7-Substituted pyrrolo[2,3-d]pyrimidines for the synthesis of new 1-deazapyrimido[1,2,3-cd]purines

Lyubov Muzychka; Iryna Yaremchuk; Oksana Muzychka; Oleg Smolii

doi:10.17721/fujcV5I2P15-23

Authors

Lyubov Muzychka
Iryna Yaremchuk
Oksana Muzychka
Oleg Smolii Institute of Bioorganic Chemistry and Petrochemistry of NAS of Ukraine

DOI:

https://doi.org/10.17721/fujcV5I2P15-23

Keywords:

pyrrolo[2, 3-d]pyrimidine, iodolactonization, 5, 6-dihydro-4H-1-deazapyrimido[1, 2, 3-cd]purine, cyclizations

Abstract

Few examples of new heterocyclic 1-deazapyrimido[1,2,3-cd]purine derivatives were synthesized by intramolecular cyclization of methyl 7-(oxiran-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylates. The latter were obtained by iodolactonization of 7-allylpyrrolo[2,3-d]pyrimidine-6-carboxylic acids.

References

Rybár A. Annulated Heterocyclo-Purines II: Fused Six- and More-Membered Heterocyclo-Purinediones, -Purinones and -Purineimines. Advances in Heterocyclic Chemistry 2005;88:175-229. https://doi.org/10.1016/s0065-2725(04)88003-6

Szymańska E, Mazurkiewicz J, Kieć-Kononowicz K. Methods for the synthesis of xanthine-derived polycyclic fused systems. Heterocyclic Communications 2013;19(5):297-310. https://doi.org/10.1515/hc-2013-0082

Šimo O, Rybár A, Alföldi J. New [c,d]-Fused Purinediones: 2-Substituted 9-Methyl-4,5-dihydro-6H,8H-pyrimido-[1,2,3-cd]purine-8,10(9H)-diones. Synthesis 1995;1995(07):837-840. https://doi.org/10.1055/s-1995-3996

Simo O, Rybár A, Alföldi J. 2-Triazolylpyrimido[1,2,3-cd]purine-8,10-dionesvia1,3-dipolar cycloadditions to 2-ethynylpyrimido[1,2,3-cd]purine-8,10-dione. Journal of Heterocyclic Chemistry 2000;37(5):1033-1039. https://doi.org/10.1002/jhet.5570370502

Qi S, Zhang S, Gao C, Li Q. Purine and Pyrimidine Derivatives from the South China Sea Gorgonian Subergorgia suberosa. CHEMICAL & PHARMACEUTICAL BULLETIN 2008;56(7):993-994. https://doi.org/10.1248/cpb.56.993

Weyler S, Hayallah A, Müller C. Versatile, convenient synthesis of pyrimido[1,2,3-cd]purinediones. Tetrahedron 2003;59(1):47-54. https://doi.org/10.1016/s0040-4020(02)01485-0

Burbiel J, Hockemeyer J, Müller C. . Beilstein Journal of Organic Chemistry 2006;2(1):20. https://doi.org/10.1186/1860-5397-2-20

Weyler S, Fülle F, Diekmann M, Schumacher B, Hinz S, Klotz K, Müller C. Improving Potency, Selectivity, and Water Solubility of Adenosine A1 Receptor Antagonists: Xanthines Modified at Position 3 and Related Pyrimido[1,2,3-cd]purinediones. ChemMedChem 2006;1(8):891-902. https://doi.org/10.1002/cmdc.200600066

Mieczkowski A, Roy V, Agrofoglio L. Preparation of Cyclonucleosides. Chemical Reviews 2010;110(4):1828-1856. https://doi.org/10.1021/cr900329y

KIKUGAWA K. Transformation of adenosine into N3,3'- and N3,5'-cycloadenosines via the reactions with sulfuryl chloride and thionyl chloride.. CHEMICAL & PHARMACEUTICAL BULLETIN 1977;25(9):2181-2188. https://doi.org/10.1248/cpb.25.2181

De Carvalho G, Fourrey J, Dodd R, Da Silva A. Synthesis of a 4′,4′-spirothietane-2′, N3-cycloadenosine as a highly constrained analogue of 5′-deoxy-5′-methylthioadenosine (MTA). Tetrahedron Letters 2009;50(4):463-466. https://doi.org/10.1016/j.tetlet.2008.11.039

Mizuno Y, Ikehara M, Watanabe K, Suzaki S, Itoh T. Synthetic Studies of Potential Antimetabolites. IX. The Anomeric Configuration of Tubercidin. The Journal of Organic Chemistry 1963;28(12):3329-3331. https://doi.org/10.1021/jo01047a012

Verves E, Kucher A, Muzychka L, Smolii O. Synthesis of 7-alkyl-4-amino-7H-pyrrolo-[2,3-d]pyrimidine-6-carboxylic acids. Chemistry of Heterocyclic Compounds 2013;48(12):1844-1852. https://doi.org/10.1007/s10593-013-1218-0

Grunewald G, Dahanukar V. Synthesis of 3-alkyl-8-substituted- and 4-hydroxy-8-substituted-2,3,4,5-tetrahydro-1H-2-benzazepines. Journal of Heterocyclic Chemistry 1994;31(6):1609-1617. https://doi.org/10.1002/jhet.5570310656

Roux M, Paugam R, Rousseau G. Evaluation ofexo-endoRatios in the Halolactonization of ω-Unsaturated Acids. The Journal of Organic Chemistry 2001;66(12):4304-4310. https://doi.org/10.1021/jo0017234

Joseph B, Putey A, Fournet G. General and Easy Access to 11-Substituted 4-Hydroxy-2,3,4,5-tetrahydro[1,4]diazepino[1,2-a]indol-1-one Derivatives. Synlett 2006;2006(17):2755-2758. https://doi.org/10.1055/s-2006-950249

Seden T, Turner R. The reaction of adenine with epichlorohydrin. Journal of Heterocyclic Chemistry 1975;12(5):1045-1046. https://doi.org/10.1002/jhet.5570120548

Harriman G, Poirot A, Abushanab E, Midgett R, Stoeckler J. Adenosine deaminase inhibitors. Synthesis and biological evaluation of C1' and nor-C1' derivatives of (+)-erythro-9-[2(S)-hydroxy-3(R)-nonyl]adenine. Journal of Medicinal Chemistry 1992;35(22):4180-4184. https://doi.org/10.1021/jm00100a025

Sund P, Kronberg L. Ring-Opening of 3-β-D-Ribofuranosyl-3,7,8,9-Tetrahydropyrimido [1,2-i]Purin-8-ol and Preparation of 2-Thio- and 2-aza-Adenosine Derivatives. Nucleosides, Nucleotides and Nucleic Acids 2008;27(12):1215-1226. https://doi.org/10.1080/15257770802458162

Robison M, Butler F, Robison B. 7-Azaindole. IV. The Hydrogenation of 7-Azaindole and Related Compounds1,2. Journal of the American Chemical Society 1957;79(10):2573-2578. https://doi.org/10.1021/ja01567a057

Savarino P, Viscardi G, Barni E, Di Modica G. Quaternary salts and polymethine dyes from 2-(methylpyridyl)-X-azolo[4,5-b]pyridine. Journal of Heterocyclic Chemistry 1987;24(4):1053-1060. https://doi.org/10.1002/jhet.5570240428

Holý A. Preparation of aliphatic analogues of S-adenosyl-L-homocysteine and related compounds. Collection of Czechoslovak Chemical Communications 1981;46(12):3134-3144. https://doi.org/10.1135/cccc19813134

Kim M, Gokel G. A molecular box, based on bibracchial lariat ethers having adenine and thymine sidearms, that self-assembles in water. Journal of the Chemical Society, Chemical Communications 1987;(22):1686. https://doi.org/10.1039/c39870001686

Shibinskaya M, Kutuzova N, Mazepa A, Lyakhov S, Andronati S, Zubritsky M, Galat V, Lipkowski J, Kravtsov V. Synthesis of 6-Aminopropyl-6H-indolo[2,3-b]quinoxaline Derivatives. Journal of Heterocyclic Chemistry 2012;49(3):678-682. https://doi.org/10.1002/jhet.805

Sundberg R, Dalvie D, Cordero J, Sabat M, Musallam H. Carbamates of (hydroxyphenoxy)methyl heteroaromatic salts as acetylcholinesterase inhibitors and protective agents against organophosphorus compounds. Chemical Research in Toxicology 1993;6(4):500-505. https://doi.org/10.1021/tx00034a017

Parlar S, Bayraktar G, Tarikogullari A, Alptüzün V, Erciyas E. Synthesis, Biological Evaluation and Molecular Docking Study of Hydrazone-Containing Pyridinium Salts as Cholinesterase Inhibitors. Chemical and Pharmaceutical Bulletin 2016;64(9):1281-1287. https://doi.org/10.1248/cpb.c16-00221