How to cite this paper
Myrko, I., Chaban, T., Matiichuk, Y., Arshad, M & Matiychuk, V. (2021). Approaches for the synthesis, chemical modification and biological properties of N-acylphenothiazines.Current Chemistry Letters, 10(4), 377-392.
Refrences
1. Pluta K., Morak-Mlodawska B., and Jelen M. (2011) Recent progress in biological activities of synthesized phenothiazines. Eur. J. Med. Chem. 46 (8) 3179–3189.
2. Ohlow M.J., and Moosmann B. (2011) Phenothiazine: the seven lives of pharmacology's first lead structure. Drug Discov. Today. 16 (3-4) 119–131.
3. Mashkovsky M.D. (1998) Medicines. Manual for doctors. In two volumes. Kharkov: "Torsing".
4. Ghinet A., Moise I.M., Rigo B., Homerin G., Farce A, Dubois J, and Bîcu E. (2016) Studies on phenothiazines: New microtubule-interacting compounds with phenothiazine A-ring as potent antineoplastic agents. Bioorg. Med. Chem. 24 (10) 2307–2317.
5. Abuhaie C.M., Bîcu E., Rigo B., Gautret P., Belei D., Farce A., Dubois J., and Ghinet A. (2013) Synthesis and anticancer activity of analogues of phenstatin, with a phenothiazine A-ring, as a new class of microtubule-targeting agents. Bioorg Med. Chem. Lett. 23 (1) 147–152.
6. Prinz H., Chamasmani B., Vogel K., Böhm K.J., Aicher B., Gerlach M., Günther E.G., Amon P., Ivanov I., and Müller K. (2011) N-Benzoylated Phenoxazines and Phenothiazines: Synthesis, Antiproliferative Activity, and Inhibition of Tubulin Polymerization. J. Med. Chem. 54 (12) 4247–4263.
7. Darvesh S., McDonald R.S., Darvesh K.V., Mataija D., Conrad S., Gomez G., Walsh R., and Martin E. (2007) Selective reversible inhibition of human butyrylcholinesterase by aryl amide derivatives of phenothiazine. Bioorg. Med. Chem. 15 (19) 6367–6378.
8. Darvesh S., McDonald R.S., Penwell A., Conrad S., Darvesh K.V., Mataija D., Gomez G., Caines A., Walsh R., and Martin E. (2005) Structure-activity relationships for inhibition of human cholinesterases by alkyl amide phenothiazine derivatives. Bioorg. Med. Chem. 13 (1) 211–222.
9. Marcu A., Schurigt U., Müller K., Moll H., Krauth-Siegel R.L., and Prinz H. (2016) Inhibitory effect of phenothiazine- and phenoxazine-derived chloroacetamides on Leishmania major growth and Trypanosoma brucei trypanothione reductase. Eur. J. Med. Chem. 108 (11) 436–443.
10. Sarmiento G.P., Vitale R.G., Afeltra J., Moltrasio G.Y., and Moglioni A.G. (2011) Synthesis and antifungal activity of some substituted phenothiazines and related compounds. Eur. J. Med. Chem. 46 (1), 101–105.
11. Naik N., Honnaiah V.K., and Veena V. (2012) Novel phenothiazine analogous: Synthesis and a new perceptivity into their antioxidant potential. Der Pharm. Lett. 4 (3) 786–794.
12. Zhang Q., Zeng S.X., Zhang Y., Ding D., Ye Q., Meroueh S.O., and Lu H. (2012) A small molecule Inauhzin inhibits SIRT1 activity and suppresses tumour growth through activation of p53. EMBO Mol. Med. 4 (4) 298–312.
13. Zhang Y., Zhang Q., Zeng S.X., Mayo L.D., and Lu H. (2012) Inauhzin and Nutlin3 synergistically activate p53 and suppress tumor growth. Cancer Biol. Ther. 13 (10) 915–924.
14. Zhang Q., Ding D., Zeng S.X., Ye Q.Z., and Lu H. (2012) Structure and Activity Analysis of Inauhzin Analogs as Novel Antitumor Compounds That Induce p53 and Inhibit Cell Growth. PLoS One. 7 (10) e46294.
15. Tasso B., Catto M., Nicolotti O., Novelli F., Tonelli M., Giangreco I., Pisani L., Sparatore A., Boido V., Carotti A., and Sparatore F. (2011) Quinolizidinyl derivatives of bi- and tricyclic systems as potent inhibitors of acetyl- and butyrylcholinesterase with potential in Alzheimer's disease. Eur. J. Med. Chem. 46 (6) 2170–2184.
16. Tasso B., Sparatore A., and Sparatore F. (2003) N-homolupinanoyl and N-(omega-lupinylthio)alkanoyl derivatives of some tricyclic systems as ligands for muscarinic M1 and M2 receptor subtypes. Farmaco. 58 (9) 669–676.
17. Novelli F., Tasso B., and Sparatore F. (1999) Synthesis and pharmacological evaluation of some thiolupinine derivatives. Farmaco. 54 (6) 354–358.
18. Bansode T.N., Rangari R.P., and Shimpi P.A. (2014) Synthesis and Biological Evaluation of Some Novel 6-(Substituted Phenyl)-4-(10H-Phenothiazin-10-YL)Pyrimidin-2(1H)-Ones/Thiones. Pharm. Chem. J. 48 (7) 430–433.
19. Bansal E., Srivastava V.K., and Kumar A. (2001) Synthesis and anti-inflammatory activity of 1-acetyl-5-substitute daryl-3-(β-aminonaphthyl)-2-pyrazolines and β-(substitute daminoethyl) amidonaphthalenes. Eur. J. Med. Chem. 36 (1) 81–92.
20. Baciu-Atudosie L., Ghinet A., Farce A., Dubois J., Belei D., and Bîcu E. (2012) Synthesis and biological evaluation of new phenothiazine derivatives bearing a pyrazole unit as protein farnesyltransferase inhibitors. Bioorg. Med. Chem. Lett. 22 (22) 6896–6902.
21. Rajasekaran A., Periasamy M., and Venkatesan S. (2010) Synthesis, characterization and biological activity of some novel azetidinones. J. Dev. Biol. Tissue Eng. 2 (1) 5–13.
22. Rajasekaran A., and Devi K.S. (2013) Synthesis and biological evaluation of 1-(3-chloro-2-oxo-4-phenylazetidin-1-yl)-3-(2-oxo-2-(10H-phenothiazin-10-yl)ethyl)urea derivatives. Med. Chem. Res. 22 (6) 2578–2588.
23. Zhang X., He Y., Liu S., Yu Z., Jiang Z.X., Yang Z., Dong Y., Nabinger S.C., Wu L., Gunawan A.M., Wang L., Chan R.J., and Zhang Z.Y. (2010) Salicylic Acid Based Small Molecule Inhibitor for the Oncogenic Src Homology-2 Domain Containing Protein Tyrosine Phosphatase-2 (SHP2). J. Med. Chem. 53 (6) 2482–2493.
24. Bansode T.N., Shelke J.V., and Dongre V.G. (2009) Synthesis and antimicrobial activity of some new N-acyl substituted phenothiazines. Eur. J. Med. Chem. 44 (12) 5094–5098.
25. Bansode T.N., Dongre P.M., and Dongre V.G. (2009) Synthesis, antibacterial and antifungal activity of 1, 3-di(2-substituted 10H-phenothiazin-10-yl)propan-1-one. Pharm. Chem. J. 43 (6) 311–314.
26. Salvi V.K., Sharma S., Sharma Ch., Bhambi D., and Talesara G.L. (2009) ChemInform Abstract: Synthesis of Phthalimido 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. 48 (B) 1583–1589.
27. Ramprasad J., Nayak N., and Dalimba U. (2015) Design of new phenothiazine-thiadiazole hybrids via molecular hybridization approach for the development of potent antitubercular agents. Eur. J. Med. Chem. 106 (12) 75–84.
28. Hui A., Chen Y., Zhu S.-J, Gan C.-S., Pan J., and Zhou A. (2014) Design and synthesis of tacrine-phenothiazine hybrids as multitarget drugs for Alzheimer’s disease. Med. Chem. Res. 23 (7) 3546–3557.
29. Takács D., Nagy I., Bombicz P., Egyed O., Jemnitz K., Riedl Z., Molnár J., Amaral L., and Hajós G. (2012) Selective hydroboration of dieneamines. Formation of hydroxyalkylphenothiazines as MDR modulators. Bioorg. Med. Chem. 20 (14) 4258–4270.
30. Bâcu E., Samson-Belei D., Nowogrocki G., Couture A., and Grandclaudon P. (2003) Benzoindolizine derivatives of N-acylphenothiazine. Synthesis and characterization. Org. Biomol. Chem. 1 (13) 2377–2382.
31. Abuhaie C.M., Ghinet A., Farce A., Dubois J., Gautret P., Rigo B., Belei D., and Bîcu E. (2013) Synthesis and biological evaluation of a new series of phenothiazine-containing protein farnesyltransferase inhibitors. Eur. J. Med. Chem. 59, 101–110.
32. Fadda A.A., Fekria A., and Bayoumy N.M. (2015) Synthesis, antimicrobial evaluation and molecular modeling of some novel phenothiazine derivatives. RSC Advances, 5(98) 80844–80852.
2. Ohlow M.J., and Moosmann B. (2011) Phenothiazine: the seven lives of pharmacology's first lead structure. Drug Discov. Today. 16 (3-4) 119–131.
3. Mashkovsky M.D. (1998) Medicines. Manual for doctors. In two volumes. Kharkov: "Torsing".
4. Ghinet A., Moise I.M., Rigo B., Homerin G., Farce A, Dubois J, and Bîcu E. (2016) Studies on phenothiazines: New microtubule-interacting compounds with phenothiazine A-ring as potent antineoplastic agents. Bioorg. Med. Chem. 24 (10) 2307–2317.
5. Abuhaie C.M., Bîcu E., Rigo B., Gautret P., Belei D., Farce A., Dubois J., and Ghinet A. (2013) Synthesis and anticancer activity of analogues of phenstatin, with a phenothiazine A-ring, as a new class of microtubule-targeting agents. Bioorg Med. Chem. Lett. 23 (1) 147–152.
6. Prinz H., Chamasmani B., Vogel K., Böhm K.J., Aicher B., Gerlach M., Günther E.G., Amon P., Ivanov I., and Müller K. (2011) N-Benzoylated Phenoxazines and Phenothiazines: Synthesis, Antiproliferative Activity, and Inhibition of Tubulin Polymerization. J. Med. Chem. 54 (12) 4247–4263.
7. Darvesh S., McDonald R.S., Darvesh K.V., Mataija D., Conrad S., Gomez G., Walsh R., and Martin E. (2007) Selective reversible inhibition of human butyrylcholinesterase by aryl amide derivatives of phenothiazine. Bioorg. Med. Chem. 15 (19) 6367–6378.
8. Darvesh S., McDonald R.S., Penwell A., Conrad S., Darvesh K.V., Mataija D., Gomez G., Caines A., Walsh R., and Martin E. (2005) Structure-activity relationships for inhibition of human cholinesterases by alkyl amide phenothiazine derivatives. Bioorg. Med. Chem. 13 (1) 211–222.
9. Marcu A., Schurigt U., Müller K., Moll H., Krauth-Siegel R.L., and Prinz H. (2016) Inhibitory effect of phenothiazine- and phenoxazine-derived chloroacetamides on Leishmania major growth and Trypanosoma brucei trypanothione reductase. Eur. J. Med. Chem. 108 (11) 436–443.
10. Sarmiento G.P., Vitale R.G., Afeltra J., Moltrasio G.Y., and Moglioni A.G. (2011) Synthesis and antifungal activity of some substituted phenothiazines and related compounds. Eur. J. Med. Chem. 46 (1), 101–105.
11. Naik N., Honnaiah V.K., and Veena V. (2012) Novel phenothiazine analogous: Synthesis and a new perceptivity into their antioxidant potential. Der Pharm. Lett. 4 (3) 786–794.
12. Zhang Q., Zeng S.X., Zhang Y., Ding D., Ye Q., Meroueh S.O., and Lu H. (2012) A small molecule Inauhzin inhibits SIRT1 activity and suppresses tumour growth through activation of p53. EMBO Mol. Med. 4 (4) 298–312.
13. Zhang Y., Zhang Q., Zeng S.X., Mayo L.D., and Lu H. (2012) Inauhzin and Nutlin3 synergistically activate p53 and suppress tumor growth. Cancer Biol. Ther. 13 (10) 915–924.
14. Zhang Q., Ding D., Zeng S.X., Ye Q.Z., and Lu H. (2012) Structure and Activity Analysis of Inauhzin Analogs as Novel Antitumor Compounds That Induce p53 and Inhibit Cell Growth. PLoS One. 7 (10) e46294.
15. Tasso B., Catto M., Nicolotti O., Novelli F., Tonelli M., Giangreco I., Pisani L., Sparatore A., Boido V., Carotti A., and Sparatore F. (2011) Quinolizidinyl derivatives of bi- and tricyclic systems as potent inhibitors of acetyl- and butyrylcholinesterase with potential in Alzheimer's disease. Eur. J. Med. Chem. 46 (6) 2170–2184.
16. Tasso B., Sparatore A., and Sparatore F. (2003) N-homolupinanoyl and N-(omega-lupinylthio)alkanoyl derivatives of some tricyclic systems as ligands for muscarinic M1 and M2 receptor subtypes. Farmaco. 58 (9) 669–676.
17. Novelli F., Tasso B., and Sparatore F. (1999) Synthesis and pharmacological evaluation of some thiolupinine derivatives. Farmaco. 54 (6) 354–358.
18. Bansode T.N., Rangari R.P., and Shimpi P.A. (2014) Synthesis and Biological Evaluation of Some Novel 6-(Substituted Phenyl)-4-(10H-Phenothiazin-10-YL)Pyrimidin-2(1H)-Ones/Thiones. Pharm. Chem. J. 48 (7) 430–433.
19. Bansal E., Srivastava V.K., and Kumar A. (2001) Synthesis and anti-inflammatory activity of 1-acetyl-5-substitute daryl-3-(β-aminonaphthyl)-2-pyrazolines and β-(substitute daminoethyl) amidonaphthalenes. Eur. J. Med. Chem. 36 (1) 81–92.
20. Baciu-Atudosie L., Ghinet A., Farce A., Dubois J., Belei D., and Bîcu E. (2012) Synthesis and biological evaluation of new phenothiazine derivatives bearing a pyrazole unit as protein farnesyltransferase inhibitors. Bioorg. Med. Chem. Lett. 22 (22) 6896–6902.
21. Rajasekaran A., Periasamy M., and Venkatesan S. (2010) Synthesis, characterization and biological activity of some novel azetidinones. J. Dev. Biol. Tissue Eng. 2 (1) 5–13.
22. Rajasekaran A., and Devi K.S. (2013) Synthesis and biological evaluation of 1-(3-chloro-2-oxo-4-phenylazetidin-1-yl)-3-(2-oxo-2-(10H-phenothiazin-10-yl)ethyl)urea derivatives. Med. Chem. Res. 22 (6) 2578–2588.
23. Zhang X., He Y., Liu S., Yu Z., Jiang Z.X., Yang Z., Dong Y., Nabinger S.C., Wu L., Gunawan A.M., Wang L., Chan R.J., and Zhang Z.Y. (2010) Salicylic Acid Based Small Molecule Inhibitor for the Oncogenic Src Homology-2 Domain Containing Protein Tyrosine Phosphatase-2 (SHP2). J. Med. Chem. 53 (6) 2482–2493.
24. Bansode T.N., Shelke J.V., and Dongre V.G. (2009) Synthesis and antimicrobial activity of some new N-acyl substituted phenothiazines. Eur. J. Med. Chem. 44 (12) 5094–5098.
25. Bansode T.N., Dongre P.M., and Dongre V.G. (2009) Synthesis, antibacterial and antifungal activity of 1, 3-di(2-substituted 10H-phenothiazin-10-yl)propan-1-one. Pharm. Chem. J. 43 (6) 311–314.
26. Salvi V.K., Sharma S., Sharma Ch., Bhambi D., and Talesara G.L. (2009) ChemInform Abstract: Synthesis of Phthalimido 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. 48 (B) 1583–1589.
27. Ramprasad J., Nayak N., and Dalimba U. (2015) Design of new phenothiazine-thiadiazole hybrids via molecular hybridization approach for the development of potent antitubercular agents. Eur. J. Med. Chem. 106 (12) 75–84.
28. Hui A., Chen Y., Zhu S.-J, Gan C.-S., Pan J., and Zhou A. (2014) Design and synthesis of tacrine-phenothiazine hybrids as multitarget drugs for Alzheimer’s disease. Med. Chem. Res. 23 (7) 3546–3557.
29. Takács D., Nagy I., Bombicz P., Egyed O., Jemnitz K., Riedl Z., Molnár J., Amaral L., and Hajós G. (2012) Selective hydroboration of dieneamines. Formation of hydroxyalkylphenothiazines as MDR modulators. Bioorg. Med. Chem. 20 (14) 4258–4270.
30. Bâcu E., Samson-Belei D., Nowogrocki G., Couture A., and Grandclaudon P. (2003) Benzoindolizine derivatives of N-acylphenothiazine. Synthesis and characterization. Org. Biomol. Chem. 1 (13) 2377–2382.
31. Abuhaie C.M., Ghinet A., Farce A., Dubois J., Gautret P., Rigo B., Belei D., and Bîcu E. (2013) Synthesis and biological evaluation of a new series of phenothiazine-containing protein farnesyltransferase inhibitors. Eur. J. Med. Chem. 59, 101–110.
32. Fadda A.A., Fekria A., and Bayoumy N.M. (2015) Synthesis, antimicrobial evaluation and molecular modeling of some novel phenothiazine derivatives. RSC Advances, 5(98) 80844–80852.