Recent progress in biological activities of synthesized phenothiazines

European Journal of Medicinal Chemistry

Volumn 46, Issue 8, 2011, Pages 3179-3189

  Pluta, Krystian ^a   Morak Młodawska, Beata ^a   Jeleń, Małgorzata ^a  

^a MEDICAL UNIVERSITY OF SILESIA   (Poland)

Author keywords

Antibacterial; Anticancer; Antifungal; Azaphenothiazines; Multi drug resistance; Phenothiazines

Indexed keywords

ANALGESIC AGENT; ANTICONVULSIVE AGENT; ANTIFILARIAL AGENT; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; ANTIINFLAMMATORY AGENT; ANTIMALARIAL AGENT; ANTINEOPLASTIC AGENT; ANTITRYPANOSOMAL AGENT; ANTIVIRUS AGENT; AZABICYCLONONANE DERIVATIVE; BENZENE; DNA; FUNCTIONAL GROUP; HETEROCYCLIC COMPOUND; IMMUNOSUPPRESSIVE AGENT; NAPHTHALENE; OXADIAZOLE DERIVATIVE; PHENOTHIAZINE DERIVATIVE; PYRAZOLE DERIVATIVE; PYRAZOLOPYRIMIDINE DERIVATIVE; PYRIDINE DERIVATIVE; PYRIMIDINE DERIVATIVE; QUINOLIZINE DERIVATIVE; SPIRO COMPOUND; TETRAZOLE DERIVATIVE; THIADIAZOLE DERIVATIVE; THIAZOLE DERIVATIVE; THIAZOLOPYRIDINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTIBACTERIAL ACTIVITY; ANTICONVULSANT ACTIVITY; ANTIFUNGAL ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; BILAYER MEMBRANE; BIOLOGICAL ACTIVITY; CHEMICAL MODIFICATION; DRUG SYNTHESIS; HUMAN; LIPID MONOLAYER; LIPOPHILICITY; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR INTERACTION; MULTIDRUG RESISTANCE; NONHUMAN; REVIEW;

ANALGESICS; ANIMALS; ANTI-BACTERIAL AGENTS; ANTI-INFLAMMATORY AGENTS; ANTICONVULSANTS; ANTIFUNGAL AGENTS; ANTIMALARIALS; ANTINEOPLASTIC AGENTS; ANTIPSYCHOTIC AGENTS; ANTIVIRAL AGENTS; BACTERIA; CELL MEMBRANE PERMEABILITY; DRUG RESISTANCE, MULTIPLE; HUMANS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; IMMUNOSUPPRESSIVE AGENTS; MICE; PHENOTHIAZINES; RABBITS; RATS; SOLUBILITY; STRUCTURE-ACTIVITY RELATIONSHIP; TRYPANOCIDAL AGENTS; VIRUSES;

EID: 79958257266     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.05.013     Document Type: Review

References (71)

1. R.R. Gupta, and M. Kumar Synthesis, properties and reactions of phenothiazines R.R. Gupta, Phenothiazines and 1,4-Benzothiazines - Chemical and Biological Aspects 1988 Elsevier 1 161
2. N. Motohashi, M. Kawase, S. Saito, and H. Sakagami Antitumor potential and possible targets of phenothiazine-related compounds Curr. Drug Targets 1 2000 237 245
3. N. Motohashi, M. Kawase, K. Satoh, and H. Sakagami Cytotoxic potential of phenothiazines Curr. Drug Targets 7 2006 1055 1066 (Pubitemid 44356007)
4. J.J. Aaron, M.D. Gaye-Seye, S. Trajkovska, and N. Motohashi Bioactive Phenothiazines and Benzo[a]phenothiazines: spectroscopic studies and biological and biomedical properties and applications Top. Heterocycl. Chem. 16 2009 153 231 Springer-Verlag, Berlin
5. A. Dasgupta, S.G. Dastridara, Y. Shirataki, and N. Motohashi Antibacterial activity of artificial phenothiazines and isoflavones from plants Top. Heterocycl. Chem. 15 2008 67 132 Springer-Verlag, Berlin
6. M.D. Gaye-Seye, J.J. Aaron, C. Parkanyi, and N. Motohashi Luminescence and photophisical properties of benzo[a]phenothiazines-therapeutic, physico-chemical and analytical applications Curr. Drug Targets 7 2006 1083 1093
7. S.C. Mitchell Phenothiazine: the parent molecule Curr. Drug Targets 7 2006 1181 1189 (Pubitemid 44356014)
8. A.D. Mosnaim, V.V. Ranade, M.E. Wolf, J. Puente, and M.A. Valenzuela Phenothiazine molecule provides the basic chemical structure for various classes of pharmacotherapeutic agents Am. J. Therapeut. 13 2006 261 273 (Pubitemid 44026194)
9. L. Amaral, and J.E. Kristiansen Phenothiazines: potential management of Creutzfeldt-Jacob disease and its variants Int. J. Antimicrob. Agents 18 2001 411 417 (Pubitemid 33065651)
10. K. Pluta, B. Morak-Młodawska, and M. Jeleń Synthesis and properties of diaza-, triaza- and tetraazaphenothiazines J. Heterocycl. Chem. 46 2009 355 391
11. A.B. Bata, J.H. Kalin, E.M. Fooksman, E.L. Amorose, C.M. Price, H.M. William, M.J. Rodig, M.O. Mitchell, S.H. Cho, Y. Wang, and S.G. Franzblau Synthesis and antitubercular activity of quaternized promazine and promathazine derivatives Bioorg. Med. Chem. Lett. 17 2007 1346 1348 (Pubitemid 46240829)
12. E.A. Weinstein, T. Yano, L.S. Li, D. Avarbock, A. Avarbock, D. Helm, A.A. McColm, K. Dunkan, J.T. Lonsdale, and H. Rubin Inhibitors of type II NADH: menaquinone oxidoreductase represent a clas of antitubercular drugs Proc. Natl. Acad. Sci. U.S.A. 102 2005 4548 4553 (Pubitemid 40397149)
13. N. Motohashi, M. Kawase, J. Molnar, L. Ferenczy, O. Wesołowska, A.B. Hendrich, M. Bobrowska-Hägerstrand, H. Hägestrand, and K. Michalak Antimicrobial activity of N-acylphenothiazines and their influence on lipid model membranes and erythrocyte membranes Arzneim.Forsch./Drug Res. 53 2003 590 599 (Pubitemid 37011510)
14. P.B. Madrid, W.E. Polgar, L. Toll, and M.J. Tanga Synthesis and antitubercular activity of phenothiazines with reduced binding to dopamine and serotonine receptors Bioorg. Med. Chem. Lett. 17 2007 3014 3017 (Pubitemid 46702642)
15. Y. Zhang, C.E. Ballard, S.L. Zheng, X. Gao, K.Ch. Ko, H. Yang, G. Brandt, X. Lou, P.C. Tai, Ch.D. Lu, and B. Wang Design, synthesis and evolution of efflux substrate-metal chelator conjugates as potential antimicrobial agents Bioorg. Med. Chem. Lett. 17 2007 707 711 (Pubitemid 46108564)
16. S.D. Srivastava, and P. Kohli Synthesis of 5-((10N-phenothiazin-yl) methyl)-4-(benzylideneamino-3-mercaptotriazoles as antibacterial and antifungal agents Proc. Natl. Acad. Sci. India 77(A) 2007 199 204
17. T.N. Bansode, J.V. Shelke, and V.G. Dongre Synthesis and antimicrobial activity of some new N-acyl substituted phenothiazines Eur. J. Med. Chem. 44 2009 5094 5098
18. T.N. Bansode, J.V. Shelke, and V.G. Dongre Synthesis, antimicrobial and antifungal activity of 1,3-di(2-substituted 10H-phenothiazin-10-yl)propan-1-one Pharm. Chem. J. 43 2009 311 314
19. V.K. Salvi, S. Sharma, Ch. Sharma, D. Bhambi, and G.L. Talesara Synthesis of phtalimido or succinimido-[2-aryl-4-oxo-3-[{2-oxo-2-(phenothiazin-10-yl) ethyl} amino]-1,3-thiazolidin-5-yl]ethanoate and their antimicrobial activities Ind. J. Chem. 48B 2009 1583 1589
20. G. Singh, N. Kumar, A.K. Yadav, and A.K. Mishra Potential antimicrobial agents trifluoromethyl-10H-phenothiazines and ribofuranosides Heteroatom. Chem. 14 2003 481 486
21. V. Gautam, M. Sharma, R.M. Samarth, N. Gautam, A. Kumar, I.K. Sharma, and D.C. Gautam Synthesis of some substituted 10 H-Phenothiazines, ribofuranosides, and their antioxidant activity Phosphorus Sulfur Silicon 182 2007 1381 1392
22. R. Dixit, Y. Dixit, N. Gautam, and D.C. Gautam Synthesis and biological activities of some new phenothiazines, their sulfones, and ribofuranosides Phosphorus Sulfur Silicon 183 2008 1 12
23. R. Dixit, N. Gautam, and D.C. Gautam Synthesis of 10 H-phenothiazines, their sulfones and ribofuranosides as potential chemotherapeutic agents Jordan J. Chem. 3 2008 357 365
24. Y. Dixit, R. Dixit, N. Gautam, and D.C. Gautam Synthesis and antimicrobial activities of novel biologically active heterocycles: 10 H-Phenothiazines, their ribofuranosides and sulfone derivatives Nucleosides Nucleotides Nucleic Acids 28 2009 998 1006
25. Y. Dixit, R. Dixit, N. Gautam, and D.C. Gautam Synthesis of bioactive fluorinated 10 H-Phenothiazines and their sulfone derivatives Eur. J. Chem. 5 S1 2008 1063 1068
26. J.P. Raval, and K.R. Desai Synthesis and antimicrobial activity of new tetrazolopyridinyl phenothiazines ARKIVOC (xiii) 2005 21 28 (Pubitemid 40397771)
27. R.K. Upadhyay, M.S. Upadhyay, and S. Jain Synthesis and antimicrobial activity of 1-[2-(10-p-chlorobenzyl)phenothiazinyl]-3-(substituted aryl)-2-propen-1-ones Eur. J. Chem. 6 S1 2009 S254 S258
28. A.R. Triverdi, A.B. Siddiqui, and V.H. Shah Design, synthesis, characterization and antitubercular activity of some 2-heterocycle-substituted phenothiazines ARKIVOC (ii) 2008 210 217
29. N. Kumar, G. Singh, S. Khatoon, and A.K. Yadav Synthesis and antimicrobial activities of novel 10 H-pyrido[3,2-b][1,4]benzo-[b]thiazine ribofuranoside Ind. J. Chem. 42 2003 2015 2018
30. K.V. Tandon, H.K. Maurya, N.N. Mishra, and P.K. Shukla Design, synthesis and biological evaluation of novel nitrogen and sulfur containing hetero-1,4-naphthoquinones as antifungal and antibacterial agents Eur. J. Med. Chem. 44 2009 3130 3137
31. K.V. Tandon, H.K. Maurya, A. Tripathi, G.B. ShivaKeshava, P.K. Shukla, P. Srivastava, and D. Panda 2,3-Disubstituted-1,4-naphthoquinones, 12H-benzo[b]phenothiazine-6,11-diones and related compounds: synthesis and biological evaluation as potential antiproliferative and antifungal agents Eur. J. Med. Chem. 44 2009 1086 1092
32. P.K. Swarnkar, P. Kriplani, G.N. Gupta, and K.G. Ojha Synthesis and antibacterial activity of some new phenothiazine derivatives Eur. J. Chem. 4 2007 14 20
33. N. Motohashi Antitumor activity of phenothiazines (phenothiazine oncology) R.R. Gupta, Phenothiazines and 1,4-Benzothiazines - Chemical and Biological Aspects 1988 Elsevier 705 770
34. H. Sakagami, H. Takahashi, H. Yoshida, M. Yamamura, K. Fukuchi, K. Gomi, N. Motohashi, and M. Takeda Induction of DNA fragmentation in human Myelogenous Leukaemic cell lines by phenothiazine-related compounds Anticancer Res. 15 1995 2533 2540 (Pubitemid 26095057)
35. N. Motohashi, H. Sakagami, K. Kamata, and Y. Yamamoto Cytotoxicity and differentiation-inducing activity of phenothiazie and benzo[a]phenothiazine derivatives Anticancer Res. 11 1991 1933 1937
36. M.A. Wuonola, M.G. Palfreyman, N. Motohashi, M. Kawase, S. Gabay, R.R. Gupta, and J. Molnár The primary in vitro anticancer activity of "half-mustard type" phenothiazines in NCI's revised anticancer screening paradigm Anticancer Res. 18 1998 337 348 (Pubitemid 28174729)
37. N. Motohashi, T. Kurihara, H. Sakagami, D. Szabo, K. Csuri, and J. Molnár Chemical structure and tumor type specificity of "half-mustard type" phenothiazines Anticancer Res. 19 1999 1859 1864 (Pubitemid 29392750)
38. S. Nagy, G. Argyelan, J. Molnár, M. Kawase, and N. Motohashi Antitumor activity of phenothiazine-related compounds Anticancer Res. 16 1996 1915 1918 (Pubitemid 26270702)
39. N. Motohashi, M. Kawase, and T. Kurihara Synthesis and antitumor activity of 1-[2(chloroethyl)-3-(-substituted-10H-phenothiazin-10-yl)]alkyl-1-ureas as potent anticancer agents Anticancer Res. 16 1996 2525 2532 (Pubitemid 26388212)
40. N. Motohashi, M. Kawase, and S. Saito Synthesis and biological activity of N-acylphenothiazines Int. J. Antimicrob. Agents 14 2000 203 207 (Pubitemid 30201544)
41. H. Okumara, J. Nakazava, K. Tsuganezawa, T. Usui, H. Osada, T. Matsumoto, A. Tanaka, and S. Yokoyama Phenothiazine and carbazole-related compounds inhibit mitotic kinesin Eg5 and trigger apoptosis in transformed culture cells Toxicol. Lett. 166 2006 44 52 (Pubitemid 44279303)
42. K.K. Rozman, S. Mission, K. Fried, P.F. Terrranova, G.I. Georg, A. Dutta, Phenothiazine derivatives and their method of use, US 2005/0288279 A1, 2005.
43. A. Bisi, M. Meli, S. Gobbi, A. Rampa, M. Tolomeo, and L. Dusonchet Multidrug resistance reverting activity and antitumor profil of new phenothiazine derivatives Bioorg. Med. Chem. 16 2008 6474 6482 (Pubitemid 351794257)
44. B. Morak-Młodawska, and K. Pluta Synthesis of novel dipyrido-1,4-thiazines Heterocycles 71 2007 1347 1361
45. M. Zimecki, J. Artym, M. Kociba, K. Pluta, B. Morak-Młodawska, and M. Jeleń The immunesuppresive activities of newly synthesized azaphenothiazines in human and mouse models Cell. Mol. Biol. Lett. 14 2009 622 635
46. K. Pluta, M. Jeleń, B. Morak-Młodawska, M. Zimecki, J. Artym, and M. Kociba Anticancer activity of newly synthesized azaphenothiazines from NCI's anticancer screening bank Pharmacol. Rep. 62 2010 319 332
47. O. Wesołowska, D. Mosidz, N. Motohashi, M. Kawase, and K. Michalak Phenothiazine maleates stimulate MRP1 transport activity in human erythrocytes Biochem. Biophys. Acta 1720 2005 52 58 (Pubitemid 43202135)
48. A.B. Hendrich, O. Wesołowska, N. Motohashi, J. Molnar, and K. Michalak New phenothiazine - type multidrug resistance modifiers: anti-MDR activity versus membrane perturbing potency Biochem. Biophys. Res. Commun. 304 2003 260 265 (Pubitemid 36444564)
49. M. Kolaczkowski, K. Michalak, and N. Motohashi Phenothiazines are potent modulators of yeast multidrug resistance Int. J. Antimicrob. Agents 22 2003 279 283 (Pubitemid 37103214)
50. A. Hilgeroth, A. Molnar, J. Molnar, and B. Voigt Correlation of calculated molecular orbital energies of some phenothiazine compounds with MDR reversal properties Eur. J. Med. Chem. 41 2006 548 551
51. J. Guan, D.E. Kyle, L. Gerena, Q. Zhang, W.K. Milhous, and A.J. Lin Design, synthesis and evaluation of new chemosensitizers in MDR Plasmodium falciparum J. Med. Chem. 45 2002 2741 2748 (Pubitemid 34627646)
52. A. Kónya, A. Andor, P. Satorhelyi, K. Nemeth, and I. Kurucz Inhibition of the MDR transporter by new phenothiazine derivatives Biochem. Biophys. Res. Commun. 346 2006 45 50 (Pubitemid 43870264)
53. I. Nagy, Z. Riedl, G. Hajos, A. Messmer, N. Gyemant, and J. Molnar Synthesis of new tetrazolyldienylphenothiazines as potential multidrug resistance inhibitory compounds Arkivoc (vii) 2004 177 182 (Pubitemid 38773723)
54. F. Barbieri, A. Alama, B. Tasso, V. Boido, C. Bruzdo, and F. Sparatore Quinolizidinyl derivatives of iminodibezyl and phenothiazine as multidrug resistance modulators in ovarian cancer cells Invest. New Drug 21 2003 413 420 (Pubitemid 38124980)
55. M. Kalkanidis, N. Klonis, L. Tillej, and L.W. Deady Novel phenothiazine antimalarials: synthesis, antimalarial activity and inhibition of the formation of β-haematin Biochim. Pharm. 63 2002 833 842 (Pubitemid 34242995)
56. M. Mayer, T. Lang, S. Gerber, P.B. Madrid, I.G. Pinto, R.K. Guy, and T.L. James Synthesis and testing of a focused phenothiazine library of binding to HIV-1 TAR RNA Chem. Biol. 13 2006 993 1000 (Pubitemid 44375171)
57. I. Mucsi, J. Molnar, and N. Motohashi Combination of benzo[a] phenothiazines with acyclovir against herpes simpex virus Int. J. Antimicrob. Agents 18 2001 67 72 (Pubitemid 32703869)
58. S. Sharma, V.K. Srivastava, and A. Kumar Synthesis and anti-inflamatory activity of some heterocyclic derivatives of phenothiazine Pharmazie 60 2005 18 20
59. 1 antagonists Bioorg. Med. Chem. Lett. 19 2009 2766 2771
60. A. Rajasekaran, and P.P. Thampi Synthesis and anti-inflammatory activity of some 1 - [(1-Acyl-1H-tetrazol-5-yl)ethyl)-10H-phenothiazines Acta Pharm. Turcica 45 2003 235 240
61. A. Rajasekaran, and P.P. Thampi Synthesis and analgesic evolution of some 5-[β-(10-phenothiazinyl)ethyl]-1-(acyl)-1,2,3,4-tetrazoles Eur. J. Med. Chem. 39 2004 273 279 (Pubitemid 38393755)
62. G.A. Silva, L.M.M. Costa, F.C.F. Brito, A.L.P. Miranda, E.J. Barreiro, and C.A.M. Fraga New class of potent antinociceptive and antiplatelet 10H-phenothiazine-1-acylhydrazone derivatives Bioorg. Med. Chem. 12 2004 3149 3158 (Pubitemid 38680704)
63. Y.S. Sadanandam, M.M. Shetty, A.B. Rao, and Y. Rambabu 10H-Phenothiazines: a new class of enzyme inhibitors for inflammatory diseases Eur. J. Med. Chem. 44 2009 197 202
64. T. Kaneko, R. Clark, N. Ohi, T. Kawahara, H. Akamatsu, F. Ozaki, A. Kamada, K. Okano, H. Yokohama, K. Muramoto, M. Ohkuro, O. Takenaka, and S. Kobayashi Inhibitors of adhesion molecules expression; the synthesis and pharmacological properties of 10 H-pyrazino[2,3- b][1,4]benzothiazine derivatives Chem. Pharm. Bull. 50 2002 922 929 (Pubitemid 41694867)
65. T. Kaneko, R. Clark, N. Ohi, F. Ozaki, T. Kawahara, A. Kamada, K. Okano, H. Yokohama, M. Ohkuro, K. Muramoto, O. Takenaka, and S. Kobayashi Piperidine carboxylic acid derivatives of 10H-pyrazino[2,3-b][1,4]benzothiazine as orally-active adhesion molecule inhibitors Chem. Pharm. Bull. 52 2004 675 687 (Pubitemid 41685504)
66. P. Archana, K. Rani, V.K. BajajSrivastava, R. Chandra, and A. Kumar Synthesis of novel indolyl phenothiazinyl substituted 2-oxo/thiobarbituric acid derivatives as potent anticonvulsant agents Arzneim.Forsch./Drug Res. 53 2003 301 306 (Pubitemid 36609823)
67. S. Darvesh, R.S. McDonald, A. Penwell, S. Condar, K.V. Darvesh, D. Mataija, G. Gomez, A. Caines, R. Walsh, and E. Martin Structure-activity relationships for inhibition of human cholinoesterases by alkyl amide phenothiazine derivatives Bioorg. Med. Chem. 13 2005 211 222 (Pubitemid 39575706)
68. S. Darvesh, R.S. McDonald, K.V. Darvesh, A. Penwell, S. Condar, D. Mataija, G. Gomez, R. Walsh, and E. Martin Selective reversible inhibition of human butyrylcholinesterase by aryl amide derivatives of phenothiazine Bioorg. Med. Chem. 15 2007 6367 6378 (Pubitemid 47212737)
69. P. Shinde, S.K. Srivastava, R. Odedara, D. Tuli, S. Munshi, J. Patel, S.P. Zambad, R. Sonawane, R.C. Gupta, V. Chauthaiwale, and Ch. Dutt Synthesis of spiro[chroman-2,4′-piperidin]-4-one derivatives as acetyl-CoA carboxylase inhibitors Bioorg. Med. Chem. Lett. 19 2009 949 953
70. B.C. Galarreta, R. Sifuentes, A.K. Carrilllo, L. Sanchez, M. Amado, and H. Maruenda The use of natural product scaffolds as leads in the search for trypanothione reductase inhibitors Bioorg. Med. Chem. Lett. 16 2008 6689 6695
71. M. Bakavoli, M. Nikpour, M. Rahimizadeh, M.R. Saberi, and H. Sadeghian Design and synthesis of pyrimido[4,5-b][1,4]benzothiazine derivatives as potent 15-lipoxygenase inhibitors Bioorg. Med. Chem. 15 2007 2120 2126 (Pubitemid 46176623)