SCOPUS 정보 검색 플랫폼

Carbohydrate Research

Volumn 345, Issue 14, 2010, Pages 1988-1997

Regioselective facile one-pot Friedländer synthesis of sugar-based heterocyclic biomolecules

(4) Nagarajan, Subbiah a Arjun, Pandian a Raaman, Nanjian a Das, Thangamuthu Mohan a

a UNIVERSITY OF MADRAS (India)

Author keywords

C Glycosylic ketones; Antimicrobial activity; Friedl nder condensation; Naphthyridines; Quinolines; Xanthones

Indexed keywords

ANOMERICS; ANTI-MICROBIAL ACTIVITY; ANTIMICROBIAL STUDY; ELEMENTAL ANALYSIS; NAPHTHYRIDINE; NAPHTHYRIDINES; NMR SPECTROSCOPY; NMR STUDIES; ONE POT; ONE-POT SYNTHESIS; QUINOLINES; REGIO-SELECTIVE; SUGAR MOIETY; XANTHONES;

CONDENSATION; KETONES; MICROORGANISMS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SUGAR (SUCROSE); SYNTHESIS (CHEMICAL);

REGIOSELECTIVITY;

2 (2,3,4 TRI O ACETYL BETA DEXTRO XYLOPYRANOSYLMETHYL) 6,8 DIBROMOQUINOLINE; 2 (4,6 O BUTYLIDENE BETA DEXTRO GLUCOPYRANOSYLMETHYL) 10H CHROMENO[3,2 B]PYRIDIN 10 ONE; 2 (4,6 O BUTYLIDENE BETA DEXTRO GLUCOPYRANOSYLMETHYL) 6,8 DIBROMOQUINOLINE; 2 (BETA DEXTRO GALACTOPYRANOSYLMETHYL) 1,8 NAPHTHYRIDINE; 2 (BETA DEXTRO GALACTOPYRANOSYLMETHYL) 10H CHROMENO[3,2 B]PYRIDIN 10 ONE; 2 (BETA DEXTRO GLUCOPYRANOSYLMETHYL) 6,8 DIBROMOQUINOLINE; 2 (BETA DEXTRO XYLOPYRANOSYLMETHYL) 10H CHROMENO[3,2 B]PYRIDIN 10 ONE; ANTIINFECTIVE AGENT; HETEROCYCLIC COMPOUND; NAPHTHYRIDINE DERIVATIVE; QUINOLINE DERIVATIVE; SUGAR; UNCLASSIFIED DRUG; XANTHONE DERIVATIVE;

ANTIMICROBIAL ACTIVITY; ARTICLE; DRUG SYNTHESIS; MICROORGANISM; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ONE POT SYNTHESIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

ANTI-INFECTIVE AGENTS; GLYCOSIDES; LACTONES; MICROBIAL SENSITIVITY TESTS; NAPHTHYRIDINES; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; QUINOLINES; XANTHONES;

EID: 77956413825 PISSN: 00086215 EISSN: None Source Type: Journal
DOI: 10.1016/j.carres.2010.07.016 Document Type: Article

Times cited : (28)

References (52)

1
- 29244453496
- W.H. Chiou, S.Y. Lee, and I. Ojima Can. J. Chem. 83 2005 681 692
- (2005) Can. J. Chem. , vol.83 , pp. 681-692
- Chiou, W.H.¹ Lee, S.Y.² Ojima, I.³

2
- 0347418211
- C. Dong, and H. Alper Tetrahedron: Asymmetry 15 2004 35 40
- (2004) Tetrahedron: Asymmetry , vol.15 , pp. 35-40
- Dong, C.¹ Alper, H.²

3
- 37049132572
- S.I. Murahashi, T. Shimamura, and I. Moritani J. Chem. Soc., Chem. Commun. 1974 931
- (1974) J. Chem. Soc., Chem. Commun. , pp. 931
- Murahashi, S.I.¹ Shimamura, T.² Moritani, I.³

4
- 0033538639
- P. Evans, R. Grigg, and M. Monteith Tetrahedron Lett. 40 1999 5247 5250
- (1999) Tetrahedron Lett. , vol.40 , pp. 5247-5250
- Evans, P.¹ Grigg, R.² Monteith, M.³

5
- 33947093389
- L.S. Hegedus, G.F. Allen, J.J. Bozell, and E.L. Waterman J. Am. Chem. Soc. 100 1978 5800 5807
- (1978) J. Am. Chem. Soc. , vol.100 , pp. 5800-5807
- Hegedus, L.S.¹ Allen, G.F.² Bozell, J.J.³ Waterman, E.L.⁴

6
- 34848812921
- L. Lee, and W.D. Jones J. Am. Chem. Soc. 129 2007 10707 10713
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 10707-10713
- Lee, L.¹ Jones, W.D.²

7
- 52949090063
- S. Madapa, Z. Tusi, and S. Batra Curr. Org. Chem. 12 2008 1116 1183
- (2008) Curr. Org. Chem. , vol.12 , pp. 1116-1183
- Madapa, S.¹ Tusi, Z.² Batra, S.³

8
- 0027447599
- A. Fournet, A.F. Barrios, V. Munoz, R. Hocquemiller, A. Cave, and J. Bruneton Antimicrob. Agents Chemother. 37 1993 859 863
- (1993) Antimicrob. Agents Chemother. , vol.37 , pp. 859-863
- Fournet, A.¹ Barrios, A.F.² Munoz, V.³ Hocquemiller, R.⁴ Cave, A.⁵ Bruneton, J.⁶

9
- 0023087057
- J.H. Musser, U.R. Chakraborty, S. Sciortino, R.J. Gordon, A. Khandwala, E.S. Neiss, T.P. Pruss, R. Van Inwegen, I. Weinryb, and S.M. Coutts J. Med. Chem. 30 1987 96 104
- (1987) J. Med. Chem. , vol.30 , pp. 96-104
- Musser, J.H.¹ Chakraborty, U.R.² Sciortino, S.³ Gordon, R.J.⁴ Khandwala, A.⁵ Neiss, E.S.⁶ Pruss, T.P.⁷ Van Inwegen, R.⁸ Weinryb, I.⁹ Coutts, S.M.¹⁰

10
- 0023265333
- R.G. Van Inwegen, A. Khandwala, R. Gordon, P. Sonnino, S. Coutts, and S. Jolly J. Pharm. Exp. Ther. 24 1987 117 124
- (1987) J. Pharm. Exp. Ther. , vol.24 , pp. 117-124
- Van Inwegen, R.G.¹ Khandwala, A.² Gordon, R.³ Sonnino, P.⁴ Coutts, S.⁵ Jolly, S.⁶

11
- 0024996155
- J.Y. Gauthier, T. Jones, E. Champion, L. Charette, R. Dehaven, A.W. Ford-Hutchinson, K. Hoogsteen, A. Lord, P. Masson, H. Piechuta, S.S. Pong, J.P. Springer, M. Therien, R. Zamboni, and R.N. Young J. Med. Chem. 33 1990 2841 2845
- (1990) J. Med. Chem. , vol.33 , pp. 2841-2845
- Gauthier, J.Y.¹ Jones, T.² Champion, E.³ Charette, L.⁴ Dehaven, R.⁵ Ford-Hutchinson, A.W.⁶ Hoogsteen, K.⁷ Lord, A.⁸ Masson, P.⁹ Piechuta, H.¹⁰ Pong, S.S.¹¹ Springer, J.P.¹² Therien, M.¹³ Zamboni, R.¹⁴ Young, R.N.¹⁵

12
- 33846458645
- V.R. Solomon, W. Haq, K. Srivastava, S.K. Puri, and S.B. Katti J. Med. Chem. 50 2007 394 398
- (2007) J. Med. Chem. , vol.50 , pp. 394-398
- Solomon, V.R.¹ Haq, W.² Srivastava, K.³ Puri, S.K.⁴ Katti, S.B.⁵

13
- 0036157389
- I. Jacquemond-Collet, F. Benoit-Vical, A. Mustofa Valentin, E. Stanislas, and M. Malliae Planta Med. 68 2002 68 69
- (2002) Planta Med. , vol.68 , pp. 68-69
- Jacquemond-Collet, I.¹ Benoit-Vical, F.² Mustofa Valentin, A.³ Stanislas, E.⁴ Malliae, M.⁵

14
- 13844275052
- C. Theeraladanon, M. Arisawa, M. Nakagawa, and A. Nisshida Tetrahedron: Asymmetry 16 2005 827 831
- (2005) Tetrahedron: Asymmetry , vol.16 , pp. 827-831
- Theeraladanon, C.¹ Arisawa, M.² Nakagawa, M.³ Nisshida, A.⁴

15
- 0035811449
- Y.L. Chen, K.C. Fang, J.Y. Sheu, S.L. Hsu, and S.S. Tzeng J. Med. Chem. 44 2001 2374 2377
- (2001) J. Med. Chem. , vol.44 , pp. 2374-2377
- Chen, Y.L.¹ Fang, K.C.² Sheu, J.Y.³ Hsu, S.L.⁴ Tzeng, S.S.⁵

16
- 0033694467
- G. Roma, M.D. Braccio, G. Grossi, F. Mattioli, and M. Ghia Eur. J. Med. Chem. 35 2000 1021 1035
- (2000) Eur. J. Med. Chem. , vol.35 , pp. 1021-1035
- Roma, G.¹ Braccio, M.D.² Grossi, G.³ Mattioli, F.⁴ Ghia, M.⁵

17
- 0026420864
- A.K. Agarwal, and S.A. Jenekhe Macromolecules 24 1991 6806 6808
- (1991) Macromolecules , vol.24 , pp. 6806-6808
- Agarwal, A.K.¹ Jenekhe, S.A.²

18
- 0033517645
- X. Zhang, A.S. Shetty, and S.A. Jenekhe Macromolecules 32 1999 7422 7429
- (1999) Macromolecules , vol.32 , pp. 7422-7429
- Zhang, X.¹ Shetty, A.S.² Jenekhe, S.A.³

19
- 0003680332
- K.A. Jacobson, J.W. Daly, V. Manganiello, Springer New York
- K.A. Jacobson, J.W. Daly, V. Manganiello, Purines in Cellular Signaling: Targets for New Drugs 1990 Springer New York
- (1990) Purines in Cellular Signaling: Targets for New Drugs

20
- 0026611985
- P.J.M. Van Galen, G.L. Stiles, G. Michaels, and K.A. Jacobson Med. Res. Rev. 12 1992 423 471
- (1992) Med. Res. Rev. , vol.12 , pp. 423-471
- Van Galen, P.J.M.¹ Stiles, G.L.² Michaels, G.³ Jacobson, K.A.⁴

21
- 0026520040
- K.A. Jacobson, P.J.M. Van Galen, and M. Williams J. Med. Chem. 35 1992 407 422
- (1992) J. Med. Chem. , vol.35 , pp. 407-422
- Jacobson, K.A.¹ Van Galen, P.J.M.² Williams, M.³

22
- 0002569437
- D.K.J.E. Von Lubitz, and K.A. Jacobson L. Belardinelli, A. Pelleg, Adenosine and Adenine Nucleotides: from Molecular Biology to Integrative Physiology 1995 Kluwer Norwell, MA 489
- (1995) Adenosine and Adenine Nucleotides: From Molecular Biology to Integrative Physiology , pp. 489
- Von Lubitz, D.K.J.E.¹ Jacobson, K.A.²

23
- 0028183014
- B.B. Fredholm, M.P. Abbracchio, G. Burnstock, J.W. Daly, T.K. Harden, K.A. Jacobson, P. Leff, and M. Williams Pharmacol. Rev. 46 1994 143 156
- (1994) Pharmacol. Rev. , vol.46 , pp. 143-156
- Fredholm, B.B.¹ Abbracchio, M.P.² Burnstock, G.³ Daly, J.W.⁴ Harden, T.K.⁵ Jacobson, K.A.⁶ Leff, P.⁷ Williams, M.⁸

24
- 0023239461
- D. Ukena, R.A. Olsson, and J.W. Daly Can. J. Physiol. Pharmacol. 65 1987 365 376
- (1987) Can. J. Physiol. Pharmacol. , vol.65 , pp. 365-376
- Ukena, D.¹ Olsson, R.A.² Daly, J.W.³

25
- 0032497636
- J.E. van Muijlwik-Koezen, H. Timmerman, R. Link, H. van der Goot, and A.P. Ijzerman J. Med. Chem. 41 1998 3994 4000
- (1998) J. Med. Chem. , vol.41 , pp. 3994-4000
- Van Muijlwik-Koezen, J.E.¹ Timmerman, H.² Link, R.³ Van Der Goot, H.⁴ Ijzerman, A.P.⁵

26
- 0028100062
- C.E. Muller, B. Grahner, and D. Heber Pharmazie 49 1994 878 880
- (1994) Pharmazie , vol.49 , pp. 878-880
- Muller, C.E.¹ Grahner, B.² Heber, D.³

27
- 17144441273
- P.L. Ferrarini, C. Mori, C. Manera, A. Martinelli, F. Mori, G. Saccomanni, P. Barili, L. Betti, G. Giannaccini, L. Trincavelli, and A. Lucacchini J. Med. Chem. 43 2000 2814 2823
- (2000) J. Med. Chem. , vol.43 , pp. 2814-2823
- Ferrarini, P.L.¹ Mori, C.² Manera, C.³ Martinelli, A.⁴ Mori, F.⁵ Saccomanni, G.⁶ Barili, P.⁷ Betti, L.⁸ Giannaccini, G.⁹ Trincavelli, L.¹⁰ Lucacchini, A.¹¹

28
- 0034623853
- V. Peres, T.J. Nagem, and F.F. Oliveira Phytochemistry 55 2000 683 710
- (2000) Phytochemistry , vol.55 , pp. 683-710
- Peres, V.¹ Nagem, T.J.² Oliveira, F.F.³

29
- 11844302205
- M.K. Schwaebe, T.J. Moran, and J.P. Whitten Tetrahedron Lett. 46 2005 827 829
- (2005) Tetrahedron Lett. , vol.46 , pp. 827-829
- Schwaebe, M.K.¹ Moran, T.J.² Whitten, J.P.³

30
- 6344279799
- M. Kenji, A. Yukihiro, Y. Hong, O. Kenji, I. Tetsuro, T. Toshiyuki, K. Emi, I. Munekazu, and N. Yoshinori Bioorg. Med. Chem. 12 2004 5799 5806
- (2004) Bioorg. Med. Chem. , vol.12 , pp. 5799-5806
- Kenji, M.¹ Yukihiro, A.² Hong, Y.³ Kenji, O.⁴ Tetsuro, I.⁵ Toshiyuki, T.⁶ Emi, K.⁷ Munekazu, I.⁸ Yoshinori, N.⁹

31
- 0036973288
- M. Pedro, F. Cerqueira, M.E. Sousa, M.S.J. Nascimento, and M. Pinto Bioorg. Med. Chem. 10 2002 3725 3730
- (2002) Bioorg. Med. Chem. , vol.10 , pp. 3725-3730
- Pedro, M.¹ Cerqueira, F.² Sousa, M.E.³ Nascimento, M.S.J.⁴ Pinto, M.⁵

32
- 32244448009
- W. Mahabusarakam, W. Nuangnaowarat, and W.C. Taylor Phytochemistry 67 2006 470 474
- (2006) Phytochemistry , vol.67 , pp. 470-474
- Mahabusarakam, W.¹ Nuangnaowarat, W.² Taylor, W.C.³

33
- 0035048669
- C. Gnerre, U. Thull, P. Gailland, P.A. Carrupt, B. Testa, E. Fernandes, F. Silva, M. Pinto, M.M.M. Pinto, J.-L. Wolfender, L. Hostettmann, and G. Cruciani Helv. Chim. Acta 84 2001 552 570
- (2001) Helv. Chim. Acta , vol.84 , pp. 552-570
- Gnerre, C.¹ Thull, U.² Gailland, P.³ Carrupt, P.A.⁴ Testa, B.⁵ Fernandes, E.⁶ Silva, F.⁷ Pinto, M.⁸ Pinto, M.M.M.⁹ Wolfender, J.-L.¹⁰ Hostettmann, L.¹¹ Cruciani, G.¹²

34
- 0035812224
- S. Poondru, S. Zhou, J. Rake, G. Shackleton, T.H. Corbett, R. Parchment, and B.R. Jasti J. Chromatogr., B: Struct. Sci. 759 2001 175 178 and references cited therein
- (2001) J. Chromatogr., B: Struct. Sci. , vol.759 , pp. 175-178
- Poondru, S.¹ Zhou, S.² Rake, J.³ Shackleton, G.⁴ Corbett, T.H.⁵ Parchment, R.⁶ Jasti, B.R.⁷

35
- 33750526231
- A. Sousa, I.C.F.R. Ferreira, R. Calhelha, P.P. Andrade, P. Valentao, R. Seabra, L. Estevinho, A. Bento, and J.A. Alberto Pereira Bioorg. Med. Chem. 14 2006 8533 8538
- (2006) Bioorg. Med. Chem. , vol.14 , pp. 8533-8538
- Sousa, A.¹ Ferreira, I.C.F.R.² Calhelha, R.³ Andrade, P.P.⁴ Valentao, P.⁵ Seabra, R.⁶ Estevinho, L.⁷ Bento, A.⁸ Alberto Pereira, J.A.⁹

36
- 0036836956
- D.C. Rowley, M.S.T. Hansen, D. Rhodes, C.A. Sotriffer, H. Ni, J.A. McCammon, F.D. Bushman, and W. Fenical Bioorg. Med. Chem. 10 2002 3619 3625
- (2002) Bioorg. Med. Chem. , vol.10 , pp. 3619-3625
- Rowley, D.C.¹ Hansen, M.S.T.² Rhodes, D.³ Sotriffer, C.A.⁴ Ni, H.⁵ McCammon, J.A.⁶ Bushman, F.D.⁷ Fenical, W.⁸

37
- 85008006254
- Y. Hamada, and L. Takeuchi Chem. Pharm. Bull. 19 1971 1857 1862
- (1971) Chem. Pharm. Bull. , vol.19 , pp. 1857-1862
- Hamada, Y.¹ Takeuchi, L.²

38
- 33746001269
- F. von Nussbaum, M. Brands, B. Hinzen, S. Weigand, and D. Häbich Angew. Chem., Int. Ed. 45 2006 5072 5129
- (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 5072-5129
- Von Nussbaum, F.¹ Brands, M.² Hinzen, B.³ Weigand, S.⁴ Häbich, D.⁵

39
- 65449126627
- S. Nagarajan, and T. Mohan Das Carbohydr. Res. 334 2009 1028 1031
- (2009) Carbohydr. Res. , vol.334 , pp. 1028-1031
- Nagarajan, S.¹ Mohan Das, T.²

40
- 67649723111
- S. Nagarajan, T. Mohan Das, P. Arjun, and N. Raaman J. Mater. Chem. 19 2009 4587 4596
- (2009) J. Mater. Chem. , vol.19 , pp. 4587-4596
- Nagarajan, S.¹ Mohan Das, T.² Arjun, P.³ Raaman, N.⁴

41
- 77953324693
- S. Nagarajan, P. Ravinder, V. Subramanian, and T. Mohan Das New J. Chem. 34 2010 123 131
- (2010) New J. Chem. , vol.34 , pp. 123-131
- Nagarajan, S.¹ Ravinder, P.² Subramanian, V.³ Mohan Das, T.⁴

42
- 73449142823
- S. Nagarajan, and T. Mohan Das New J. Chem. 33 2009 2391 2396
- (2009) New J. Chem. , vol.33 , pp. 2391-2396
- Nagarajan, S.¹ Mohan Das, T.²

43
- 67651172851
- K. Karthik Kumar, M. Elango, V. Subramanian, and T. Mohan Das New J. Chem. 33 2009 1570 1577
- (2009) New J. Chem. , vol.33 , pp. 1570-1577
- Karthik Kumar, K.¹ Elango, M.² Subramanian, V.³ Mohan Das, T.⁴

44
- 77953323525
- S. Nagarajan, K. Anupa, V. Babu, and T. Mohan Das Carbohydr. Res. 345 2010 1077 1083
- (2010) Carbohydr. Res. , vol.345 , pp. 1077-1083
- Nagarajan, S.¹ Anupa, K.² Babu, V.³ Mohan Das, T.⁴

45
- 0000576905
- R.L. Mellis, C.L. Mehltretter, and C.E. Rist J. Am. Chem. Soc. 73 1951 294 296
- (1951) J. Am. Chem. Soc. , vol.73 , pp. 294-296
- Mellis, R.L.¹ Mehltretter, C.L.² Rist, C.E.³

46
- 37049042379
- T.G. Bonner, E.J. Bourne, and D. Lewis J. Chem. Soc. 1965 7453 7458
- (1965) J. Chem. Soc. , pp. 7453-7458
- Bonner, T.G.¹ Bourne, E.J.² Lewis, D.³

47
- 17144423235
- N. Bragnier, and M.-C. Scherrmann Synthesis 5 2005 814 818
- (2005) Synthesis , vol.5 , pp. 814-818
- Bragnier, N.¹ Scherrmann, M.-C.²

48
- 0034699895
- F. Rodrigues, Y. Canac, and A. Lubineau Chem. Commun. (Cambridge) 2000 2049 2050
- (2000) Chem. Commun. (Cambridge) , pp. 2049-2050
- Rodrigues, F.¹ Canac, Y.² Lubineau, A.³

49
- 0036303578
- I. Riemann, M.A. Papadopoulos, M. Knorst, and W.D. Fessner Aust. J. Chem. 55 2002 147 154
- (2002) Aust. J. Chem. , vol.55 , pp. 147-154
- Riemann, I.¹ Papadopoulos, M.A.² Knorst, M.³ Fessner, W.D.⁴

50
- 0141741623
- Y.-Z. Hu, G. Zhang, and R.P. Thummel Org. Lett. 5 2003 2251 2253
- (2003) Org. Lett. , vol.5 , pp. 2251-2253
- Hu, Y.-Z.¹ Zhang, G.² Thummel, R.P.³

51
- 52649161380
- C. Palomo, J.M. Aizpurua, E. Balentova, I. Azcune, J.I. Santos, J. Jimenez-Barbero, J. Canada, and J.I. Miranda Org. Lett. 10 2008 2227 2230
- (2008) Org. Lett. , vol.10 , pp. 2227-2230
- Palomo, C.¹ Aizpurua, J.M.² Balentova, E.³ Azcune, I.⁴ Santos, J.I.⁵ Jimenez-Barbero, J.⁶ Canada, J.⁷ Miranda, J.I.⁸

52
- 0000200150
- C. Perez, M. Pauli, and P. Bazerque Acta Biol. Med. Exp. 15 1990 113 115
- (1990) Acta Biol. Med. Exp. , vol.15 , pp. 113-115
- Perez, C.¹ Pauli, M.² Bazerque, P.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.