Diprotected Triflylguanidines:  A New Class of Guanidinylation Reagents

Feichtinger, Konrad; Zapf, Christoph W.; Sings, Heather L.; Goodman, Murray

doi:10.1021/jo980425s

Cited by 238 publications

(178 citation statements)

References 10 publications

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“…45 Di-Boc-triflylguanidine 110 and di -Cbz-triflylguanidine 113 are efficiently converted by various primary amines into guanidines 111, 114. [45][46][47] …”

Section: Triflyl Guanidinesmentioning

confidence: 99%

Recent developments in guanylating agents

Katritzky¹,

Rogovoy²

2005

Arkivoc

144

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Dedicated to Professor Nikolai Zefirov on the occasion of his 70th birthday (received 26 Oct 04; accepted 08 Jan 05; published on the web 05 Jan 05) AbstractGuanidines are important molecules with a wide range of interesting properties. In this overview we summarize recent advances in the development of guanylating reagents which we define as compounds forming a guanidine structure by a chemical transformation. We cover important classes of guanylating agents developed in the last two decades and representative examples are reported.

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“…45 Di-Boc-triflylguanidine 110 and di -Cbz-triflylguanidine 113 are efficiently converted by various primary amines into guanidines 111, 114. [45][46][47] …”

Section: Triflyl Guanidinesmentioning

confidence: 99%

Recent developments in guanylating agents

Katritzky¹,

Rogovoy²

2005

Arkivoc

144

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“…Compounds 49 and 50 were synthesized with typical acylation methods. Compound 51 was prepared using di-Boc-protected triflylguanidine, 20 and the deprotection of one or both of the Boc groups gave a mixture of compounds 52 (30%) and 53 (57%).…”

Section: Resultsmentioning

confidence: 99%

Quinazolines as adenosine receptor antagonists: SAR and selectivity for A2B receptors

Webb

Lvovskiy

Kim

et al. 2003

Bioorganic & Medicinal Chemistry

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We have recently reported the discovery of numerous new compounds that are selective inhibitors of all of the subtypes of the adenosine receptor family via a pharmacophore database searching and screening strategy. During the course of this work we made the unexpected discovery of a potent A 2B receptor antagonist, 4-methyl-7-methoxyquinazolyl-2-(2′-amino-4′-imidazolinone) (38, CMB 6446), which showed selectivity for this receptor and functioned as an antagonist, with a binding K i value of 112 nM. We explored the effects of both substituent-and ring-structural variations on the receptor affinity in this series of derivatives, which were found to be mostly nonselective adenosine receptor ligands with K i values in the micromolar range. Since no enhancement of A 2B receptor affinity of 38 was achieved, the previously reported pharmacophorebased searching strategy yielded the most potent and selective structurally-related hit in the database originally searched.

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“…Our strategy (Scheme 1) incorporated the stereochemical element using commercially available (S)-allylglycine, thus avoiding the use of chiral templates. The reliable olefin cross-metathesis reaction 13 provided the necessary chain elongation and established guanidation methodology 14 was then applied for the required primary amine to guanidine functional group transformation. This strategy of amino acid chain elongation via olefin cross-metathesis could potentially be used to prepare a variety of unnatural amino acids and amino acid homologues rapidly, with the advantage of incorporating the C2-chiral stereocentre from the outset.…”

Section: Resultsmentioning

confidence: 99%

A Convenient and Efficient Synthesis of (S)‐Lysine and (S)‐Arginine Homologues via Olefin Cross‐Metathesis.

Boyle¹,

Bremner²,

Coates³

et al. 2005

ChemInform

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A convenient and efficient synthesis of (S)-lysine and (S)-arginine homologues via olefin cross-metathesis, Tetrahedron, 61(30), 2005, 7271-7276. Original journal article available here A convenient and efficient synthesis of (S)-lysine and (S)-arginine homologues via olefin cross-metathesis AbstractA convenient five step synthesis of (S)-homolysine, incorporating a key olefin cross-metathesis step in the chain extension methodology, has been developed, together with a six step related synthesis of a new homologue of arginine, (S)-bishomoarginine. Abstract: A convenient five step synthesis of (S)-homolysine, incorporating a key olefin crossmetathesis step in the chain extension methodology, has been developed, together with a six step related synthesis of a new homologue of arginine, (S)-bishomoarginine. A Convenient and Efficient Synthesis of (S)-Lysine and (S)-Arginine Homologues via Olefin Cross Metathesis

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Diprotected Triflylguanidines: A New Class of Guanidinylation Reagents

Cited by 238 publications

References 10 publications

Recent developments in guanylating agents

Recent developments in guanylating agents

Quinazolines as adenosine receptor antagonists: SAR and selectivity for A2B receptors

A Convenient and Efficient Synthesis of (S)‐Lysine and (S)‐Arginine Homologues via Olefin Cross‐Metathesis.

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