Iron/Copper Co-Catalyzed Cross-Coupling Reaction for the Synthesis of 6-Substituted 7-Deazapurines and the Corresponding Nucleosides

Li, Qingfeng; Persoons, Leentje; Daelemans, Dirk; Herdewijn, Piet

doi:10.1021/acs.joc.9b02414

Cited by 15 publications

(20 citation statements)

References 36 publications

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“…4‐Ethyl‐N7‐(2’,3’,5’‐tri‐O‐benzoyl‐β‐ d –ribofuranosyl)‐7 H ‐pyrrolo[2,3‐ d ]‐pyrimidine (66) [50] . 62 [23,49] (700 mg, 1.17 mmol) and Pd(PPh 3 ) 4 (135 mg, 0.12 mmol, 0.1 eq.)…”

Section: Methodsmentioning

confidence: 99%

“…[a] Cpd. R or structure T. cruzi [a] EC 50 [μM] MRC-5 [b] EC 50 Table 3. Comparison of activity of compound 14 and the corresponding 3'-deoxy-analogue against intracellular T. cruzi amastigotes.…”

Section: Cpdmentioning

confidence: 99%

“…[a] Cpd. Structure T. cruzi [a] EC 50 [μM] MRC-5 [b] EC 50 elicited a 3-fold weaker anti-T. cruzi activity than its ribose congener 14.…”

Section: Cpdmentioning

confidence: 99%

“…1 66). [50] 62 [23,49] (700 mg, 1.17 mmol) and Pd-(PPh 3 ) 4 (135 mg, 0.12 mmol, 0.1 eq.) was placed into a 50 mL round bottom flask.…”

Section: N7-(β-d-ribofuranosyl)-7h-pyrrolo[23-d]-pyrimidine (63)mentioning

confidence: 99%

“…Then, the reaction solution was evaporated till dryness, purified by column chromatography (0!10 % MeOH/ DCM) to afford 68 (165 mg, 0.46 mmol) as a white solid in 88 % yield. 1 [50] 4-Chloro-7H-pyrrolo [2,3-d]pyrimidine (300 mg, 1.95 mmol), phenylboronic acid (480 mg, 3.91 mmol, 2 eq. ), K 2 CO 3 (808 mg, 5.85 mmol, 3 eq.)…”

Section: -Ethyl-5-bromo-n7-(β-d-ribofuranosyl)-7h-pyrrolo[23-d]-pyrimidine (68)mentioning

confidence: 99%

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6‐Methyl‐7‐Aryl‐7‐Deazapurine Nucleosides as Anti‐Trypanosoma cruzi Agents: Structure‐Activity Relationship and in vivo Efficacy

et al. 2021

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Chagas disease is a tropical infectious disease resulting in progressive organ-damage and currently lacks efficient treatment and vaccine options. The causative pathogen, Trypanosoma cruzi, requires uptake and processing of preformed purines from the host because it cannot synthesize these de novo, instigating the evaluation of modified purine nucleosides as potential trypanocides. By modifying the pyrimidine part of a previously identified 7-aryl-7-deazapurine nucleoside, we found that substitution of a 6-methyl for a 6-amino group allows retaining T. cruzi amastigote growth inhibitory activity but confers improved selectivity towards mammalian cells. By keeping the 6-methyl group unaltered, and introducing different 7-aryl groups, we identified several analogues with submicromolar antitrypanosomal activity. The 7-(4-chlorophenyl) analogue 14, which was stable in microsomes, was evaluated in an acute mouse model. Oral administration of 25 mg/kg b.i.d. suppressed peak parasitemia and protected mice from infection-related mortality, gave similar reductions as the reference drug of blood parasite loads determined by qPCR, but as benznidazole failed to induce sterile cure in the short time period of drug exposure (5 days).

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Section: Methodsmentioning

confidence: 99%

Section: Cpdmentioning

confidence: 99%

“…[a] Cpd. Structure T. cruzi [a] EC 50 [μM] MRC-5 [b] EC 50 elicited a 3-fold weaker anti-T. cruzi activity than its ribose congener 14.…”

Section: Cpdmentioning

confidence: 99%

“…1 66). [50] 62 [23,49] (700 mg, 1.17 mmol) and Pd-(PPh 3 ) 4 (135 mg, 0.12 mmol, 0.1 eq.) was placed into a 50 mL round bottom flask.…”

Section: N7-(β-d-ribofuranosyl)-7h-pyrrolo[23-d]-pyrimidine (63)mentioning

confidence: 99%

Section: -Ethyl-5-bromo-n7-(β-d-ribofuranosyl)-7h-pyrrolo[23-d]-pyrimidine (68)mentioning

confidence: 99%

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6‐Methyl‐7‐Aryl‐7‐Deazapurine Nucleosides as Anti‐Trypanosoma cruzi Agents: Structure‐Activity Relationship and in vivo Efficacy

et al. 2021

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Iron‐Based Multi‐Catalysis: Eco‐Compatible Alternative for Complex Molecules Synthesis

Quintard

2020

Chemistry A European J

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Iron–Copper Dual Catalysis Enabling C−C and C−X (X=N, B, P, S, Sn) Bond Formation

Huo

Shi

2022

Eur J Org Chem

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Dedicated to Professor Zhen Yang on the occasion of his 63rd birthdayThe dual-catalysis tactics where two types of catalysts are connected in one single reaction operation are highly prized in the novel bond constructions that are difficult or unattainable to be achieved with current mono-catalysis. In recent years, increased emphasis on sustainable catalytic methods on more economic and eco-friendly processes has shifted the focus to catalysis with earth-abundant transition metals, such as iron, copper, and so on. As two of the most inexpensive and environmentally friendly metals on earth, the research and development based on either iron or copper catalysis are flourishing, and iron-copper dual-catalyzed reactions appeal more and more attention. In this review, we mainly cover the construction of CÀ C, CÀ N, CÀ B, CÀ P, CÀ S and CÀ Sn bonds enabled by iron-copper dual-catalysis published in the literature from 2011.

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Iron/Copper Co-Catalyzed Cross-Coupling Reaction for the Synthesis of 6-Substituted 7-Deazapurines and the Corresponding Nucleosides

Cited by 15 publications

References 36 publications

6‐Methyl‐7‐Aryl‐7‐Deazapurine Nucleosides as Anti‐Trypanosoma cruzi Agents: Structure‐Activity Relationship and in vivo Efficacy

6‐Methyl‐7‐Aryl‐7‐Deazapurine Nucleosides as Anti‐Trypanosoma cruzi Agents: Structure‐Activity Relationship and in vivo Efficacy

Iron‐Based Multi‐Catalysis: Eco‐Compatible Alternative for Complex Molecules Synthesis

Iron–Copper Dual Catalysis Enabling C−C and C−X (X=N, B, P, S, Sn) Bond Formation

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