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Volumn 16, Issue 5 A, 1996, Pages 2525-2532

Synthesis and antitumor activity of 1-[2-(chloroethyl)-3-(2-substituted-10H-phenothiazin-10-yl)alkyl-1- ureas as potent anticancer agents

Author keywords

10 N (phthalimido)alkyl 2 substituted 10H phenothiazines,1 (2 ; Antitumor activity; chloroethyl) 3 (2 substituted 10H phenothiazin 10 yl)alkyl 1 ureas; Structure activity relationship

Indexed keywords

PHENOTHIAZINE DERIVATIVE; UREA DERIVATIVE;

EID: 0029966193     PISSN: 02507005     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (38)

References (32)
  • 1
    • 1842268447 scopus 로고
    • Antitumor activities of phenothiazines (Phenothiazine Oncology)
    • Gupta RR (ed), Elsevier
    • Motohashi N: Antitumor activities of phenothiazines (Phenothiazine Oncology) In: Gupta RR (ed), Phenothiazines and 1,4-Benzothiazines, Bioactive Molecules. Vol 4, Elsevier, 1988, pp 705-770.
    • (1988) Phenothiazines and 1,4-Benzothiazines, Bioactive Molecules , vol.4 , pp. 705-770
    • Motohashi, N.1
  • 2
    • 0025689995 scopus 로고
    • Interaction of chlorpromazine with DNA
    • Motohashi N, Kamata K and Meyer R: Interaction of chlorpromazine with DNA. Anticancer Res 10: 1611-1614, 1990.
    • (1990) Anticancer Res , vol.10 , pp. 1611-1614
    • Motohashi, N.1    Kamata, K.2    Meyer, R.3
  • 3
    • 0022357199 scopus 로고
    • Cancer therapy: Phenothiazines in an unexpected role
    • Jones GRN: Cancer therapy: Phenothiazines in an unexpected role. Tumori 71: 563-569, 1985.
    • (1985) Tumori , vol.71 , pp. 563-569
    • Jones, G.R.N.1
  • 4
    • 0027372218 scopus 로고
    • Enhancement of immune response by phenothiazine administration in vivo
    • Ghosh N and Chattopadhyay U: Enhancement of immune response by phenothiazine administration in vivo. In Vivo 7: 435-440, 1993.
    • (1993) In Vivo , vol.7 , pp. 435-440
    • Ghosh, N.1    Chattopadhyay, U.2
  • 5
    • 0015325643 scopus 로고
    • Hydrophobic and ionic interactions of phenothiazine derivatives with bovine serum albumin
    • Krieglstein J, Meiler W and Staab J: Hydrophobic and ionic interactions of phenothiazine derivatives with bovine serum albumin. Biochem Pharmacol 21: 985-997, 1972.
    • (1972) Biochem Pharmacol , vol.21 , pp. 985-997
    • Krieglstein, J.1    Meiler, W.2    Staab, J.3
  • 6
    • 0018948952 scopus 로고
    • 2+)-ATPase and its antagonism by phenothiazines
    • 2+)-ATPase and its antagonism by phenothiazines. Mol Pharmacol 18: 253-258, 1980.
    • (1980) Mol Pharmacol , vol.18 , pp. 253-258
    • Raess, B.U.1    Vincenzi, F.F.2
  • 7
    • 0019394118 scopus 로고
    • Plasma membrane calcium (2+) ion transport: Antagonism by several potential inhibitors
    • Hinds TR, Raess BU and Vincenzi FF: Plasma membrane calcium (2+) ion transport: antagonism by several potential inhibitors. J Membrane Biol 58: 57-65, 1981.
    • (1981) J Membrane Biol , vol.58 , pp. 57-65
    • Hinds, T.R.1    Raess, B.U.2    Vincenzi, F.F.3
  • 8
    • 0018278265 scopus 로고
    • Regulation of a plasma membrane calcium pump: A speculative model
    • (a) Vincenzi FF: Regulation of a plasma membrane calcium pump: a speculative model. Ann NY Acad Sci 307: 229-231, 1978.
    • (1978) Ann NY Acad Sci , vol.307 , pp. 229-231
    • Vincenzi, F.F.1
  • 9
    • 84921123438 scopus 로고
    • The plasma membrane calcium pump: A potential target for drug action
    • abstract
    • (b) Vincenzi FF, Raess BU, Larsen FL, Jung NSGT and Hinds TR: The plasma membrane calcium pump: a potential target for drug action. Pharmacologist 20 (3): 257 (abstract), 1978.
    • (1978) Pharmacologist , vol.20 , Issue.3 , pp. 257
    • Vincenzi, F.F.1    Raess, B.U.2    Larsen, F.L.3    Jung, N.S.G.T.4    Hinds, T.R.5
  • 10
    • 0019158565 scopus 로고
    • A semi-automated method for the determination of multiple membrane ATPase activities
    • (a) Raess BU and Vincenzi FK: A semi-automated method for the determination of multiple membrane ATPase activities. J Pharmacol Methods 4(3): 273-283, 1980.
    • (1980) J Pharmacol Methods , vol.4 , Issue.3 , pp. 273-283
    • Raess, B.U.1    Vincenzi, F.K.2
  • 11
    • 10544240573 scopus 로고
    • 2+ transport: Inhibition by trifluoroperazine
    • 2+ transport: Inhibition by trifluoroperazine. Pharmacologist 21: 697, 1929.
    • (1929) Pharmacologist , vol.21 , pp. 697
    • Raess, B.U.1    Hinds, T.R.2
  • 12
    • 0023661342 scopus 로고
    • Calmodulin is involved in regulation of cell proliferation
    • Rasmussen CD and Means AR: Calmodulin is involved in regulation of cell proliferation. EMBO J 6: 3961-3968, 1987.
    • (1987) EMBO J , vol.6 , pp. 3961-3968
    • Rasmussen, C.D.1    Means, A.R.2
  • 13
    • 0022516721 scopus 로고
    • Calmodulin: A potential target for cancer chemotherapeutic agents
    • Hait WN and Lazo JS: Calmodulin: A potential target for cancer chemotherapeutic agents. J Clin Oncol 4: 994-1012, 1986.
    • (1986) J Clin Oncol , vol.4 , pp. 994-1012
    • Hait, W.N.1    Lazo, J.S.2
  • 14
    • 0023836456 scopus 로고
    • Most drugs that reverse multidrug resistance also inhibit photoaffinity labeling of P-glycoprotein by a vinblastine analog
    • Akiyama S, Cornwell MM, Kuwano M, Pastan I and Gottesman MM: Most drugs that reverse multidrug resistance also inhibit photoaffinity labeling of P-glycoprotein by a vinblastine analog. Mol Pharmacol 33: 144-147, 1988.
    • (1988) Mol Pharmacol , vol.33 , pp. 144-147
    • Akiyama, S.1    Cornwell, M.M.2    Kuwano, M.3    Pastan, I.4    Gottesman, M.M.5
  • 15
    • 0020591753 scopus 로고
    • Enhancement of sensitivity to adriamycin in resistant P388 leukemia by the calmodulin inhibitor trifluoroperazine
    • Ganapathi R and Grabowski D: Enhancement of sensitivity to adriamycin in resistant P388 leukemia by the calmodulin inhibitor trifluoroperazine. Cancer Res 43: 3696-3699, 1983.
    • (1983) Cancer Res , vol.43 , pp. 3696-3699
    • Ganapathi, R.1    Grabowski, D.2
  • 16
    • 0023205811 scopus 로고
    • The cell biology of multiple drug resistance
    • Beck WT: The cell biology of multiple drug resistance. Biochem Pharmacol 36: 2879-2887, 1987.
    • (1987) Biochem Pharmacol , vol.36 , pp. 2879-2887
    • Beck, W.T.1
  • 17
    • 0021856764 scopus 로고
    • Reduced drug accumulation in multiply drug-resistant human KB carcinoma cell lines
    • Fojo A, Akiyama S, Gottesman MM and Pastan I: Reduced drug accumulation in multiply drug-resistant human KB carcinoma cell lines. Cancer Res 45: 3002-3007, 1985.
    • (1985) Cancer Res , vol.45 , pp. 3002-3007
    • Fojo, A.1    Akiyama, S.2    Gottesman, M.M.3    Pastan, I.4
  • 18
    • 0001463656 scopus 로고
    • Membrane vesicles from multidrug-resistant human cancer cells contain a specific 150- to 170-kDa protein detected by photoaffinity labeling
    • Cornwell MM, Safa AR, Felsted RL, Gottesman MM and Pastan I: Membrane vesicles from multidrug-resistant human cancer cells contain a specific 150- to 170-kDa protein detected by photoaffinity labeling. Proc Natl Acad Sci USA 83: 3847-3850, 1986.
    • (1986) Proc Natl Acad Sci USA , vol.83 , pp. 3847-3850
    • Cornwell, M.M.1    Safa, A.R.2    Felsted, R.L.3    Gottesman, M.M.4    Pastan, I.5
  • 19
    • 0028272272 scopus 로고
    • Similar toxic effect of 1,3-bis(2-chloroethyl)-1-nitrosourea on lymphocytes from human subjects differing in the expression of glutathione transferase M1-1
    • Jungnelius U, Ridderström M, Hansson J, Ringborg U and Mannervik B: Similar toxic effect of 1,3-bis(2-chloroethyl)-1-nitrosourea on lymphocytes from human subjects differing in the expression of glutathione transferase M1-1. Biochem Pharmacol 47: 1777-1780, 1994.
    • (1994) Biochem Pharmacol , vol.47 , pp. 1777-1780
    • Jungnelius, U.1    Ridderström, M.2    Hansson, J.3    Ringborg, U.4    Mannervik, B.5
  • 21
    • 0017641428 scopus 로고
    • Interstrand cross-linking of DNA by 1,3-bis(2-chloroethyl)-1-nitrosoureas and other 1-(2-haloethyl)-Initrosoureas
    • Kohn KW: Interstrand cross-linking of DNA by 1,3-bis(2-chloroethyl)-1-nitrosoureas and other 1-(2-haloethyl)-Initrosoureas. Cancer Res 37: 1450-1454, 1977.
    • (1977) Cancer Res , vol.37 , pp. 1450-1454
    • Kohn, K.W.1
  • 22
    • 10544239763 scopus 로고
    • Modification of DNA and RNA bases by the nitrosoureas
    • Ludlum DB and Tong WP: Modification of DNA and RNA bases by the nitrosoureas. INSERM Symposium 19: 21-31, 1981.
    • (1981) INSERM Symposium , vol.19 , pp. 21-31
    • Ludlum, D.B.1    Tong, W.P.2
  • 23
    • 0025876394 scopus 로고
    • Synthesis of the piperidinone metabolites of piperidine type phenothiazine antipsychotic drugs via Ruthenium tetroxide oxidation
    • Lin G, Midha KK and Hawes EM: Synthesis of the piperidinone metabolites of piperidine type phenothiazine antipsychotic drugs via Ruthenium tetroxide oxidation. J Heterocyclic Chem 28: 215-219, 1991.
    • (1991) J Heterocyclic Chem , vol.28 , pp. 215-219
    • Lin, G.1    Midha, K.K.2    Hawes, E.M.3
  • 24
    • 0019814581 scopus 로고
    • A new class of nitrosoureas. I. Synthesis and antitumor activity of 1-(2-chloroethyl)-3,3-disubstituted-1-nitrosoureas having a hydroxyl group at the ß-position of the substituents
    • Japan
    • Tsujihara K, Ozeki M, Morikawa T and Arai Y: A new class of nitrosoureas. I. Synthesis and antitumor activity of 1-(2-chloroethyl)-3,3-disubstituted-1-nitrosoureas having a hydroxyl group at the ß-position of the substituents. Chem Pharm Bull (Japan) 29: 2509-2515, 1981.
    • (1981) Chem Pharm Bull , vol.29 , pp. 2509-2515
    • Tsujihara, K.1    Ozeki, M.2    Morikawa, T.3    Arai, Y.4
  • 25
    • 10544237879 scopus 로고
    • Studies on the syntheses of phenothiazine derivatives. 11. on the reduction of 10-ß-cyanoethylphenothiazines
    • Fujii K: Studies on the syntheses of phenothiazine derivatives. 11. On the reduction of 10-ß-cyanoethylphenothiazines. Yakugaku Zasshi (in Japanese) 76: 640-644, 1956.
    • (1956) Yakugaku Zasshi (in Japanese) , vol.76 , pp. 640-644
    • Fujii, K.1
  • 26
    • 0017106877 scopus 로고
    • Inhibition of human neutrophil chemotaxis in vitro by phenothiazines and related compounds
    • Björksten B and Quie PG: Inhibition of human neutrophil chemotaxis in vitro by phenothiazines and related compounds. Infect Immun 14: 948-950, 1976.
    • (1976) Infect Immun , vol.14 , pp. 948-950
    • Björksten, B.1    Quie, P.G.2
  • 27
    • 0013508682 scopus 로고
    • A retrovirus carrying an MDR1 cDNA confers multidrug resistance and polarized expression of P-glycoprotein in MDCK cells
    • Pastan I, Gottesman MM, Ueda K, Lovelace E, Rutherford AV and Willingham MC: A retrovirus carrying an MDR1 cDNA confers multidrug resistance and polarized expression of P-glycoprotein in MDCK cells. Proc Natl Acad Sci USA 85: 4486-4490, 1988.
    • (1988) Proc Natl Acad Sci USA , vol.85 , pp. 4486-4490
    • Pastan, I.1    Gottesman, M.M.2    Ueda, K.3    Lovelace, E.4    Rutherford, A.V.5    Willingham, M.C.6
  • 28
    • 0027195754 scopus 로고
    • The effect of ion channel blockers, immunosuppressive agents, and other drugs on the activity of the multi-drug transporter
    • Weaver JL, Szabo G, Pine PS, Gottesman MM, Goldenberg S and Aszalos A: The effect of ion channel blockers, immunosuppressive agents, and other drugs on the activity of the multi-drug transporter. Int J Cancer 54: 456-461, 1993.
    • (1993) Int J Cancer , vol.54 , pp. 456-461
    • Weaver, J.L.1    Szabo, G.2    Pine, P.S.3    Gottesman, M.M.4    Goldenberg, S.5    Aszalos, A.6
  • 29
    • 0024794496 scopus 로고
    • Exploring multidrug resistance using Rhodamine 123
    • Kessel D: Exploring multidrug resistance using Rhodamine 123. Cancer Commun 1: 145-149, 1989.
    • (1989) Cancer Commun , vol.1 , pp. 145-149
    • Kessel, D.1
  • 30
    • 0020533372 scopus 로고
    • Revised methods for the Salmonella mutagenicity test
    • Maron DM and Ames BN: Revised methods for the Salmonella mutagenicity test. Mutation Res 113: 173-215, 1983.
    • (1983) Mutation Res , vol.113 , pp. 173-215
    • Maron, D.M.1    Ames, B.N.2
  • 31
    • 0026777319 scopus 로고
    • Human wild-type p53 adopts a unique conformational and phosphorylation state in vivo during growth arrest of glioblastoma cells
    • Ullrich SJ, Mercer WE and Appella E: Human wild-type p53 adopts a unique conformational and phosphorylation state in vivo during growth arrest of glioblastoma cells. Oncogene 7: 1635-1643, 1992.
    • (1992) Oncogene , vol.7 , pp. 1635-1643
    • Ullrich, S.J.1    Mercer, W.E.2    Appella, E.3
  • 32
    • 0025221676 scopus 로고
    • Addition of fresh medium induces cell cycle and conformation changes in p53, a tumor suppressor protein
    • Milner J and Watson JV: Addition of fresh medium induces cell cycle and conformation changes in p53, a tumor suppressor protein. Oncogene 5: 1683-1690, 1990.
    • (1990) Oncogene , vol.5 , pp. 1683-1690
    • Milner, J.1    Watson, J.V.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.