Synthesis of some new thiazolopyrane and thiazolopyranopyrimidine derivatives bearing a sulfonamide moiety for evaluation as anticancer and radiosensitizing agents

Medicinal Chemistry Research

Volumn 21, Issue 9, 2012, Pages 2395-2407

  El Ella, Dalal A Abou ^a   Ghorab, Mostafa M ^c   Heiba, Helmy I ^b   Soliman, Aiten M ^b  

^a Ain Shams University   (Egypt)

^b NATIONAL CENTER FOR RADIATION RESEARCH AND TECHNOLOGY   (Egypt)

^c KING SAUD UNIVERSITY   (Saudi Arabia)

Author keywords

Anticancer; Radiosensitizing activities; Sulfonamide; Thiazole; Thiazolopyrane; Thiazolopyranopyrimidine

Indexed keywords

2 METHYL 8 OXO 7 ( 3,4 DIMETHOXYPHENYL) 7H [ 2 ( 4 SULFAMOYLPHENYLAMINO)]THIAZOLO[4,5 B]PYRANO[2,3 D]PYRIMIDINE; 2 METHYL 8 OXO 7 ( 4 NITROPHENYL) 7H [ 2 ( 4 SULFAMOYLPHENYLAMINO)]THIAZOLO[4,5 B]PYRANO[2,3 D]PYRIMIDINE; 4 ( 4 OXO 4,5 DIHYDROTHIAZOL 2 YLAMINO)BENZENESULFONAMIDE; 4 ( 5 AMINO 6 CYANO 7 ( 3,4 DIMETHOXYPHENYL) 7H PYRANO[2,3 D]THIAZOL 2 YLAMINO)BENZENESULFONAMIDE; 4 ( 5 AMINO 6 CYANO 7 ( 4 NITROPHENYL) 7H PYRANO[2,3 D]THIAZOL 2 YLAMINO)BENZENESULFONAMIDE; 4 ( 5 AMINO 7 ( 2 CHLOROPHENYL) 6 CYANO 7H PYRANO[2,3 D]THIAZOL 2 YLAMINO)BENZENESULFONAMIDE; 4 ( 5 AMINO 7 ( 3 BROMOPHENYL) 6 CYANO 7H PYRANO[2,3 D]THIAZOL 2 YLAMINO)BENZENESULFONAMIDE; 4 ( 6 CYANO 7 ( 4 NITROPHENYL) 2 ( 4 SULFAMOYLPHENYLAMINO) 7H PYRANO[2,3 D]THIAZOL 5 YLAMINO) 4 OXOBUTANOIC ACID; 5 ( 6 CYANO 5 ( 2,5 DIOXOPYRROLIDINYL) 7 ( 4 NITROPHENYL) 7H PYRANO[2,3 D]THIAZOL 2 YLAMINO)BENZENESULFONAMIDE; 8 AMINO 2 OXO 7 ( 4 NITROPHENYL) 7H [ 2 ( 4 SULFAMOYLPHENYLAMINO)]THIAZOLO[4,5 B]PYRANO[2,3 D]PYRIMIDINE; 8 AMINO 2 THIOXO 7 ( 4 NITROPHENYL) 7H [ 2 ( 4 SULFAMOYLPHENYLAMINO)]THIAZOLO[4,5 B]PYRANO[2,3 D]PYRIMIDINE; 8 AMINO 7 ( 4 NITROPHENYL) 7H [ 2 ( 4 SULFAMOYLPHENYLAMINO)]THIAZOLO[4,5 B]PYRANO[2,3 D]PYRIMIDINE; 8 IMINO 2 THIOXO 7 ( 3,4 DIMETHOXYPHENYL) 7H 1 N PHENYL[ 2 ( 4 SULFAMOYLPHENYLAMINO)]THIAZOLO[4,5 B]PYRANO[2,3 D]PYRIMIDINE; 8 OXO 7 ( 3,4 DIMETHOXYPHENYL) 7H [ 2 ( 4 SULFAMOYLPHENYLAMINO)]THIAZOLO[4,5 B]PYRANO[2,3 D]PYRIMIDINE; 8 OXO 7 ( 4 NITROPHENYL) 7H [ 2 ( 4 SULFAMOYLPHENYLAMINO)]THIAZOLO[4,5 B]PYRAZNO[2,3 D]PYRIMIDINE; ANTINEOPLASTIC AGENT; CARBONATE DEHYDRATASE II; CYTOTOXIC AGENT; DOXORUBICIN; INDISULAM; N ( 6 CYANO 7 ( 4 NITROPHENYL) 2 ( 4 SULFAMOYLPHENYLAMINO) 7H PYRANO[2,3 D]THIAZOL 5 YL) 3 OXOBUTANAMIDE; PYRIMIDINE DERIVATIVE; RADIOSENSITIZING AGENT; SULFONAMIDE; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CANCER CELL CULTURE; CONTROLLED STUDY; CRYSTAL STRUCTURE; CYTOTOXICITY; DATA ANALYSIS SOFTWARE; DRUG BINDING; DRUG DESIGN; DRUG POTENCY; DRUG SYNTHESIS; GAMMA RADIATION; GENE OVEREXPRESSION; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; LIVER CANCER; MOLECULAR DOCKING; MOLECULAR DYNAMICS; RADIOSENSITIZATION; STRUCTURE ACTIVITY RELATION;

EID: 84866415279     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-011-9751-9     Document Type: Article

References (33)

1. Abbate F, Casini A, Owa T, Scozzafava A, Supuran CT (2004) Carbonic anhydrase inhibitors: E7070, a sulfonamide anticancer agent, potently inhibits cytosolic isozymes I and II, and transmembrane, tumor-associated isozyme IX. Bioorg Med Chem Lett 14:217-223 (Pubitemid 38010223)
2. Al-Said MS, Ghorab MM, Al-Dosari MS, Hamed MM (2011) Synthesis and in vitro anticancer evaluation of some novel hexahydroquinoline derivatives having a benzene sulfonamide moiety. Eur J Med Chem 46:201-207
3. Amr AE, Mohamed AM, Mohamed SF, Abdel-Hafez NA, Hammam AG (2006) Anticancer activities of some newly synthesized pyridine, pyrane and pyrimidine derivatives. Bioorg Med Chem 14:5481-5488 (Pubitemid 43994482)
4. Boyd AE III (1988) Sulfonylurea receptors, ion channels, and fruit flies. Diabetes 37:847-850
5. Casini A, Scozzafava A, Mastrolorenzo A, Supuran CT (2002) Sulfonamides and sulfonylated derivatives as anticancer agents. Curr Cancer Drug Targets 2:55-75 (Pubitemid 34627379)
6. Chegwidden WR, Spencer IM (1995) Sulphonamide inhibitors of carbonic anhydrase inhibit the growth of human lymphoma cells in culture. Inflammopharmacol 3:231-239
7. Chegwidden WR, Dodgson SJ, Spencer IM (2000) The roles of carbonic anhydrase in metabolism, cell growth and cancer in animals. EXS 90:343-363
8. Dean WD, Papadopoules EP (1982) N-ethoxycarbonylamidines as starting materials and intermediates in the synthesis of heterocyclic compounds. J Heterocycl Chem 19:171-176
9. Donkor IO, Abdel-Ghany YS, Kador PF, Mizoguchi T, Bartoszko-Malik A, Miller DD (1998) Synthesis and biological activities of aldose reductase inhibitors bearing acyl benzenesulfonamides as carboxylic acid surrogates. Eur J Med Chem 33:15-22 (Pubitemid 28123509)
10. Drews J (2000) Drug discovery: a historical perspective. Science 287:1960-1964 (Pubitemid 30158662)
11. Geng C, Zeng Z, Wang J, Xuan S, Lin C (2005) Docetaxel shows radiosensitization in human hepatocellular carcinoma cells. World J Gastroenterol 11(19):2990-2993 (Pubitemid 40790075)
12. Ghorab MM, Noaman E, Ismail MM, Heiba HI, Ammar YA, Sayed MY (2006) Novel antitumor and radioprotective sulfonamides containing pyrrolo[2,3-d] pyrimidines. Arzneimittelforschung 56:405-413 (Pubitemid 44047519)
13. Ghorab MM, Ragab FA, Heiba HI, Youssef HA, El-Gazzar MG (2010) Synthesis of novel pyrrole and pyrrolo[2,3-d] pyrimidine derivatives bearing sulfonamide moiety for evaluation as anticancer and radiosensitizing agents. Bioorg Med Chem Lett 20:6316-6320
14. Kavallaris M, Habefvb M, Norris MD, Pittmana SM, Reed C, Stewart BW (1990) Phenotypic and cytogenetic analysis of atypical multidrug resistance in human leukaemic cells selected with methotrexate at high concentration. Cancer Lett 51:193-201 (Pubitemid 20175815)
15. Kivela AJ, Kivela J, Saarnio J, Parkkila S (2005) Carbonic anhydrases in normal gastrointestinal tract and gastrointestinal tumours. World J Gastroenterol 11:155-163 (Pubitemid 40125196)
16. Lv PC, Zhou CF, Chen J, Liu PG, Wang KR, Mao WJ, Li HQ, Yang Y, Xiong J, Zhu HL (2010) Design, synthesis and biological evaluation of thiazolidinone derivatives as potential EGFR and HER-2 kinase inhibitors. Bioorg Med Chem 18:314-319
17. Maren TH (1976) Relations between structure and biological activity of sulfonamides. Annu Rev Pharmacol Toxicol 16:309-327
18. Pastorekova S, Parkkila S, Pastorek J, Supuran CT (2004) Carbonic anhydrases: current state of the art, therapeutic applications and future prospects. J Enzyme Inhib Med Chem 19:199-229 (Pubitemid 39004275)
19. Rostom SA (2006) Synthesis and in vitro antitumor evaluation of some indeno [1,2-c] pyrazol(in)es substituted with sulfonamide, sulfonylurea(- thiourea) pharmacophores, and some derived thiazole ring systems. Bioorg Med Chem 14:6475-6485 (Pubitemid 44233325)
20. Saczewski F, Slawinski J, Kornicka A, Brzozowski Z, Pomarnacka E, Innocenti A, Scozzafava A, Supuran CT (2006) Carbonic anhydrase inhibitors. Inhibition of the human cytosolic isozymes I and II, and the transmembrane, tumor associated isozymes IX and XII with substituted aromatic sulfonamides activatable in hypoxic tumors. Bioorg Med Chem Lett 16:4846-4851 (Pubitemid 44177775)
21. Saczewski F, Innocenti A, Slawinski J, Kornicka A, Brzozowski Z, Pomarnacka E, Scozzafava A, Temperini C, Supuran CT (2008) Carbonic anhydrase inhibitors: inhibition of human cytosolic isozymes I and II and tumor-associated isozymes IX and XII with S-substituted 4-chloro-2-mercapto-5-methyl- benzenesulfonamides. Bioorg Med Chem 16:3933-3940 (Pubitemid 351484021)
22. Sasai K, Iwai H, Yoshizawa T, Nishimoto S, Shibamoto Y, Oya N, Shibata T, Abe M (1994) Fluorinated 2-nitroimidazole derivative hypoxic cell radiosensitizers: radiosensitizing activities and pharmacokinetics. J Radiat oncol biol phys 29:579-582 (Pubitemid 24187932)
23. Siavosh M, Andreas S, Heymo H, Emerich E, Thomas B, Mathias S, Thomas M, Josef SF, Thomas BL (2006) [4-(Imidazol-1-yl)-thiazol-2-yl]phenylamines-a novel class of highly potent colchicine site binding tubulin polymerization inhibitors: synthesis and cytotoxic activity on some human cancer cell lines. J Med Chem 49:5769-5776
24. Skehan P, Storeng R (1990) New colorimetric cytotoxicity assay for anticancer-drug screening. J Natl Cancer Inst 82:1107-1112 (Pubitemid 20213250)
25. Supuran CT (2008) Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discov 7:168-181 (Pubitemid 351194064)
26. Supuran CT, Scozzafava A (2000) Carbonic anhydrase inhibitors and their therapeutic potential. Exp Opin Ther Patents 10:575-600 (Pubitemid 30251754)
27. Supuran CT, Scozzafava A (2001) Carbonic anhydrase inhibitors. Curr Med Chem Immunol Endocr Metabol Agents 1:61-97
28. Supuran CT, Scozzafava A (2007) Carbonic anhydrases as targets for medicinal chemistry. Bioorg Med Chem 15:4336-4350 (Pubitemid 46777288)
29. Supuran CT, Scozzafava A, Casini A (2003) Carbonic anhydrase inhibitors. Med Res Rev 23:146-189 (Pubitemid 36241096)
30. Supuran CT, Casini A, Mastrolorenzo A, Scozzafava A (2004) COX-2 selective inhibitors, carbonic anhydrase inhibition and anticancer properties of sulfonamides belonging to this class of pharmacological agents. Mini-Rev Med Chem 4:625-632 (Pubitemid 38961227)
31. Thiry A, Ledecq M, Cecchi A, Dogne JM, Wouters J, Supuran CT (2006) Indansulfonamides as carbonic anhydrase inhibitors toward structure-based design of selective inhibitors of the tumor associated isozyme CAIX. J Med Chem 49:2743-2749
32. Thornber CW (1979) Isosterism and molecular modification in drug design. Chem Soc Rev 8:563-580
33. Yoshino H, Ueda N, Niijima J, Sugumi H, Kotake Y, Koyanagi N, Yoshimatsu K, Asada M, Watanabe T, Nagasu T, Tsukahara K, Iijima A, Kitoh K (1992) Novel sulfonamides as potential, systemically active antitumor agents. J Med Chem 35:2496-2497