Synthesis of Purines and Other Fused Imidazoles from Acyclic Amidines and Guanidines

Szczepankiewicz, Bruce G.; Rohde, Jeffrey J.; Kurukulasuriya, Ravi

doi:10.1021/ol0504751

Cited by 44 publications

(25 citation statements)

References 6 publications

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“…Abbott disclosed a series of compounds that were xanthine mimetics as DPP-IV inhibitors [58,59] (Fig. (14)).…”

Section: Xanthines and Xanthine-based Hetero-cyclesmentioning

confidence: 99%

See 1 more Smart Citation

Aromatic Heterocycle-Based DPP-IV Inhibitors: Xanthines and Related Structural Types.

Szczepankiewicz¹,

Kurukulasuriya²

2007

CTMC

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Xanthines and xanthine-like DPP-IV inhibitors were first disclosed in 2002. Since then, several dozen accounts of xanthine-based DPP-IV inhibitors have been published. Only a few presentations and journal articles have appeared, with the vast majority of information coming from the patent literature. DPP-IV inhibitors related to the xanthines include purine analogues with other arrangements of the nitrogen atoms in the core structure, imidazoles, uracils, pyrimidines, pyridines, and some fused pyridines. At least one compound derived from the xanthines has advanced into clinical trials, making it likely that these molecules will play a major role in the DPP-IV inhibition arena over the next several years.

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“…Abbott disclosed a series of compounds that were xanthine mimetics as DPP-IV inhibitors [58,59] (Fig. (14)).…”

Section: Xanthines and Xanthine-based Hetero-cyclesmentioning

confidence: 99%

“…A 2005 patent by Takeda (Japan) disclosed a series of pyridine-based DPP-IV inhibitors (57)(58)(59) including IC 50 data [60] (Fig. (16)).…”

Section: Pyridine-and Pyrimidine-based Dpp-iv Inhibitorsmentioning

confidence: 99%

Aromatic Heterocycle-Based DPP-IV Inhibitors: Xanthines and Related Structural Types.

Szczepankiewicz¹,

Kurukulasuriya²

2007

CTMC

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“…Moreover, these compounds have found wide application as adenosine receptor ligands [15,16], antiparasitic agents [17], cyclin-dependent kinase inhibitors [18], antitumor [19], and antiviral compounds [20]. A systematic perusal of literature survey reveals that a number of synthetic routes are available for the construction of substituted purine nucleus deriving from amidines or guanidines with retrosynthetic disconnection at the ring fusion [21], inverse electron demand Diels-Alder cycloaddition (IEDDAC) reaction [22], metal-catalyzed cross-coupling reactions [23], S N Ar displacement in anilines and amines followed by N-alkylation and N-arylation [24]. However, the methods reported so far are tedious with low outcome of the overall yields.…”

Section: Introductionmentioning

confidence: 99%

Calix[n]arenes mediated phase‐transfer catalytic synthesis of purine derivatives

Sharma

Kumar

Sahu

et al. 2008

Int J of Chemical Kinetics

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A new route was designed to achieve the synthesis of purine derivatives under phase-transfer catalysis conditions using calix[n]arenes TAC n A (n = 4, 6, and 8) as phasetransfer catalyst for the first time in this particular type of synthesis. The compounds were synthesized in excellent yields (70%-80%) and the structures were established on the basis of consistent IR, 1 H NMR, FAB-Mass, and elemental analyses data. Their purity has been ascertained by chromatographic resolution using acetonitrile, methanol, and water (50:30:20, v/v) as eluenting system. Moreover, the kinetics of the reaction was studied and it was found to obey first-order kinetics. Effect of various parameters, namely, temperature, amount of catalyst, stirring speed, and so on was also investigated. C

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“…Ring closure proceeds using Cu(I), with no special ligands required. The method allowed for easy modification of the heterocyclic nucleus and has proven useful for the preparation of potent DPPIV inhibitors, and it will make the preparation of new purines and other fused imidazole systems simpler than is possible using previous methods [134]. Synthesis of fused imidazoles © 2005 American Chemical Society3.1.12.…”

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confidence: 99%

Guanidines from ‘toxic substances’ to compounds with multiple biological applications – Detailed outlook on synthetic procedures employed for the synthesis of guanidines

Tahir

Badshah

Hussain

2015

Bioorganic Chemistry

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Synthesis of Purines and Other Fused Imidazoles from Acyclic Amidines and Guanidines

Cited by 44 publications

References 6 publications

Aromatic Heterocycle-Based DPP-IV Inhibitors: Xanthines and Related Structural Types.

Aromatic Heterocycle-Based DPP-IV Inhibitors: Xanthines and Related Structural Types.

Calix[n]arenes mediated phase‐transfer catalytic synthesis of purine derivatives

Guanidines from ‘toxic substances’ to compounds with multiple biological applications – Detailed outlook on synthetic procedures employed for the synthesis of guanidines

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