EPSP Synthase: The Design and Synthesis of Bisubstrate Inhibitors Incorporating Novel 3-Phosphate Mimics

Sikorski, James A.; Miller, Michael J.; Braccolino, Diane S.; Cleary, Darryl G.; Corey, Susan D.; Font, Josep; Gruys, Kenneth J.; Han, Chao; Lin, Ko-Chung; Pansegrau, Paul D.; Ream, Joel E.; Schnur, Dora M.; Shah, Ajit S.; Walker, Mark C.

doi:10.1080/10426509308032372

Cited by 131 publications

(27 citation statements)

References 9 publications

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“…One of the most frequently encountered heterocycle in medicinal chemistry is quinoline with wide applications including antibacterial 1 , antifungal 2 , anti-malarial 3 , antiviral 4 , antiasthamatic 5 , antihypertensive 6 , analgesic 7, antiinflammatory 8 , cytotoxic 9 , anti-platelet 10 , antiprion 11 , H+/K+ATPase inhibitor 12 , leukotrien 13 and biosynthesis inhibitor activity. Interesting pharmacological properties have been associated with 2-chloroquinoline-3-carbaldehydes and their derivatives 14,15 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis Characterisation and Antimicrobial Activity of N-(2-Chloroquinolin-3-yl)methylene)- isonicotinohydrazide

2017

Chem Sci Trans

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A series of novel N′-(2-chloro-substituted quinolin-3-yl)methylene)isonicotinohydrazide (3a-h) were prepared by condensation of 2-chloro-3-formylquinoline (1a-h) with isonicotinohydrazide (2) in the presence of catalytic quantity of acetic acid in methanol under reflux in good yield. Newly synthesized compounds were characterized by IR, 1 H NMR and mass. The newly synthesized compound (3a-h) has been screened for their antibacterial and antifungal activities. All compounds exhibited significant antibacterial and antifungal activity.

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Section: Introductionmentioning

confidence: 99%

Synthesis Characterisation and Antimicrobial Activity of N-(2-Chloroquinolin-3-yl)methylene)- isonicotinohydrazide

2017

Chem Sci Trans

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“…Additionally, the phosphonic acids and their derivatives may be considered as long life analogues of transition states for tetrahedral intermediates in amide/ester hydrolysis [16]. Among others, these compounds also possess enzyme inhibition properties and consequently they can serve as antibacterial and anticancer drugs [17][18][19][20][21][22][23][24][25][26][27][28][29][30][31]. Phosphorylated alkenes are also synthetically useful [32][33][34][35] and are commonly used in organic synthesis [36][37][38][39][40].…”

Section: Introductionmentioning

confidence: 99%

Conformation of Sterically Hindered 4-Methyl-2-oxo-2-trityl-1,3,2-dioxaphosphorinane in the Solid State and the Solution

Kruszyński

Czubacka

Trzęsowska-Kruszyńska

et al. 2011

J Chem Crystallogr

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The cis-and trans-2-methyl-2-oxo-2-trityl-1,3,2-dioxaphosphorinanes were obtained in the Arbuzov reaction of 2-methoxy-4-methyl-1,3,2-dioxaphosphorinane with trityl chloride. The NMR spectra ( 1 H, 13 C and 31 P) in solution indicated that trans isomer exists in the form of two noncongruent molecules and it adopts two different conformations: a halfchair and a sofa, while the cis isomer exists as the mixed half/chair-sofa conformer. The compounds crystallise as a pure chiral forms and as a racemates. The solid state structural studies show that NMR data are consistent with the single crystal X-ray analysis, but the conformation existing in the crystal structure is more complex than it can be supposed on sole NMR determination. Crystal data: cis-isomer chiral form: space group P3 2 , a = 8.

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“…They can be used as inhibitors of synthase [1], HIV protease [2], PTPases [3,4], rennin [5], enzymes [6], antibiotics [7], herbicides [8], etc.…”

Section: Introductionmentioning

confidence: 99%

Kabachnik-Fields and Prins- Ritter Synthesis: Application of Ce(III) Supported on a Weakly Acidic Cation-exchanger Resin in Comparative Study

2015

J Chem Appl

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We described results of comparative studies of the application of Ce(III) cation supported on macroporous weakly acidic polyacrylate resin as catalyst in two model three-component domino syntheses, i.e. Kabachnik-Fields domino synthesis of α-aminophosphonates, and Prins-Ritter domino synthesis of 4-amidotetrahydropyrane derivatives, respectively. It was discovered that cation Ce(III) supported on a weak acid macroporous cation-exchanger shown in the studied reactions at least the same or better catalytic activity as salt CeCl3.7H2O, eventually doped by NaI. Further, we found that reactivity of the low reactive 4-methoxybenzaldehyde as carbonyl compounds in the presence of Ce(III) catalyst increases, while the reactivity of the highly reactive 4-nitrobenzaldehyde in this case strongly decreases due to its low coordination with the catalyst. Finally, the presented synthetic protocols using cerium(III) supported on low-cost industrial resin further increases green impact of studied domino syntheses of α-aminophosphonates, and 4-amidotetrahydropyrane derivatives.

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EPSP Synthase: The Design and Synthesis of Bisubstrate Inhibitors Incorporating Novel 3-Phosphate Mimics

Cited by 131 publications

References 9 publications

Synthesis Characterisation and Antimicrobial Activity of N-(2-Chloroquinolin-3-yl)methylene)- isonicotinohydrazide

Synthesis Characterisation and Antimicrobial Activity of N-(2-Chloroquinolin-3-yl)methylene)- isonicotinohydrazide

Conformation of Sterically Hindered 4-Methyl-2-oxo-2-trityl-1,3,2-dioxaphosphorinane in the Solid State and the Solution

Kabachnik-Fields and Prins- Ritter Synthesis: Application of Ce(III) Supported on a Weakly Acidic Cation-exchanger Resin in Comparative Study

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