38949102610 scopus 로고    scopus 로고
    • Highly chemo- and diastereoselective synthesis of substituted tetrahydropyran-4-ones via organocatalytic oxa-Diels-Alder reactions of acyclic α,β-unsaturated ketones with aldehydes
    • Lu, L.-Q.; Xing, X.-N.; Wang, X.-F.; Ming, Z.-H.; Wang, H.-M.; Xiao, W.-J. Highly chemo- and diastereoselective synthesis of substituted tetrahydropyran-4-ones via organocatalytic oxa-Diels-Alder reactions of acyclic α,β-unsaturated ketones with aldehydes Tetrahedron Lett. 2008, 49, 1631-1635
    • (2008) Tetrahedron Lett. , vol.49 , pp. 1631-1635
    • Lu, L.-Q.1    Xing, X.-N.2    Wang, X.-F.3    Ming, Z.-H.4    Wang, H.-M.5    Xiao, W.-J.6
  • 46
    • 0002491291 scopus 로고
    • Hetero-Diels-Alder reaction in highly functionalized natural product synthesis
    • Schmidt, R. R. Hetero-Diels-Alder reaction in highly functionalized natural product synthesis Acc. Chem. Res. 1986, 19, 250-259
    • (1986) Acc. Chem. Res. , vol.19 , pp. 250-259
    • Schmidt, R.R.1
  • 47
    • 4644256135 scopus 로고    scopus 로고
    • Efficient enanatioslective synthesis of functionalized tetrahydropyrans by Ru-catalyzed asymmetric ring-opening metathesis/cross-metathesis (AROM/CM)
    • references therein
    • Gillingham, D. G.; Kataoka, O.; Garber, S. B.; Hoveyda, A. H. Efficient enanatioslective synthesis of functionalized tetrahydropyrans by Ru-catalyzed asymmetric ring-opening metathesis/cross-metathesis (AROM/CM) J. Am. Chem. Soc. 2004, 126, 12288-12290 and references therein
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 12288-12290
    • Gillingham, D.G.1    Kataoka, O.2    Garber, S.B.3    Hoveyda, A.H.4
  • 48
    • 0035830571 scopus 로고    scopus 로고
    • Diastereoslective synthesis of polysubstituted tetrahydropyrans and thiacyclohexanes via indium trichloride mediated cyclizations
    • Yang, X.-F.; Mague, J. T.; Li, C.-J. Diastereoslective synthesis of polysubstituted tetrahydropyrans and thiacyclohexanes via indium trichloride mediated cyclizations J. Org. Chem. 2001, 66, 739-747
    • (2001) J. Org. Chem. , vol.66 , pp. 739-747
    • Yang, X.-F.1    Mague, J.T.2    Li, C.-J.3
  • 49
    • 32644432747 scopus 로고    scopus 로고
    • Convenient synthesis of highly optically active 2,3,4,6-tetrasubstituted tetrahydropyrans via Prins cyclization reaction (PCR) of optically active homoallylic alcohols with aldehydes
    • Kataoka, K.; Ode, Y.; Matsumoto, M.; Nokami, J. Convenient synthesis of highly optically active 2,3,4,6-tetrasubstituted tetrahydropyrans via Prins cyclization reaction (PCR) of optically active homoallylic alcohols with aldehydes Tetrahedron 2006, 62, 2471-2483
    • (2006) Tetrahedron , vol.62 , pp. 2471-2483
    • Kataoka, K.1    Ode, Y.2    Matsumoto, M.3    Nokami, J.4
  • 50
    • 64149115053 scopus 로고    scopus 로고
    • Stereoslective one-pot, three-component synthesis of 4- aryltetrahydropyran via Prins-Friedel-Craft reaction
    • Reddy, U. C.; Bondalapati, S.; Saikia, A. K. Stereoslective one-pot, three-component synthesis of 4-aryltetrahydropyran via Prins-Friedel-Craft reaction J. Org. Chem. 2009, 74, 2605-2608
    • (2009) J. Org. Chem. , vol.74 , pp. 2605-2608
    • Reddy, U.C.1    Bondalapati, S.2    Saikia, A.K.3
  • 51
    • 33751435646 scopus 로고    scopus 로고
    • Stereochemical Prins cyclization: Electronic versus steric effects on the synthesis of 2,4,6-trisubstituted tetrahydropyran rings
    • Chan, K.-P.; Seow, A.-H.; Loh, T.-P. Stereochemical Prins cyclization: electronic versus steric effects on the synthesis of 2,4,6-trisubstituted tetrahydropyran rings Tetrahedron Lett. 2007, 48, 37-41
    • (2007) Tetrahedron Lett. , vol.48 , pp. 37-41
    • Chan, K.-P.1    Seow, A.-H.2    Loh, T.-P.3
  • 52
    • 33847063493 scopus 로고    scopus 로고
    • Iodine as a versatile reagent for the Prins-cyclization: An expeditious synthesis of 4-iodotetrahydropyran derivatives
    • Yadav, J. S.; Reddy, B. V. S.; Kumar, G. G. K. S. N.; Swamy, T. Iodine as a versatile reagent for the Prins-cyclization: an expeditious synthesis of 4-iodotetrahydropyran derivatives Tetrahedron Lett. 2007, 48, 2205-2208
    • (2007) Tetrahedron Lett. , vol.48 , pp. 2205-2208
    • Yadav, J.S.1    Reddy, B.V.S.2    Kumar, G.G.K.S.N.3    Swamy, T.4
  • 53
    • 4043069147 scopus 로고    scopus 로고
    • Axial selective Prins cyclizations by solvolysis of α-bromo ethers
    • Jasti, R.; Vitale, J.; Rychnovsky, S. D. Axial selective Prins cyclizations by solvolysis of α-bromo ethers J. Am. Chem. Soc. 2004, 126, 9904-9905
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 9904-9905
    • Jasti, R.1    Vitale, J.2    Rychnovsky, S.D.3
  • 54
    • 0001126230 scopus 로고    scopus 로고
    • Lewis base-catalyzed, asymmetric aldol additions of methyl ketone enolates
    • Denmark, S. E.; Stavenger, R. A.; Wong, K.-T. Lewis base-catalyzed, asymmetric aldol additions of methyl ketone enolates J. Org. Chem. 1998, 63, 918-919
    • (1998) J. Org. Chem. , vol.63 , pp. 918-919
    • Denmark, S.E.1    Stavenger, R.A.2    Wong, K.-T.3
  • 55
    • 33847804804 scopus 로고
    • New cross-aldol reactions. Reactions of silyl enol ethers with carbonyl compounds activated by titanium tetrachloride
    • Mukaiyama, T.; Banno, K.; Narasaka, K. New cross-aldol reactions. Reactions of silyl enol ethers with carbonyl compounds activated by titanium tetrachloride J. Am. Chem. Soc. 1974, 27, 7503-7509
    • (1974) J. Am. Chem. Soc. , vol.27 , pp. 7503-7509
    • Mukaiyama, T.1    Banno, K.2    Narasaka, K.3
  • 57
    • 4644248174 scopus 로고    scopus 로고
    • Catalytic asymmetric allylation of ketones and a tandem asymmetric allylation/diastereoselective epoxidation of cyclic ketones
    • Kim, J. G.; Waltz, K. M.; Garcia, I. F.; Kwiatkowski, D.; Walsh, P. J. Catalytic asymmetric allylation of ketones and a tandem asymmetric allylation/diastereoselective epoxidation of cyclic ketones J. Am. Chem. Soc. 2004, 126, 12580-12585
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 12580-12585
    • Kim, J.G.1    Waltz, K.M.2    Garcia, I.F.3    Kwiatkowski, D.4    Walsh, P.J.5
  • 58
    • 0002313620 scopus 로고    scopus 로고
    • Chiral allylic and allenic stannanes as reagents for asymmetric synthesis
    • Marshall, J. A. Chiral allylic and allenic stannanes as reagents for asymmetric synthesis Chem. Rev. 1996, 96, 31-48
    • (1996) Chem. Rev. , vol.96 , pp. 31-48
    • Marshall, J.A.1
  • 59
    • 0037467855 scopus 로고    scopus 로고
    • Indium mediated allylation of carbonyl compounds with an allylic bromide in aqueous media: Anomalous syn -diastereoselectivity regardless of allylic bromide geometry
    • Loh, T.-P.; YZ.; Song, H.-Y.; Tan, K.-L. Indium mediated allylation of carbonyl compounds with an allylic bromide in aqueous media: Anomalous syn -diastereoselectivity regardless of allylic bromide geometry Tetrahedron Lett. 2003, 44, 911-914
    • (2003) Tetrahedron Lett. , vol.44 , pp. 911-914
    • Loh, T.-P.1    Yin, Z.2    Song, H.-Y.3    Tan, K.-L.4
  • 60
    • 0029933487 scopus 로고    scopus 로고
    • β with heteroatomic functional groups. Analysis of the modulation in diastereoselectivity attainable in aqueous, organic and mixed solvent systems
    • β with heteroatomic functional groups. Analysis of the modulation in diastereoselectivity attainable in aqueous, organic and mixed solvent systems J. Am. Chem. Soc. 1996, 118, 1931-1937
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 1931-1937
    • Paquette, L.A.1    Mitzel, T.M.2
  • 61
    • 0033543497 scopus 로고    scopus 로고
    • Organic synthesis using indium mediated and catalyzed reactions in aqueous media
    • Li, C. J.; Chan, T.-H. Organic synthesis using indium mediated and catalyzed reactions in aqueous media Tetrahedron 1999, 55, 11149-11176
    • (1999) Tetrahedron , vol.55 , pp. 11149-11176
    • Li, C.J.1    Chan, T.-H.2
  • 62
    • 33748699338 scopus 로고    scopus 로고
    • Synthetic use of molecular iodine for organic synthesis
    • Togo, H.; Lida, S. Synthetic use of molecular iodine for organic synthesis Synlett 2006, 2159-2175
    • (2006) Synlett , pp. 2159-2175
    • Togo, H.1    Lida, S.2
  • 63
    • 77952066771 scopus 로고    scopus 로고
    • COX-inhibitor screening assay kits (cat. no. 560101) were obtained from Cayman Chemical, and the standard protocol, as supplied along with the kit, was followed for evaluations of COX-1/2 inhibitory activities
    • COX-inhibitor screening assay kits (cat. no. 560101) were obtained from Cayman Chemical, and the standard protocol, as supplied along with the kit, was followed for evaluations of COX-1/2 inhibitory activities.
  • 64
    • 34247585524 scopus 로고    scopus 로고
    • 2,3,5-Substituted tetrahydrofurans as cancer chemopreventives. Part 1: Synthesis and anti-cancer activities of 5-hydroxymethyl-2,3-diary-tetrahydro- furan-3-ols
    • Singh, P.; Mittal, A.; Kumar, S. 2,3,5-Substituted tetrahydrofurans as cancer chemopreventives. Part 1: Synthesis and anti-cancer activities of 5-hydroxymethyl-2,3-diary-tetrahydro-furan-3-ols Bioorg. Med. Chem. 2007, 15, 3990-3996
    • (2007) Bioorg. Med. Chem. , vol.15 , pp. 3990-3996
    • Singh, P.1    Mittal, A.2    Kumar, S.3
  • 65
    • 0042825578 scopus 로고    scopus 로고
    • Nutritional and botanical modulation of the inflammatory cascade - Eicosanoids, cyclooxygenases and lipoxygenases - As an adjunct in cancer therapy
    • Wallace, J. M. Nutritional and botanical modulation of the inflammatory cascade - eicosanoids, cyclooxygenases and lipoxygenases - as an adjunct in cancer therapy Integr. Cancer Ther. 2002, 1, 7-37
    • (2002) Integr. Cancer Ther. , vol.1 , pp. 7-37
    • Wallace, J.M.1
  • 66
    • 70349134371 scopus 로고    scopus 로고
    • version 4.0.1; Thompson Planaria Software LLC: Seattle, WA
    • Mark, A. ArgusLab, version 4.0.1; Thompson Planaria Software LLC: Seattle, WA; http://www.arguslab.com.
    • ArgusLab
    • Mark, A.1
  • 67
    • 0006683046 scopus 로고    scopus 로고
    • version 7.1; Tripos Inc. (St. Louis, MO 63144-2913)
    • SYBYL Molecular Modeling System, version 7.1; Tripos Inc. (St. Louis, MO 63144-2913).
    • SYBYL Molecular Modeling System


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.