Derivatives of Purinethiols. Purine Thiolcarbonates and Related Compounds<sup>1</sup>

Dyer, Elizabeth; Bender, Howard S.

doi:10.1021/jm00331a003

Cited by 14 publications

(2 citation statements)

References 2 publications

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“…The most informative proof for the structure of compound 6 was 1 H NMR spectrum, as it revealed two singlets at δ 2.93 and 3.16 ppm corresponding to thiazepine CH 2 and CH–C 6 H 5 protons, respectively. In 1964, Dyer and Bender reported the synthesis of ethyl purin‐6‐yl thiocarbonate through stirring of 6‐mercaptopurine 1 with ethyl chloroformate in dry dimethylformamide containing potassium carbonate as a catalyst. In this work, 6‐mercaptopurine 1 was refluxed with ethyl chloroformate in presence of sodium ethoxide as a base to yield the thiazolo[3,4,5‐ gh ]purin derivative 7 .…”

Section: Resultsmentioning

confidence: 99%

Design, Synthesis, and Anticancer Activity of Novel Fused Purine Analogues

Hassan

Sarg

Bayoumi

et al. 2017

Journal of Heterocyclic Chem

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6‐Mercaptopurine has been utilized for the synthesis of various fused purine analogues through different chemical reactions to yield [1,4]thiazino[4,3,2‐gh]purines 2, 3, 10a,b, 14, (8‐oxo‐[1,4]thiazino[4,3,2‐gh]purin‐7(8H)‐ylidene) acetate 4, [1,4]thiazepino[4,3,2‐gh]purine 6, thiazolo[3,4,5‐gh]purine 7, imidazo[1,5,4‐gh]purin‐5‐amine 8, 5‐methylimidazo[1,5,4‐gh]purine 9, [1,2,4]triazino[4,3‐i]purines 16, 18, 21, [1,2,4]triazino[4,5,6‐gh]purine 20, 5‐methyl‐2‐(7H‐purin‐6‐yl)‐1H‐pyrazol‐3(2H)‐one 22, [1,2,4]triazolo[4,3‐i]purine 23, [1,2,5]triazepino[5,4,3‐gh]purine 24, and ethyl 6‐(2‐(ethoxycarbonyl)hydrazinyl)‐9H‐purine‐9‐carboxylate 26. Seventeen of the newly synthesized compounds were selected by the NCI, Maryland, USA, and were tested for their anticancer activity in an initial single high dose in the full NCI 60 cell line panel among which [1,4]thiazino[4,3,2‐gh]purine‐7,8‐dione 2, 7‐benzyl‐[1,4]thiazino[4,3,2‐gh]purine 10b, and 3‐(2,4‐dimethoxyphenyl)‐7H‐[1,2,4]triazolo[4,3‐i]purine 23 were found to possess very potent anticancer activity against most of the cancer cell lines.

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Section: Resultsmentioning

confidence: 99%

Design, Synthesis, and Anticancer Activity of Novel Fused Purine Analogues

Hassan

Sarg

Bayoumi

et al. 2017

Journal of Heterocyclic Chem

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show abstract

“…Thiocarbonates have been used as protecting group for thiols, [1] synthetic intermediates in the preparation of other valuable substances, [2,3] heat stabilizers for polymers, [4] polymerization inhibitors, [5] bioactive compounds, [6] radiographic contrast agents, [7] precursors to polymercaptanes, [8] and as biological toxicants, particularly as mematocides. [9] The usual syntheses of thiocarbonates involve reactions of primary and benzyl alcohols with carbon dioxide, methanesulfonic anhydride, and thiols under basic conditions, [10] the treatment of thiols and disulfides with chloroformates, [7b] the reaction of b-nitroalcohols and 2,2,2-trihaloethanols with ethyl chlorothiolformate, [11] nucleophilic addition of potassium monothiocarbonates to epoxides or alkyl halides, [12] the rearrangement of diaryl thiocarbonates, [13] the reaction of aryloxide salts, carbonyl sulfide, and alkyl halides, [14] the reaction of trimethylsilyl enol ethers with phenyl thiofluoroformate in the presence of a naked fluoride ion catalyst, [15] selenium-catalyzed reaction of alcohols, carbon monoxide, sulfur, and alkyl halides, [16] and sulfur-assisted O-carbonylation of alcohols with carbon monoxide in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU).…”

Section: Introductionmentioning

confidence: 99%