메뉴 건너뛰기




Volumn 27, Issue 6, 2009, Pages 534-542

Synthesis of novel 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole derivatives as antiproliferative agents: A structure-activity relationship study

Author keywords

2 benzisoxazole; 6 fluoro 3 (4 piperidinyl) 1; Acid chloride; Antiproliferative activity; Cancer therapy; Cell proliferation.; Isonipecotic acid; MTT assay

Indexed keywords

(3 BROMOPHENYL)(4 (6 FLUOROBENZISOXAZOL 3 YL)PIPERIDIN 1 YL)METHANONE; (4 (6 FLUOROBENZISOXAZOL 3 YL)PIPERIDIN 1 YL) (4 METHYLPIPERAZIN 1 YL)METHANONE; (4 (6 FLUOROBENZISOXAZOL 3 YL)PIPERIDIN 1 YL)(2 FLUOROPHENYL)METHANONE; (4 (6 FLUOROBENZISOXAZOL 3 YL)PIPERIDIN 1 YL)(2,4 DICHLORO PHENYL)METHANONE; (4 (6 FLUOROBENZISOXAZOL 3 YL)PIPERIDIN 1 YL)(2,6 DIFLUOROPHENYL)METHANONE; (4 (6 FLUOROBENZISOXAZOL 3 YL)PIPERIDIN 1 YL)(3 METHOXYPHENYL)METHANONE; (4 (6 FLUOROBENZISOXAZOL 3 YL)PIPERIDIN 1 YL)(3,5 DINITRO PHENYL)METHANONE; (4 (6 FLUOROBENZISOXAZOL 3 YL)PIPERIDIN 1 YL)(MORPHOLINO)METHANONE; (4 (6 FLUOROBENZISOXAZOL 3 YL)PIPERIDIN 1 YL)(P TOLYL)METHANONE; (4 (6 FLUOROBENZISOXAZOL 3 YL)PIPERIDIN 1 YL)(PYRROLIDIN 1 YL)METHANONE; (4 CHLOROPHENYL)(4 (6 FLUOROBENZISOXAZOL 3 YL)PIPERIDIN 1 YL)METHANONE; (4 TERT BUTYLPHENYL)(4 (6 FLUOROBENZISOXAZOL 3 YL) PIPERIDIN 1 YL)METHANONE; 1 (4 (6 FLUOROBENZISOXAZOL 3 YL)PIPERIDIN 1 YL) 2 PHENYL ETHANONE; 3 (4,5 DIMETHYL 2 THIAZOLYL) 2,5 DIPHENYLTETRAZOLIUM BROMIDE; 6 FLUORO 3 (4 PIPERIDINYL) 1,2 BENZISOXAZOLE DERIVATIVE; ANTINEOPLASTIC AGENT; AROMATIC CARBOXYLIC ACID; HETEROCYCLIC COMPOUND; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 70450252406     PISSN: 01676997     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10637-008-9205-5     Document Type: Article
Times cited : (18)

References (22)
  • 1
    • 0033859256 scopus 로고    scopus 로고
    • Achievements and future of chemotherapy
    • DOI 10.1016/S0959-8049(00)00133-7, PII S0959804900001337
    • J Verweij MJA Jonge 2000 Achievements and future of chemotherapy Eur J Cancer 36 1479 1487 10.1016/S0959-8049(00)00133-7 1:STN:280: DC%2BD3cvotVekuw%3D%3D 10930795 doi:10.1016/S0959-8049(00)00133-7 (Pubitemid 30619000)
    • (2000) European Journal of Cancer , vol.36 , Issue.12 , pp. 1479-1487
    • Verweij, J.1    De Jonge, M.J.A.2
  • 2
    • 0035015868 scopus 로고    scopus 로고
    • Incidence and prevalence of all cancerous diseases in Italy: Trends and implications
    • DOI 10.1016/S0959-8049(01)00094-6, PII S0959804901000946
    • A Verdecchia A Mariotto R Capocaccia G Gatta A Micheli M Sant F Berrino 2001 Incidence and prevalence of all cancerous diseases in Italy: trends and implications Eur J Cancer 37 1149 1157 10.1016/S0959-8049(01)00094-6 1:STN:280:DC%2BD3M3pslektQ%3D%3D 11378346 doi:10.1016/S0959-8049(01)00094-6 (Pubitemid 32520889)
    • (2001) European Journal of Cancer , vol.37 , Issue.9 , pp. 1149-1157
    • Frouin, I.1    Prosperi, E.2    Denegri, M.3    Negri, C.4    Donzelli, M.5    Rossi, L.6    Riva, F.7    Stefanini, M.8    Scovassi, A.I.9
  • 3
    • 0033402254 scopus 로고    scopus 로고
    • Discovering novel chemotherapeutic drugs for the third millennium
    • DOI 10.1016/S0959-8049(99)00280-4, PII S0959804999002804
    • MD Garret P Workman 1999 Discovering novel chemotherapeutic drugs for the third millennium Eur J Cancer 35 2010 2030 10.1016/S0959-8049(99)00280-4 doi:10.1016/S0959-8049(99)00280-4 (Pubitemid 30026222)
    • (1999) European Journal of Cancer , vol.35 , Issue.14 , pp. 2010-2030
    • Garrett, M.D.1    Workman, P.2
  • 4
    • 27544446579 scopus 로고    scopus 로고
    • Promiscuous drugs compared to selective drugs (promiscuity can be a virtue)
    • DOI 10.1186/1472-6904-5-3
    • SK Mencher LG Wang 2005 Promiscuous drugs compared to selective drugs (promiscuity can be a virtue) BMC Clin Pharmacol 5 3 10.1186/1472-6904-5-3 15854222 doi:10.1186/1472-6904-5-3 (Pubitemid 41534964)
    • (2005) BMC Clinical Pharmacology , vol.5 , pp. 3
    • Mencher, S.K.1    Wang, L.G.2
  • 5
    • 33746232407 scopus 로고    scopus 로고
    • Multitargeted therapy: Can promiscuity be praised in an era of political correctness?
    • DOI 10.1016/j.critrevonc.2006.01.005, PII S1040842806000199
    • A Jimeno M Hidalgo 2006 Multitargeted therapy: can promiscuity be praised in an era of political correctness Crit Rev Oncol Hematol 59 150 158 10.1016/j.critrevonc.2006.01.005 16843676 doi:10.1016/j.critrevonc.2006.01.005 (Pubitemid 44094107)
    • (2006) Critical Reviews in Oncology/Hematology , vol.59 , Issue.2 , pp. 150-158
    • Jimeno, A.1    Hidalgo, M.2
  • 7
    • 0025094689 scopus 로고
    • Pilot clinical investigation of risperidone in the treatment of psychotic patients
    • 10.1055/s-2007-1014509 1:STN:280:DyaK3M%2FmslOntg%3D%3D 1701262 doi:10.1055/s-2007-1014509
    • YG Gelders SLE Heylen BG Vander AJM Reyntjens PAJ Janssen 1990 Pilot clinical investigation of risperidone in the treatment of psychotic patients Pharmacopsychiatry 23 206 211 10.1055/s-2007-1014509 1:STN:280: DyaK3M%2FmslOntg%3D%3D 1701262 doi:10.1055/s-2007-1014509
    • (1990) Pharmacopsychiatry , vol.23 , pp. 206-211
    • Gelders, Y.G.1    Heylen, S.L.E.2    Vander, B.G.3    Reyntjens, A.J.M.4    Janssen, P.A.J.5
  • 8
    • 0004047129 scopus 로고    scopus 로고
    • Churchill Livingstone Edinburgh, UK
    • Dollery C (1999) Therapeutic drugs. Churchill Livingstone, Edinburgh, UK
    • (1999) Therapeutic Drugs
    • Dollery, C.1
  • 9
    • 0028074997 scopus 로고
    • Effects of fluorine substitution on drug metabolism: Pharmacological and toxicological implications
    • 10.3109/03602539408998319 1:CAS:528:DyaK2cXmslSqtbc%3D 7924905 doi:10.3109/03602539408998319
    • BK Park NR Kitteringham 1994 Effects of fluorine substitution on drug metabolism: pharmacological and toxicological implications Drug Metab Rev 26 605 643 10.3109/03602539408998319 1:CAS:528:DyaK2cXmslSqtbc%3D 7924905 doi:10.3109/03602539408998319
    • (1994) Drug Metab Rev , vol.26 , pp. 605-643
    • Park, B.K.1    Kitteringham, N.R.2
  • 10
    • 32944470419 scopus 로고    scopus 로고
    • Synthesis and anti-HIV activity of new alkenyldiarylmethane (ADAM) non-nucleoside reverse transcriptase inhibitors (NNRTIs) incorporating benzoxazolone and benzisoxazole rings
    • DOI 10.1016/j.bmc.2005.11.014, PII S0968089605010783
    • BL Deng MD Cullen Z Zhou TL Hartman RW Buckheit Jr C Pannecouque ED Clercq PE Fanwick M Cushmana 2006 Synthesis and anti-HIV activity of new alkenyldiarylmethane (ADAM) non-nucleoside reverse transcriptase inhibitors (NNRTIs) incorporating benzoxazolone and benzisoxazole rings Bioorg Med Chem 14 2366 2374 10.1016/j.bmc.2005.11.014 1:CAS:528:DC%2BD28XhsFKqtrg%3D 16321539 doi:10.1016/j.bmc.2005.11.014 (Pubitemid 43256690)
    • (2006) Bioorganic and Medicinal Chemistry , vol.14 , Issue.7 , pp. 2366-2374
    • Deng, B.-L.1    Cullen, M.D.2    Zhou, Z.3    Hartman, T.L.4    Buckheit Jr., R.W.5    Pannecouque, C.6    Clercq, E.D.7    Fanwick, P.E.8    Cushman, M.9
  • 11
    • 0345412552 scopus 로고    scopus 로고
    • 1,2-Benzisoxazole Phosphorodiamidates as Novel Anticancer Prodrugs Requiring Bioreductive Activation
    • DOI 10.1021/jm020581y
    • M Jain CH Kwon 2003 1,2-Benzisoxazole phosphorodiamidates as novel anticancer prodrugs requiring bioreductive activation J Med Chem 46 25 5428 5436 10.1021/jm020581y 1:CAS:528:DC%2BD3sXovVOisLc%3D 14640551 doi:10.1021/jm020581y (Pubitemid 37490375)
    • (2003) Journal of Medicinal Chemistry , vol.46 , Issue.25 , pp. 5428-5436
    • Jain, M.1    Kwon, C.-H.2
  • 12
    • 0018601171 scopus 로고
    • Potential antiinflammatory compounds. II. Acidic antiinflammatory 1,2-benzisoxazoles
    • DOI 10.1021/jm00198a026
    • JC Saunders WR Williamson 1979 Potential antiinflammatory compounds. 2. Acidic antiinflammatory 1,2-benzisoxazoles J Med Chem 22 12 1554 1558 10.1021/jm00198a026 1:CAS:528:DyaE1MXmtVCnsL8%3D 537000 doi:10.1021/jm00198a026 (Pubitemid 10190310)
    • (1979) Journal of Medicinal Chemistry , vol.22 , Issue.12 , pp. 1554-1558
    • Saunders, J.C.1    Williamson, W.R.N.2
  • 13
    • 0029957641 scopus 로고    scopus 로고
    • Synthesis and binding affinities of a series of 1,2-benzisoxazole-3- carboxamides to dopamine and serotonin receptors
    • DOI 10.1016/S0223-5234(97)86174-0
    • A Nuhrich MV Lembege J Vercauteren R Dokhan P Renard G Devaux 1996 Synthesis and binding affinities of a series of 1,2-benzisoxazole-3-carboxamides to dopamine and serotonin receptors Eur J Med Chem 31 957 964 10.1016/S0223-5234(97)86174-0 1:CAS:528:DyaK2sXhvVKlsA%3D%3D doi:10.1016/S0223-5234(97)86174-0 (Pubitemid 26418439)
    • (1996) European Journal of Medicinal Chemistry , vol.31 , Issue.12 , pp. 957-964
    • Nuhrich, A.1    Varache-Lembege, M.2    Vercauteren, J.3    Dokhan, R.4    Renard, P.5    Devaux, G.6
  • 14
    • 0026580133 scopus 로고
    • Reductive metabolism of the anticonvulsant agent zonisamide, a 1,2-benzisoxazole derivative
    • 10.3109/00498259209053097 1:CAS:528:DyaK38Xht1Sgt7Y%3D 1615700
    • DD Stiff JT Robicheau MA Zemaitis 1992 Reductive metabolism of the anticonvulsant agent zonisamide, a 1,2-benzisoxazole derivative Xenobiotica 22 1 1 11 10.3109/00498259209053097 1:CAS:528:DyaK38Xht1Sgt7Y%3D 1615700
    • (1992) Xenobiotica , vol.22 , Issue.1 , pp. 1-11
    • Stiff, D.D.1    Robicheau, J.T.2    Zemaitis, M.A.3
  • 15
    • 0032916931 scopus 로고    scopus 로고
    • 11C]methoxy-3-[2[1- (phenylmethyl)-4- piperidinyl]ethyl]-1,2-benzisoxazole as an in vivo radioligand for acetylcholinesterase
    • DOI 10.1016/S0969-8051(98)00078-X, PII S096980519800078X
    • 11C]Methoxy-3-[2- [1-(phenylmethyl)-4-piperidinyl]ethyl]-1,2- benzisoxazole as an in vivo radioligand for acetylcholinesterase Nucl Med Biol 26 1 99 103 10.1016/S0969-8051(98)00078-X doi:10.1016/S0969-8051(98)00078-X (Pubitemid 29030528)
    • (1999) Nuclear Medicine and Biology , vol.26 , Issue.1 , pp. 99-103
    • Brown-Proctor, C.1    Snyder, S.E.2    Sherman, P.S.3    Kilbourn, M.R.4
  • 16
    • 14844330802 scopus 로고    scopus 로고
    • Synthesis and characterization of novel 6-fluoro-4-piperidinyl-1,2- benzisoxazole amides and 6-fluoro-chroman-2-carboxamides: Antimicrobial studies
    • DOI 10.1016/j.bmc.2005.01.026
    • BS Priya Basappa SN Swamy KS Rangappa 2005 Synthesis and characterization of novel 6-fluoro-4-piperidinyl-1,2-benzisoxazole amides and 6-fluoro-chroman-2-carboxamides: antimicrobial studies Bioorg Med Chem 13 7 2623 2628 10.1016/j.bmc.2005.01.026 1:CAS:528:DC%2BD2MXitVartb8%3D 15846867 doi:10.1016/j.bmc.2005.01.026 (Pubitemid 40341664)
    • (2005) Bioorganic and Medicinal Chemistry , vol.13 , Issue.7 , pp. 2623-2628
    • Priya, B.S.1    Basappa2    Swamy, S.N.3    Rangappa, K.S.4
  • 17
    • 50249101608 scopus 로고    scopus 로고
    • Synthesis and in vitro antiproliferative activity against human cancer cell lines of novel 5-(4-methyl-benzylidene)-thiazolidine-2,4-diones
    • 10.1007/s10637-008-9130-7 1:CAS:528:DC%2BD1cXhtVSku7fO 18473120 doi:10.1007/s10637-008-9130-7
    • S Chandrappa SB Benaka Prasad K Vinaya CS Ananda Kumar NR Thimmegowda KS Rangappa 2008 Synthesis and In vitro antiproliferative activity against human cancer cell lines of novel 5-(4-methyl-benzylidene)-thiazolidine-2,4-diones Invest New Drugs 26 437 444 10.1007/s10637-008-9130-7 1:CAS:528: DC%2BD1cXhtVSku7fO 18473120 doi:10.1007/s10637-008-9130-7
    • (2008) Invest New Drugs , vol.26 , pp. 437-444
    • Chandrappa, S.1    Benaka Prasad, S.B.2    Vinaya, K.3    Ananda Kumar, C.S.4    Thimmegowda, N.R.5    Rangappa, K.S.6
  • 18
    • 66949117121 scopus 로고    scopus 로고
    • Synthesis and antiproliferative activity of substituted diazaspiro hydantoins: A structure-activity relationship study
    • doi: 10.1007/s10637-008-9150-3
    • Ananda Kumar CS, Benaka Prasad SB, Vinaya K, Chandrappa S, Thimmegowda NR Sanjay Swarup, Rangappa KS (2008) Synthesis and antiproliferative activity of substituted diazaspiro hydantoins: a structure-activity relationship study. Invest New Drugs. doi: 10.1007/s10637-008-9150-3.
    • (2008) Invest New Drugs
    • Ananda Kumar, C.S.1    Benaka Prasad, S.B.2    Vinaya, K.3    Chandrappa, S.4    Swarup Sanjay T.Nr5    Rangappa, K.S.6
  • 19
    • 40549101901 scopus 로고    scopus 로고
    • Synthesis and evaluation of 1-benzhydryl-sulfonyl-piperazine derivatives as inhibitors of MDA-MB-231 human breast cancer cell proliferation
    • DOI 10.1007/s00044-007-9022-y
    • CS Ananda Kumar S Nanjunda Swamy NR Thimmegowda SB Benaka Prasad WY George KS Rangappa 2007 Synthesis and evaluation of 1-benzhydryl-sulfonyl- piperazine derivatives as inhibitors of MDA-MB-231 human breast cancer cell proliferation Med Chem Res 16 179 187 10.1007/s00044-007-9022-y 1:CAS:528:DC%2BD1cXit12itb4%3D doi:10.1007/s00044-007-9022-y (Pubitemid 351363183)
    • (2007) Medicinal Chemistry Research , vol.16 , Issue.4 , pp. 179-187
    • Ananda Kumar, C.S.1    Nanjunda Swamy, S.2    Thimmegowda, N.R.3    Benaka Prasad, S.B.4    Yip, G.W.5    Rangappa, K.S.6
  • 21
    • 7644233081 scopus 로고    scopus 로고
    • A simple and efficient method for the synthesis 1,2-benzisoxazoles: A series of its potent acetylcholinesterase inhibitors
    • Basappa K Mantelingu MP Sadashiva KS Rangappa 2004 A simple and efficient method for the synthesis 1,2-benzisoxazoles: a series of its potent acetylcholinesterase inhibitors Indian J Chem 43 B 1954 1957
    • (2004) Indian J Chem , vol.43 , Issue.B , pp. 1954-1957
    • Basappa1    Mantelingu, K.2    Sadashiva, M.P.3    Rangappa, K.S.4
  • 22
    • 0023792919 scopus 로고
    • Evaluation of a soluble tetrazolium/formazan assay for cell growth and drug sensitivity in culture using human and other tumor cell lines
    • 1:CAS:528:DyaL1cXls1arsrk%3D 3409223
    • DA Scudiero RH Shoemaker KD Paull A Monks S Tierney TH Nofziger MJ Currens D Seni MR Boyd 1988 Evaluation of a soluble tetrazolium/formazan assay for cell growth and drug sensitivity in culture using human and other tumor cell lines Cancer Res 48 4827 4833 1:CAS:528:DyaL1cXls1arsrk%3D 3409223
    • (1988) Cancer Res , vol.48 , pp. 4827-4833
    • Scudiero, D.A.1    Shoemaker, R.H.2    Paull, K.D.3    Monks, A.4    Tierney, S.5    Nofziger, T.H.6    Currens, M.J.7    Seni, D.8    Boyd, M.R.9


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.