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Synthesis and antifolate properties of 10-alkyl-5,10-dideaza analogs of methotrexate and tetrahydrofolic acid

Cite this: J. Med. Chem. 1990, 33, 2, 673–677
Publication Date (Print):February 1, 1990
https://doi.org/10.1021/jm00164a033
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    5. Paul A. Keller, Mohammed K. Abdel-Hamid, Ashraf M. Abdel-Megeed. Ring Synthesis. 2013, 15-152. https://doi.org/10.1016/B978-0-12-385235-9.00002-3
    6. Abdel-Sattar S Hamad Elgazwy, DaliaH S Soliman, Saad R Atta-Allah, Diaa A Ibrahim. Three-dimensional quantitative structure activity relationship (QSAR) of cytotoxic active 3,5-diaryl-4,5-dihydropyrazole analogs: a comparative molecular field analysis (CoMFA) revisited study. Chemistry Central Journal 2012, 6 (1) https://doi.org/10.1186/1752-153X-6-50
    7. Mahmoud A. Mohamed. Synthesis of some new bipyridines, thieno[2,3-b]pyridines, and pyrazolo[3,4-b]pyridines. Journal of Heterocyclic Chemistry 2012, 49 (1) , 200-203. https://doi.org/10.1002/jhet.802
    8. Mahmoud A. Mohamed. Synthesis of some new pyridones, fused pyrimidines, and fused 1,2,4-triazines. Journal of Heterocyclic Chemistry 2010, 101 , NA-NA. https://doi.org/10.1002/jhet.351
    9. Osama M. Ahmed, Mahmoud A. Mohamed, Rasha R. Ahmed, Sayed A. Ahmed. Synthesis and anti-tumor activities of some new pyridines and pyrazolo[1,5-a]pyrimidines. European Journal of Medicinal Chemistry 2009, 44 (9) , 3519-3523. https://doi.org/10.1016/j.ejmech.2009.03.042
    10. Nagy M. Khalifa, Mostafa M. Ramla, Abd El-Galil E. Amr, Mohamed M. Abdulla. Synthesis and Anti-Inflammatory Activities of Some Novel S-Pyridyl Glycosides Derivatives. Phosphorus, Sulfur, and Silicon and the Related Elements 2008, 183 (12) , 3046-3062. https://doi.org/10.1080/10426500802059885
    11. Adel M. Attia, Galal H. Elgemeie, Lamies A. Shahada. Synthesis of some novel condensed pyridine-2(1H)-thiones and related glycosides. Tetrahedron 1997, 53 (51) , 17441-17448. https://doi.org/10.1016/S0040-4020(97)10192-2
    12. Wolfgang Pfleiderer. Bicyclic 6-6 Systems: Pteridines. 1996, 679-736. https://doi.org/10.1016/B978-008096518-5.00162-3
    13. . Volume 7 References. 1996, 947-1044. https://doi.org/10.1016/B978-008096518-5.00253-7
    14. Galal E.H. Elgemeie, Badria A.W. Hussain. A convenient synthesis of 5-deaza nonclassical antifolates: Reaction of cyanothioacetamide with sodium salts of 2-(hydroxymethylene)-1-cycloalkanones. Tetrahedron 1994, 50 (1) , 199-204. https://doi.org/10.1016/S0040-4020(01)80745-6
    15. Robert J. Mullin, Barry R. Keith, Eric C. Bigham, David S. Duch, Robert Ferone, Louise S. Heath, Sara Singer, Kathleen A. Waters, H.Robert Wilson. In vivo antitumor activity and metabolism of a series of 5-deazaacyclotetrahydrofolate (5-DACTHF) analogues. Biochemical Pharmacology 1992, 43 (7) , 1627-1634. https://doi.org/10.1016/0006-2952(92)90222-5
    16. Richard G. Moran. Folate antimetabolites inhibitory to de novo purine synthesis. 1992, 65-87. https://doi.org/10.1007/978-1-4615-3876-9_4
    17. Aleem Gangjee, Rajesh Devraj, Fu-Tyan Lin. Synthesis of 2,4-diamino-5,10-dideaza nonclassical antifolates. Journal of Heterocyclic Chemistry 1991, 28 (7) , 1747-1751. https://doi.org/10.1002/jhet.5570280717
    18. E. M. Birinberg, I. P. Rudakova. Search for new anti-tumor drugs among compounds inhibiting enzymes involved in folic acid metabolism (a review). Pharmaceutical Chemistry Journal 1991, 25 (9) , 611-622. https://doi.org/10.1007/BF00777683
    19. Gerrit Jansen, G. Robbin Westerhof, Ietje Kathmann, Gert Rijksen, Jan H. Schornagel. Growth-inhibitory effects of 5,10-dideazatetrahydrofolic acid on variant murine L1210 and human CCRF-CEM leukemia cells with different membrane-transport characteristics for (anti)folate compounds. Cancer Chemotherapy and Pharmacology 1991, 28 (2) , 115-117. https://doi.org/10.1007/BF00689699
    20. J. I. DEGRAW, P. H. CHRISTIE, R. L. KISLIUK, Y. GAUMONT, F. M. SIROTNAK. ChemInform Abstract: Synthesis and Antifolate Properties of 10-Alkyl-5,10-dideaza Analogues of Methotrexate and Tetrahydrofolic Acid.. ChemInform 1990, 21 (25) https://doi.org/10.1002/chin.199025188

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