Synthesis and structure-activity relationships of new cephalosporins with aminoimidazoles at C-7. Effect of the pKa of the C-7 aminoimidazole on antibacterial spectrum and .BETA.-lactamase stability.

Jung, F.; Boucherot, D.; Delvare, C.; Olivier, A.; Davies, Gareth; Betts, Michael J.; Brown, Randi L.; Stevenson, Ralph J.; Joseph, Mejo; Kingston, John F.; Pittam, J. D.

doi:10.7164/antibiotics.46.992

Cited by 12 publications

(6 citation statements)

References 14 publications

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“…Benzimidazoles and 2‐aminobenzimidazoles are very powerful compounds because of their applications in therapeutic and biological sciences (Figure ) . These compounds were used as neuropeptide YY1 receptor antagonist, N ‐methyl‐D‐aspartate (NMDA) antagonist, factor Xa(FXa) inhibitor, poly(ADP‐ribose)polymerase (PARP) inhibitor and non‐peptide thrombin inhibitor .…”

Section: Figurementioning

confidence: 99%

Synthesis of Benzimidazoles via Domino Intra and Intermolecular C‐N Cross‐Coupling Reaction

2018

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The synthesis of aminobenzimidazoles has been demonstrated under mild reaction conditions using cobalt catalyst in one pot reaction. This methodology involved domino intra and intermolecular C-N cross-coupling reaction. In addition, functional group tolerance has been also explored.Benzimidazoles [1][2][3][4][5][6][7][8][9][10] and 2-aminobenzimidazoles [11][12][13][14][15][16][17][18][19][20][21] are very powerful compounds because of their applications in therapeutic [22][23] and biological sciences ( Figure 1). [24][25] These compounds were used as neuropeptide YY1 receptor antagonist, [26] N-methyl-D-aspartate (NMDA) antagonist, [27] factor Xa(FXa) inhibitor, [28] poly(ADP-ribose)polymerase (PARP) inhibitor [29] and non-peptide thrombin inhibitor. [30] In addition, these compounds show anti-inflammatory, antimicrobial and antibacterial activities. [31] Apart from that, these compounds can also be used for the synthesis of dyes and high-temperature resistance polymers. [32] Therefore, the construction of benzimidazole derivatives were developed by many researchers via both traditional methods [33][34][35] and C-N cross-coupling reactions using various transition metals such as Cu, [36][37][38][39][40] Pd, [41][42][43] Co, [44] Zn, [45][46][47] and Ru. [48] In this connection, we would like to demonstrate the methodology for the synthesis of benzimidazoles from thiourea in one pot reaction via desulphurization/substitution/domino C-N cross-coupling reaction using cobalt source as catalyst under mild reaction conditions.

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Section: Figurementioning

confidence: 99%

Synthesis of Benzimidazoles via Domino Intra and Intermolecular C‐N Cross‐Coupling Reaction

2018

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“…The 2-aminoimidazole has been utilized as a building block has led to the development of several medicinally relevant small molecules. Researchers at Zeneca delivered a series of broad spectrum antibiotics 7a-c, inspired by the well studied cephalosporins [28,29]. They were further able to show that substitution on N1 of the aminoimidazole led to inactive compounds, again suggesting that this motif may make an acid hydrogen bond contact ( Fig.…”

Section: The 2-aminoimidazole In Appendage Diversitymentioning

confidence: 99%

2-Aminoimidazoles from Leucetta Sponges: Synthesis and Biology of an Important Pharmacophore

Sullivan¹,

Giles²,

Looper³

2009

CBC

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This review will focus on the ability of the 2-aminoimidazole to occupy a unique subset of chemical space which makes it an ideal pharmacophore for the development of small molecule collections for discovery based research. These observations rely both on the use of 2-aminoimidazoles as building blocks in medicinal chemistry as well as the recent discovery of alkaloids from sponges of the genus Leucetta which exhibit a diverse range of biological activities around a relatively limited structural core. The preparation of these compounds will also be highlighted.

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“…A broad range of substituents on the 4-position of the imidazole ring were used to provide a series of compounds that were studied with respect to b-lactamase stability and for activity against gram-positive organisms. 126 …”

Section: Fluorinated Purines and Benzimidazolesmentioning

confidence: 99%

Fluorinated Five‐Membered Nitrogen‐Containing Heterocycles

Kirk¹

2009

Fluorinated Heterocyclic Compounds

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Synthesis and structure-activity relationships of new cephalosporins with aminoimidazoles at C-7. Effect of the pKa of the C-7 aminoimidazole on antibacterial spectrum and .BETA.-lactamase stability.

Cited by 12 publications

References 14 publications

Synthesis of Benzimidazoles via Domino Intra and Intermolecular C‐N Cross‐Coupling Reaction

Synthesis of Benzimidazoles via Domino Intra and Intermolecular C‐N Cross‐Coupling Reaction

2-Aminoimidazoles from Leucetta Sponges: Synthesis and Biology of an Important Pharmacophore

Fluorinated Five‐Membered Nitrogen‐Containing Heterocycles

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