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Volumn 23, Issue 2, 2014, Pages 896-904

Greener synthesis and photo-antiproliferative activity of novel fluorinated benzothiazolo[2, 3-b]quinazolines

Author keywords

Antiproliferative activity; Fluorinated benzothiazolo 2,3 b quinazolines; Ionic liquid; Microwaves

Indexed keywords

5,5 DIMETHYL 1,3 CYCLOHEXANEDIONE; 8 CHLORO 12 (2 FLUOROPHENYL) 2,3,4,12 TETRAHYDRO 3,3 DIMETHYL 1H BENZOTHIAZOLO[2,3 B]QUINAZOLIN 1 ONE; 8 CHLORO 12 (4' CHLOROPHENYL) 2,3,4,12 TETRAHYDRO 3,3 DIMETHYL 1H BENZOTHIAZOLO[2,3 B]QUINAZOLIN 1 ONE; 9 CHLORO 3,3 DIMETHYL 2,4,6 TRIHYDRO(5H)BENZOTHIAZOLO[2,3 B]QUINAZOLIN 5 ONE; 9 CHLORO 3,3 DIMETHYL 6 (2' TRIFLUOROMETHYL PHENYL) 2,4,6 TRIHYDRO(5H)BENZOTHIAZOLO[2,3 B]QUINAZOLIN 5 ONE; 9 CHLORO 3,3 DIMETHYL 6 (3' FLUORO PHENYL)2,4,6 TRIHYDRO(5H)BENZOTHIAZOLO[2,3 B]QUINAZOLIN 5 ONE; 9 CHLORO 3,3 DIMETHYL 6 (3' TRIFLUOROMETHYL PHENYL) 2,4,6 TRIHYDRO(5H)BENZOTHIAZOLO[2,3 B]QUINAZOLIN 5 ONE; 9 CHLORO 3,3 DIMETHYL 6 (4' FLUORO PHENYL)2,4,6 TRIHYDRO(5H)BENZOTHIAZOLO[2,3 B]QUINAZOLIN 5 ONE; 9 CHLORO 3,3 DIMETHYL 6 (4' METHYLPHENYL) 2,4,6 TRIHYDRO(5H)BENZOTHIAZOLO[2,3 B]QUINAZOLIN 5 ONE; 9 CHLORO 3,3 DIMETHYL 6 (4' TRIFLUOROMETHYL PHENYL) 2,4,6 TRIHYDRO(5H)BENZOTHIAZOLO[2,3 B]QUINAZOLIN 5 ONE; 9 CHLORO 3,3 DIMETHYL 6 (5' CHLORO 2' FLUORO PHENYL) 2,4,6 TRIHYDRO(5H)BENZOTHIAZOLO[2,3 B]QUINAZOLIN 5 ONE; ANTINEOPLASTIC AGENT; BENZALDEHYDE DERIVATIVE; BENZOTHIAZOLE DERIVATIVE; DNA; FLUOROURACIL; QUINAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 84893775497     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-013-0689-y     Document Type: Article
Times cited : (19)

References (34)
  • 1
    • 78651104965 scopus 로고    scopus 로고
    • Microwave induced preparation of biologically important benzothiazolo [2,3-b] quinazolines, and comparison with ultrasonic and classical heating
    • 10.1007/s00706-010-0361-x
    • Arya K, Dandia A, Khaturia S, Jain AK (2010) Microwave induced preparation of biologically important benzothiazolo [2,3-b] quinazolines, and comparison with ultrasonic and classical heating. Monatsh Chem 141:979-985
    • (2010) Monatsh Chem , vol.141 , pp. 979-985
    • Arya, K.1    Dandia, A.2    Khaturia, S.3    Jain, A.K.4
  • 2
    • 84869986976 scopus 로고    scopus 로고
    • Proline confined FAU zeolite: Heterogeneous hybrid catalyst for the synthesis of spiroheterocycles via a Mannich type reaction
    • 1:CAS:528:DC%2BC38XhslaqtLjK 10.1039/c2gc35822k
    • Arya K, Rajesh UC, Rawat DS (2012) Proline confined FAU zeolite: heterogeneous hybrid catalyst for the synthesis of spiroheterocycles via a Mannich type reaction. Green Chem 14:3344
    • (2012) Green Chem , vol.14 , pp. 3344
    • Arya, K.1    Rajesh, U.C.2    Rawat, D.S.3
  • 3
    • 84883464414 scopus 로고    scopus 로고
    • Synthesis, anti-inflammatory activity, and QSAR study of some Schiff bases derived from 5-mercapto-3-(4′-pyridyl)-4H-1,2,4-triazol-4-yl- thiosemicarbazide
    • doi: 10.1007/s00044-013-0507-6
    • Arya K, Sachdeva H, Dwivedi D, Khaturia S, Saroj R (2013) Synthesis, anti-inflammatory activity, and QSAR study of some Schiff bases derived from 5-mercapto-3-(4′-pyridyl)-4H-1,2,4-triazol-4-yl-thiosemicarbazide. Med Chem Res. doi: 10.1007/s00044-013-0507-6
    • (2013) Med Chem Res
    • Arya, K.1    Sachdeva, H.2    Dwivedi, D.3    Khaturia, S.4    Saroj, R.5
  • 5
    • 0001191030 scopus 로고
    • Studies on 2-aminobenzothiazoles
    • 1:CAS:528:DyaG1MXhtVGms7o%3D
    • Bhargava PN, Baliga BT (1958) Studies on 2-aminobenzothiazoles. J Indian Chem Soc 35:807-810
    • (1958) J Indian Chem Soc , vol.35 , pp. 807-810
    • Bhargava, P.N.1    Baliga, B.T.2
  • 6
    • 7344246555 scopus 로고    scopus 로고
    • Influence of 2-(4-aminophenyl)benzothiazoles on growth of human ovarian carcinoma cells in vitro and in vivo
    • 1:CAS:528:DyaK1cXlslWjtb0%3D 2063080 9716022 10.1038/bjc.1998.510
    • Bradshaw TD, Shi DF, Schultz RJ, Paull KD, Wilson A, Garner C, Fiebig HH, Wrigley S, Stevens MFG (1998) Influence of 2-(4-aminophenyl)benzothiazoles on growth of human ovarian carcinoma cells in vitro and in vivo. Br J Cancer 78:421-429
    • (1998) Br J Cancer , vol.78 , pp. 421-429
    • Bradshaw, T.D.1    Shi, D.F.2    Schultz, R.J.3    Paull, K.D.4    Wilson, A.5    Garner, C.6    Fiebig, H.H.7    Wrigley, S.8    Stevens, M.F.G.9
  • 7
    • 0037156957 scopus 로고    scopus 로고
    • In vitro evaluation of amino acid prodrugs of novel antitumour 2-(4-amino-3-methylphenyl)benzothiazoles
    • 1:CAS:528:DC%2BD38XksVSmtbo%3D 2375326 11953897 10.1038/sj.bjc.6600225
    • Bradshaw TD, Chua MS, Browne HL, Trapani V, Suasville EA, Stevens MFG (2002) In vitro evaluation of amino acid prodrugs of novel antitumour 2-(4-amino-3-methylphenyl)benzothiazoles. Br J Cancer 86:1348-1352
    • (2002) Br J Cancer , vol.86 , pp. 1348-1352
    • Bradshaw, T.D.1    Chua, M.S.2    Browne, H.L.3    Trapani, V.4    Suasville, E.A.5    Stevens, M.F.G.6
  • 8
    • 4243545125 scopus 로고    scopus 로고
    • Oxidative nucleobase modifications leading to strand scission
    • 1:CAS:528:DyaK1cXis12htrY%3D 11848927 10.1021/cr960421s
    • Burrows CJ, Muller JG (1998) Oxidative nucleobase modifications leading to strand scission. Chem Rev 98:1109-1152
    • (1998) Chem Rev , vol.98 , pp. 1109-1152
    • Burrows, C.J.1    Muller, J.G.2
  • 9
    • 31544434530 scopus 로고    scopus 로고
    • Recent developments in isocyanide based multicomponent reactions in applied chemistry
    • 16402771 10.1021/cr0505728
    • Dömling A (2006) Recent developments in isocyanide based multicomponent reactions in applied chemistry. Chem Rev 106:17-89
    • (2006) Chem Rev , vol.106 , pp. 17-89
    • Dömling, A.1
  • 10
    • 0036364137 scopus 로고    scopus 로고
    • Excited-state properties and in vitro phototoxicity studies of three phenothiazine derivatives
    • 1:CAS:528:DC%2BD38XptFeitA%3D%3D 11837323 10.1562/0031-8655(2002) 075<0011:ESPAIV>2.0.CO;2
    • Elisei F, Aloisi G, Latterini L, Mazzuccato U, Viola G, Miolo G, Vedaldi D, Dall'Acqua F (2002) Excited-state properties and in vitro phototoxicity studies of three phenothiazine derivatives. Photochem Photobiol 75:11-21
    • (2002) Photochem Photobiol , vol.75 , pp. 11-21
    • Elisei, F.1    Aloisi, G.2    Latterini, L.3    Mazzuccato, U.4    Viola, G.5    Miolo, G.6    Vedaldi, D.7    Dall'Acqua, F.8
  • 11
    • 0033800306 scopus 로고    scopus 로고
    • Synthesis of certain pyrimido[2,1-b]benzothiazole and benzothiazolo[2,3-b]quinazoline derivatives for in vitro antitumor and antiviral activities
    • 1:CAS:528:DC%2BD3cXnslOis74%3D
    • El-Sherbeny MA (2000) Synthesis of certain pyrimido[2,1-b]benzothiazole and benzothiazolo[2,3-b]quinazoline derivatives for in vitro antitumor and antiviral activities. Arzeneim Forsch 50:848-853
    • (2000) Arzeneim Forsch , vol.50 , pp. 848-853
    • El-Sherbeny, M.A.1
  • 12
    • 0016336604 scopus 로고
    • Fluorinated compounds of medicinal interest
    • 1:CAS:528:DyaE2MXhs1Cnu7Y%3D
    • Filler R (1974) Fluorinated compounds of medicinal interest. Chem Tech 4:752-756
    • (1974) Chem Tech , vol.4 , pp. 752-756
    • Filler, R.1
  • 13
    • 1842815265 scopus 로고    scopus 로고
    • Synthesis, crystal structure and antiproliferative evaluation of some new substituted benzothiazoles and styrylbenzothiazoles
    • 15081347 10.1016/j.farmac.2004.01.008
    • Grdisa CM, Mrvos-Sermek D, Cetina M, Tralić-Kulenović VK, Pavelić G, Karminski-Zamola G (2004) Synthesis, crystal structure and antiproliferative evaluation of some new substituted benzothiazoles and styrylbenzothiazoles. Farmaco 59:297-305
    • (2004) Farmaco , vol.59 , pp. 297-305
    • Grdisa, C.M.1    Mrvos-Sermek, D.2    Cetina, M.3    Tralić-Kulenović, V.K.4    Pavelić, G.5    Karminski-Zamola, G.6
  • 14
    • 0000319695 scopus 로고    scopus 로고
    • Azido/tetrazole equilibrium in the thiazoloacridinone series
    • 1:CAS:528:DyaK28XkvF2itLg%3D 10.1002/jhet.5570330337
    • Hanoun JP, Faure R, Galy JP (1996) Azido/tetrazole equilibrium in the thiazoloacridinone series. J Heterocycl Chem 33:747-750
    • (1996) J Heterocycl Chem , vol.33 , pp. 747-750
    • Hanoun, J.P.1    Faure, R.2    Galy, J.P.3
  • 15
    • 0033533836 scopus 로고    scopus 로고
    • Antitumor benzothiazoles. 8. Synthesis, metabolic formation, and biological properties of the C- and N-oxidation products of antitumor 2-(4-aminophenyl)benzothiazoles
    • 1:CAS:528:DyaK1MXls1Ojsr0%3D 10514287 10.1021/jm990104o
    • Kashiyama E, Hutchinson I, Chua MS, Stinson SF, Phillips LR, Kaur G, Sausville EA, Bradshaw TD, Westwell AD, Stevens MF (1999) Antitumor benzothiazoles. 8. Synthesis, metabolic formation, and biological properties of the C- and N-oxidation products of antitumor 2-(4-aminophenyl)benzothiazoles. J Med Chem 42(20):4172-4184
    • (1999) J Med Chem , vol.42 , Issue.20 , pp. 4172-4184
    • Kashiyama, E.1    Hutchinson, I.2    Chua, M.S.3    Stinson, S.F.4    Phillips, L.R.5    Kaur, G.6    Sausville, E.A.7    Bradshaw, T.D.8    Westwell, A.D.9    Stevens, M.F.10
  • 16
    • 84921846095 scopus 로고    scopus 로고
    • Diversity oriented one-pot three-component sequential synthesis of annulated benzothiazoloquinazolines
    • 1:CAS:528:DC%2BC38XktFakur0%3D 3349974 22381142 10.1186/2191-2858-2-10
    • Kumar M, Sharma K, Sharma DK (2012) Diversity oriented one-pot three-component sequential synthesis of annulated benzothiazoloquinazolines. Org Med Chem Lett 2:10
    • (2012) Org Med Chem Lett , vol.2 , pp. 10
    • Kumar, M.1    Sharma, K.2    Sharma, D.K.3
  • 17
    • 33748921576 scopus 로고    scopus 로고
    • Direct access to heterocyclic scaffolds by new multicomponent Ugi-smiles couplings
    • 10.1021/ol061605o
    • Laurent EK, Gizolme M, Grimaud L, Oble J (2006) Direct access to heterocyclic scaffolds by new multicomponent Ugi-smiles couplings. Org Lett 8:4019-4021
    • (2006) Org Lett , vol.8 , pp. 4019-4021
    • Laurent, E.K.1    Gizolme, M.2    Grimaud, L.3    Oble, J.4
  • 18
    • 12344263872 scopus 로고    scopus 로고
    • In vitro, in vivo, and in silico analyses of the antitumor activity of 2-(4-amino-3-methylphenyl)-5-fluorobenzothiazoles
    • 1:CAS:528:DC%2BD2MXmtFSg 15634650
    • Leong CO, Suggitt M, Swaine DJ, Bibby MC, Stevens MFG, Bradshaw TD (2004) In vitro, in vivo, and in silico analyses of the antitumor activity of 2-(4-amino-3-methylphenyl)-5-fluorobenzothiazoles. Mol Cancer Ther 3:1565-1575
    • (2004) Mol Cancer Ther , vol.3 , pp. 1565-1575
    • Leong, C.O.1    Suggitt, M.2    Swaine, D.J.3    Bibby, M.C.4    Stevens, M.F.G.5    Bradshaw, T.D.6
  • 19
    • 11444269801 scopus 로고    scopus 로고
    • Novel anticancer targets and drug discovery in post genomic age
    • 1:CAS:528:DC%2BD2MXhvFKlsw%3D%3D 15720261 10.2174/1568011053352631
    • Li Q, Xu W (2005) Novel anticancer targets and drug discovery in post genomic age. Curr Med Chem Anticancer Agents 5(1):53-63
    • (2005) Curr Med Chem Anticancer Agents , vol.5 , Issue.1 , pp. 53-63
    • Li, Q.1    Xu, W.2
  • 20
    • 0035819998 scopus 로고    scopus 로고
    • Phase-separable catalysis using room temperature ionic liquids and supercritical carbon dioxide
    • 10.1039/b009701m
    • Liu F, Abrams MB, Baker RT, Tumas W (2001) Phase-separable catalysis using room temperature ionic liquids and supercritical carbon dioxide. Chem Commun 5:433-434
    • (2001) Chem Commun , vol.5 , pp. 433-434
    • Liu, F.1    Abrams, M.B.2    Baker, R.T.3    Tumas, W.4
  • 21
    • 0000331562 scopus 로고
    • Marine pyridoacridine alkaloid: Structure, synthesis and biological chemistry
    • 1:CAS:528:DyaK3sXkvFGrtbc%3D 10.1021/cr00021a009
    • Molinski TF (1993) Marine pyridoacridine alkaloid: structure, synthesis and biological chemistry. Chem Rev 93:1825-1838
    • (1993) Chem Rev , vol.93 , pp. 1825-1838
    • Molinski, T.F.1
  • 22
    • 84866434883 scopus 로고    scopus 로고
    • Convenient approach for the one-pot, three-component synthesis of triheterocyclic 4H-pyrimido[2,1-b]benzothiazole derivatives using TBAHS
    • 1:CAS:528:DC%2BC38XhtlWnsrzJ 10.1080/00397911.2011.592624
    • Nagarapu L, Gaikwad HK, Palem JD, Venkatesh R, Bantu R, Sridhar B (2013) Convenient approach for the one-pot, three-component synthesis of triheterocyclic 4H-pyrimido[2,1-b]benzothiazole derivatives using TBAHS. Synth Commun 43:93-104
    • (2013) Synth Commun , vol.43 , pp. 93-104
    • Nagarapu, L.1    Gaikwad, H.K.2    Palem, J.D.3    Venkatesh, R.4    Bantu, R.5    Sridhar, B.6
  • 23
    • 34547403674 scopus 로고    scopus 로고
    • IBX-mediated oxidative ugi-type multicomponent reactions: Application to the N and C1 functionalization of tetrahydroisoquinoline
    • 1:CAS:528:DC%2BD2sXosFGmsL8%3D 10.1002/anie.200701603
    • Ngouansavanh T, Zhu J (2007) IBX-mediated oxidative ugi-type multicomponent reactions: application to the N and C1 functionalization of tetrahydroisoquinoline. Angew Chem Int Ed 46:5775-5778
    • (2007) Angew Chem Int Ed , vol.46 , pp. 5775-5778
    • Ngouansavanh, T.1    Zhu, J.2
  • 24
    • 0028450105 scopus 로고
    • Analysing DNA complexes by circular and linear dichroism
    • 1:CAS:528:DyaK2cXmt1Ggs7g%3D 7826674 10.1002/jmr.300070211
    • Norden B, Kurucsev T (1994) Analysing DNA complexes by circular and linear dichroism. J Mol Recognit 7:141-156
    • (1994) J Mol Recognit , vol.7 , pp. 141-156
    • Norden, B.1    Kurucsev, T.2
  • 25
    • 38349047179 scopus 로고    scopus 로고
    • Applications of ionic liquids in the chemical industry
    • 1:CAS:528:DC%2BD1cXmtVWhsQ%3D%3D 18197338 10.1039/b006677j
    • Plechkova NV, Seddon KR (2008) Applications of ionic liquids in the chemical industry. Chem Soc Rev 37:123-150
    • (2008) Chem Soc Rev , vol.37 , pp. 123-150
    • Plechkova, N.V.1    Seddon, K.R.2
  • 26
    • 0036008105 scopus 로고    scopus 로고
    • Control of the reaction between 2-aminobenzothiazoles and Mannich bases: Synthesis of pyrido[2,1-b][1,3]benzothiazoles versus [1,3]benzothiazolo[2,3-b] quinazolines
    • 10.1039/b109676a
    • Quiroga J, Hernandez P, Insuasty B, Abonia R, Cobo J, Sanchez A, Nogueras M, Low JN (2002) Control of the reaction between 2-aminobenzothiazoles and Mannich bases: synthesis of pyrido[2,1-b][1,3]benzothiazoles versus [1,3]benzothiazolo[2,3-b]quinazolines. J Chem Soc Perkin Trans 1(4):555-559
    • (2002) J Chem Soc Perkin Trans , vol.1 , Issue.4 , pp. 555-559
    • Quiroga, J.1    Hernandez, P.2    Insuasty, B.3    Abonia, R.4    Cobo, J.5    Sanchez, A.6    Nogueras, M.7    Low, J.N.8
  • 27
    • 84868704776 scopus 로고    scopus 로고
    • Hydrotalcite: Recyclable, novel heterogeneous catalyst for facile, environmentally benign and high yielding multi-component synthesis and mechanistic study under solvent free conditions
    • 1:CAS:528:DC%2BC38Xhs1ekurbK 10.1039/c2cy20067h
    • Sahu PK, Jain R, Yadav R, Agarwal DD (2012) Hydrotalcite: recyclable, novel heterogeneous catalyst for facile, environmentally benign and high yielding multi-component synthesis and mechanistic study under solvent free conditions. Catal Sci Technol 2:2465-2475
    • (2012) Catal Sci Technol , vol.2 , pp. 2465-2475
    • Sahu, P.K.1    Jain, R.2    Yadav, R.3    Agarwal, D.D.4
  • 28
    • 27644463562 scopus 로고    scopus 로고
    • A novel one-pot three-component reaction: Synthesis of triheterocyclic 4H-pyrimido[2,1-b]benzazoles ring systems
    • 1:CAS:528:DC%2BD2MXhtFOrsLrI 16236502 10.1016/j.bmcl.2005.08.101
    • Shaabani A, Rahmati A, Naderi S (2005) A novel one-pot three-component reaction: synthesis of triheterocyclic 4H-pyrimido[2,1-b]benzazoles ring systems. Bioorg Med Chem Lett 15:5553-5557
    • (2005) Bioorg Med Chem Lett , vol.15 , pp. 5553-5557
    • Shaabani, A.1    Rahmati, A.2    Naderi, S.3
  • 29
    • 0029780539 scopus 로고    scopus 로고
    • Antitumor benzothiazoles. 3. Synthesis of 2-(4-aminophenyl)benzothiazoles and evaluation of their activities against breast cancer cell lines in vitro and in vivo
    • 1:CAS:528:DyaK28XksFahsbc%3D 8765521 10.1021/jm9600959
    • Shi DF, Bradshaw TD, Wrigley S, McCall CJ, Lelieveld P, Fichtner I, Stevens MFG (1996) Antitumor benzothiazoles. 3. Synthesis of 2-(4-aminophenyl)benzothiazoles and evaluation of their activities against breast cancer cell lines in vitro and in vivo. J Med Chem 39:3375-3384
    • (1996) J Med Chem , vol.39 , pp. 3375-3384
    • Shi, D.F.1    Bradshaw, T.D.2    Wrigley, S.3    McCall, C.J.4    Lelieveld, P.5    Fichtner, I.6    Stevens, M.F.G.7
  • 31
    • 38949096876 scopus 로고    scopus 로고
    • Microwave-assisted efficient synthesis of benzo[4,5]imidazo[1,2-a]- pyrimidine derivatives in water under catalyst-free conditions
    • 1:CAS:528:DC%2BD2sXhtlartL3M 10.1002/jhet.5570440625
    • Tu S, Shao Q, Zhou D, Cao L, Shi F, Li C (2007) Microwave-assisted efficient synthesis of benzo[4,5]imidazo[1,2-a]-pyrimidine derivatives in water under catalyst-free conditions. J Heterocycl Chem 44:1401-1406
    • (2007) J Heterocycl Chem , vol.44 , pp. 1401-1406
    • Tu, S.1    Shao, Q.2    Zhou, D.3    Cao, L.4    Shi, F.5    Li, C.6
  • 34
    • 1642561840 scopus 로고    scopus 로고
    • Determination of the Lewis acidity of ionic liquids by means of an IR spectroscopic probe
    • 10.1039/b311615h
    • Yang YI, Kou Y (2004) Determination of the Lewis acidity of ionic liquids by means of an IR spectroscopic probe. Chem Commun 2:226-227
    • (2004) Chem Commun , vol.2 , pp. 226-227
    • Yang, Y.I.1    Kou, Y.2


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