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Volumn 15, Issue 3, 2011, Pages 781-789

Base catalyzed multicomponent synthesis of spiroheterocycles with fused heterosystems

Author keywords

Benzothiazolochromenopyrimidines; Benzothiazolodioxanopyrimidines; Benzothiazolopyranopyrimidines; Benzothiazolopyrimidopyrimidines; Benzothiazoloquinazolines; Multicomponent reactions; Spiroheterocycles; Spirooxindole

Indexed keywords

1,3 DIKETONE; 1,3,9 TRIMETHYLSPIRO[BENZOTHIAZOLO(2,3 B)PYRIMIDO(5,4 E)PYRIMIDINE 5,3' INDOLINE] 2,2',4(1H,3H)TRIONE; 2,2,8,10 TETRAMETHYL 2,3 DIHYDRO 1H SPIRO[BENZOTHIAZOLO(2,3 B)QUINAZOLINE-5,3' INDOLINE] 2',4 DIONE; 2,2,8,10 TETRAMETHYLSPIRO[BENZOTHIAZOLO(2,3 B) 1,3 DIOXANO(5,4 E)PYRIMIDINE 5,3' INDOLINE] 2',4 DIONE; 2,2,9 TRIMETHYL 2,3 DIHYDRO 1H SPIRO[BENZOTHIAZOLO(2,3 B)QUINAZOLINE 5,3' INDOLINE] 2',4 DIONE; 2,2,9 TRIMETHYLSPIRO[BENZOTHIAZOLO(2,3 B) 1,3 DIOXANO(5,4 E)PYRIMIDINE 5,3' INDOLINE] 2',4 DIONE; 2,8,10 TRIMETHYLSPIRO[BENZOTHIAZOLO(2,3 B)PYRANO(3,4 E)PYRIMIDINE 5,3' INDOLINE] 2',4 DIONE; 2,9 DIMETHYLSPIRO[BENZOTHIAZOLO(2,3 B)PYRANO(3,4 E)PYRIMIDINE 5,3' INDOLINE] 2',4 DIONE; 8,10 DIMETHYLSPIRO[BENZOTHIAZOLO(2,3 B)PYRIMIDO(5,4 E)PYRIMIDINE 5,3' INDOLINE] 2,2',4(1H,3H)TRIONE; 9 BROMO 2,2,7 TRIMETHYL 2,3 DIHYDRO 1H SPIRO[BENZOTHIAZOLO(2,3 B)QUINAZOLIN 5,3' INDOLINE] 2',4 DIONE; 9 BROMO 2,2,7 TRIMETHYLSPIRO[BENZOTHIAZOLO(2,3 B) 1,3 DIOXANO(5,4 E)PYRIMIDINE 5,3' INDOLINE] 2',4-DIONE; 9 BROMO 2,7 DIMETHYLSPIRO[BENZOTHIAZOLO(2,3 B)PYRANO(3,4 E)PYRIMIDINE 5,3' INDOLINE] 2',4 DIONE; 9 BROMO 7 METHYLSPIRO[BENZOTHIAZOLO(2,3 B)PYRIMIDO(5,4 E)PYRIMIDINE 5,3' INDOLINE] 2,2',4(1H,3H)TRIONE; 9 METHYLSPIRO[BENZOTHIAZOLO(2,3 B])PYRIMIDO(5,4 E)PYRIMIDINE 5,3' INDOLINE] 2,2',4(1H,3H)TRIONE; BENZOTHIAZOLE DERIVATIVE; BENZOTHIAZOLOCHROMENOPYRIMIDINE; BENZOTHIAZOLODIOXANOPYRIMIDINE; BENZOTHIAZOLOPYRANOPYRIMIDINE; BENZOTHIAZOLOPYRIMIDOPYRIMIDINE; BENZOTHIAZOLOQUINAZOLINE; HETEROCYCLIC COMPOUND; ISATIN; TRIETHYLAMINE; UNCLASSIFIED DRUG;

EID: 80051582567     PISSN: 13811991     EISSN: 1573501X     Source Type: Journal    
DOI: 10.1007/s11030-011-9309-2     Document Type: Article
Times cited : (41)

References (26)
  • 1
    • 0037366605 scopus 로고    scopus 로고
    • The combinatorial synthesis of bicyclic privileged structures or privileged substructures
    • 10.1021/cr020033s 12630855 10.1021/cr020033s 1:CAS:528: DC%2BD3sXhtlGkt7k%3D
    • DA Horton GT Bourne ML Smythe 2003 The combinatorial synthesis of bicyclic privileged structures or privileged substructures Chem Rev 103 893 930 10.1021/cr020033s 12630855 10.1021/cr020033s 1:CAS:528:DC%2BD3sXhtlGkt7k%3D
    • (2003) Chem Rev , vol.103 , pp. 893-930
    • Horton, D.A.1    Bourne, G.T.2    Smythe, M.L.3
  • 2
    • 46849121202 scopus 로고    scopus 로고
    • Tuning of chemo- and regioselectivities in multicomponent condensations of 5-aminopyrazoles, dimedone, and aldehydes
    • DOI 10.1021/jo800825c
    • VA Chebanov VE Saraev SM Desenko VN Chernenko IV Knyazeva U Groth TN Glasnov CO Kappe 2008 Tuning of chemo- and regioselectivities in multicomponent condensations of 5-aminopyrazoles, dimedone, and aldehydes J Org Chem 73 5110 5118 10.1021/jo800825c 18512991 10.1021/jo800825c 1:CAS:528:DC%2BD1cXms1GitLw%3D (Pubitemid 351956576)
    • (2008) Journal of Organic Chemistry , vol.73 , Issue.13 , pp. 5110-5118
    • Chebanov, V.A.1    Saraev, V.E.2    Desenko, S.M.3    Chernenko, V.N.4    Knyazeva, I.V.5    Groth, U.6    Glasnov, T.N.7    Kappe, C.O.8
  • 3
    • 67649804836 scopus 로고    scopus 로고
    • Cytotoxic and anticancer activities of isatin and its derivatives: A comprehensive review from 2000-2008
    • 1:CAS:528:DC%2BD1MXlslOlsrs%3D
    • KL Vine L Matesic JM Locke M Ranson D Skropeta 2009 Cytotoxic and anticancer activities of isatin and its derivatives: a comprehensive review from 2000-2008 Anti-cancer Agents Med Chem 9 397 414 1:CAS:528:DC%2BD1MXlslOlsrs%3D
    • (2009) Anti-cancer Agents Med Chem , vol.9 , pp. 397-414
    • Vine, K.L.1    Matesic, L.2    Locke, J.M.3    Ranson, M.4    Skropeta, D.5
  • 4
    • 77954559449 scopus 로고    scopus 로고
    • Efficient one-pot synthesis of novel spirooxindole derivatives via three-component reaction in aqueous medium
    • 10.1021/cc100056p 20515044 10.1021/cc100056p 1:CAS:528: DC%2BC3cXmslelsLs%3D
    • H Chen S Daqing 2010 Efficient one-pot synthesis of novel spirooxindole derivatives via three-component reaction in aqueous medium J Comb Chem 12 571 576 10.1021/cc100056p 20515044 10.1021/cc100056p 1:CAS:528:DC%2BC3cXmslelsLs%3D
    • (2010) J Comb Chem , vol.12 , pp. 571-576
    • Chen, H.1    Daqing, S.2
  • 5
    • 1842767304 scopus 로고    scopus 로고
    • Synthesis and evaluation of some new spiro indoline-based heterocycles as potentially active antimicrobial agents
    • DOI 10.1016/j.bmc.2003.10.063, PII S096808960400121X
    • AH Abdel-Rahman EM Keshk MA Hanna SM El-Bady 2004 Synthesis and evaluation of some new spiro indoline-based heterocycles as potentially active antimicrobial agents Bioorg Med Chem 12 2483 2488 10.1016/j.bmc.2003.10.063 15080944 10.1016/j.bmc.2003.10.063 1:CAS:528:DC%2BD2cXjtVOjs7w%3D (Pubitemid 38471731)
    • (2004) Bioorganic and Medicinal Chemistry , vol.12 , Issue.9 , pp. 2483-2488
    • Abdel-Rahman, A.H.1    Keshk, E.M.2    Hanna, M.A.3    El-Bady, Sh.M.4
  • 6
    • 36749025633 scopus 로고    scopus 로고
    • Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents
    • DOI 10.1002/anie.200701342
    • CV Galliford KA Scheidt 2007 Pyrrolidinyl-spirooxindole natural products as inspirations for the development of therapeutic agents Angew Chem Int Ed 46 8748 8758 0.1002/anie.200701342 10.1002/anie.200701342 1:CAS:528: DC%2BD2sXhsVait73K (Pubitemid 350207923)
    • (2007) Angewandte Chemie - International Edition , vol.46 , Issue.46 , pp. 8748-8758
    • Galliford, C.V.1    Scheidt, K.A.2
  • 7
    • 67650504633 scopus 로고    scopus 로고
    • Facile synthesis and antimycobacterial evaluation of novel spiro-pyrido-pyrrolizines and pyrrolidines
    • 10.1016/j.ejmech.2009.05.01 10.1016/j.ejmech.2009.05.010
    • RR Kumar S Perumal P Senthilkumar P Yogeeswari D Sriram 2009 Facile synthesis and antimycobacterial evaluation of novel spiro-pyrido-pyrrolizines and pyrrolidines Eur J Med Chem 44 3821 3829 10.1016/j.ejmech.2009.05.01 10.1016/j.ejmech.2009.05.010
    • (2009) Eur J Med Chem , vol.44 , pp. 3821-3829
    • Kumar, R.R.1    Perumal, S.2    Senthilkumar, P.3    Yogeeswari, P.4    Sriram, D.5
  • 10
    • 32044469592 scopus 로고    scopus 로고
    • Biomimetic synthesis, antimicrobial, antileishmanial and antimalarial activities of euglobals and their analogues
    • DOI 10.1016/j.bmc.2005.10.027, PII S0968089605010096
    • SB Bharate KK Bhutani SI Khan BL Tekwani MR Jacob IA Khan IP Singh 2006 Biomimetic synthesis, antimicrobial, antileishmanial and antimalarial activities of euglobals and their analogues Bioorg Med Chem 14 1750 1760 10.1016/j.bmc.2005.10.02 16274995 10.1016/j.bmc.2005.10.027 1:CAS:528: DC%2BD28XhtlKmu70%3D (Pubitemid 43199509)
    • (2006) Bioorganic and Medicinal Chemistry , vol.14 , Issue.6 , pp. 1750-1760
    • Bharate, S.B.1    Bhutani, K.K.2    Khan, S.I.3    Tekwani, B.L.4    Jacob, M.R.5    Khan, I.A.6    Singh, I.P.7
  • 11
    • 0022381194 scopus 로고
    • Synthesis, absolute configuration, and conformation of the aldose reductase inhibitor sorbinil
    • DOI 10.1021/jm00149a030
    • R Sarges J Bordner BW Dominy MJ Peterson EB Whipple 1985 Synthesis, absolute configuration, and conformation of the aldose reductase inhibitor sorbinil J Med Chem 28 1716 1720 10.1021/jm00149a030 3934383 10.1021/jm00149a030 1:CAS:528:DyaL2MXls1Sntrw%3D (Pubitemid 16204843)
    • (1985) Journal of Medicinal Chemistry , vol.28 , Issue.11 , pp. 1716-1720
    • Sarges, R.1    Bordner, J.2    Dominy, B.W.3
  • 12
    • 0028059377 scopus 로고
    • Synthesis and aldose reductase inhibitory activity of 2-substituted 6- fluoro-2,3-dihydrospiro[4H-1-benzopyran-4,4'-imidazolidine]-2',5'-diones
    • R Unno T Yamaguchi T Usui T Kakigami M Fukushima K Mizuno Y Baba M Kurono 1994 Synthesis and aldose reductase inhibitory activity of 2-substituted 6-fluoro-2,3-dihydrospiro[4H-1-benzopyran-4,4'-imidazolidine]-2',5'-diones Chem Pharm Bull 42 1474 1478 7923471 1:CAS:528:DyaK2MXivVamtrs%3D (Pubitemid 24244094)
    • (1994) Chemical and Pharmaceutical Bulletin , vol.42 , Issue.7 , pp. 1474-1478
    • Unno, R.1    Yamaguchi, T.2    Usui, T.3    Kakigami, T.4    Fukushima, M.5    Mizuno, K.6    Baba, Y.7    Kurono, M.8
  • 13
    • 0024562454 scopus 로고
    • Antitumor and antiviral activity of synthetic α- and β-ribonucleosides of certain substituted pyrimido[5,4-d]pyrimidines: A new synthetic strategy for exocyclic aminonucleosides
    • DOI 10.1021/jm00123a022
    • YS Sanghvi SB Larson SS Matsumoto LD Nord DF Smee RC Willis TH Avery RK Robins GR Revankar 1989 Antitumor and antiviral activity of synthetic. alpha.- and.beta.-ribonucleosides of certain substituted pyrimido[5,4-d]pyrimidines: a new synthetic strategy for exocyclic aminonucleosides J Med Chem 32 629 637 10.1021/jm00123a022 2918511 10.1021/jm00123a022 1:CAS:528:DyaL1MXhtFGht7g%3D (Pubitemid 19075716)
    • (1989) Journal of Medicinal Chemistry , vol.32 , Issue.3 , pp. 629-637
    • Sanghvi, Y.S.1    Larson, S.B.2    Matsumoto, S.S.3    Nord, L.D.4    Smee, D.F.5    Willis, R.C.6    Avery, T.L.7    Robins, R.K.8    Revankar, G.R.9
  • 14
    • 0035180517 scopus 로고    scopus 로고
    • Inhibition of herpes simplex virus reactivation by dipyridamole
    • DOI 10.1128/AAC.45.12.3657-3659.2001
    • RB Tenser A Gaydos KA Hay 2001 Inhibition of herpes simplex virus reactivation by dipyridamole Antimicrob Agents Chemother 45 3657 3659 10.1128/AAC.45.12.3657-3659 11709364 10.1128/AAC.45.12.3657-3659.2001 1:CAS:528:DC%2BD3MXovVOktrw%3D (Pubitemid 33107902)
    • (2001) Antimicrobial Agents and Chemotherapy , vol.45 , Issue.12 , pp. 3657-3659
    • Tenser, R.B.1    Gaydos, A.2    Hay, K.A.3
  • 15
    • 33750949952 scopus 로고    scopus 로고
    • Synthesis and pharmacological evaluation of some 3-phenyl-2-substituted- 3H-quinazolin-4-one as analgesic, anti-inflammatory agents
    • DOI 10.1016/j.bmc.2006.09.065, PII S0968089606008108
    • V Alagarsamy SV Raja K Dhanabal 2007 Synthesis and pharmacological evaluation of some 3-phenyl-2-substituted-3H-quinazolin-4-one as analgesic, anti-inflammatory agents Bioorg Med Chem 15 235 241 10.1016/j.bmc.2006.09.065 17079148 10.1016/j.bmc.2006.09.065 1:CAS:528:DC%2BD28Xht1CmtrbE (Pubitemid 44738581)
    • (2007) Bioorganic and Medicinal Chemistry , vol.15 , Issue.1 , pp. 235-241
    • Alagarsamy, V.1    Raja Solomon, V.2    Dhanabal, K.3
  • 16
    • 20944432343 scopus 로고    scopus 로고
    • Discovery of 3-[(4,5,7-trifluorobenzothiazol-2-yl)methyl]indole-N-acetic acid (lidorestat) and congeners as highly potent and selective inhibitors of aldose reductase for treatment of chronic diabetic complications
    • DOI 10.1021/jm0492094
    • MC Van Zandt ML Jones DE Gunn LS Geraci JH Jones DR Sawicki J Sredy JL Jacot AT DiCioccio T Petrove A Mitschler AD Podjarny 2005 Discovery of 3-[(4,5,7-trifluorobenzothiazol-2-yl)methyl]indole-N-acetic acid (lidorestat) and congeners as highly potent and selective inhibitors of aldose reductase for treatment of chronic diabetic complications J Med Chem 48 3141 3152 10.1021/jm0492094 15857120 10.1021/jm0492094 1:CAS:528:DC%2BD2MXislWqtrg%3D (Pubitemid 40628034)
    • (2005) Journal of Medicinal Chemistry , vol.48 , Issue.9 , pp. 3141-3152
    • Van Zandt, M.C.1    Jones, M.L.2    Gunn, D.E.3    Geraci, L.S.4    Jones, J.H.5    Sawicki, D.R.6    Sredy, J.7    Jacot, J.L.8    DiCioccio, A.T.9    Petrova, T.10    Mitschler, A.11    Podjarny, A.D.12
  • 17
    • 64349120832 scopus 로고    scopus 로고
    • Novel cyano and amidinobenzothiazole derivatives: Synthesis, antitumor evaluationand X-ray quantitative structure-activity relationship (QSAR) analysis
    • 10.1021/jm801566q 19265399 10.1021/jm801566q 1:CAS:528: DC%2BD1MXislOitrk%3D
    • I Caleta M Kralj B Bertosa S Tomic G Pavlovic K Pavelic G Karminski-Zamola 2009 Novel cyano and amidinobenzothiazole derivatives: synthesis, antitumor evaluationand X-ray quantitative structure-activity relationship (QSAR) analysis J Med Chem 52 1744 1756 10.1021/jm801566q 19265399 10.1021/jm801566q 1:CAS:528:DC%2BD1MXislOitrk%3D
    • (2009) J Med Chem , vol.52 , pp. 1744-1756
    • Caleta, I.1    Kralj, M.2    Bertosa, B.3    Tomic, S.4    Pavlovic, G.5    Pavelic, K.6    Karminski-Zamola, G.7
  • 19
    • 41149106860 scopus 로고    scopus 로고
    • Development and evaluation of compounds for imaging of β-amyloid plaque by means of positron emission tomography
    • 10.1007/s00259-007-0705-x 10.1007/s00259-007-0705-x
    • G Henriksen BH Yousefi A Drzezga HJ Wester 2008 Development and evaluation of compounds for imaging of β-amyloid plaque by means of positron emission tomography Eur J Nucl Med Mol Imaging 35 75 81 10.1007/s00259-007-0705-x 10.1007/s00259-007-0705-x
    • (2008) Eur J Nucl Med Mol Imaging , vol.35 , pp. 75-81
    • Henriksen, G.1    Yousefi, B.H.2    Drzezga, A.3    Wester, H.J.4
  • 21
    • 73949084441 scopus 로고    scopus 로고
    • Hybrid pharmacophore design and synthesis of isatin-benzothiazole analogs for their anti-breast cancer activity
    • 10.1016/j.bmc.2009.08.068 19804979 10.1016/j.bmc.2009.08.068 1:CAS:528:DC%2BD1MXht1ylurzE
    • VR Solomon C Hu H Lee 2009 Hybrid pharmacophore design and synthesis of isatin-benzothiazole analogs for their anti-breast cancer activity Bioorg Med chem 17 7585 7592 10.1016/j.bmc.2009.08.068 19804979 10.1016/j.bmc.2009.08.068 1:CAS:528:DC%2BD1MXht1ylurzE
    • (2009) Bioorg Med Chem , vol.17 , pp. 7585-7592
    • Solomon, V.R.1    Hu, C.2    Lee, H.3
  • 22
    • 77956182123 scopus 로고    scopus 로고
    • Synthesis and antioxidant activity of quinolinobenzothiazinones
    • 10.1016/j.ejmech.2010.07.006 20691512 10.1016/j.ejmech.2010.07.006 1:CAS:528:DC%2BC3cXhtV2itbfJ
    • M Kumar K Sharma RM Samarth A Kumar 2010 Synthesis and antioxidant activity of quinolinobenzothiazinones Eur J Med Chem 45 4467 4472 10.1016/j.ejmech.2010.07.006 20691512 10.1016/j.ejmech.2010.07.006 1:CAS:528:DC%2BC3cXhtV2itbfJ
    • (2010) Eur J Med Chem , vol.45 , pp. 4467-4472
    • Kumar, M.1    Sharma, K.2    Samarth, R.M.3    Kumar, A.4
  • 24
    • 33745610170 scopus 로고    scopus 로고
    • Synthesis of 7-chloro-5-trifluoromethyl/7-fluoro/7-trifluoromethyl-4H-1, 4-benzothiazines as antimicrobial agents
    • DOI 10.1016/j.bmc.2006.04.009, PII S0968089606002902
    • BS Rathore M Kumar 2006 Synthesis of 7-chloro-5-trifluoromethyl/7-fluoro/ 7-trifluoromethyl-4H-1,4-benzothiazines as antimicrobial agents Bioorg Med Chem 14 5678 5682 10.1016/j.bmc.2006.04.009 16650998 10.1016/j.bmc.2006.04.009 1:CAS:528:DC%2BD28Xmslyqs7w%3D (Pubitemid 43994454)
    • (2006) Bioorganic and Medicinal Chemistry , vol.14 , Issue.16 , pp. 5678-5682
    • Rathore, B.S.1    Kumar, M.2
  • 25
    • 33846880466 scopus 로고    scopus 로고
    • Synthesis of 7-chloro-9-trifluoromethyl-/7-fluorophenothiazines
    • DOI 10.1002/hc.20235
    • BS Rathore V Gupta RR Gupta M Kumar 2007 Synthesis of 7-chloro-9-trifluoromethyl-/7-fluorophenothiazines Heteroat Chem 18 81 86 10.1002/hc.20235 10.1002/hc.20235 1:CAS:528:DC%2BD2sXpsVymtw%3D%3D (Pubitemid 46225950)
    • (2007) Heteroatom Chemistry , vol.18 , Issue.1 , pp. 81-86
    • Rathore, B.S.1    Gupta, V.2    Gupta, R.R.3    Kumar, M.4
  • 26
    • 77955031573 scopus 로고    scopus 로고
    • One-pot multicomponent sequential synthesis of benzothiazoloquinazolinones
    • 10.1080/00397910903243807 10.1080/00397910903243807
    • BK Sharma PK Sharma M Kumar 2010 One-pot multicomponent sequential synthesis of benzothiazoloquinazolinones Synth Commun 40 2341 2346 10.1080/00397910903243807 10.1080/00397910903243807
    • (2010) Synth Commun , vol.40 , pp. 2341-2346
    • Sharma, B.K.1    Sharma, P.K.2    Kumar, M.3


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