메뉴 건너뛰기




Volumn 50, Issue 7, 2007, Pages 1528-1536

Synthesis and anti-cancer activity of C-ring-functionalized prodigiosin analogues

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE; ESTER; ETHYL 5 [3 METHOXY 5 (1H PYRROL 2 YL)METHYLENE] 2,4 DIMETHYL 5H PYRROLE 3 CARBOXYLATE; PRODIGIOSIN; UNCLASSIFIED DRUG;

EID: 34147186738     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm061088f     Document Type: Article
Times cited : (69)

References (49)
  • 1
    • 0000487689 scopus 로고    scopus 로고
    • Synthesis, proton-affinity and anti-cancer properties of the prodigiosin-group natural products
    • Manderville, R. A. Synthesis, proton-affinity and anti-cancer properties of the prodigiosin-group natural products. Curr. Med. Chem.: Anti-Cancer Agents 2001, 1, 195-218.
    • (2001) Curr. Med. Chem.: Anti-Cancer Agents , vol.1 , pp. 195-218
    • Manderville, R.A.1
  • 2
    • 0037303304 scopus 로고    scopus 로고
    • Montaner, B.; Pérez,-Tomás, R. The prodigiosins: a new family of anticancer drugs. Curr. Cancer Drug Targets 2003, 3, 57-65.
    • Montaner, B.; Pérez,-Tomás, R. The prodigiosins: a new family of anticancer drugs. Curr. Cancer Drug Targets 2003, 3, 57-65.
  • 3
    • 17744417463 scopus 로고    scopus 로고
    • Chemistry and biology of roseophilin and the prodigiosin alkaloids: A survey of the last 2500 years
    • Fürstner, A. Chemistry and biology of roseophilin and the prodigiosin alkaloids: a survey of the last 2500 years. Angew. Chem., Int. Ed. 2003, 42, 3582-3603.
    • (2003) Angew. Chem., Int. Ed , vol.42 , pp. 3582-3603
    • Fürstner, A.1
  • 4
    • 0032555603 scopus 로고    scopus 로고
    • Prodigiosins as a new group of H+/CI- symporters that uncouple proton translocators
    • Sato, T.; Konno, H.; Tanaka, Y.; Kataoka, T.; Nagai, K.; et al. Prodigiosins as a new group of H+/CI- symporters that uncouple proton translocators. J. Biol. Chem. 1998, 273, 21455-21462.
    • (1998) J. Biol. Chem , vol.273 , pp. 21455-21462
    • Sato, T.1    Konno, H.2    Tanaka, Y.3    Kataoka, T.4    Nagai, K.5
  • 5
    • 27644474427 scopus 로고    scopus 로고
    • Non-apoptotic concentrations of prodigiosin (H+/CI- symporter) inhibit the acidification of lysosomes and induce cell cycle blockage in colon cancer cells
    • Castillo-Avila, W.: Abal, M.; Robine. S.; Perez-Tomas. R. Non-apoptotic concentrations of prodigiosin (H+/CI- symporter) inhibit the acidification of lysosomes and induce cell cycle blockage in colon cancer cells. Life Sci. 2005, 78, 121-127.
    • (2005) Life Sci , vol.78 , pp. 121-127
    • Castillo-Avila, W.1    Abal, M.2    Robine, S.3    Perez-Tomas, R.4
  • 6
    • 0033856757 scopus 로고    scopus 로고
    • Cycloprodigiosin hydrochloride, a H+/CI- symporter, induces apoptosis and differentiation in HL-60 cell lines
    • Yamamoto, D.; Uemura, Y.; Tanaka, K.; Nakai, K.; Yamamoto, C.; et al. Cycloprodigiosin hydrochloride, a H+/CI- symporter, induces apoptosis and differentiation in HL-60 cell lines. Int. J. Cancer 2000, 88, 121-128.
    • (2000) Int. J. Cancer , vol.88 , pp. 121-128
    • Yamamoto, D.1    Uemura, Y.2    Tanaka, K.3    Nakai, K.4    Yamamoto, C.5
  • 7
    • 0034068796 scopus 로고    scopus 로고
    • Cycloprodigiosin hydrochloride, a H(+)/CI(-) symporter, induces apoptosis in human breast cancer cell lines
    • Yamamoto, D.; Kiyozuka, Y.; Uemura, Y.; Yamamoto, C.; Takemoto, H.; et al. Cycloprodigiosin hydrochloride, a H(+)/CI(-) symporter, induces apoptosis in human breast cancer cell lines. J. Cancer Rex. Clin. Oncol. 2000, 126, 191-197.
    • (2000) J. Cancer Rex. Clin. Oncol , vol.126 , pp. 191-197
    • Yamamoto, D.1    Kiyozuka, Y.2    Uemura, Y.3    Yamamoto, C.4    Takemoto, H.5
  • 8
    • 0032860986 scopus 로고    scopus 로고
    • Cycloprodigiosin hydrochloride, a new H(+)/CI(-) symporter, induces apoptosis in human and rat hepatocellular cancer cell lines in vitro and inhibits the growth of hepatocellular carcinoma xenografts in nude mice
    • Yamamoto, C.; Takemoto, H.; Kuno, K.; Yamamoto. D.; Tsubura, A.; et al. Cycloprodigiosin hydrochloride, a new H(+)/CI(-) symporter, induces apoptosis in human and rat hepatocellular cancer cell lines in vitro and inhibits the growth of hepatocellular carcinoma xenografts in nude mice. Hepatology 1999, 30, 894-902.
    • (1999) Hepatology , vol.30 , pp. 894-902
    • Yamamoto, C.1    Takemoto, H.2    Kuno, K.3    Yamamoto, D.4    Tsubura, A.5
  • 9
    • 29744433479 scopus 로고    scopus 로고
    • Prodigiosin is a chloride carrier that can function as an anion exchanger
    • Seganish, J. L.; Davis, J. T. Prodigiosin is a chloride carrier that can function as an anion exchanger. Chem. Commun. 2005, 5781-5783.
    • (2005) Chem. Commun , pp. 5781-5783
    • Seganish, J.L.1    Davis, J.T.2
  • 10
    • 20544435208 scopus 로고    scopus 로고
    • DNA interaction and dual topoisomerase I and II inhibition properties of the anti-tumor drug prodigiosin
    • Montaner, B.; Castillo-Avila, W.; Martinell, M.; Oellinger, R.; Aymami, J.; et al. DNA interaction and dual topoisomerase I and II inhibition properties of the anti-tumor drug prodigiosin. Toxicol. Sci. 2005, 85, 870-879.
    • (2005) Toxicol. Sci , vol.85 , pp. 870-879
    • Montaner, B.1    Castillo-Avila, W.2    Martinell, M.3    Oellinger, R.4    Aymami, J.5
  • 11
    • 0035802124 scopus 로고    scopus 로고
    • Studies on DNA cleavage by cytotoxic pyrrole alkaloids reveal the distinctly different behavior of roseophilin and prodigiosin derivatives
    • Fürstner, A.; Grabowski, E. J. Studies on DNA cleavage by cytotoxic pyrrole alkaloids reveal the distinctly different behavior of roseophilin and prodigiosin derivatives. ChemBioChem 2001, 2, 706-709.
    • (2001) ChemBioChem , vol.2 , pp. 706-709
    • Fürstner, A.1    Grabowski, E.J.2
  • 12
    • 0036096264 scopus 로고    scopus 로고
    • Influence of the A-ring on the redox and nuclease properties of the prodigiosins: Importance of the bipyrrole moiety in oxidative DNA cleavage
    • Melvin, M. S.; Calcutt, M. W.; Noftlet, R. E.; Manderville, R. A. Influence of the A-ring on the redox and nuclease properties of the prodigiosins: importance of the bipyrrole moiety in oxidative DNA cleavage. Chem. Res. Toxicol. 2002, 15, 742-748.
    • (2002) Chem. Res. Toxicol , vol.15 , pp. 742-748
    • Melvin, M.S.1    Calcutt, M.W.2    Noftlet, R.E.3    Manderville, R.A.4
  • 13
    • 0032885667 scopus 로고    scopus 로고
    • DNA binding by 4-methoxypyrrolic natural products. Preference for intercalation at AT sites by tambjamine E and prodigiosin
    • Melvin. M. S.; Ferguson, D. C.; Lindquist, N.; Manderville, R. A. DNA binding by 4-methoxypyrrolic natural products. Preference for intercalation at AT sites by tambjamine E and prodigiosin. J. Org. Chem. 1999, 64, 6861-6869.
    • (1999) J. Org. Chem , vol.64 , pp. 6861-6869
    • Melvin, M.S.1    Ferguson, D.C.2    Lindquist, N.3    Manderville, R.A.4
  • 14
    • 0036095547 scopus 로고    scopus 로고
    • Influence of the A-ring on the proton affinity and anticancer properties of the prodigiosins
    • Melvin, M. S.; Tomlinson, J. T.; Park, G.; Day, C. S.; Saluta, G. R.; et al. Influence of the A-ring on the proton affinity and anticancer properties of the prodigiosins. Chem. Res. Toxicol. 2002, 15, 734-741.
    • (2002) Chem. Res. Toxicol , vol.15 , pp. 734-741
    • Melvin, M.S.1    Tomlinson, J.T.2    Park, G.3    Day, C.S.4    Saluta, G.R.5
  • 16
    • 0035197804 scopus 로고    scopus 로고
    • Copper-nuclease efficiency correlates with cytotoxicity for the 4-methoxypyrrolic natural products
    • Melvin, M. S.; Wooton, K. E.; Rich, C. C.; Saluta, G. R.: Kucera, G. L.; et al. Copper-nuclease efficiency correlates with cytotoxicity for the 4-methoxypyrrolic natural products. J. Inorg. Biochem. 2001, 87, 129-135.
    • (2001) J. Inorg. Biochem , vol.87 , pp. 129-135
    • Melvin, M.S.1    Wooton, K.E.2    Rich, C.C.3    Saluta, G.R.4    Kucera, G.L.5
  • 17
    • 0038341812 scopus 로고    scopus 로고
    • Zinc and copper complexes of prodigiosin: Implications for copper-mediated double-strand DNA cleavage
    • Park, G.; Tomlinson, J. T.; Melvin, M. S.; Wright, M. W.; Day, C. S.; et al. Zinc and copper complexes of prodigiosin: implications for copper-mediated double-strand DNA cleavage. Org. Lett. 2003, 5, 113-116.
    • (2003) Org. Lett , vol.5 , pp. 113-116
    • Park, G.1    Tomlinson, J.T.2    Melvin, M.S.3    Wright, M.W.4    Day, C.S.5
  • 18
    • 0014703256 scopus 로고
    • Prodigiosene [5-(2-pyrryl)-2,2'-dipyrrylmethene] and some substitited prodigiosenes
    • Hearn, W. R.; Elson, M. K.; Williams, R. H.; Medina-Castro, J. Prodigiosene [5-(2-pyrryl)-2,2'-dipyrrylmethene] and some substitited prodigiosenes. J. Org. Chem. 1970, 35, 142-146.
    • (1970) J. Org. Chem , vol.35 , pp. 142-146
    • Hearn, W.R.1    Elson, M.K.2    Williams, R.H.3    Medina-Castro, J.4
  • 19
    • 33646828179 scopus 로고    scopus 로고
    • Cytotoxic proteins combined with prodigiosin obtained from Serratia marcescens have both broad and selective cytotoxic activity on tumor cells
    • Abrahantes-Perez, M. C.; Reyes-Gonzalez, J.; Rios, G. V.; Bequet-Romero, M.; Riera, R. G.; et al. Cytotoxic proteins combined with prodigiosin obtained from Serratia marcescens have both broad and selective cytotoxic activity on tumor cells. J. Chemother. 2006, 18, 172-181.
    • (2006) J. Chemother , vol.18 , pp. 172-181
    • Abrahantes-Perez, M.C.1    Reyes-Gonzalez, J.2    Rios, G.V.3    Bequet-Romero, M.4    Riera, R.G.5
  • 20
    • 33750369211 scopus 로고    scopus 로고
    • Photoinduced cytotoxicity and thioadduct formation by a prodigiosin analog
    • Tomlinson, J. T.; Park, G.; Misenheimer, J. A.; Kucera, G. L.; Hesp, K.; et al. Photoinduced cytotoxicity and thioadduct formation by a prodigiosin analog. Org. Lett. 2006, 8, 4951-4954.
    • (2006) Org. Lett , vol.8 , pp. 4951-4954
    • Tomlinson, J.T.1    Park, G.2    Misenheimer, J.A.3    Kucera, G.L.4    Hesp, K.5
  • 21
    • 33749512427 scopus 로고    scopus 로고
    • Protein assembly line components in prodigiosin biosynthesis: Characterization of PigA,G,H,I.J
    • Garneau-Tsodikova, S.; Dorrestein, P. C.: Kelleher, N. L.; Walsh, C. T. Protein assembly line components in prodigiosin biosynthesis: characterization of PigA,G,H,I.J. J. Am. Chem. Soc. 2006, 128, 12600-12601.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 12600-12601
    • Garneau-Tsodikova, S.1    Dorrestein, P.C.2    Kelleher, N.L.3    Walsh, C.T.4
  • 22
    • 34147163576 scopus 로고    scopus 로고
    • Rioux, E.; Billot, X.; Dairi, K.; Gonzalez, G.; Lavallée, J.-F.; et al. SAR study on aryl and heteroaryl bipyrrole inhibitors of Bcl antiapoptotic proteins and potent antitumor activity in vivo. J. Mex. Chem. Soc. (IUPAC-ICOS-16 special issue) 2006, 50, 209.
    • Rioux, E.; Billot, X.; Dairi, K.; Gonzalez, G.; Lavallée, J.-F.; et al. SAR study on aryl and heteroaryl bipyrrole inhibitors of Bcl antiapoptotic proteins and potent antitumor activity in vivo. J. Mex. Chem. Soc. (IUPAC-ICOS-16 special issue) 2006, 50, 209.
  • 23
    • 33644898091 scopus 로고    scopus 로고
    • Two-step synthesis of the bipyrrole precursor of prodigiosins
    • Dairi, K.; Tripathy, S.; Attardo, G.; Lavallée. J.-F. Two-step synthesis of the bipyrrole precursor of prodigiosins. Tetrahedron Lett. 2006, 47, 2605-2606.
    • (2006) Tetrahedron Lett , vol.47 , pp. 2605-2606
    • Dairi, K.1    Tripathy, S.2    Attardo, G.3    Lavallée, J.-F.4
  • 24
    • 29544435126 scopus 로고    scopus 로고
    • Indoloprodigiosins from the C-10 bipyrrolic precursor: New antiproliferative prodigiosin analogs
    • Baldino, C. M.; Parr, J.; Wilson, C. J.; Ng, S.-C; Yohannes, D.; et al. Indoloprodigiosins from the C-10 bipyrrolic precursor: New antiproliferative prodigiosin analogs. Bioorg. Med Chem. Lett. 2006, 16, 701-704.
    • (2006) Bioorg. Med Chem. Lett , vol.16 , pp. 701-704
    • Baldino, C.M.1    Parr, J.2    Wilson, C.J.3    Ng, S.-C.4    Yohannes, D.5
  • 25
    • 0033595888 scopus 로고    scopus 로고
    • Pyrrole-singlet oxygen reactions leading to a,a'-bipyrroles. Synthesis of prodigiosin and analogs
    • Wasserman, H. H.; Petersen, A. K.; Xia, M.; Wang, J. Pyrrole-singlet oxygen reactions leading to a,a'-bipyrroles. Synthesis of prodigiosin and analogs. Tetrahedron Lett. 1999, 40, 7587-7589.
    • (1999) Tetrahedron Lett , vol.40 , pp. 7587-7589
    • Wasserman, H.H.1    Petersen, A.K.2    Xia, M.3    Wang, J.4
  • 26
    • 3342931241 scopus 로고    scopus 로고
    • Singlet oxygen reactions of 3-methoxy-2-pyrrole carboxylic acid tert-butyl esters. A route to 5-substituted pyrrole precursors of prodigiosin and analogs
    • Wasserman, H. H.; Xia, M.; Wang, J.; Petersen, A. K.; Jorgensen, M.; et al. Singlet oxygen reactions of 3-methoxy-2-pyrrole carboxylic acid tert-butyl esters. A route to 5-substituted pyrrole precursors of prodigiosin and analogs. Tetrahedron 2004, 60, 7419-7425.
    • (2004) Tetrahedron , vol.60 , pp. 7419-7425
    • Wasserman, H.H.1    Xia, M.2    Wang, J.3    Petersen, A.K.4    Jorgensen, M.5
  • 28
    • 23744434373 scopus 로고    scopus 로고
    • Amidopyrroles: From anion receptors to membrane transport agents
    • Gale, P. A. Amidopyrroles: from anion receptors to membrane transport agents. Chem. Commun. 2005, 3761-3772.
    • (2005) Chem. Commun , pp. 3761-3772
    • Gale, P.A.1
  • 29
    • 33646460395 scopus 로고    scopus 로고
    • Synthesis and anion binding properties of N,N'-bispyrrol-2-yl-2,5-diamidopyrrole
    • Sessler, J. L.; Pantos, G. D.; Gale, P. A.; Light, M. E. Synthesis and anion binding properties of N,N'-bispyrrol-2-yl-2,5-diamidopyrrole. Org. Lett. 2006, 8, 1593-1596.
    • (2006) Org. Lett , vol.8 , pp. 1593-1596
    • Sessler, J.L.1    Pantos, G.D.2    Gale, P.A.3    Light, M.E.4
  • 30
    • 33846161944 scopus 로고    scopus 로고
    • 4-Alkoxy- and 4-amino-2-2'-bipyrrole synthesis
    • Jolicoeur, B.; Lubell, W. D. 4-Alkoxy- and 4-amino-2-2'-bipyrrole synthesis. Org. Lett. 2006, 8, 6107-6110.
    • (2006) Org. Lett , vol.8 , pp. 6107-6110
    • Jolicoeur, B.1    Lubell, W.D.2
  • 31
    • 0034729730 scopus 로고    scopus 로고
    • Synthesis and immunosuppressive activity of novel prodigiosin derivatives
    • D'Alessio, R.; Bargiotti, A.; Carlini, O.; Colotta, F.; Ferrari, M.; et al. Synthesis and immunosuppressive activity of novel prodigiosin derivatives. J. Med. Chem. 2000, 43, 2557-2565.
    • (2000) J. Med. Chem , vol.43 , pp. 2557-2565
    • D'Alessio, R.1    Bargiotti, A.2    Carlini, O.3    Colotta, F.4    Ferrari, M.5
  • 32
    • 25144509595 scopus 로고    scopus 로고
    • Synthesis, anion-binding properties, and in vitro anticancer activity of prodigiosin analogues
    • Sessler, J. L.; Eller, L. R.; Cho, W.-S.; Nicolaou, S.; Aguilar, A. L., J. T.; et al. Synthesis, anion-binding properties, and in vitro anticancer activity of prodigiosin analogues. Angew. Chem., Int. Ed. 2005, 44, 5989-5992.
    • (2005) Angew. Chem., Int. Ed , vol.44 , pp. 5989-5992
    • Sessler, J.L.1    Eller, L.R.2    Cho, W.-S.3    Nicolaou, S.4    Aguilar, A.L.J.T.5
  • 33
    • 34147174479 scopus 로고    scopus 로고
    • Targeted chimeric molecules for cancer therapy comprising a targeting moiety and an anti-cell proliferation moiety
    • PCT Int. Appl. WO 2006074451 A2 20060713
    • Rosenblum, M. G.; Ellington, A. D. Targeted chimeric molecules for cancer therapy comprising a targeting moiety and an anti-cell proliferation moiety. PCT Int. Appl. WO 2006074451 A2 20060713, 2006.
    • (2006)
    • Rosenblum, M.G.1    Ellington, A.D.2
  • 34
    • 0001750476 scopus 로고    scopus 로고
    • Short synthesis of undecylprodigiosin. A new route to 2,2'-bipyrrolyl-pyrromethylene systems
    • D'Alessio, R.; Rossi, A. Short synthesis of undecylprodigiosin. A new route to 2,2'-bipyrrolyl-pyrromethylene systems. Synlett 1996, 6, 513-514.
    • (1996) Synlett , vol.6 , pp. 513-514
    • D'Alessio, R.1    Rossi, A.2
  • 35
    • 37049135531 scopus 로고
    • A synthesis of 2,6-diacetyldeuterioporphyrin II dimethyl ester
    • Davies, J. L. A synthesis of 2,6-diacetyldeuterioporphyrin II dimethyl ester. J. Chem. Soc. C 1968, 1392-1396.
    • (1968) J. Chem. Soc. C , pp. 1392-1396
    • Davies, J.L.1
  • 36
    • 0000832208 scopus 로고
    • Synthesis of 5-substituted 4-O-methyl tetramates
    • Jones, R. C. F.; Bates, A. D. Synthesis of 5-substituted 4-O-methyl tetramates. Tetrahedron Lett. 1986, 27, 5285-5288.
    • (1986) Tetrahedron Lett , vol.27 , pp. 5285-5288
    • Jones, R.C.F.1    Bates, A.D.2
  • 38
    • 0026573801 scopus 로고
    • Methyl (E)-4-chloro-3- methoxy-2-butenoate: An extremely versatile four carbon building block
    • Due, L.; McGarrity, J. F.; Meul, T.; Warm, A. Methyl (E)-4-chloro-3- methoxy-2-butenoate: an extremely versatile four carbon building block. Synthesis 1992, 391-394.
    • (1992) Synthesis , pp. 391-394
    • Due, L.1    McGarrity, J.F.2    Meul, T.3    Warm, A.4
  • 39
    • 0006860745 scopus 로고
    • Syntheses of protoporphyrin IX analogues bearing acetic and butyric side chains
    • Smith, K. M.; Eivazi, F.; Martynenko, Z. Syntheses of protoporphyrin IX analogues bearing acetic and butyric side chains. J. Org. Chem. 1981, 46, 2189-2193.
    • (1981) J. Org. Chem , vol.46 , pp. 2189-2193
    • Smith, K.M.1    Eivazi, F.2    Martynenko, Z.3
  • 41
    • 84971036320 scopus 로고
    • Chemistry of pyrrolic compounds. VII. Synthesis of 5,5'-diformyldipyrrylmethanes
    • Chong, R.; Clezy, P. S.; Liepa, A. J.; Nichol, A. W. Chemistry of pyrrolic compounds. VII. Synthesis of 5,5'-diformyldipyrrylmethanes. Aust. J. Chem. 1969, 22, 229-238.
    • (1969) Aust. J. Chem , vol.22 , pp. 229-238
    • Chong, R.1    Clezy, P.S.2    Liepa, A.J.3    Nichol, A.W.4
  • 42
    • 37049081932 scopus 로고
    • Synthesis and inhibitory properties of alpha-(chlorofluoromethyl) a-amino acids, a novel class of irreversible inactivators of decarboxylases
    • Schirlin, D.; Ducep, J. B.; Baltzer, S.; Bey, P.; Piriou, F.; et al. Synthesis and inhibitory properties of alpha-(chlorofluoromethyl) a-amino acids, a novel class of irreversible inactivators of decarboxylases. J. Chem. Soc., Perkin Trans. 1992, 1, 1053-1064.
    • (1992) J. Chem. Soc., Perkin Trans , vol.1 , pp. 1053-1064
    • Schirlin, D.1    Ducep, J.B.2    Baltzer, S.3    Bey, P.4    Piriou, F.5
  • 43
    • 33845423856 scopus 로고    scopus 로고
    • Microwave-accelerated synthesis of benzyl 3,5-dimethyl-pyrrole-2-carboxylate
    • Regourd, J.; Comeau, I. M.; Beshara, C. S.; Thompson, A. Microwave-accelerated synthesis of benzyl 3,5-dimethyl-pyrrole-2-carboxylate. J. Heterocycl. Chem. 2006, 43, 1709-1714.
    • (2006) J. Heterocycl. Chem , vol.43 , pp. 1709-1714
    • Regourd, J.1    Comeau, I.M.2    Beshara, C.S.3    Thompson, A.4
  • 44
    • 0343772050 scopus 로고
    • Improved synthesis of covalemly strapped porphyrins. Application to highly deformed porphyrin synthesis
    • Wijesekera, T. P.; Paine, J. B., III; Dolphin, D. Improved synthesis of covalemly strapped porphyrins. Application to highly deformed porphyrin synthesis. J. Org. Chem. 1988, 53, 1345-1352.
    • (1988) J. Org. Chem , vol.53 , pp. 1345-1352
    • Wijesekera, T.P.1    Paine III, J.B.2    Dolphin, D.3
  • 46
    • 17744373696 scopus 로고    scopus 로고
    • Stereochemically stable double-helicate dinuclear complexes of bis(dipyrromethene)s: A chiroptical study
    • Wood, T. E.; Dalgleish, N. D.; Power, E. D.; Thompson, A.; Chen, X.; et al. Stereochemically stable double-helicate dinuclear complexes of bis(dipyrromethene)s: a chiroptical study. J. Am. Chem. Soc. 2005, 127, 5740-5741.
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 5740-5741
    • Wood, T.E.1    Dalgleish, N.D.2    Power, E.D.3    Thompson, A.4    Chen, X.5
  • 47
    • 33845279106 scopus 로고
    • Total synthesis of prodigiosin, prodigiosene, and desmethoxyprodigiosin: Diels-Alder reactions of heterocyclic azadienes and development of an effective palladium(II)-promoted 2,2'-bipyrrole coupling procedure
    • Boger, D. L.; Patel, M. Total synthesis of prodigiosin, prodigiosene, and desmethoxyprodigiosin: Diels-Alder reactions of heterocyclic azadienes and development of an effective palladium(II)-promoted 2,2'-bipyrrole coupling procedure. J. Org. Chem. 1988, 53, 1405-1415.
    • (1988) J. Org. Chem , vol.53 , pp. 1405-1415
    • Boger, D.L.1    Patel, M.2
  • 48
    • 0007384331 scopus 로고
    • New synthesis of beta-keto esters of the type RCOCH2CO2Et
    • Breslow, D. S.; Baumgarten, E.; Hauser, C. R. New synthesis of beta-keto esters of the type RCOCH2CO2Et. J. Am. Chem. Soc. 1944, 66, 1286-1288.
    • (1944) J. Am. Chem. Soc , vol.66 , pp. 1286-1288
    • Breslow, D.S.1    Baumgarten, E.2    Hauser, C.R.3
  • 49
    • 4444225021 scopus 로고    scopus 로고
    • Design, synthesis, and evaluation of aza inhibitors of chorismate mutase
    • Hediger, M. E. Design, synthesis, and evaluation of aza inhibitors of chorismate mutase. Bioorg. Med. Chem. 2004, 12, 4995-5010.
    • (2004) Bioorg. Med. Chem , vol.12 , pp. 4995-5010
    • Hediger, M.E.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.