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Arzneimittelforschung 2008; 58(01): 35-41
DOI: 10.1055/s-0031-1296464
Antibiotics · Antimycotics · Antiviral Drugs · Chemotherapeutics · Cytostatics
Editio Cantor Verlag Aulendorf (Germany)

Utility of 4-(5,5-Dimethyl-3-oxo-cyclohex-l-enylamino)benzenesulfonamide in the Synthesis of Novel Quinolines as Possible Anticancer and Radioprotective Agents

Mostafa M. Ghorab
1   Department of Drug Radiation Research, National Centre for Radiation Research and Technology, Atomic Energy Authority, Nasr City, Cairo, Egypt
,
Fatma A. Ragab
2   Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Cairo University, Cairo, Egypt
,
Eman Noaman
3   Department of Radiation Biology, National Centre for Radiation Research and Technology, Atomic Energy Authority, Nasr City, Cairo, Egypt
,
Helmy I. Heiba
1   Department of Drug Radiation Research, National Centre for Radiation Research and Technology, Atomic Energy Authority, Nasr City, Cairo, Egypt
,
Ebaa M. El-Hossary
1   Department of Drug Radiation Research, National Centre for Radiation Research and Technology, Atomic Energy Authority, Nasr City, Cairo, Egypt
› Author Affiliations
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Publication History

Publication Date:
15 December 2011 (online)

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Abstract

The present work reports the possible utility of 4-(5,5-dimethyl-3-oxo-cyclohex-1-enylamino)benzenesulfonamide in the synthesis of some novel 4-(quinolin-l-yl) benzenesulfonamide derivatives (6a-o). Structures of the newly synthesized compounds were confirmed by elemental analyses and spectral data. All the newly synthesized compounds were evaluated for their in vitro anticancer activity. Compounds 6k, 6j) and 6m showed interesting cytotoxic activity compared with doxorubicin (CAS 23214-92-8) as a reference drug. Additionally, compound 6c exhibited in vivo radioprotective activity, against γ-irradiation, in mice.

Key words

Anticancer drugs - Quinolines, anticancer activity, radioprotective activity, sulfonamide moiety - Radioprotective drugs - Sulfonamides
 

  • References

  • 1 Abdel-Gawad SM, El-Gaby MSA, Heiba HI, Ali HM, Ghorab MM. Synthesis and radiation stability of some new biologically active hydroquinoline and pyrimido[4,5-b]quinoline derivatives. J. Chin. Chem. Soc. 2005; 52: 1227-1236
    CrossrefPubMedSearch in Google Scholar
  • 2 El-Gaby MS, Abdel Gawad SM, Ghorab MM, Heiba HI, Ali HM. Synthesis and biological activity of some novel thieno[2,3-d]quinoline, quinolino[3,2:4,5]thieno[3,2-d]pyrimidine and pyrido[2,3:4,5]thieno[2,3-d]quinoline derivatives. Phosphorus Sulfur Silicon. 2006; 181: 279-297
    CrossrefPubMedSearch in Google Scholar
  • 3 Ghorab MM, Abdel-Hamide SG, Farrag HA. Synthesis of novel quinolines, pyranoquinolines, furoquinolines, thienoquinolines and their effect on the ultrastructure of some pathogenic microorganisms. Acta Pol Pharm Drug Res. 2001; 58 (3) 175-184
    PubMedSearch in Google Scholar
  • 4 Chen YL, Huang CJ, Huang ZY, Tseng CH, Chang FS, Yang SH et al. Synthesis and antiproliferative evaluation of certain 4-anilino-8-methoxy-2-phenylquinoline and 4-anilino-8-hydroxy-2-phenylquinoline derivatives. Bioorg Med Chem. 2006; 14: 3098-3105
    CrossrefPubMedSearch in Google Scholar
  • 5 Zhao YL, Chen YL, Chang FS, Tzeng CC. Synthesis and Cytotoxic evaluation of certain 4-anilino-2-phenylquinoline derivatives. Eu. J Med Chem. 2005; 40: 792-797
    PubMedSearch in Google Scholar
  • 6 Kim YH, Shin KJ, Lee TG, Kim E, Lee MS, Rya SH et al. G2 arrest and apoptosis by 2-amino-N-quinoline-8-yl-benzenesulfonamide (QBS), a novel cytotoxic compound. Biochem Pharmacol. 2005; 69: 1333-1341
    CrossrefPubMedSearch in Google Scholar
  • 7 Gopal M, Shenoy S, Doddamani LS. Antitumor activity of 4-amino and 8-methyl-4-(3-diethylaminopropylamino)pyrimido[4’,5’:4,5]thieno(2,3-b)quinolines. J Photochem Photobiol B. 2003; 72: 69-78
    CrossrefPubMedSearch in Google Scholar
  • 8 Kouznetsov VV, Puentes CO, Bohorquez ARR, Zacchino SA, Sortino M, Gupta M et al. A straightforward synthetic approach to antitumoral pyridinyl substituted 7H- 1ndeno [2][1-c]quinoline derivatives via three-component imino Diels-Alder reaction. Letters Org Chem. 2006; 3 (4) 300-304
    PubMedSearch in Google Scholar
  • 9 Ghorab MM, Ismail ZH, Abdel-Gawad SM, Abdel-Aziem A. Antimicrobial activity of amino acid, imidazole and sulfonamide derivatives of pyrazolo[3,4-d]pyrimidine. Heteroatom Chem. 2004; 15: 57-62
    CrossrefPubMedSearch in Google Scholar
  • 10 Ghorab MM. New biologically active N-(tetrahydrobenzo-thienopyrimidin-4-yl)-amino acids, thiourethane, sulfonamides and related compounds. Phosphorus Sulfur Silicon. 2000; 165: 221-235
    CrossrefPubMedSearch in Google Scholar
  • 11 Melagraki G, Afantitis A, Sarimveis H, Igglessi-Markopoulou O, Supuran CT. QSAR study on para-substituted aromatic sulfonamides as carbonic anhydrase II inhibitors using topological information indices. Bioorg Med Chem. 2006; 14: 1108-1114
    CrossrefPubMedSearch in Google Scholar
  • 12 Özensoy Ö, Puccetti L, Fasolis G, Arslan O, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors: Inhibition of tumor-associated isozymes IX and XII with a library of aromatic and heteroaromatic sulfonamides. Bioorg Med Chem Lett. 2005; 15: 4862-4866
    CrossrefPubMedSearch in Google Scholar
  • 13 Poulsen S, Bornaghi LF, Healy PC. Synthesis and structure-activity relationships of novel benzene sulfonamides with potent binding affinity for bovine carbonic anhydrase II. Bioorg Med Chem Lett. 2005; 15: 5429-5433
    CrossrefPubMedSearch in Google Scholar
  • 14 Ismail MMF, Ghorab MM, Noaman E, Ammar YA, Heiba HI, Sayed MY. Novel synthesis of pyrrolo[2,3-d]pyrimidines bearing sulfonamide moieties as potential antitumor and radioprotective agents. Arzneimittel-Forschung (Drug Research). 2006; 56 (4) 301-308
    Thieme ConnectPubMedSearch in Google Scholar
  • 15 Ghorab MM, Noaman E, Ismail MMF, Heiba HI, Ammar YA, Sayed MY. Novel antitumor and radioprotective sulfonamides containing pyrrolo[2,3-d]pyrimidines. Arzneimittel-Forschung (Drug Research). 2006; 56 (6) 405-413
    Thieme ConnectPubMedSearch in Google Scholar
  • 16 Rostom SAF. Synthesis and in vitro antitumor evaluation of some indeno[l,2-c]-pyrazol(in)es substituted with sulfonamide, sulfonylurea(-thiourea) pharmacophores, and some derived thiazole ring systems. Bioorg Med Chem. 2006; 14: 64756485
    PubMedSearch in Google Scholar
  • 17 Supuran CT, Casini A, Mastrolorenzo A, Scozzafava A. COX-2 selective inhibitors, carbonic anhydrase inhibition and anticancer properties of sulfonamides belonging to this class of pharmacological agents. Mini Rev Med Chem. 2004; 4 (6) 625-632
    CrossrefPubMedSearch in Google Scholar
  • 18 Abbate F, Casini A, Owa T, Scozzafava A, Supuran CT. 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. 2004; 14 (1) 217-223
    CrossrefPubMedSearch in Google Scholar
  • 19 Casini A, Scozzafava A, Mastrolorenzo A, Supuran CT. Su-lonamides and sulfonylated derivatives as anticancer agents. Current Cancer Drug Targets. 2002; 2: 55-75
    CrossrefPubMedSearch in Google Scholar
  • 20 Bump EA, Hoffman SJ, Foye WO. Burger’s Medicinal Chemistry and Drug Discovery. 6th ed. Vol. 5. New York: John Wiley & Sons; 2003: 152-167
    Search in Google Scholar
  • 21 Ghorab MM, Ragab FA, Noaman E, Heiba HI, Galal M. Synthesis of certain new thieno[2,3-d]pyrimidines as potential antitumor and radioprotective agents. Arzneimittel-Forschung (Drug Research). 2006; 56 (7) 553-560
    Thieme ConnectPubMedSearch in Google Scholar
  • 22 Heiba HI, Ragab FA, Noaman E, Ghorab MM, Galal M. Synthesis of some novel sulphur containing triazolothienopyrimidines and biscompounds as possible antitumor and radioprotective agents. Arzneimittel-Forschung (Drug Research). 2006; 56 (8) 593-599
    Thieme ConnectPubMedSearch in Google Scholar
  • 23 Ghorab MM, Osman AN, Noaman E, Heiba HI, Zaher NH. The synthesis of some new sulfur heterocyclic compounds as potential radioprotective and anticancer agents. Phosphorous Sulphur Silicon. 2006; 181: 1935-1950
    PubMedSearch in Google Scholar
  • 24 Donkor IO, Zhou X, Schmidt J, Agrawal KC, Kishore V. Synthesis and radioprotective effects of adamantyl substituted 1,4-dihydropyridine derivatives. Bioorg Med Chem. 1998; 6: 563-568
    CrossrefPubMedSearch in Google Scholar
  • 25 Georgieva R, Tsevi R, Kossev K, Kusheva R, Balgjiska M, Petrova R et al. Immobilization of aminothiols on poly (oxyalkylene phosphates). Formation of poly(oxyethylene phosphates)/cysteamine Complexes and their radioprotective efficiency. J. Med. Chem. 2002; 45: 5797-5801
    CrossrefPubMedSearch in Google Scholar
  • 26 Banq ZM, Dechamps G, Fischer P, Herve A, Lebihan H, Lecomte J et. al Protection against X-rays and therapy of radiation sickness with beta-mercaptoethylamine. Science. 1953; 117: 633-636
    CrossrefPubMedSearch in Google Scholar
  • 27 Brusick DJ. Cytogenetic assays, aberrations and SCE techniques in carcinogenesis and mutagenesis testing. Clifton (New Jersey): Human Press; 1984: 265-276
    Search in Google Scholar
  • 28 Yoshioka T, Kawada K, Shimada T, Mori M. Lipid peroxidation in maternal and cord blood and protective mechanism against activated oxygen toxicity in the blood. Am J Obestet Gynecol. 1979; 135: 372-376
    PubMedSearch in Google Scholar
  • 29 Beutler E, Duron O, Kelly DM. Improved method of the determination of blood glutathione. J Lab Clin Med. 1963; 61: 882-888
    PubMedSearch in Google Scholar
  • 30 Minami M, Yoshikawa H. A simplified assay method of superoxide dismutase. Clin. Chim. Acta. 1979; 92: 337-342
    CrossrefPubMedSearch in Google Scholar
  • 31 Snedecor GW, Cochron WG. Statistical Methods. 8th ed Ames (Iowa): Louis State University Press; 1989
    Search in Google Scholar
  • 32 Sohal RS, Weindruch R. Oxidative stress, caloric restriction and aging. Science. 1996; 273: 59-63
    CrossrefPubMedSearch in Google Scholar
  • 33 Beckman KB, Ames BN. The free radical theory of aging matures. Physiol Rev. 1998; 78: 547-581
    CrossrefPubMedSearch in Google Scholar
  • 34 Bonnefont D, Rousselot J. Irrradiation of cell membranes. J Chim Phys Physico Chim Biol. 1994; 91: 968-983
    PubMedSearch in Google Scholar
  • 35 Tenchova V. Acute gamma irradiation effect on lipid oxidation and antioxidant activity in rat hemopoietic organs and plasma. Rentgenologiya I Radiologiya. 1994; 33 (4) 49
    PubMedSearch in Google Scholar