Deamination, involving ring opening, in reactions of 1-aminopurinium mesitylenesulfonates with methanolic amonia

Kos, N.J.; Jongejan, H.; Plas, H. C. Van Der

doi:10.1016/s0040-4020(01)87667-5

Cited by 8 publications

(15 citation statements)

References 11 publications

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“…Thus, the addition of 15 N-labelled ammonia to the C-2 position of purine with concomitant ring opening yielded 176, which cyclized to the 15 N-1-labelled purines 177 (Scheme 28). [139] Electrophilic amination of adenines 178 with DNPA produced 1-aminoadenines 179 that displayed similar properties to N-oxides (Scheme 29). For instance, the ring opening in strongly alkaline media was accompanied by further cyclization to triazoles 180 a-b.…”

Section: Ring Opening Of N-1-quaternized Purinesmentioning

confidence: 99%

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Applications of Purine Ring Opening in the Synthesis of Imidazole, Pyrimidine, and New Purine Derivatives

et al. 2021

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Purines, which are regarded as relatively stable heterocyclic systems, can be opened at both pyrimidine and imidazole rings. Purine ring opening also serves as a tool for the preparation of ring-modified purines through rearrangement/recyclization mechanisms. The obtained imidazole, pyrimidine, and purine derivatives are privileged molecular scaffolds in medicinal and agricultural chemistry. Purine ring-opening approach is a useful alternative for their synthesis, which competes well with de novo approach or modification of a conserved heterocyclic core. The substitution patterns and groups that activate purines towards ring opening are reviewed. Moreover, mechanistic studies using labelled substrates, which are leading to rearranged purine derivatives are covered. Furthermore, an insight into imidazole ring opening upon exposure of purine system to DNA damaging agents is provided.

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Section: Ring Opening Of N-1-quaternized Purinesmentioning

confidence: 99%

“…Thus, the addition of 15 N ‐labelled ammonia to the C ‐2 position of purine with concomitant ring opening yielded 176 , which cyclized to the 15 N ‐1‐labelled purines 177 (Scheme 28). [139] …”

Section: Ring Opening Of the Pyrimidine Moiety In Purinesmentioning

confidence: 99%

Applications of Purine Ring Opening in the Synthesis of Imidazole, Pyrimidine, and New Purine Derivatives

et al. 2021

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“…To provide a reference point for these studies, the 6-substituent was deleted entirely. Thus, the 6-unsubstituted intermediate 64 was prepared from 2-fluoro-6-chloropurine ( 63 ) [ 27 ], by selective dehalogenation of the 6-chloro group using catalytic transfer hydrogenation [ 28 , 29 ]. Coupling of 64 with the appropriate anilines gave derivatives 65 and 66 , with 66 being converted to amide 67 (Scheme 4 ).…”

Section: Resultsmentioning

confidence: 99%

Structure-guided design of purine-based probes for selective Nek2 inhibition

et al. 2016

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Nek2 (NIMA-related kinase 2) is a cell cycle-dependent serine/threonine protein kinase that regulates centrosome separation at the onset of mitosis. Overexpression of Nek2 is common in human cancers and suppression can restrict tumor cell growth and promote apoptosis. Nek2 inhibition with small molecules, therefore, offers the prospect of a new therapy for cancer. To achieve this goal, a better understanding of the requirements for selective-inhibition of Nek2 is required. 6-Alkoxypurines were identified as ATP-competitive inhibitors of Nek2 and CDK2. Comparison with CDK2-inhibitor structures indicated that judicious modification of the 6-alkoxy and 2-arylamino substituents could achieve discrimination between Nek2 and CDK2. In this study, a library of 6-cyclohexylmethoxy-2-arylaminopurines bearing carboxamide, sulfonamide and urea substituents on the 2-arylamino ring was synthesized. Few of these compounds were selective for Nek2 over CDK2, with the best result being obtained for 3-((6-(cyclohexylmethoxy)-9H-purin-2-yl)amino)-N,N-dimethylbenzamide (CDK2 IC50 = 7.0 μM; Nek2 IC50 = 0.62 μM) with >10-fold selectivity. Deletion of the 6-substituent abrogated activity against both Nek2 and CDK2. Nine compounds containing an (E)-dialkylaminovinyl substituent at C-6, all showed selectivity for Nek2, e.g. (E)-6-(2-(azepan-1-yl)vinyl)-N-phenyl-9H-purin-2-amine (CDK2 IC50 = 2.70 μM; Nek2 IC50 = 0.27 μM). Structural biology of selected compounds enabled a partial rationalization of the observed structure activity relationships and mechanism of Nek2 activation. This showed that carboxamide 11 is the first reported inhibitor of Nek2 in the DFG-in conformation.

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“…The 15 N content of the final products is in the range of 4-8%. 58 A pathway to introduce a selective 15 N labeling at N-7 is outlined in Scheme 6.…”

Section: Methodsmentioning

confidence: 99%

Chemical Synthesis of 13C and 15N Labeled Nucleosides

Lagoja¹,

Herdewijn²

2002

Synthesis

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The chemical synthesis of 13 C and 15 N labeled nucleosides for site-specific incorporation in RNA or DNA oligonucleotides is herein reviewed. The review covers the following aspects: 1: single-and multiple site chemical 13 C and/or 15 N labeling of purine bases, 2: single-and multiple site chemical 13 C and/or 15 N labeling of pyrimidine bases, 3: single-and multiple site chemical 13 C labeling of the sugar residues.

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Deamination, involving ring opening, in reactions of 1-aminopurinium mesitylenesulfonates with methanolic amonia

Cited by 8 publications

References 11 publications

Applications of Purine Ring Opening in the Synthesis of Imidazole, Pyrimidine, and New Purine Derivatives

Applications of Purine Ring Opening in the Synthesis of Imidazole, Pyrimidine, and New Purine Derivatives

Structure-guided design of purine-based probes for selective Nek2 inhibition

Chemical Synthesis of 13C and 15N Labeled Nucleosides

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