메뉴 건너뛰기




Volumn 13, Issue 1, 2011, Pages 65-71

Natural product inspired diversity oriented synthesis of tetrahydroquinoline scaffolds as antitubercular agent

Author keywords

Antitubercular agent; Benzopyran; Cellulose sulfuric acid; Diversity oriented synthesis; Natural product inspired synthesis; Tetrahydroquinoline

Indexed keywords

1,2,3,4 TETRAHYDROQUINOLINE; 1,2,3,4-TETRAHYDROQUINOLINE; BIOLOGICAL PRODUCT; QUINOLINE DERIVATIVE; TUBERCULOSTATIC AGENT;

EID: 78651436768     PISSN: 21568952     EISSN: None     Source Type: Journal    
DOI: 10.1021/co100022h     Document Type: Article
Times cited : (108)

References (45)
  • 1
    • 33846211453 scopus 로고    scopus 로고
    • Structure-Based Organic Synthesis of Drug Prototypes: A Personal Odyssey
    • Hanessian, S. Structure-Based Organic Synthesis of Drug Prototypes: A Personal Odyssey Chem. Med. Chem. 2006, 1, 1300-1330
    • (2006) Chem. Med. Chem. , vol.1 , pp. 1300-1330
    • Hanessian, S.1
  • 2
    • 34247109045 scopus 로고    scopus 로고
    • Natural Products as Sources of New Drugs over the Last 25 Years
    • Newman, D. J.; Cragg, G. M. Natural Products as Sources of New Drugs over the Last 25 Years J. Nat. Prod. 2007, 70, 461-477
    • (2007) J. Nat. Prod. , vol.70 , pp. 461-477
    • Newman, D.J.1    Cragg, G.M.2
  • 3
    • 58149358949 scopus 로고    scopus 로고
    • Organic chemistry: Molecular diversity by design
    • Schreiber, S. L. Organic chemistry: Molecular diversity by design Nature 2009, 457, 153-154
    • (2009) Nature , vol.457 , pp. 153-154
    • Schreiber, S.L.1
  • 4
  • 8
    • 0034678033 scopus 로고    scopus 로고
    • Target-Oriented and Diversity-Oriented Organic Synthesis in Drug Discovery
    • Schreiber, S. L. Target-Oriented and Diversity-Oriented Organic Synthesis in Drug Discovery Science 2000, 287, 1964-1969
    • (2000) Science , vol.287 , pp. 1964-1969
    • Schreiber, S.L.1
  • 9
    • 48149108752 scopus 로고    scopus 로고
    • Natural products as an inspiration in the diversity-oriented synthesis of bioactive compound libraries
    • Cordier, C.; Morton, D.; Murrison, S.; Nelson, A.; O′Leary-Steele, C. Natural products as an inspiration in the diversity-oriented synthesis of bioactive compound libraries Nat. Prod. Rep. 2008, 25, 719-737
    • (2008) Nat. Prod. Rep. , vol.25 , pp. 719-737
    • Cordier, C.1    Morton, D.2    Murrison, S.3    Nelson, A.4    Oleary-Steele, C.5
  • 11
    • 0012815011 scopus 로고    scopus 로고
    • Total Synthesis of the Alkaloids Martinelline and Martinellic Acid via a Hetero Diels-Alder Multicomponent Coupling Reaction
    • Powell, D. A.; Batey, R. A. Total Synthesis of the Alkaloids Martinelline and Martinellic Acid via a Hetero Diels-Alder Multicomponent Coupling Reaction Org. Lett. 2002, 4, 2913-2916
    • (2002) Org. Lett. , vol.4 , pp. 2913-2916
    • Powell, D.A.1    Batey, R.A.2
  • 12
    • 0026749637 scopus 로고
    • 2-Carboxytetrahydroquinolines. Conformational and stereochemical requirements for antagonism of the glycine site on the N-methyl-D-aspartate (NMDA) receptor
    • Carling, R. W.; Lesson, P. D.; Moseley, A. M.; Baker, R.; Foster, A. C.; Grimwood, S.; Kemp, J. A.; Marshal, G. R. 2-Carboxytetrahydroquinolines. Conformational and stereochemical requirements for antagonism of the glycine site on the N-methyl-D-aspartate (NMDA) receptor J. Med. Chem. 1992, 35, 1942-1953
    • (1992) J. Med. Chem. , vol.35 , pp. 1942-1953
    • Carling, R.W.1    Lesson, P.D.2    Moseley, A.M.3    Baker, R.4    Foster, A.C.5    Grimwood, S.6    Kemp, J.A.7    Marshal, G.R.8
  • 14
    • 0029017727 scopus 로고
    • Synthesis, Structure-Activity Relationships, and Pharmacological Evaluation of Pyrrolo[3,2,1-ij]quinoline Derivatives: Potent Histamine and Platelet Activating Factor Antagonism and 5-Lipoxygenase Inhibitory Properties. Potential Therapeutic Application in Asthma
    • Paris, D.; Cottin, M.; Demonchaux, P.; Augert, G.; Dupassieux, P.; Lenoir, P.; Peck, M. J.; Jasserand, D. Synthesis, Structure-Activity Relationships, and Pharmacological Evaluation of Pyrrolo[3,2,1-ij]quinoline Derivatives: Potent Histamine and Platelet Activating Factor Antagonism and 5-Lipoxygenase Inhibitory Properties. Potential Therapeutic Application in Asthma J. Med. Chem. 1995, 38, 669-685
    • (1995) J. Med. Chem. , vol.38 , pp. 669-685
    • Paris, D.1    Cottin, M.2    Demonchaux, P.3    Augert, G.4    Dupassieux, P.5    Lenoir, P.6    Peck, M.J.7    Jasserand, D.8
  • 15
    • 64949123222 scopus 로고    scopus 로고
    • Diversity oriented synthesis of benzimidazole and benzoxa/(thia)zole libraries through polymer-supported hypervalent iodine reagent
    • Kumar, A.; Maurya, R. A.; Ahmad, P. Diversity oriented synthesis of benzimidazole and benzoxa/(thia)zole libraries through polymer-supported hypervalent iodine reagent J. Comb. Chem. 2009, 11, 198-201
    • (2009) J. Comb. Chem. , vol.11 , pp. 198-201
    • Kumar, A.1    Maurya, R.A.2    Ahmad, P.3
  • 16
    • 74049113723 scopus 로고    scopus 로고
    • Diversity Oriented Synthesis of Benzoxanthene and Benzochromene Libraries via One-Pot, Three-Component Reactions and Their Anti-proliferative Activity
    • Kumar, A.; Sharma, S.; Maurya, R. A.; Sarkar, J. Diversity Oriented Synthesis of Benzoxanthene and Benzochromene Libraries via One-Pot, Three-Component Reactions and Their Anti-proliferative Activity J. Comb. Chem. 2010, 12, 20-24
    • (2010) J. Comb. Chem. , vol.12 , pp. 20-24
    • Kumar, A.1    Sharma, S.2    Maurya, R.A.3    Sarkar, J.4
  • 17
    • 77954555240 scopus 로고    scopus 로고
    • Diversity Oriented Synthesis of Pyrrolidines via Natural Carbohydrate Solid Acid Catalyst
    • Kumar, A.; Gupta, G.; Srivastava, S. Diversity Oriented Synthesis of Pyrrolidines via Natural Carbohydrate Solid Acid Catalyst J. Comb. Chem 2010, 12, 458-462
    • (2010) J. Comb. Chem , vol.12 , pp. 458-462
    • Kumar, A.1    Gupta, G.2    Srivastava, S.3
  • 18
    • 67650092641 scopus 로고    scopus 로고
    • Design and synthesis of 3,5-diarylisoxazole derivatives as novel class of anti-hyperglycemic and lipid lowering agents
    • Kumar, A.; Maurya, R. A.; Sharma, S.; Ahmad, P.; Singh, A. B.; Tamrakar, A. K.; Srivastava, A. K. Design and synthesis of 3,5-diarylisoxazole derivatives as novel class of anti-hyperglycemic and lipid lowering agents Bioorg. Med. Chem. 2009, 17, 5285-5292
    • (2009) Bioorg. Med. Chem. , vol.17 , pp. 5285-5292
    • Kumar, A.1    Maurya, R.A.2    Sharma, S.3    Ahmad, P.4    Singh, A.B.5    Tamrakar, A.K.6    Srivastava, A.K.7
  • 19
    • 73549089481 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of N -aryl-1,4-dihydropyridines as novel antidyslipidemic and antioxidant agents
    • Kumar, A.; Maurya, R. A.; Sharma, S.; Kumar, M.; Bhatia, G. Synthesis and biological evaluation of N -aryl-1,4-dihydropyridines as novel antidyslipidemic and antioxidant agents Eur. J. Med. Chem. 2010, 45, 501-509
    • (2010) Eur. J. Med. Chem. , vol.45 , pp. 501-509
    • Kumar, A.1    Maurya, R.A.2    Sharma, S.3    Kumar, M.4    Bhatia, G.5
  • 21
    • 67649993673 scopus 로고    scopus 로고
    • 2: An efficient biomimetic catalyst system providing metabolites of drug candidates
    • 2: An efficient biomimetic catalyst system providing metabolites of drug candidates Bioorg. Med. Chem. Lett. 2009, 19, 4432-4436
    • (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 4432-4436
    • Kumar, A.1    Maurya, R.A.2    Sharma, S.3
  • 22
    • 57949110112 scopus 로고    scopus 로고
    • Novel 2-aryl-naphtho[1,2- d ]oxazole derivatives as potential PTP-1B inhibitors showing antihyperglycemic activities
    • Kumar, A.; Ahmad, P.; Maurya, R. A.; Singh, A. B.; Srivastava, A. K. Novel 2-aryl-naphtho[1,2- d ]oxazole derivatives as potential PTP-1B inhibitors showing antihyperglycemic activities Eur. J. Med. Chem. 2009, 44, 109-116
    • (2009) Eur. J. Med. Chem. , vol.44 , pp. 109-116
    • Kumar, A.1    Ahmad, P.2    Maurya, R.A.3    Singh, A.B.4    Srivastava, A.K.5
  • 23
    • 0032516298 scopus 로고    scopus 로고
    • Convenient synthesis of pyrano[3,2- c ]quinolines and indeno[2,1- c ] quinolines by imino Diels-Alder reactions
    • Babu, G.; Perumal, P. T. Convenient synthesis of pyrano[3,2- c ]quinolines and indeno[2,1- c ] quinolines by imino Diels-Alder reactions Tetrahedron Lett. 1998, 39, 3225-3228
    • (1998) Tetrahedron Lett. , vol.39 , pp. 3225-3228
    • Babu, G.1    Perumal, P.T.2
  • 24
    • 0033588330 scopus 로고    scopus 로고
    • Lanthanide Chloride Catalyzed Imino Diels-Alder Reaction. One-Pot Synthesis of Pyrano[3,2- c ]- and Furo[3,2- c ]quinolines
    • Ma, Y.; Qian, C.; Xie, M.; Sun, J. Lanthanide Chloride Catalyzed Imino Diels-Alder Reaction. One-Pot Synthesis of Pyrano[3,2- c ]- and Furo[3,2- c ]quinolines J. Org. Chem. 1999, 64, 6462-6467
    • (1999) J. Org. Chem. , vol.64 , pp. 6462-6467
    • Ma, Y.1    Qian, C.2    Xie, M.3    Sun, J.4
  • 25
    • 0029813591 scopus 로고    scopus 로고
    • A New Methodology for Combinatorial Synthesis. Preparation of Diverse Quinoline Derivatives Using a Novel Polymer-Supported Scandium Catalyst
    • Kobayashi, S.; Nagayama, S. A New Methodology for Combinatorial Synthesis. Preparation of Diverse Quinoline Derivatives Using a Novel Polymer-Supported Scandium Catalyst J. Am. Chem. Soc. 1996, 118, 8977-8978
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 8977-8978
    • Kobayashi, S.1    Nagayama, S.2
  • 26
    • 33747322715 scopus 로고    scopus 로고
    • Phosphomolybdic acid-catalyzed efficient one-pot three-component aza-Diels-Alder reactions under solvent-free conditions: A facile synthesis of trans -fused pyrano- and furanotetrahydroquinolines
    • Nagaiah, K.; Sreenu, D.; Srinivasa., R.; Rao, G. V.; Yadav, J. S. Phosphomolybdic acid-catalyzed efficient one-pot three-component aza-Diels-Alder reactions under solvent-free conditions: a facile synthesis of trans -fused pyrano- and furanotetrahydroquinolines Tetrahedron Lett. 2006, 47, 4409-4413
    • (2006) Tetrahedron Lett. , vol.47 , pp. 4409-4413
    • Nagaiah, K.1    Sreenu, D.2    Srinivasa, R.3    Rao, G.V.4    Yadav, J.S.5
  • 27
    • 0030573985 scopus 로고    scopus 로고
    • Catalytic asymmetric aza Diels-Alder reactions using a chiral lanthanide Lewis acid. Enantioselective synthesis of tetrahydroquinoline derivatives using a catalytic amount of a chiral source
    • Ishitani, H.; Kobayashi, S. Catalytic asymmetric aza Diels-Alder reactions using a chiral lanthanide Lewis acid. Enantioselective synthesis of tetrahydroquinoline derivatives using a catalytic amount of a chiral source Tetrahedron Lett. 1996, 37, 7357-7360
    • (1996) Tetrahedron Lett. , vol.37 , pp. 7357-7360
    • Ishitani, H.1    Kobayashi, S.2
  • 29
    • 0035897147 scopus 로고    scopus 로고
    • Triphenyl phosphonium perchlorate-an efficient catalyst for the imino Diels-Alder reaction of imines with electron rich dienophiles. Synthesis of pyranoquinoline, furoquinoline and phenanthridine derivatives
    • Nagarajan, R.; Chitra, S.; Perumal, P. T. Triphenyl phosphonium perchlorate-an efficient catalyst for the imino Diels-Alder reaction of imines with electron rich dienophiles. Synthesis of pyranoquinoline, furoquinoline and phenanthridine derivatives Tetrahedron 2001, 57, 3419-3423
    • (2001) Tetrahedron , vol.57 , pp. 3419-3423
    • Nagarajan, R.1    Chitra, S.2    Perumal, P.T.3
  • 31
    • 0035128465 scopus 로고    scopus 로고
    • Litheum perchlorare/diethylether ctalyzed aza-diels-alder reaction: An expeditious synthesis of pyrani, indeno qunolines and phenathridines
    • Yadav, J. S.; Reddy, B. V. S.; Srinivas, R.; Madhuri, C.; Ramalingam, T. Litheum perchlorare/diethylether ctalyzed aza-diels-alder reaction: An expeditious synthesis of pyrani, indeno qunolines and phenathridines Synlett 2001, 240-242
    • (2001) Synlett , pp. 240-242
    • Yadav, J.S.1    Reddy, B.V.S.2    Srinivas, R.3    Madhuri, C.4    Ramalingam, T.5
  • 33
    • 0000354729 scopus 로고
    • α -Unsaturated ethers and their analogues in reactions of diene synthesis
    • Povarov, L. S. α -Unsaturated ethers and their analogues in reactions of diene synthesis Russ. Chem. Rev. 1967, 36, 656
    • (1967) Russ. Chem. Rev. , vol.36 , pp. 656
    • Povarov, L.S.1
  • 34
    • 33846336715 scopus 로고    scopus 로고
    • Synthesis of polyhydroquinoline derivatives through unsymmetric Hantzsch reaction using organocatalysts
    • DOI 10.1016/j.tet.2006.12.074, PII S0040402006020412
    • Kumar, A.; Maurya, R. A. Synthesis of polyhydroquinoline derivatives through unsymmetric Hantzsch reaction using organocatalysts Tetrahedron 2007, 63, 1946-1952 (Pubitemid 46136373)
    • (2007) Tetrahedron , vol.63 , Issue.9 , pp. 1946-1952
    • Kumar, A.1    Maurya, R.A.2
  • 35
    • 39849106140 scopus 로고    scopus 로고
    • Organocatalysed three-component domino synthesis of 1,4-dihydropyridines under solvent free conditions
    • Kumar, A.; Maurya, R. A. Organocatalysed three-component domino synthesis of 1,4-dihydropyridines under solvent free conditions Tetrahedron 2008, 64, 3477-3482
    • (2008) Tetrahedron , vol.64 , pp. 3477-3482
    • Kumar, A.1    Maurya, R.A.2
  • 36
    • 71649083229 scopus 로고    scopus 로고
    • Supramolecular carbohydrate scaffold-catalyzed synthesis of tetrahydroquinolines
    • Kumar, A.; Srivastava, S.; Gupta, G. Supramolecular carbohydrate scaffold-catalyzed synthesis of tetrahydroquinolines Tetrahedron Lett. 2010, 51, 517-520
    • (2010) Tetrahedron Lett. , vol.51 , pp. 517-520
    • Kumar, A.1    Srivastava, S.2    Gupta, G.3
  • 38
    • 0034583449 scopus 로고    scopus 로고
    • Solid acids and their use as environmentally friendly catalysts in organic synthesis
    • Wilson, K.; Clark, J. H. Solid acids and their use as environmentally friendly catalysts in organic synthesis Pure Appl. Chem. 2000, 72, 1313-1319
    • (2000) Pure Appl. Chem. , vol.72 , pp. 1313-1319
    • Wilson, K.1    Clark, J.H.2
  • 39
    • 21844444274 scopus 로고    scopus 로고
    • Catalysis of liquid phase organic reactions using chemically modified mesoporous inorganic solids
    • Clark, J. H.; Macquarrie, D. J. Catalysis of liquid phase organic reactions using chemically modified mesoporous inorganic solids Chem. Commun. 1998, 853
    • (1998) Chem. Commun. , pp. 853
    • Clark, J.H.1    MacQuarrie, D.J.2
  • 40
    • 0033531748 scopus 로고    scopus 로고
    • A three-component coupling protocol for the synthesis of substituted hexahydropyrrolo[3,2- c ]quinolines
    • Batey, R. A.; Simoncic, P. D.; Lin, D.; Smyj, R. P.; Lough, A. J. A three-component coupling protocol for the synthesis of substituted hexahydropyrrolo[3,2- c ]quinolines Chem. Commun. 1999, 651-652
    • (1999) Chem. Commun. , pp. 651-652
    • Batey, R.A.1    Simoncic, P.D.2    Lin, D.3    Smyj, R.P.4    Lough, A.J.5
  • 41
    • 47049125207 scopus 로고    scopus 로고
    • Molecular iodine-catalyzed diastereoselective synthesis of cis-fused pyranobenzopyrans and furanobenzopyrans
    • Wang, J.; Xu, F.-X.; Lin, X.-F.; Wang, Y.-G. Molecular iodine-catalyzed diastereoselective synthesis of cis-fused pyranobenzopyrans and furanobenzopyrans Tetrahedron Lett. 2008, 49, 5208-5210
    • (2008) Tetrahedron Lett. , vol.49 , pp. 5208-5210
    • Wang, J.1    Xu, F.-X.2    Lin, X.-F.3    Wang, Y.-G.4
  • 43
    • 0037164634 scopus 로고    scopus 로고
    • Diastereoselective synthesis of cis -fused pyrano and furanobenzopyrans catalyzed by indium trichloride or triphenyl phosphonium perchlorate
    • Anniyappan, M.; Muralidharan, D.; Perumal, P. T. Diastereoselective synthesis of cis -fused pyrano and furanobenzopyrans catalyzed by indium trichloride or triphenyl phosphonium perchlorate Tetrahedron 2002, 58, 10301-10307
    • (2002) Tetrahedron , vol.58 , pp. 10301-10307
    • Anniyappan, M.1    Muralidharan, D.2    Perumal, P.T.3
  • 44
    • 0030903133 scopus 로고    scopus 로고
    • Microplate alamar blue assay versus BACTEC 460 system for high- throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium
    • Collins, L. A.; Franzblan, S. G. Microplate alamar blue assay versus BACTEC 460 system for high- throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium Antimicrob. Agents Chemother. 1997, 41, 1004-1009
    • (1997) Antimicrob. Agents Chemother. , vol.41 , pp. 1004-1009
    • Collins, L.A.1    Franzblan, S.G.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.