Collect. Czech. Chem. Commun.
1964, 29, 2060-2076
https://doi.org/10.1135/cccc19642060
Nucleic acids components and their analogues. LI. Synthesis of 1-glycosyl derivatives of 5-azauracil and 5-azacytosine
A. Pískala and F. Šorm
Crossref Cited-by Linking
- del Campo-Balguerías Almudena, Ocaña Alberto, Bravo Iván, Alonso-Moreno Carlos: Guanidine-based drugs in cancer therapy. Bioorganic Chemistry 2026, 181, 110295. <https://doi.org/10.1016/j.bioorg.2026.110295>
- Penteado André Berndt, Hassanie Haifa, Sousa Gustavo Henrique Marques, Vinha Thabata Corazza Navarro, Soares Artur Caminero Gomes, Calil Raisa Ludmila, Santos Thiago dos, Novais Raul Marques, Emery Flávio da Silva, Ganesan A., Trossini Gustavo Henrique Goulart: From design to clinic: Medicinal chemistry and pharmacology of approved epigenetic drugs. European Journal of Medicinal Chemistry 2026, 318, 119198. <https://doi.org/10.1016/j.ejmech.2026.119198>
- Umezawa Akari, Tsunoda Takeshi, Nakashima Yu, Wang Yung-Lin, Yoneda Tomoki, Maruyama Chitose, Hsu Ning-Shian, Matsuyama Taro, Miyamoto Kazunori, Sato Hajime, Shimose Asuha, Takazawa Reo, Hamano Yoshimitsu, Li Tsung-Lin, Inokuma Yasuhide, Uchiyama Masanobu, Ogasawara Yasushi, Morita Hiroyuki, Dairi Tohru: Enzymatic skeletal editing reaction forming the 1,3,5-triazine core during biosynthesis of the anticancer nucleoside analogue 5-azacytidine. Nat Catal 2026. <https://doi.org/10.1038/s41929-026-01611-x>
- Scandolara Thalita Basso, Siqueira Isabelle Vasconcelos Menegoy, Ribeiro Pinto Luis Felipe, Soares-Lima Sheila Coelho: The power and the promise of epigenetic drugs in oncology. Front. Genet. 2026, 16. <https://doi.org/10.3389/fgene.2025.1622115>
- Khandazhinskaya A. L., Matyugina E. S., Kochetkov S. N., Novikov M. S.: Pyrimidine nucleoside analogues and antitumour drugs based on them: fifty years in therapy. RUSS CHEM REV 2026, 95, RCR5197. <https://doi.org/10.59761/RCR5197>
- Wojciechowski Marek, Czapinska Honorata, Krwawicz Joanna, Rafalski Dominik, Bochtler Matthias: Cytosine analogues as DNA methyltransferase substrates. Nucleic Acids Research 2024, 52, 9267. <https://doi.org/10.1093/nar/gkae568>
- Stein Richard A., Gomaa Faris E., Raparla Pranaya, Riber Leise: Now and then in eukaryotic DNA methylation. Physiological Genomics 2024, 56, 741. <https://doi.org/10.1152/physiolgenomics.00091.2024>
- Yue Xinru, Zhang Xun, Zhang Derong, Zhang Zhigang, Tang Lingkai, Ou Zuoxin, Cao Yujie, Li Jing, Li Ying, Liang Li, Liu Wei, Hu Jianping: Research Progress on hCNT3 Structure/Function and Nucleoside Anticancer Drugs. CPPS 2024, 25, 120. <https://doi.org/10.2174/1389203724666230905110952>
- Maria Catarina, Rauter Amélia P.: Nucleoside analogues: N-glycosylation methodologies, synthesis of antiviral and antitumor drugs and potential against drug-resistant bacteria and Alzheimer's disease. Carbohydrate Research 2023, 532, 108889. <https://doi.org/10.1016/j.carres.2023.108889>
- Holdgate Geoffrey A., Bardelle Catherine, Lanne Alice, Read Jon, O'Donovan Daniel H., Smith James M., Selmi Nidhal, Sheppard Robert: Drug discovery for epigenetics targets. Drug Discovery Today 2022, 27, 1088. <https://doi.org/10.1016/j.drudis.2021.10.020>
- Šimoničová Kristína, Janotka Ľuboš, Kavcová Helena, Sulová Zdena, Breier Albert, Messingerova Lucia: Different mechanisms of drug resistance to hypomethylating agents in the treatment of myelodysplastic syndromes and acute myeloid leukemia. Drug Resistance Updates 2022, 61, 100805. <https://doi.org/10.1016/j.drup.2022.100805>
- Singh Manoj, Kumar Vikas, Sehrawat Nirmala, Yadav Mukesh, Chaudhary Mayank, Upadhyay Sushil K., Kumar Sunil, Sharma Varruchi, Kumar Sandeep, Dilbaghi Neeraj, Sharma Anil K.: Current paradigms in epigenetic anticancer therapeutics and future challenges. Seminars in Cancer Biology 2022, 83, 422. <https://doi.org/10.1016/j.semcancer.2021.03.013>
- Gorica Era, Mohammed Shafeeq A., Ambrosini Samuele, Calderone Vincenzo, Costantino Sarah, Paneni Francesco: Epi-Drugs in Heart Failure. Front. Cardiovasc. Med. 2022, 9. <https://doi.org/10.3389/fcvm.2022.923014>
- Onaciu Anca, Toma Valentin, Moldovan Cristian, Țigu Adrian Bogdan, Cenariu Diana, Culic Carina, Borșa Rareș Mario, David Luca, Știufiuc Gabriela Fabiola, Tetean Romulus, Tomuleasa Ciprian, Știufiuc Rareș Ionuț: Nanoscale Investigation of DNA Demethylation in Leukemia Cells by Means of Ultrasensitive Vibrational Spectroscopy. Sensors 2022, 23, 346. <https://doi.org/10.3390/s23010346>
- Straube Jasmin, Lane Steven W., Vu Therese: Optimizing DNA hypomethylating therapy in acute myeloid leukemia and myelodysplastic syndromes. BioEssays 2021, 43. <https://doi.org/10.1002/bies.202100125>
- Cao Chang, Gilbert Elizabeth R., Cline Mark A.: DNA methylation-modifiers reduced food intake in juvenile chickens (Gallus gallus) and Japanese quail (Coturnix japonica). Neuroscience Letters 2021, 764, 136230. <https://doi.org/10.1016/j.neulet.2021.136230>
- Vaidergorn Miguel M., da Silva Emery Flavio, Ganesan A.: From Hit Seeking to Magic Bullets: The Successful Union of Epigenetic and Fragment Based Drug Discovery (EPIDD + FBDD). J. Med. Chem. 2021, 64, 13980. <https://doi.org/10.1021/acs.jmedchem.1c00787>
- Janotka Ľuboš, Messingerová Lucia, Šimoničová Kristína, Kavcová Helena, Elefantová Katarína, Sulová Zdena, Breier Albert: Changes in Apoptotic Pathways in MOLM-13 Cell Lines after Induction of Resistance to Hypomethylating Agents. IJMS 2021, 22, 2076. <https://doi.org/10.3390/ijms22042076>
- Sorrentino Vincent G., Thota Srijan, Gonzalez Edward A., Rameshwar Pranela, Chang Victor T., Etchegaray Jean-Pierre: Hypomethylating Chemotherapeutic Agents as Therapy for Myelodysplastic Syndromes and Prevention of Acute Myeloid Leukemia. Pharmaceuticals 2021, 14, 641. <https://doi.org/10.3390/ph14070641>
- Cook Nicola, Parker Darren J., Tauber Eran, Pannebakker Bart A., Shuker David M.: Validating the Demethylating Effects of 5-aza-2′-deoxycytidine in Insects Requires a Whole-Genome Approach. The American Naturalist 2019, 194, 432. <https://doi.org/10.1086/704248>
- Ganesan A., Arimondo Paola B., Rots Marianne G., Jeronimo Carmen, Berdasco María: The timeline of epigenetic drug discovery: from reality to dreams. Clin Epigenet 2019, 11. <https://doi.org/10.1186/s13148-019-0776-0>
- Ichikawa Yoshiyasu: The Dawn, Evolution and Personal Reminiscences in Studies of Glycosyl Isocyanates and Isocyanides. HETEROCYCLES 2018, 96, 1691. <https://doi.org/10.3987/REV-18-892>
- Bozhok T. S., Kalinichenko E. N., Kuz’mitskii B. B., Golubeva M. B.: Synthesis, Hydrolytic Stability, and Antileukemic Activity of Azacytidine Nucleoside Analogs. Pharm Chem J 2016, 49, 804. <https://doi.org/10.1007/s11094-016-1375-4>
- Shelton Jadd, Lu Xiao, Hollenbaugh Joseph A., Cho Jong Hyun, Amblard Franck, Schinazi Raymond F.: Metabolism, Biochemical Actions, and Chemical Synthesis of Anticancer Nucleosides, Nucleotides, and Base Analogs. Chem. Rev. 2016, 116, 14379. <https://doi.org/10.1021/acs.chemrev.6b00209>
- Hennessy Conor, McKernan Declan P: Epigenetics and innate immunity: the ‘unTolld’ story. Immunol Cell Biol 2016, 94, 631. <https://doi.org/10.1038/icb.2016.24>
- Jahanfar Farhad, Hasani Akbar, Shanebandi Dariush, Rahmati Mohammad, Hamishehkar Hamed: Enhanced in Vitro Anti-Tumor Activity of 5-Azacytidine by Entrapment into Solid Lipid Nanoparticles. Adv Pharm Bull 2016, 6, 367. <https://doi.org/10.15171/apb.2016.048>
- Bhat Jaydeep, Kabelitz Dieter: γδ T cells and epigenetic drugs: A useful merger in cancer immunotherapy?. OncoImmunology 2015, 4. <https://doi.org/10.1080/2162402X.2015.1006088>
- Khatun Amina, Shabir Nadeem, Yoon Kyoung-Jin, Kim Won-Il: Effects of ribavirin on the replication and genetic stability of porcine reproductive and respiratory syndrome virus. BMC Vet Res 2015, 11. <https://doi.org/10.1186/s12917-015-0330-z>
- Michigami Kyosuke, Uchida Satoshi, Adachi Miho, Hayashi Masahiko: Synthesis of novel nucleosides and stereoselectivity of N-glycosidation. Tetrahedron 2013, 69, 595. <https://doi.org/10.1016/j.tet.2012.11.017>
- Vujjini Satish Kumar, Varanasi Ganesh, Arevelli Srinivas, Kandala Sreenatha Charyulu, Tirumalaraju Satyanarayana Raju, Bandichhor Rakeshwar, Kagga Mukkanti, Cherukupally Praveen: An Improved and Scalable Process for the Synthesis of 5-Azacytidine: An Antineoplastic Drug. Org. Process Res. Dev. 2013, 17, 303. <https://doi.org/10.1021/op300192e>
- Krečmerová Marcela, Otmar Miroslav: 5-Azacytosine Compounds In Medicinal Chemistry: Current Stage And Future Perspectives. Future Med. Chem. 2012, 4, 991. <https://doi.org/10.4155/fmc.12.36>
- Tochitani Tomoaki, Kanemitsu Hiroyuki, Yamauchi Hirofumi, Uchida Kazuyuki, Nakayama Hiroyuki: 5-azacytidine, a chemotherapeutic drug, induces TRAIL-mediated apoptosis in mouse thymocytes in vivo. Experimental and Toxicologic Pathology 2011, 63, 237. <https://doi.org/10.1016/j.etp.2009.12.005>
- Lim Sue Ping, Neilsen Paul, Kumar Raman, Abell Andrew, Callen David F.: The Application of Delivery Systems for DNA Methyltransferase Inhibitors. BioDrugs 2011, 25, 227. <https://doi.org/10.2165/11592770-000000000-00000>
- Matoušová Marika, Votruba Ivan, Otmar Miroslav, Tloušťová Eva, Günterová Jana, Mertlíková-Kaiserová Helena: 2´-deoxy-5,6-dihydro-5-azacytidine - a less toxic alternative of 2´-deoxy-5-azacytidine. Epigenetics 2011, 6, 769. <https://doi.org/10.4161/epi.6.6.16215>
- Krečmerová Marcela, Masojídková Milena, Holý Antonín: Acyclic nucleoside phosphonates with 5-azacytosine base moiety substituted in C-6 position. Bioorganic & Medicinal Chemistry 2010, 18, 387. <https://doi.org/10.1016/j.bmc.2009.10.044>
- Mieczkowski Adam, Roy Vincent, Agrofoglio Luigi A.: Preparation of Cyclonucleosides. Chem. Rev. 2010, 110, 1828. <https://doi.org/10.1021/cr900329y>
- Quintás-Cardama Alfonso, Santos Fabio P. S., Garcia-Manero Guillermo: Therapy with azanucleosides for myelodysplastic syndromes. Nat Rev Clin Oncol 2010, 7, 433. <https://doi.org/10.1038/nrclinonc.2010.87>
- Yu Jian-Ning, Xue Chun-Yang, Wang Xu-Guang, Lin Fei, Liu Chun-Yi, Lu Fu-Zeng, Liu Hong-Lin: 5-AZA-2′-deoxycytidine (5-AZA-CdR) leads to down-regulation of Dnmt1o and gene expression in preimplantation mouse embryos. Zygote 2009, 17, 137. <https://doi.org/10.1017/S0967199408005169>
- Dračínský Martin, Krečmerová Marcela, Holý Antonín: Study of chemical stability of antivirally active 5-azacytosine acyclic nucleoside phosphonates using NMR spectroscopy. Bioorganic & Medicinal Chemistry 2008, 16, 6778. <https://doi.org/10.1016/j.bmc.2008.05.058>
- Guo Gang, Li Gang, Liu Dan, Yang Qian-Jiao, Liu Yu, Jing Yong-Kui, Zhao Lin-Xiang: Synthesis and Antiproliferative Activities of 5-Azacytidine Analogues in Human Leukemia Cells. Molecules 2008, 13, 1487. <https://doi.org/10.3390/molecules13071487>
- Liu Zhongfa, Marcucci Guido, Byrd John C., Grever Michael, Xiao Jim, Chan Kenneth K.: Characterization of decomposition products and preclinical and low dose clinical pharmacokinetics of decitabine (5‐aza‐2′‐deoxycytidine) by a new liquid chromatography/tandem mass spectrometry quantification method. Rapid Comm Mass Spectrometry 2006, 20, 1117. <https://doi.org/10.1002/rcm.2423>
- Fenaux Pierre: Inhibitors of DNA methylation: beyond myelodysplastic syndromes. Nat Rev Clin Oncol 2005, 2, S36. <https://doi.org/10.1038/ncponc0351>
- Zsoldos‐Mády Virág, Sohár Pál, Kovács József, Pintér István, Szakács Zoltán: New Carbohydrate Derivatives of Norfloxacin. Journal of Carbohydrate Chemistry 2005, 24, 19. <https://doi.org/10.1081/CAR-200049410>
- Ichikawa Yoshiyasu, Matsukawa Yohei, Nishiyama Taihei, Isobe Minoru: Synthesis, Characterization, and Reaction of Crystalline Fischer’s Glucopyranosyl Isocyanate. Eur J Org Chem 2004, 2004, 586. <https://doi.org/10.1002/ejoc.200300617>
- Pískala Alois, Hanna Naeem B., Masojídková Milena, Fiedler Pavel, Votruba Ivan: Synthesis of N4-Amino and N4-Hydroxy Derivatives of 5-Azacytidine. A Facile Rearrangement of the N4-Amino Derivative to 5-(3-β-D-Ribofuranosylureido)-1H-1,2,4-triazole. Collect. Czech. Chem. Commun. 2004, 69, 905. <https://doi.org/10.1135/cccc20040905>
- Dowell Jonathan E., Minna John D.: Cancer Chemotherapy Targeted at Reactivating the Expression of Epigenetically Inactivated Genes. JCO 2004, 22, 1353. <https://doi.org/10.1200/JCO.2004.01.947>
- Pískala Alois, Hanna Naeem B., Masojídková Milena, Otmar Miroslav, Fiedler Pavel, Ubik Karel: Synthesis of N4-Alkyl-5-azacytidines and Their Base-Pairing with Carbamoylguanidines - A Contribution to Explanation of the Mutagenicity of 2'-Deoxy-5-azacytidine. Collect. Czech. Chem. Commun. 2003, 68, 711. <https://doi.org/10.1135/cccc20030711>
- Christman Judith K: 5-Azacytidine and 5-aza-2′-deoxycytidine as inhibitors of DNA methylation: mechanistic studies and their implications for cancer therapy. Oncogene 2002, 21, 5483. <https://doi.org/10.1038/sj.onc.1205699>
- Goffin J., Eisenhauer E.: DNA methyltransferase inhibitors—state of the art. Annals of Oncology 2002, 13, 1699. <https://doi.org/10.1093/annonc/mdf314>
- Katritzky Alan R., Rogovoy Boris V., Vvedensky Vladimir Y., Hebert Normand, Forood Behrouz: Synthesis of Substituted 4(6)-Amino-1,3,5-triazin-2-ones and -1,3,5-triazin-2-thiones. J. Org. Chem. 2001, 66, 6797. <https://doi.org/10.1021/jo010416a>
- Gaubert Gilles, Mathé Christophe, Imbach Jean-Louis, Eriksson Staffan, Vincenzetti Silvia, Salvatori Daniela, Vita Alberto, Maury Georges: Unnatural enantiomers of 5-azacytidine analogues: Syntheses and enzymatic properties. European Journal of Medicinal Chemistry 2000, 35, 1011. <https://doi.org/10.1016/S0223-5234(00)01184-3>
- Wang Zhiwei, Prudhomme Daniel R., Buck Jason R., Park Minnie, Rizzo Carmelo J.: Stereocontrolled Syntheses of Deoxyribonucleosides via Photoinduced Electron-Transfer Deoxygenation of Benzoyl-Protected Ribo- and Arabinonucleosides. J. Org. Chem. 2000, 65, 5969. <https://doi.org/10.1021/jo0003652>
- Hossain Mokbul, Nakayama Hiroyuki, Shinozuka Junko, Katayama Kei-ichi, Suzuki Kazuhiko, Doi Kunio: 5-Azacytidine-induced Apoptosis in Lymphoid and Hematopoietic Organs of Adult Mice. Journal of Toxicologic Pathology 2000, 13, 231. <https://doi.org/10.1293/tox.13.231>
- Jackson-Grusby Laurie, Laird Peter W., Magge Suresh N., Moeller Benjamin J., Jaenisch Rudolf: Mutagenicity of 5-aza-2′-deoxycytidine is mediated by the mammalian DNA methyltransferase. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 4681. <https://doi.org/10.1073/pnas.94.9.4681>
- Hanna + Naeem B., Zajíček ++ Jaroslav, Pískala Alois: 6-Methyl-5-Azacytidine-Synthesis, Conformational Properties and Biological Activity. A Comparison of Molecular Conformation with 5-Azacytidine. Nucleosides and Nucleotides 1997, 16, 129. <https://doi.org/10.1080/07328319708002528>
- Ramsahoye B.H., Davies C.S., Mills K.I.: DNA methylation: biology and significance. Blood Reviews 1996, 10, 249. <https://doi.org/10.1016/S0268-960X(96)90009-0>
- Pintér István, Kovács József, Tóth Gábor: Synthesis of sugar ureas via phosphinimines. Carbohydrate Research 1995, 273, 99. <https://doi.org/10.1016/0008-6215(95)00029-S>
- Hammons G.J., Warren G.J., Blann E., Nichols J., Lyn-Cook B.D.: Increased DT-diaphorase activity in transformed and tumorigenic pancreatic acinar cells. Cancer Letters 1995, 96, 9. <https://doi.org/10.1016/0304-3835(95)03911-F>
- Hossain Mokbul Md., Nakayama Hiroyuki, Goto Naoaki: Apoptosis in the Central Nervous System of Developing Mouse Fetuses from 5-Azacytidine-Administered Dams. Toxicol Pathol 1995, 23, 367. <https://doi.org/10.1177/019262339502300313>
- Hayashibara Kathleen C., Verdine Gregory L.: Template-directed interference footprinting of cytosine contacts in a protein-DNA complex: potent interference by 5-aza-2'-deoxycytidine. Biochemistry 1992, 31, 11265. <https://doi.org/10.1021/bi00161a002>
- Lim Benjamin B., Marquez Victor E., Dobyns Kathryn A., Cooney David A., Clercq Erik De: Synthesis and Biological Study of the Cyclopentenyl Carbocyclic Nucleoside Analogue of 5-Azacytidine. Nucleosides and Nucleotides 1992, 11, 1123. <https://doi.org/10.1080/07328319208018331>
- Kalinich J.F., Catravas G.N., Snyder S.L.: Radioprotective Properties of DNA Methylation-disrupting Agents. International Journal of Radiation Biology 1991, 59, 1217. <https://doi.org/10.1080/09553009114551091>
- Avramis Vassilios I., Powell William C., Mecum Robert A.: Cellular metabolism of 5,6-dihydro-5-azacytidine and its incorporation into DNA and RNA of human lymphoid cells CEM/O and CEM/dCk(-). Cancer Chemother. Pharmacol. 1989, 24, 155. <https://doi.org/10.1007/BF00300235>
- Avramis Vassilios I., Powell William C., Mecum Robert A.: Cellular metabolism of 1-?-d-arabinofuranosyl-5-azacytosine and incorporation into DNA and RNA of human lymphoid CEM/0 and CEM/dCk(?) cells. Cancer Chemother. Pharmacol. 1989, 25, 19. <https://doi.org/10.1007/BF00694333>
- Hiebl Johann, Zbiral Erich: Synthese von Glycofuranosylformamiden, ‐isocyaniden und ‐isocyanaten ausgehend von den entsprechenden Glycosylaziden. Liebigs Ann. Chem. 1988, 1988, 765. <https://doi.org/10.1002/jlac.198819880811>
- Johnson-Thompson Marian, Albury Denise: Azapyrimidine analogues: Inhibition of viral DNA synthesis and protein synthesis in SV40 infected BSC-1 cells. In Vitro Cell Dev Biol 1988, 24, 1114. <https://doi.org/10.1007/BF02620813>
- Hassel Tillmann, Müller Hanns Peter: Glycosyl-isocyaniddichloride – neue Synthesebausteine für die Zuckerchemie. Angew. Chem. 1987, 99, 368. <https://doi.org/10.1002/ange.19870990429>
- Hassel Tillmann, Müller Hanns Peter: Glycosyl Isocyanide Dichlorides—Novel Synthetic Building Blocks in Sugar Chemistry. Angew. Chem. Int. Ed. Engl. 1987, 26, 359. <https://doi.org/10.1002/anie.198703591>
- Rustum Abu M., Hoffman Norman E.: High-performance liquid chromatographic determination of. Journal of Chromatography B: Biomedical Sciences and Applications 1987, 421, 387. <https://doi.org/10.1016/0378-4347(87)80422-X>
- Riley Timothy A., Hennen William J., Dalley N. Kent, Wilson Bruce E., Robins Roland K.: Synthesis of 2‐(β‐D‐ribofuranosyl)[1,3,5]triazines. Journal of Heterocyclic Chem 1986, 23, 1709. <https://doi.org/10.1002/jhet.5570230621>
- Avalos Gonzalez Martin, Fuentes Mota Jose, Gomez Monterrey Isabel Ma., Jimenez Requejo Jose L., Palacios Albarran Juan C., Ortiz Mellet Maria C.: Synthesis of 1,3,4,6-tetra-O-acetyl-2-[3-alkyl-(aryl)-thioreido]-2-deoxy-α-d-glucopyranoses and their transformation into 2-alkyl(aryl)amino-(1,2-dideoxy-α-d-glucopyrano)[2,1-d]-2-thiazolines. Carbohydrate Research 1986, 154, 49. <https://doi.org/10.1016/S0008-6215(00)90021-1>
- Hawtrey A.O, Ariatti M: A possible model for the methylation of deoxycytidine in DNA. Medical Hypotheses 1984, 15, 125. <https://doi.org/10.1016/0306-9877(84)90117-8>
- Huguenin Philipp N., Jayaram Hiremagalur N., Kelley James A.: Reverse Phase HPLC Determination OF 5,6-Dihydro-5-azacytidine in Biological Fluids. Journal of Liquid Chromatography 1984, 7, 1433. <https://doi.org/10.1080/01483918408074056>
- Cech Dieter, König Joachim, Meinelt Barbara: Synthese eines Imidazol‐2‐thion‐nucleosids. Zeitschrift fuer Chemie 1982, 22, 58. <https://doi.org/10.1002/zfch.19820220219>
- Paluska E., Hrubá Alena, Madar J., Činátl J., Chudomel V., Nezvalová Jana, Čihák A.: Inhibitory effects of 5-azapyrimidine nucleosides on cellular immunity. Immunobiology 1982, 162, 288. <https://doi.org/10.1016/S0171-2985(11)80008-2>
- Yakhontov L. N., Vakhatova G. M.: Search for medicinal preparations in the series of 1,3,5-triazines (review). Pharm Chem J 1981, 15, 546. <https://doi.org/10.1007/BF00758588>
- Kelly Cecil J., Coles Eric, Gaudio Linda, Yesair David W.: Characterization of the urinary metabolites of 5-azacytidine in mice. Biochemical Pharmacology 1980, 29, 609. <https://doi.org/10.1016/0006-2952(80)90384-6>
- Lu Lee-Jane Wang, Chiang Grace H., Randerath Kurt: Effects of 5-azacytidine on transfer RNA modification: Comparative study on normal and malignant tissues. Life Sciences 1980, 27, 577. <https://doi.org/10.1016/0024-3205(80)90307-0>
- Rada Břetislav, Doskočil Jiři: Azapyrimidine nucleosides. Pharmacology & Therapeutics 1980, 9, 171. <https://doi.org/10.1016/S0163-7258(80)80018-0>
- Chan Kenneth K., Giannini Donald D., Staroscik James A., Sadee Wolfgang: 5-Azacytidine Hydrolysis Kinetics Measured by High-Pressure Liquid Chromatography and 13C-NMR Spectroscopy. Journal of Pharmaceutical Sciences 1979, 68, 807. <https://doi.org/10.1002/jps.2600680705>
- Bellet Robert E., Catalano R. B., Mastrangelo Michael J., Berd David: Phase II study of subcutaneously administered 5‐azacytidine (NSC‐102816) in patients with metastatic malignant melanoma. Med. Pediatr. Oncol. 1978, 4, 11. <https://doi.org/10.1002/mpo.2950040104>
- Veselý Jiří, Čihák Alois: 5-Azacytidine: Mechanism of action and biological effects in mammalian cells. Pharmacology & Therapeutics. Part A: Chemotherapy, Toxicology and Metabolic Inhibitors 1978, 2, 813. <https://doi.org/10.1016/0362-5478(78)90016-5>
- SHNIDER BRUCE I., BAIG MAHMOODULLAH, COLSKY JACOB: A Phase I Study of 5‐Azacytidine (NSC‐102816). The Journal of Clinical Pharma 1976, 16, 205. <https://doi.org/10.1002/j.1552-4604.1976.tb01519.x>
- Revankar Ganapathi R., Robins Roland K.: Synthesis of certain 1,2,4‐Thiadiazole nucleosides. Journal of Heterocyclic Chem 1976, 13, 169. <https://doi.org/10.1002/jhet.5570130140>
- Lee Thomas T., Karon Myron R.: Inhibition of protein synthesis in 5-azacytidine-treated HeLa cells. Biochemical Pharmacology 1976, 25, 1737. <https://doi.org/10.1016/0006-2952(76)90407-X>
- Carter Stephen K., Slavik Milan: Investigational drugs under study by the United States National Cancer Institute. Cancer Treatment Reviews 1976, 3, 43. <https://doi.org/10.1016/S0305-7372(76)80016-3>
- VON HOFF DANIEL D., SLAVIK MILAN, MUGGIA FRANCO M.: 5-Azacytidine. Ann Intern Med 1976, 85, 237. <https://doi.org/10.7326/0003-4819-85-2-237>
- Coburn Robert A., Bhooshan Bharat: Mesoionie 1,3‐disubstituted s‐triazine‐4,6‐diones and their thione derivatives. Journal of Heterocyclic Chem 1975, 12, 187. <https://doi.org/10.1002/jhet.5570120138>
- Chu Chung K., Watanabe Kyoichi A., Fox Jack J.: Nucleosides XCII. A facile synthesis of 5‐(β‐d‐ribofuranosyl)‐ isocytosine (ψ‐isocytidine). Journal of Heterocyclic Chem 1975, 12, 817. <https://doi.org/10.1002/jhet.5570120448>
- Notari Robert E., Deyoung Joyce L.: Kinetics and Mechanisms of Degradation of the Antileukemic Agent 5‐Azacytidine in Aqueous Solutions. Journal of Pharmaceutical Sciences 1975, 64, 1148. <https://doi.org/10.1002/jps.2600640704>
- Wentworth David F., Wolfenden Richard: Interaction of 3,4,5,6-tetrahydrouridine with human liver cytidine deaminase. Biochemistry 1975, 14, 5099. <https://doi.org/10.1021/bi00694a012>
- Bloch Alexander: THE STRUCTURE OF NUCLEOSIDES IN RELATION TO THEIR BIOLOGICAL AND BIOCHEMICAL ACTIVITY: A SUMMARY. Annals of the New York Academy of Sciences 1975, 255, 576. <https://doi.org/10.1111/j.1749-6632.1975.tb29262.x>
- Shone Robert L.: A synthesis of 3-deazathymidine. Tetrahedron Letters 1973, 14, 3079. <https://doi.org/10.1016/S0040-4039(01)96324-5>
- Carter Stephen K.: New drugs on the horizon in bronchogenic carcinoma. Cancer 1972, 30, 1402. <https://doi.org/10.1002/1097-0142(197211)30:5<1402::AID-CNCR2820300539>3.0.CO;2-N>
- Burchenal Joseph H., Carter Stephen K.: New cancer chemotherapeutic agents. Cancer 1972, 30, 1639. <https://doi.org/10.1002/1097-0142(197212)30:6<1639::AID-CNCR2820300633>3.0.CO;2-4>
- Fučík V., Zadražil S., Jurovčík M., Šormová Z.: Mechanism of resistance to 5-azacytidine inBacillus Subtilis. Folia Microbiol 1972, 17, 517. <https://doi.org/10.1007/BF02872738>
- Doskočil J.: The components of the nucleoside-transporting system in Escherichia coli. Biochimica et Biophysica Acta (BBA) - Biomembranes 1972, 282, 393. <https://doi.org/10.1016/0005-2736(72)90344-6>
- Langman Jan, Shimada Morimi: Cerebral cortex of the mouse after prenatal chemical insult. Am. J. Anat. 1971, 132, 355. <https://doi.org/10.1002/aja.1001320306>
- Currie Bruce L., Robins Roland K., Robins Morris J.: The synthesis of 3‐deazapyrimidine nucleosides related to uridine and cytidine and their derivatives. Journal of Heterocyclic Chem 1970, 7, 323. <https://doi.org/10.1002/jhet.5570070211>
- Zee-Cheng Kwang-Yuen, Cheng C.C.: Common Receptor-Complement Feature Among Some Antileukemic Compounds. Journal of Pharmaceutical Sciences 1970, 59, 1630. <https://doi.org/10.1002/jps.2600591118>
- Fuǔík Vladimír, Michaelis Arnd, Rieger Rigomar: On the induction of segment extension and chromatid structural changes in Vicia faba chromosomes after treatment with 5-azacytidine and 5-azadeoxycytidine. Mutation Research 1970, 9, 599. <https://doi.org/10.1016/0027-5107(70)90105-3>
- Vorbrüggen H., Niedballa U.: Eine einfache synthese von 5-azapyrimidin-nucleosiden. Tetrahedron Letters 1970, 11, 3571. <https://doi.org/10.1016/S0040-4039(01)98530-2>
- Doskočil J., ŠOrm F.: The Mode of Action of 5‐Aza‐2′‐Deoxycytidine in Escherichia coli. European Journal of Biochemistry 1970, 13, 180. <https://doi.org/10.1111/j.1432-1033.1970.tb00916.x>
- Evans J. S., Haňka L. J.: The in vivo activity of combinations of 5-azacytidine and cytidine on leukemia L-1210. Experientia 1968, 24, 922. <https://doi.org/10.1007/BF02138656>
- Seifertová M., Veselý J., Šorm F.: Effect of 5-azacytidine on developing mouse embryo. Experientia 1968, 24, 487. <https://doi.org/10.1007/BF02144408>
- Pačes V., Doskočil J., Šorm F.: Incorporation of 5-Azacytidine into nucleic acids of Escherichia coli. Biochimica et Biophysica Acta (BBA) - Nucleic Acids and Protein Synthesis 1968, 161, 352. <https://doi.org/10.1016/0005-2787(68)90113-5>
- Veselý J., Čihák A., Šorm F.: Biochemical mechanism of drug resistance—VII. Biochemical Pharmacology 1968, 17, 519. <https://doi.org/10.1016/0006-2952(68)90267-0>
- Pačes V., Doskočil J., Šorm F.: The effect of 5‐azacytidine on the synthesis of ribosomes in escherichia coli. FEBS Letters 1968, 1, 55. <https://doi.org/10.1016/0014-5793(68)80017-1>
- Veselý J., Čihák A., Šorm F.: Biochemical mechanisms of drug resistance IV. Development of resistance to 5‐azacytidine and simultaneous depression of pyrimidine metabolism in leukemic mice. Intl Journal of Cancer 1967, 2, 639. <https://doi.org/10.1002/ijc.2910020625>
- Doskočil J., Pačes V., Šorm F.: Inhibition of protein synthesis by 5-azacytidine in Escherichia coli. Biochimica et Biophysica Acta (BBA) - Nucleic Acids and Protein Synthesis 1967, 145, 771. <https://doi.org/10.1016/0005-2787(67)90136-0>
- Doskočil J., Šorm F.: The action of 5-azacytidine on bacteria infected with bacteriophage T4. Biochimica et Biophysica Acta (BBA) - Nucleic Acids and Protein Synthesis 1967, 145, 780. <https://doi.org/10.1016/0005-2787(67)90137-2>
- Veselý J., Seifert J., Čihák A., Šorm F.: Biochemical changes associated with the development of resistance to 5‐azacytidine in AKR leukemic mice. Intl Journal of Cancer 1966, 1, 31. <https://doi.org/10.1002/ijc.2910010106>
- Fox Jack J., Miller Naishun C., Cushley Robert J.: Nucleosides XXXVI. Transformation of arabinopyrimidine nucleosides. Tetrahedron Letters 1966, 7, 4927. <https://doi.org/10.1016/S0040-4039(00)70117-1>

