메뉴 건너뛰기




Volumn 5, Issue 11, 2010, Pages 1731-1736

A rapid and efficient route to benzazole heterocycles

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL ISOTHIOCYANATE; ANILINE DERIVATIVE; ARYL ISOTHIOCYANATE; BENZAZOLE DERIVATIVE; CYANAMIDE; HETEROCYCLIC COMPOUND; HYDROGEN SULFIDE; INDOLE DERIVATIVE; ISOTHIOCYANIC ACID DERIVATIVE; NUCLEOPHILE; THIOUREA; UNCLASSIFIED DRUG;

EID: 78049410391     PISSN: 17542189     EISSN: 17502799     Source Type: Journal    
DOI: 10.1038/nprot.2010.132     Document Type: Article
Times cited : (16)

References (46)
  • 1
    • 0032600672 scopus 로고    scopus 로고
    • Beyond mere diversity: Tailoring combinatorial libraries for drug discovery
    • Martin, E.J. & Critchlow, R.E. Beyond mere diversity: tailoring combinatorial libraries for drug discovery. J. Comb. Chem. 1, 32-45 (1999).
    • (1999) J. Comb. Chem. , vol.1 , pp. 32-45
    • Martin, E.J.1    Critchlow, R.E.2
  • 2
    • 64349103355 scopus 로고    scopus 로고
    • Structure-activity relationship of new anti-hepatitis C virus agents: Heterobicycle-coumarin conjugates
    • Neyts, J. et al. Structure-activity relationship of new anti-hepatitis C virus agents: heterobicycle-coumarin conjugates. J. Med. Chem. 52, 1486-1490 (2009).
    • (2009) J. Med. Chem. , vol.52 , pp. 1486-1490
    • Neyts, J.1
  • 3
    • 33750227695 scopus 로고    scopus 로고
    • Inhibitors of Polo-like kinase reveal roles in spindle-pole maintenance
    • McInnes, C. et al. Inhibitors of Polo-like kinase reveal roles in spindle-pole maintenance. Nat. Chem. Biol. 2, 608-617 (2006).
    • (2006) Nat. Chem. Biol. , vol.2 , pp. 608-617
    • McInnes, C.1
  • 4
    • 61449229868 scopus 로고    scopus 로고
    • Novel non-peptide nociceptin/orphanin FQ receptor agonist, 1-[1-(1-methylcyclooctyl)-4-piperidinyl]-2-[(3R)-3-piperidinyl] -1H-benzimidazole: Design, synthesis, and structure-activity relationship of oral receptor occupancy in the brain for orally potent antianxiety drug
    • Hayashi, S. et al. Novel non-peptide nociceptin/orphanin FQ receptor agonist, 1-[1-(1-methylcyclooctyl)-4-piperidinyl]-2-[(3R)-3-piperidinyl]-1H- benzimidazole: design, synthesis, and structure-activity relationship of oral receptor occupancy in the brain for orally potent antianxiety drug. J. Med. Chem. 52, 610-625 (2009).
    • (2009) J. Med. Chem. , vol.52 , pp. 610-625
    • Hayashi, S.1
  • 5
    • 51849112827 scopus 로고    scopus 로고
    • Novel dual-targeting benzimidazole urea inhibitors of DNA gyrase and topoisomerase IV possessing potent antibacterial activity: Intelligent design and evolution through the judicious use of structure-guided design and structure-activity relationships
    • Charifson, P.S. et al. Novel dual-targeting benzimidazole urea inhibitors of DNA gyrase and topoisomerase IV possessing potent antibacterial activity: intelligent design and evolution through the judicious use of structure-guided design and structure-activity relationships. J. Med. Chem. 51, 5243-5263 (2008).
    • (2008) J. Med. Chem. , vol.51 , pp. 5243-5263
    • Charifson, P.S.1
  • 6
    • 49449095466 scopus 로고    scopus 로고
    • Synthesis of new arylpiperazinylalkylthiobenzimidazole, benzothiazole, or benzoxazole derivatives as potent and selective 5-HT1A serotonin receptor ligands
    • Siracusa, M.A. et al. Synthesis of new arylpiperazinylalkylthiobenzimidazole, benzothiazole, or benzoxazole derivatives as potent and selective 5-HT1A serotonin receptor ligands. J. Med. Chem. 51, 4529-4538 (2008).
    • (2008) J. Med. Chem. , vol.51 , pp. 4529-4538
    • Siracusa, M.A.1
  • 7
    • 64549100244 scopus 로고    scopus 로고
    • Discovery of 6-({4-[2-(4-tert-butylphenyl)-1H-benzimidazol-4-yl] piperazin-1-yl}methyl)quinoxaline (WAY-207024): An orally active antagonist of the gonadotropin releasing hormone receptor (GnRH-R)
    • Pelletier, J.C. et al. Discovery of 6-({4-[2-(4-tert-butylphenyl)-1H- benzimidazol-4-yl]piperazin-1-yl}methyl)quinoxaline (WAY-207024): an orally active antagonist of the gonadotropin releasing hormone receptor (GnRH-R). J. Med. Chem. 52, 2148-2152 (2009).
    • (2009) J. Med. Chem. , vol.52 , pp. 2148-2152
    • Pelletier, J.C.1
  • 8
    • 47749128453 scopus 로고    scopus 로고
    • Identifcation of a potent, selective, and orally active leukotriene A4 hydrolase inhibitor with anti-infammatory activity
    • Grice, C.A. et al. Identifcation of a potent, selective, and orally active leukotriene A4 hydrolase inhibitor with anti-infammatory activity. J. Med. Chem. 51, 4150-4169 (2008).
    • (2008) J. Med. Chem. , vol.51 , pp. 4150-4169
    • Grice, C.A.1
  • 9
    • 39749111209 scopus 로고    scopus 로고
    • Rh(I)-catalyzed arylation of heterocycles via C-H bond activation: Expanded scope through mechanistic insight
    • Lewis, J.C., Berman, A.M., Bergman, R.G. & Ellman, J.A. Rh(I)-catalyzed arylation of heterocycles via C-H bond activation: expanded scope through mechanistic insight. J. Am. Chem. Soc. 130, 2493-2500 (2008).
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 2493-2500
    • Lewis, J.C.1    Berman, A.M.2    Bergman, R.G.3    Ellman, J.A.4
  • 10
    • 63149091152 scopus 로고    scopus 로고
    • Design, selection, and characterization of thiofavin-based intercalation compounds with metal chelating properties for application in Alzheimer's disease
    • Rodriguez-Rodriguez, C. et al. Design, selection, and characterization of thiofavin-based intercalation compounds with metal chelating properties for application in Alzheimer's disease. J. Am. Chem. Soc. 131, 1436-1451 (2009).
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 1436-1451
    • Rodriguez-Rodriguez, C.1
  • 11
    • 64349094401 scopus 로고    scopus 로고
    • Synthesis, cytotoxicity, and DNA interactions of new cisplatin analogues containing substituted benzimidazole ligands
    • Gumus, F. et al. Synthesis, cytotoxicity, and DNA interactions of new cisplatin analogues containing substituted benzimidazole ligands. J. Med. Chem. 52, 1345-1357 (2009).
    • (2009) J. Med. Chem. , vol.52 , pp. 1345-1357
    • Gumus, F.1
  • 12
    • 67649518187 scopus 로고    scopus 로고
    • Effcient synthesis of regioisomerically pure bis(trifuoromethyl)- substituted 3,4,9,10-perylene tetracarboxylic bis(benzimidazole)
    • Yuan, Z., Xiao, Y., Li, Z. & Qian, X. Effcient synthesis of regioisomerically pure bis(trifuoromethyl)-substituted 3,4,9,10-perylene tetracarboxylic bis(benzimidazole). Org. Lett. 11, 2808-2811 (2009).
    • (2009) Org. Lett. , vol.11 , pp. 2808-2811
    • Yuan, Z.1    Xiao, Y.2    Li, Z.3    Qian, X.4
  • 13
    • 61549117103 scopus 로고    scopus 로고
    • Characterization of new benz-x-azole dye derivatives and metal complexes
    • Son, Y.-A., Kim, B.-S., Choi, M.-S. & Kim, S.-H. Characterization of new benz-x-azole dye derivatives and metal complexes. Mol. Cryst. Liq. Cryst. 498, 158-164 (2009).
    • (2009) Mol. Cryst. Liq. Cryst. , vol.498 , pp. 158-164
    • Son, Y.-A.1    Kim, B.-S.2    Choi, M.-S.3    Kim, S.-H.4
  • 14
    • 8144225722 scopus 로고    scopus 로고
    • Synthetic strategies towards benzoxazole ring systems: A review
    • Kumar, R.V. Synthetic strategies towards benzoxazole ring systems: a review. Asian J. Chem. 16, 1241-1260 (2004).
    • (2004) Asian J. Chem. , vol.16 , pp. 1241-1260
    • Kumar, R.V.1
  • 15
    • 42449103107 scopus 로고    scopus 로고
    • General and practical synthesis of benzothiazoles
    • Mase, T. & Itoh, T. General and practical synthesis of benzothiazoles. Pure Appl. Chem. 80, 707-715 (2008).
    • (2008) Pure Appl. Chem. , vol.80 , pp. 707-715
    • Mase, T.1    Itoh, T.2
  • 16
    • 50949127251 scopus 로고    scopus 로고
    • Synthesis reactivity and biological activity of benzimidazoles
    • Alamgir, M., Black, D.St.C. & Kumar, N. Synthesis, reactivity and biological activity of benzimidazoles. Top. Heterocycl. Chem. 9, 87-118 (2007).
    • (2007) Top. Heterocycl. Chem. , vol.9 , pp. 87-118
    • Alamgir, M.1    Black, D.St.C.2    Kumar, N.3
  • 17
    • 57749092640 scopus 로고    scopus 로고
    • Synthesis of 5-and 6-substituted 2-(4-dimethylaminophenyl)-1,3- benzoxazoles and their in vitro and in vivo evaluation as imaging agents for amyloid plaque
    • Hausner, S.H. et al. Synthesis of 5-and 6-substituted 2-(4-dimethylaminophenyl)-1,3-benzoxazoles and their in vitro and in vivo evaluation as imaging agents for amyloid plaque. Bioorg. Med. Chem. Lett. 19, 543-545 (2009).
    • (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 543-545
    • Hausner, S.H.1
  • 18
    • 34347380861 scopus 로고    scopus 로고
    • Phenylpropanoic acid derivatives bearing a benzothiazole ring as PPAR?-selective agonists
    • Fujieda, H. et al. Phenylpropanoic acid derivatives bearing a benzothiazole ring as PPAR?-selective agonists. Bioorg. Med. Chem. Lett. 17, 4351-4357 (2007).
    • (2007) Bioorg. Med. Chem. Lett. , vol.17 , pp. 4351-4357
    • Fujieda, H.1
  • 19
    • 58249096372 scopus 로고    scopus 로고
    • Formation and structures of Pd(II) N,S-heterocyclic carbene-pyridyl mixed-ligand complexes
    • Yen, S.K., Koh, L.L., Huynh, H.V. & Andy Hor, T.S. Formation and structures of Pd(II) N,S-heterocyclic carbene-pyridyl mixed-ligand complexes. J. Organomet. Chem. 694, 332-338 (2009).
    • (2009) J. Organomet. Chem. , vol.694 , pp. 332-338
    • Yen, S.K.1    Koh, L.L.2    Huynh, H.V.3    Andy Hor, T.S.4
  • 20
    • 58249118877 scopus 로고    scopus 로고
    • Palladium-catalyzed direct arylations of heteroarenes with tosylates and mesylates
    • Ackermann, L., Althammer, A. & Fenner, S. Palladium-catalyzed direct arylations of heteroarenes with tosylates and mesylates. Angew. Chem. Int. Ed. 48, 201-204 (2009).
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 201-204
    • Ackermann, L.1    Althammer, A.2    Fenner, S.3
  • 23
    • 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. 11, 198-201 (2009).
    • (2009) J. Comb. Chem. , vol.11 , pp. 198-201
    • Kumar, A.1    Maurya, R.A.2    Ahmad, P.3
  • 24
    • 56449089532 scopus 로고    scopus 로고
    • Effcient aerobic oxidative synthesis of 2-substituted benzoxazoles, benzothiazoles, and benzimidazoles catalyzed by 4-methoxy-TEMPO
    • Chen, Y.-X., Qian, L.-F., Zhang, W. & Han, B. Effcient aerobic oxidative synthesis of 2-substituted benzoxazoles, benzothiazoles, and benzimidazoles catalyzed by 4-methoxy-TEMPO. Angew. Chem. Int. Ed. 47, 9330-9333 (2008).
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 9330-9333
    • Chen, Y.-X.1    Qian, L.-F.2    Zhang, W.3    Han, B.4
  • 25
    • 0020363114 scopus 로고
    • 2-(2-Benzimidazolylamin o)benzothiazoles and 2-(2imidazolidinylidenamino) benzothiazoles
    • Merchan, F.L., Garin, J., Melendez, E. & Tejero, T. 2-(2-Benzimidazolylamin o)benzothiazoles and 2-(2imidazolidinylidenamino) benzothiazoles. Synthesis 1066-1067 (1982).
    • (1982) Synthesis , pp. 1066-1067
    • Merchan, F.L.1    Garin, J.2    Melendez, E.3    Tejero, T.4
  • 26
    • 84986438897 scopus 로고
    • A facile synthesis of dimethyl N-aryldithiocarbonimidates and 2-arylaminobenzimidazoles
    • Garin, J., Melendez, E., Merchan, F.L., Tejel, C. & Tejero, T. A facile synthesis of dimethyl N-aryldithiocarbonimidates and 2- arylaminobenzimidazoles. Synthesis 375-376 (1983).
    • (1983) Synthesis , pp. 375-376
    • Garin, J.1    Melendez, E.2    Merchan, F.L.3    Tejel, C.4    Tejero, T.5
  • 27
    • 33646080577 scopus 로고    scopus 로고
    • A one-pot method for the synthesis of 2-aminobenzimidazoles and related heterocycles
    • Cee, V.J. & Downing, N.S. A one-pot method for the synthesis of 2-aminobenzimidazoles and related heterocycles. Tetrahedron Lett. 47, 3747-3750 (2006).
    • (2006) Tetrahedron Lett. , vol.47 , pp. 3747-3750
    • Cee, V.J.1    Downing, N.S.2
  • 28
    • 70349765825 scopus 로고    scopus 로고
    • Effcient one-step synthesis of benzazoles in aqueous media
    • Boeini, H.Z. & Najafabadi, K.H. Effcient one-step synthesis of benzazoles in aqueous media. Eur. J. Org. Chem. 2009, 4926-4929 (2009).
    • (2009) Eur. J. Org. Chem. , vol.2009 , pp. 4926-4929
    • Boeini, H.Z.1    Najafabadi, K.H.2
  • 29
    • 57349191553 scopus 로고    scopus 로고
    • Desulfurization mediated by hypervalent iodine(III): A novel strategy for the construction of heterocycles
    • Ghosh, H., Yella, R., Nath, J. & Patel, B.K. Desulfurization mediated by hypervalent iodine(III): a novel strategy for the construction of heterocycles. Eur. J. Org. Chem. 2008, 6189-6196 (2008).
    • (2008) Eur. J. Org. Chem. , vol.2008 , pp. 6189-6196
    • Ghosh, H.1    Yella, R.2    Nath, J.3    Patel, B.K.4
  • 30
    • 68049084761 scopus 로고    scopus 로고
    • TBAF-assisted copper-catalyzed N-arylation and benzylation of benzazoles with aryl and benzyl halides under the ligand/base/solvent-free conditions
    • Lee, H.-G. et al. TBAF-assisted copper-catalyzed N-arylation and benzylation of benzazoles with aryl and benzyl halides under the ligand/base/solvent-free conditions. J. Org. Chem. 74, 5675-5678 (2009).
    • (2009) J. Org. Chem. , vol.74 , pp. 5675-5678
    • Lee, H.-G.1
  • 31
    • 4644226156 scopus 로고    scopus 로고
    • A convenient method for the synthesis of 2-amino substituted aza-heterocycles from N,N′-disubstituted thioureas using TsCl/NaOH
    • Heinelt, U. et al. A convenient method for the synthesis of 2-amino substituted aza-heterocycles from N,N′-disubstituted thioureas using TsCl/NaOH. Tetrahedron 60, 9883-9888 (2004).
    • (2004) Tetrahedron , vol.60 , pp. 9883-9888
    • Heinelt, U.1
  • 32
    • 34347250848 scopus 로고    scopus 로고
    • Rapid preparation of the mitotic kinesin Eg5 inhibitor monastrol using controlled microwave-assisted synthesis
    • Dallinger, D. & Kappe, C.O. Rapid preparation of the mitotic kinesin Eg5 inhibitor monastrol using controlled microwave-assisted synthesis. Nat. Protoc. 2, 317-321 (2007).
    • (2007) Nat. Protoc. , vol.2 , pp. 317-321
    • Dallinger, D.1    Kappe, C.O.2
  • 33
    • 34548493472 scopus 로고    scopus 로고
    • Automated generation of a dihydropyrimidine compound library using microwave-assisted processing
    • Dallinger, D. & Kappe, C.O. Automated generation of a dihydropyrimidine compound library using microwave-assisted processing. Nat. Protoc. 2, 1713-1721 (2007).
    • (2007) Nat. Protoc. , vol.2 , pp. 1713-1721
    • Dallinger, D.1    Kappe, C.O.2
  • 34
    • 38449099548 scopus 로고    scopus 로고
    • Rapid solid-phase synthesis of a calmodulin-binding peptide using controlled microwave irradiation
    • Bacsa, B. & Kappe, C.O. Rapid solid-phase synthesis of a calmodulin-binding peptide using controlled microwave irradiation. Nat. Protoc. 2, 2222-2227 (2007).
    • (2007) Nat. Protoc. , vol.2 , pp. 2222-2227
    • Bacsa, B.1    Kappe, C.O.2
  • 37
    • 0031980058 scopus 로고    scopus 로고
    • Contact hypersensitivity to dicyclohexylcarbodiimide and diisopropylcarbodiimide in female B6C3F1 mice
    • Hayes, B.B., Gerber, P.C., Griffey, S.S. & Meade, B.J. Contact hypersensitivity to dicyclohexylcarbodiimide and diisopropylcarbodiimide in female B6C3F1 mice. Drug Chem. Toxicol. 1, 195-206 (1998).
    • (1998) Drug Chem. Toxicol. , vol.1 , pp. 195-206
    • Hayes, B.B.1    Gerber, P.C.2    Griffey, S.S.3    Meade, B.J.4
  • 38
    • 0032932094 scopus 로고    scopus 로고
    • Induction of micronucleated erythrocytes in rodents by diisopropylcarbodiimide and dicyclohexylcarbodiimide: Dependence on exposure protocol
    • Witt, K.L., Tice, R.R., Shelby, M.D., Chhabra, R.S. & Zeiger, E. Induction of micronucleated erythrocytes in rodents by diisopropylcarbodiimide and dicyclohexylcarbodiimide: dependence on exposure protocol. Environ. Mol. Mutagen. 33, 65-74 (1999).
    • (1999) Environ. Mol. Mutagen. , vol.33 , pp. 65-74
    • Witt, K.L.1    Tice, R.R.2    Shelby, M.D.3    Chhabra, R.S.4    Zeiger, E.5
  • 40
    • 84987322826 scopus 로고
    • Methods for preparing benzimidazo[2,1-b] quinazolin-12-ones and related compounds
    • Lunn, W.H.W. & Harper, R.W. Methods for preparing benzimidazo[2,1-b] quinazolin-12-ones and related compounds. J. Heterocycl. Chem. 8, 141-147 (1971).
    • (1971) J. Heterocycl. Chem. , vol.8 , pp. 141-147
    • Lunn, W.H.W.1    Harper, R.W.2
  • 41
    • 33846044053 scopus 로고    scopus 로고
    • Microwave-mediated heterocyclization to benzimidazo[2,1-b]quinazolin- 12(5H)-ones
    • Carpenter, R.D., Lam, K.S. & Kurth, M.J. Microwave-mediated heterocyclization to benzimidazo[2,1-b]quinazolin-12(5H)-ones. J. Org. Chem. 72, 284-287 (2007).
    • (2007) J. Org. Chem. , vol.72 , pp. 284-287
    • Carpenter, R.D.1    Lam, K.S.2    Kurth, M.J.3
  • 42
    • 33644853780 scopus 로고    scopus 로고
    • The impact of microwave synthesis on drug discovery
    • Kappe, C.O. & Dallinger, D. The impact of microwave synthesis on drug discovery. Nat. Rev. Drug Discov. 5, 51-63 (2006).
    • (2006) Nat. Rev. Drug Discov. , vol.5 , pp. 51-63
    • Kappe, C.O.1    Dallinger, D.2
  • 43
    • 34047184163 scopus 로고    scopus 로고
    • Contrasting chemoselectivities in the ultrasound and microwave assisted bromination reactions of substituted alkylaromatics with N-bromosuccinimide
    • Heropoulos, G.A., Cravotto, G., Screttas, C.G. & Steele, B.R. Contrasting chemoselectivities in the ultrasound and microwave assisted bromination reactions of substituted alkylaromatics with N-bromosuccinimide. Tetrahedron Lett. 48, 3247-3250 (2007).
    • (2007) Tetrahedron Lett. , vol.48 , pp. 3247-3250
    • Heropoulos, G.A.1    Cravotto, G.2    Screttas, C.G.3    Steele, B.R.4
  • 44
    • 77954374488 scopus 로고    scopus 로고
    • Halogenated benzimidazole carboxamides target integrin alpha4 beta1 on T and B cell lymphomas
    • Carpenter, R.D. et al. Halogenated benzimidazole carboxamides target integrin alpha4 beta1 on T and B cell lymphomas. Cancer Res. 70, 5448-5456 (2010).
    • (2010) Cancer Res. , vol.70 , pp. 5448-5456
    • Carpenter, R.D.1
  • 45
    • 78049361773 scopus 로고    scopus 로고
    • accessed on July 2010
    • http://www.mrl.ucsb.edu/mrl/centralfacilities/polymer/mconditions-1.html (accessed on July 2010).
  • 46
    • 84932242838 scopus 로고
    • New synthesis of aromatic isothiocyanates
    • Jochims, J.C. Carbodiimides. IV. New synthesis of aromatic isothiocyanates. Chem. Ber. 101, 1746-1752 (1968).
    • (1968) Chem. Ber. , vol.101 , pp. 1746-1752
    • Jochims, J.C.1    Carbodiimides., I.V.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.