Synthesis and antitumor evaluation of novel tetrahydrobenzo[4′,5′]thieno[3′,2′:5,6]pyrimido[1,2-b]isoquinoline derivatives

References

• Katada, J.; Iijima, K.; Muramatsu, M.; Takami, M.; Yasuda, E.; Hayashi, M.; Hattori, M.; Hayashi, Y. Cytotoxic Effects of NSL-1406, A New Thienopyrimidine Derivative, on Leukocytes and Osteoclasts. Bioorg. Med. Chem. Lett. 1999, 9, 797–802. DOI: 10.1016/s0960-894x(99)00088-8.
   PubMed Web of Science ®Google Scholar
• Amr, A. E.; Mohamed, A. M.; Mohamed, S. F.; Abdel-Hafez, N. A.; Hammam, A. G. Anticancer Activities of Some Newly Synthesized Pyridine, Pyrane, and Pyrimidine Derivatives. Bioorg. Med. Chem. 2006, 14, 5481–5488. DOI: 10.1016/j.bmc.2006.04.045.
   PubMed Web of Science ®Google Scholar
• Rheault, T. R.; Caferro, T. R.; Dickerson, S. H.; Donaldson, K. H.; Gaul, M. D.; Goetz, A. S.; Mullin, R. J.; McDonald, O. B.; Petrov, K. G.; Rusnak, David W.; et al. Thienopyrimidine-Based Dual EGFR/ErbB-2 Inhibitors. Bioorg. Med. Chem. Lett. 2009, 19, 817–820. DOI: 10.1016/j.bmcl.2008.12.011.
   PubMed Web of Science ®Google Scholar
• Dai, Y.; Guo, Y.; Frey, R. R.; Ji, Z.; Curtin, M. L.; Ahmed, A. A.; Albert, D. H.; Arnold, L.; Arries, S. S.; Barlozzari, T.; et al. Thienopyrimidine Ureas as Novel and Potent Multitargeted Receptor Tyrosine Kinase Inhibitors. J. Med. Chem. 2005, 48, 6066–6083. DOI: 10.1021/jm050458h.
   PubMed Web of Science ®Google Scholar
• Pédeboscq, S.; Gravier, D.; Casadebaig, F.; Hou, G.; Gissot, A.; De Giorgi, F.; Ichas, F.; Cambar, J.; Pometan, J. P. Synthesis and Study of Antiproliferative Activity of Novel Thienopyrimidines on Glioblastoma Cells. Eur. J. Med. Chem. 2010, 45, 2473–2479. DOI: 10.1016/j.ejmech.2010.02.032.
   PubMed Web of Science ®Google Scholar
• Wang, Y. D.; Johnson, S.; Powell, D.; McGinnis, J. P.; Miranda, M.; Rabindran, S. K. Inhibition of Tumor Cell Proliferation by thieno[2,3-d]pyrimidin-4(1H)-one-Based Analogs. Bioorg. Med. Chem. Lett. 2005, 15, 3763–3766. DOI: 10.1016/j.bmcl.2005.05.127.
   PubMed Web of Science ®Google Scholar
• Jennings, L. D.; Kincaid, S. L.; Wang, Y. D.; Krishnamurthy, G.; Beyer, C. F.; McGinnis, J. P.; Miranda, M.; Discafani, C. M.; Rabindran, S. K. Parallel Synthesis and Biological Evaluation of 5,6,7,8-tetrahydrobenzothieno[2,3-d]pyrimidin-4(3H)-one Cytotoxic Agents Selective for p21-Deficient Cells. Bioorg. Med. Chem Lett. 2005, 15, 4731–4735. DOI: 10.1016/j.bmcl.2005.07.072.
   PubMed Web of Science ®Google Scholar
• Horiuchi, T.; Chiba, J.; Uoto, K.; Soga, T. Discovery of Novel thieno[2,3-d]pyrimidin-4-yl hydrazone-based Inhibitors of Cyclin D1-CDK4: Synthesis, Biological Evaluation, and Structure-Activity Relationships. Bioorg. Med. Chem. Lett. 2009, 19, 305–308. DOI: 10.1016/j.bmcl.2008.11.090.
   PubMed Web of Science ®Google Scholar
• Horiuchi, T.; Nagata, M.; Kitagawa, M.; Akahane, K.; Uoto, K. Discovery of Novel thieno[2,3-d]pyrimidin-4-yl hydrazone-based Inhibitors of Cyclin D1-CDK4: Synthesis, Biological Evaluation and Structure-Activity Relationships. Part 2. Bioorg. Med. Chem. 2009, 17, 7850–7860. DOI: 10.1016/j.bmc.2009.10.039.
   PubMed Web of Science ®Google Scholar
• Janin, Y. L. ATPase Inhibitors of Heat Shock Protein 90, Second Season. Drug Discov. Today. 2010, 15, 342–353. DOI: 10.1016/j.drudis.2010.03.002.
   PubMed Web of Science ®Google Scholar
• Porter, J. R.; Fritz, C. C.; Depew, K. M. Discovery and Development of Hsp90 Inhibitors: A Promising Pathway for Cancer Therapy. Curr. Opin. Chem. Biol. 2010, 14, 412–420. DOI: 10.1016/j.cbpa.2010.03.019.
   PubMed Web of Science ®Google Scholar
• Tserng, K. Y.; Bauer, L. Synthesis of 3-hydroxythieno pyrimidine-2,4-(1H,3H)-dionesfrom 2,3 and 3,4 Thiophenedicarboxylic Acids. J. Org. Chem. 1975, 40, 172–175. DOI: 10.1021/jo00890a004.
   Web of Science ®Google Scholar
• Nielsen, K. E.; Pederson, E. B. Phosphoramides, VII: Phenyl N,N-dimethyl Phosphordiamidateas a Reagent for Synthesis of 3-methylthieno[2,3-d]pyrimidine Derivatives. Acta Chem. Scand. 1978, B32, 302.
   Google Scholar
• Bhuiyan, M. H.; Rahman, M.; Hossain, K.; Rahim, A.; Hossain, M. I.; Abu Naser, M. Synthesis and Antimicrobial Evaluation of Some New Thienopyrimidine Derivatives. Acta Pharm. 2006, 56, 441. DOI: 10.3329/jsr.v1i2.2299.
   PubMedGoogle Scholar
• Bedair, A. H.; El-Hady, N. A.; Abdel-Latif, M. S.; Fakery, A. H.; El-Agrody, A. M.4-Hydroxycoumarin in Heterocyclic Synthesis, Part II: Synthesis of Some New pyrano[2,3-d]pyrimidine, 2-substituted[1,2,4]triazolo[1,5-c]pyrimidine, and pyrimido[1,6-b][1,2,4]triazine Derivatives. Farmaco. 2000, 55, 708–714. DOI: 10.1016/s0014-827x(00)00097-5.
   PubMedGoogle Scholar
• Ghorab, M. M.; Abdel-Gawad, S. M.; El-Gaby, M. S. A. Synthesis and Evaluation of Some New Fluorinated Hydroquinazoline Derivatives as Antifungal Agents. Farmaco. 2000, 55, 249–255. DOI: 10.1016/s0014-827x(00)00029-x.
   PubMedGoogle Scholar
• El-Gaby, M. S. A.; Abdel-Hamide, S. G.; Ghorab, M. M.; El-Sayed, S. M. Synthesis and Anticancer Activity in vitro of Some New Pyrimidines. Acta Pharm. 1999, 49, 149–158. DOI: 10.1002/jhet.1886.
   Web of Science ®Google Scholar
• Nasr, M. N. Gineinah, M. M. Pyrido[2,3-d]pyrimidines and pyrimido[5,4:5,6]pyrido[2,3-d]pyrimidines as New Antiviral Agents: Synthesis and Biological Activity. Arch. Pharm. 2002, 335, 289–295. DOI: 10.1002/1521-4184(200208)335:6<289::aid-ardp289>3.0.co;2-z.
   PubMed Web of Science ®Google Scholar
• Baraldi, P. G.; Pavani, M. G.; Nunez, M.; Brigidi, P.; Vitali, B.; Gambari, R.; Romagnoli, R. Antimicrobial and Antitumor Activity of n-hetero-immine-1,2,3-dithiazoles and Their Transformation in triazolo-, imidazo-, and pyrazolopyrimidines. Bioorg. Med. Chem. 2002, 10, 449–456.
   PubMed Web of Science ®Google Scholar
• Sondhi, S. M.; Johar, M.; Rajvanshi, S.; Dastidar, S. G.; Shukla, R.; Raghubir, R.; Lown, J. W. Anticancer, Anti-Inflammatory, and Analgesic Activity Evaluation of Heterocyclic Compounds Synthesized by Reaction of 4-isothiocyanato-4-methylpentan-2-one with Substituted Phenylene Diamines, o-diamino pyridine and (un)substituted. Australian J. Chem. 2001, 54, 69–74.
   Web of Science ®Google Scholar
• Shishoo, C. J.; Shirsath, V. S.; Rathod, I. S.; Patil, M. J.; Bhargava, S. S. Design, Synthesis and Antihistaminic (H1) Activity of Some Condensed 2-(substituted) Aryl Aminoethylpyrimidin-4(3H)-ones. Arzneiun. Forch. 2001, 51, 221. DOI: 10.1055/s-0031-1300028.
   PubMed Web of Science ®Google Scholar
• Bruno, O.; Brullo, C.; Schenone, S.; Ranise, A.; Bondavalli, F.; Barocelli, E.; Tognolini, M.; Magnanini, F.; Bollabeni, V. Progress in 5H[1]benzopyrano[4,3-d]pyrimidin-5-Amineseries: 2-Methoxy Derivatives Effective as Antiplatet Agents with Analgesic Activity. Farmaco. 2002, 57, 753–758. DOI: 10.1016/s0014-827x(02)01269-7.
   PubMedGoogle Scholar
• Laporte, M. G.; Lessen, T. A.; Leister, L.; Cebzanov, D.; Amparo, E.; Faust, C.; Ortlip, D.; Bailey, T. R.; Nitz, T. J.; Chunduru, S. K.; et al. Tetrahydrothiopheneinhibitors of Hepatitis C Virus NS5B Polymerase. Bioorg. & Med. Chem. Lett. 2006, 16, 100–103. DOI: 10.1016/j.bmcl.2005.09.047.
   PubMed Web of Science ®Google Scholar
• Mahmoud, M. R.; Shiba, S. A.; El-Ziaty, A. K.; Abu El-Azm, F. S. M.; Ismail, M. F. Synthesis and Reactions of Novel 2,5-Disubistituted 1,3,4-Thiadiazoles. Synth. Commun. 2014, 44, 1094–1102. DOI: 10.1080/00397911.2013.846381.
   Web of Science ®Google Scholar
• Mahmoud, M. R.; Abu El-Azm, F. S. M.; Ali, A. T.; Ali, Y. M. Design, Synthesis and Antimicrobial Evaluation of Novel Thienopyrimidines and Triazolopyrimidines. Synth. Commun. 2015, 45, 982–992. DOI: 10.1080/00397911.2014.999340.
   Web of Science ®Google Scholar
• Mahmoud, M. R.; Abu El-Magd, W. S. I.; El-Shahawi, M. M.; Hekal, M. H. Novel Synthesis of Isoquinoline Derivatives Derived from (Z)-4-(1,3-diphenylpyrazol-4-yl)isochromene-1,3-dione. Synth Commun. 2015, 45, 1632–1641. DOI: 10.1080/00397911.2015.1030760.
   Web of Science ®Google Scholar
• Mahmoud, M. R.; Abu El-Azm, F. S. M.; Ali, A. T.; Ali, Y. M. Synthesis and Antimicrobial Evaluation of Some Novel Dithiolane, Thiophene, Coumarin, and 2-Pyridone Derivatives. Synth. Commun. 2017, 47, 1591–1600. DOI: 10.1080/00397911.2017.1336776.
   Web of Science ®Google Scholar
• Mahmoud, M. R.; Derbala, H. A. Y. Heteroannulated Quinazoline and Quinazolinone Derivatives from (z)-2-[1-benzamido-2-(3,4,5-trimethoxy phenyl) vinyl-3,1-benzoxazin-4(3H)one]. Synth. commun. 2010, 40, 1516–1529. DOI: 10.1080/00397910903098722.
   Web of Science ®Google Scholar
• Bischoff, G.; Hoffmann, S. DNA-Binding of Drugs used in Medicinal Therapies. Curr Med Chem. 2002, 9, 321–348. DOI: 10.2174/0929867023371085.
   Web of Science ®Google Scholar
• Martinez, R.; Chacon-Garcia, L. The Search of DNA-Intercalators as Antitumoral Drugs: What it Worked and What Did Not Work. Curr Med Chem. 2005, 12, 127–151. DOI: 10.2174/0929867053363414.
   PubMed Web of Science ®Google Scholar
• Mosmann, T. Rapid Colorimetric Assay for Cellular Growth and Survival: Application to Proliferation and Cytotoxicity Assays. J. Immunol Methods. 1983, 65, 55. DOI: 10.1016/0022-1759(83)90303-4.
   PubMed Web of Science ®Google Scholar
• Denizot, F.; Lang, R. Rapid Colorimetric Assay for Cell Growth and Survival: Modifications to the Tetrazolium Dye Procedure Giving Improved Sensitivity and Reliability. J. Immunol Methods. 1986, 89, 271–277. DOI: 10.1016/0022-1759(86)90368-6.
   PubMed Web of Science ®Google Scholar
• Mauceri, H. J.; Hanna, N. N.; Beckett, M. A.; Gorski, D. H.; Staba, M.; Stellato, K. A.; Bigelow, K.; Heimann, R.; Gately, S.; Dhanabal, M.; et al. Combined Effects of Angiostatinionizing Radiation in Antitumour Therapy. Nature. 1998, 394, 287–291. DOI: 10.1038/28412.
   PubMed Web of Science ®Google Scholar