833486-94-5

Usage

Uses

Used in Chemical Synthesis:
4-Amino-3-Nitrophenylboronic Acid, Pinacol Ester is used as a reagent in chemical synthesis for its enhanced reactivity, particularly in reactions that require the formation of new carbon-carbon or carbon-heteroatom bonds.
Used in Coupling Reactions:
In the field of organic chemistry, 4-Amino-3-Nitrophenylboronic Acid, Pinacol Ester is used as a coupling agent in reactions such as the Suzuki-Miyaura cross-coupling. This reaction is a powerful method for the formation of carbon-carbon bonds, which is crucial in the synthesis of complex organic molecules and pharmaceutical compounds.
Used in Research Applications:
4-Amino-3-Nitrophenylboronic Acid, Pinacol Ester is used as a research tool in various scientific studies, including the investigation of new reaction mechanisms, the development of novel synthetic pathways, and the exploration of its potential applications in material science and medicinal chemistry.

InChI:InChI=1/C12H17BN2O4/c1-11(2)12(3,4)19-13(18-11)8-5-6-9(14)10(7-8)15(16)17/h5-7H,14H2,1-4H3

Synthetic route

4-Bromo-2-nitroaniline (875-51-4) + bis(pinacol)diborane (73183-34-3) → 4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5)

Conditions	Yield
With potassium acetate; palladium diacetate In N,N-dimethyl-formamide at 85℃; for 5h;	92%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane for 2h; Inert atmosphere;	91.9%
With potassium acetate; 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane at 85℃;	86%

4-Chloro-2-nitroaniline (89-63-4) + bis(pinacol)diborane (73183-34-3) → 4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5)

Conditions	Yield
With potassium phosphate tribasic heptahydrate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); XPhos In ethanol at 20℃; for 1.5h;	63%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + 4,6-dichloro-5-methoxypyrimidine (5018-38-2) → 4-(6-chloro-5-methoxypyrimidin-4-yl)-2-nitroaniline

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 80℃; for 3h; Suzuki Coupling;	100%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + 2-chloro-4,6-diphenyl-1,3,5-triazine (3842-55-5) → C21H15N5O2

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 12h; Reflux;	100%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + 2-bromo-5-methoxy-1,3-benzothiazole (2941-58-4) → 2-(4'-amino-3-nitrophenyl)-6-methoxybenzothiazole (132064-21-2)

Conditions	Yield
Stage #1: 4-amino-3-nitrophenylboronic acid pinacol ester; 2-bromo-6-methoxy-1,3 benzothiazole With potassium carbonate In water; N,N-dimethyl-formamide for 1h; Suzuki-Miyaura Coupling; Inert atmosphere; Stage #2: With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In water; N,N-dimethyl-formamide at 80℃; for 2h; Suzuki-Miyaura Coupling; Inert atmosphere;	99%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + 6-hydroxy-2-bromo-benzothiazole (808755-67-1) → 2-(4'-amino-3-nitrophenyl)-6-hydroxybenzothiazole (1448780-05-9)

Conditions	Yield
Stage #1: 4-amino-3-nitrophenylboronic acid pinacol ester; 6-hydroxy-2-bromo-benzothiazole With potassium carbonate In water; N,N-dimethyl-formamide for 1h; Suzuki-Miyaura Coupling; Inert atmosphere; Stage #2: With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In water; N,N-dimethyl-formamide at 80℃; for 1.5h; Temperature; Time; Suzuki-Miyaura Coupling; Inert atmosphere;	98%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + 4-iodo-5-methyl-1,2-oxazole (7064-38-2) → 4-(5-methylisoxazol-4-yl)-2-nitroaniline

Conditions	Yield
Stage #1: 4-amino-3-nitrophenylboronic acid pinacol ester; 4-iodo-5-methyl-1,2-oxazole With caesium carbonate In 1,4-dioxane; water at 0.2℃; for 0.25h; Stage #2: With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,4-dioxane; water at 100℃; for 0.5h; Inert atmosphere;	96%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + 2,7-dibromo-2',7'-di-[5-[3,4-bis[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]phenyl]-1,3,4-oxadiazole-2-yl]-9,9'-spirobifluorene (1274238-86-6) → 2,7-di-(4-amino-3-nitrophenyl)-2',7'-di-[5-[3,4-bis[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]phenyl]-1,3,4-oxadiazole-2-yl]-9,9'-spirobifluorene (1274238-87-7)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran; water for 12h; Suzuki coupling; Inert atmosphere; Reflux;	94%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + (S)-3-((S)-1-(4-bromophenyl)ethyl)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one (1110641-70-7) → 3-[(S)-1-(4'-amino-3'-nitrobiphenyl-4-yl)ethyl]-(S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-[1,3]oxazinan-2-one (1114573-37-3)

Conditions	Yield
Stage #1: 4-amino-3-nitrophenylboronic acid pinacol ester; (S)-3-((S)-1-(4-bromophenyl)ethyl)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one With sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In water at 100℃; Inert atmosphere; Stage #2: With citric acid In water pH=5 - 6;	93%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + methyl 3-[methyl(propan-2-yl)amino]-2-[(trifluoromethane)sulfonyloxy]quinoxaline-6-carboxylate (1394973-22-8) → methyl 2-(4-amino-3-nitrophenyl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate (1396753-37-9)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 90℃; for 0.666667h; Inert atmosphere;	93%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) → 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzene-1,2-diamine (851883-08-4)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In ethyl acetate under 3102.97 Torr;	91%
With hydrogen; palladium 10% on activated carbon In methanol; dichloromethane at 20℃;
With hydrogen; palladium 10% on activated carbon In methanol under 2475.25 Torr; for 2h;

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + 1-bromo-2,6-difluorobenzene (64248-56-2) → 2',6'-difluoro-3-nitro-[1,1'-biphenyl]-4-amine (1259026-54-4)

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,2-dimethoxyethane; water at 90℃; for 18h; Suzuki coupling; Inert atmosphere;	91%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + 3-(2-(1H-indol-3-yl) ethyl)-6-bromoquinazolin-4(3H)-one → 3-(2-(1H-indol-3-yl)ethyl)-6-(4-amino-3-nitrophenyl)quinazolin-4(3H)-one

Conditions	Yield
Stage #1: 4-amino-3-nitrophenylboronic acid pinacol ester; 3-(2-(1H-indol-3-yl) ethyl)-6-bromoquinazolin-4(3H)-one With potassium carbonate In 1,4-dioxane; water at 100℃; for 0.25h; Suzuki-Miyaura Coupling; Stage #2: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; water at 100℃; Suzuki-Miyaura Coupling; Inert atmosphere;	89.4%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + 7-bromo-4-{[4-(difluoromethyl)piperidine-1-yl]carbonyl}-2,3,4,5-tetrahydro-1,4-benzoxazepine (1257320-91-4) → 4-(4-{[4-(difluoromethyl)piperidin-1-yl]carbonyl}-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-2-nitroaniline (1257320-92-5)

Conditions	Yield
With caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,4-dioxane; water at 90℃; for 12h;	86%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + 3-bromo-4-fluorobenzaldehyde (77771-02-9) → 4'-amino-6-fluoro-3'-nitro-[1,1'-biphenyl]-3-carbaldehyde

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In 1,4-dioxane; water at 98℃; for 18h; Inert atmosphere;	86%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + 6-bromo-3-(2-morpholino-2-oxoethyl)quinazolin-4(3H)-one → 6-(4-amino-3-nitrophenyl)-3-(2-morpholino-2-oxoethyl)quinazolin-4(3H)-one

Conditions	Yield
Stage #1: 4-amino-3-nitrophenylboronic acid pinacol ester; 6-bromo-3-(2-morpholino-2-oxoethyl)quinazolin-4(3H)-one With potassium carbonate In 1,4-dioxane; water at 100℃; for 0.25h; Suzuki-Miyaura Coupling; Stage #2: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; water at 100℃; Suzuki-Miyaura Coupling; Inert atmosphere;	86%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + 5-bromo-furan-2-carboxylic acid ((S)-cyclohexyl-methylcarbamoyl-methyl)-amide (1191923-17-7) → 5-(4-amino-3-nitro-phenyl)-furan-2-carboxylic acid ((S)-cyclohexyl-methylcarbamoyl-methyl)-amide (1222809-30-4)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 100℃; for 4h;	85%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + C70H101BrN2O4 (1268673-68-2) → C76H106N4O6 (1435751-05-5)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 90℃; for 8h; Suzuki Coupling;	85%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + (1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-2-en-3-yl trifluoromethanesulfonate → 4-((1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-2-en-3-yl)-2-nitroaniline

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 16h; Inert atmosphere;	83%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + 6-bromo-3-methyl-2-(morpholinomethyl)quinazolin-4(3H)-one → 6-(4-amino-3-nitrophenyl)-3-methyl-2-(morpholinomethyl)quinazolin-4(3H)-one

Conditions	Yield
Stage #1: 4-amino-3-nitrophenylboronic acid pinacol ester; 6-bromo-3-methyl-2-(morpholinomethyl)quinazolin-4(3H)-one With potassium carbonate In 1,4-dioxane; water at 100℃; for 0.25h; Suzuki-Miyaura Coupling; Stage #2: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; water at 100℃; Suzuki-Miyaura Coupling; Inert atmosphere;	82.8%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + 6-bromo-3-butyl-4(3H)-quinazolinone → 6-(4-amino-3-nitrophenyl)-3-butylquinazolin-4(3H)-one

Conditions	Yield
Stage #1: 4-amino-3-nitrophenylboronic acid pinacol ester; 6-bromo-3-butylquinazolin-4(3H)-one With potassium carbonate In 1,4-dioxane; water at 100℃; for 0.25h; Suzuki-Miyaura Coupling; Stage #2: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; water at 100℃; Suzuki-Miyaura Coupling; Inert atmosphere;	82.3%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + 6-bromo-3-(2-(4-morpholino)ethyl)quinazolin-4(3H)-one → 6-(4-amino-3-nitrophenyl)-3-(2-morpholinoethyl)quinazolin-4(3H)-one

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 100℃; for 4h; Inert atmosphere;	82.2%
Stage #1: 4-amino-3-nitrophenylboronic acid pinacol ester; 6-bromo-3-(2-(4-morpholino)ethyl)quinazolin-4(3H)-one With potassium carbonate In 1,4-dioxane; water at 100℃; for 0.25h; Suzuki-Miyaura Coupling; Stage #2: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; water at 100℃; Suzuki-Miyaura Coupling; Inert atmosphere;	81.1%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + 6-bromo-3-N-methylquinazoline-4(3H)-one (57573-59-8) → 6-(4-amino-3-nitrophenyl)-3-methylquinazolin-4(3H)-one

Conditions	Yield
Stage #1: 4-amino-3-nitrophenylboronic acid pinacol ester; 6-bromo-3-N-methylquinazoline-4(3H)-one With potassium carbonate In 1,4-dioxane; water at 100℃; for 0.25h; Suzuki-Miyaura Coupling; Stage #2: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; water at 100℃; Suzuki-Miyaura Coupling; Inert atmosphere;	82.1%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + 6-bromo-3-(2-(piperidin-1-yl)ethyl)quinazolin-4(3H)-one → 6- (4-amino-3-nitrophenyl)-3-(2-(piperidin-1-yl)ethyl)quinazolin-4(3H)-one

Conditions	Yield
Stage #1: 4-amino-3-nitrophenylboronic acid pinacol ester; 6-bromo-3-(2-(piperidin-1-yl)ethyl)quinazolin-4(3H)-one With potassium carbonate In 1,4-dioxane; water at 100℃; for 0.25h; Suzuki-Miyaura Coupling; Stage #2: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; water at 100℃; Suzuki-Miyaura Coupling; Inert atmosphere;	81.3%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + 6-bromo-3-(3-morpholinylpropyl)-4(3H)-quinazolinone (878743-68-1) → 6-(4-amino-3-nitrophenyl)-3-(3-morpholinopropyl)quinazolin-4(3H)-one

Conditions	Yield
Stage #1: 4-amino-3-nitrophenylboronic acid pinacol ester; 6-bromo-3-(3-morpholinylpropyl)-4(3H)-quinazolinone With potassium carbonate In 1,4-dioxane; water at 100℃; for 0.25h; Suzuki-Miyaura Coupling; Stage #2: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; water at 100℃; Suzuki-Miyaura Coupling; Inert atmosphere;	80.3%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + methyl iodide (74-88-4) → N-methyl-2-nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Conditions	Yield
Stage #1: 4-amino-3-nitrophenylboronic acid pinacol ester With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃;	80%
Stage #1: 4-amino-3-nitrophenylboronic acid pinacol ester With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h;	80%

4-amino-3-nitrophenylboronic acid pinacol ester (833486-94-5) + 4-bromo-2,2-difluoro-1,3-benzodioxole (144584-66-7) → 4-(2,2-difluorobenzo[d][1,3]dioxol-4-yl)-2-nitroaniline (1259026-52-2)

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,2-dimethoxyethane; water at 90℃; for 18h; Suzuki coupling; Inert atmosphere;	79%

Upstream product

• 89-63-4 4-Chloro-2-nitroaniline 
• 73183-34-3 bis(pinacol)diborane 
• 875-51-4 4-Bromo-2-nitroaniline 

Downstream Products

• 956822-01-8 C₂₁H₂₆N₈O₃ 
• 1228653-84-6 3'-fluoro-3,4'-dinitrobiphenyl-4-amine 
• 1274238-87-7 2,7-di-(4-amino-3-nitrophenyl)-2',7'-di-[5-[3,4-bis[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]phenyl]-1,3,4-oxadiazole-2-yl]-9,9'-spirobifluorene 
• 863328-18-1 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-2-amine 
• 710348-69-9 5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1,3-dihydro-2H-benzo[d]imidazol-2-one 
• 1448780-09-3 2-(4'-amino-3-nitrophenyl)-6-nitrobenzothiazole 
• 1448780-07-1 4-(6-methyl-1,3-benzothiazol-2-yl)-2-nitroaniline 
• 132064-21-2 2-(4'-amino-3-nitrophenyl)-6-methoxybenzothiazole 
• 1448780-05-9 2-(4'-amino-3-nitrophenyl)-6-hydroxybenzothiazole 
• 1435751-05-5 C₇₆H₁₀₆N₄O₆ 

Relevant academic research and scientific papers

6-(2-amino-1H-benzo[d]imidazole-6-yl)quinazoline-4(3H)-one compound

The invention discloses a 6-(2-amino-1H-benzo[d]imidazole-6-yl)quinazoline-4(3H)-one compound,a preparation method and applications thereof, wherein the structural general formula (I) of the compoundis defined in the specification, R1 is hydrogen atom, morpholinomethyl, piperazinomethyl or substituted piperazinomethyl, R2 is hydrogen atom, butyl, morpholine substituted alkyl, benzyl, substitutedbenzyl, tryptamine, substituted tryptamine or N,N-dimethylamino, R3 is-C(O)R4 or-SO2R5, R4 and R5 are alkyl (C3-C6 alkyl), cycloalkyl (3-6-membered ring), alkoxy or alkyl substituted amino, and n is 1, 2, 3 or 4. The compound of the invention has inhibition activity on breast cancer, prostate cancer and human neuroblastoma.

Design, synthesis, biological evaluation of 6-(2-amino-1H-benzo[d]imidazole-6-yl)quinazolin-4(3H)-one derivatives as novel anticancer agents with Aurora kinase inhibition

Aurora A kinase, a member of the Aurora kinase family, is frequently overexpressed in various human cancers. In addition, Overexpression of Aurora A kinase is associated with drug resistance and poor prognosis in many cancers including breast cancer. Therefore, Aurora A kinase has been considered as an attractive anticancer target for the treatment of human cancers. Herein, A series of 6-(2-amino-1H-benzo[d]imidazole-6-yl)quinazolin-4(3H)-one derivatives were designed, synthesized, and evaluated as Aurora A kinase inhibitors. The cell-based cytotoxicity assays showed that compound 16h was the most potent cytotoxic agent against all tested cancer cells and had a lower IC50 value than ENMD-2076 against MDA-MB-231 cells. Meanwhile, Aurora A kinase assay and Western blot analysis showed that 16h inhibited Aurora A kinase with an IC50 value of 21.94 nM and suppressed the phosphorylation of Histone H3 on Ser10 and Aurora A kinase on Thr288, which were consistent with the activation of Aurora A kinase. Accordingly, 16h caused aberrant mitotic phenotypes and obvious G2/M phase arrest in MDA-MB-231 cells and induced caspase-dependent apoptosis in MDA-MB-231 cells. These results demonstrated that 16h is a potential candidate for the development of anticancer agents targeting Aurora A kinase.

Room-temperature borylation and one-pot two-step borylation/Suzuki-Miyaura cross-coupling reaction of aryl chlorides

A highly efficient room-temperature borylation strategy of aryl chlorides is described. Utilizing Buchwald's second-generation preformed catalyst, boronate esters were obtained for a wide range of substrates in high yield. The method was also applied to Suzuki-Miyaura cross-coupling reaction in a one-pot two-step sequential manner, providing a facile and convenient access to the direct synthesis of biaryl compounds from aryl chlorides.

ORGANIC ELECTROLUMINESCENT COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME

The present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. By using the organic electroluminescent compound of the present disclosure, an organic electroluminescent device having low driving voltage, high luminous efficiency, and/or excellent lifespan characteristic can be produced.

BENZIMIDAZOLONE AND BENZOTHIAZOLONE COMPOUNDS AND THEIR USE AS AMPA RECEPTOR MODULATORS

Provided herein are compounds of Formula (I), and pharmaceutically acceptable salts, N-oxides, or solvates thereof, Also provided herein are pharmaceutical compositions comprising compounds of Formula (I) and methods of using compounds of Formula (I).

METALLO-BETA-LACTAMASE INHIBITORS

The present invention relates to compounds of formula (I) that are metallo-β-lactamase inhibitors, the synthesis of such compounds, and the use of such compounds for use with β-lactam antibiotics for overcoming resistance.

METALLO-BETA-LACTAMASE INHIBITORS

The present invention relates to compounds of formula I that are metallo-β-lactamase inhibitors, the synthesis of such compounds, and the use of such compounds for use with β-lactam antibiotics for overcoming resistance.

N-aryl-2-aminobenzimidazoles: Novel, efficacious, antimalarial lead compounds

From the phenotypic screening of the AstraZeneca corporate compound collection, N-aryl-2-aminobenzimidazoles have emerged as novel hits against the asexual blood stage of Plasmodium falciparum (Pf). Medicinal chemistry optimization of the potency against Pf and ADME properties resulted in the identification of 12 as a lead molecule. Compound 12 was efficacious in the P. berghei (Pb) model of malaria. This compound displayed an excellent pharmacokinetic profile with a long half-life (19 h) in rat blood. This profile led to an extended survival of animals for over 30 days following a dose of 50 mg/kg in the Pb malaria model. Compound 12 retains its potency against a panel of Pf isolates with known mechanisms of resistance. The fast killing observed in the in vitro parasite reduction ratio (PRR) assay coupled with the extended survival highlights the promise of this novel chemical class for the treatment of malaria.

ENZYME INHIBITORS

The present subject matter relates generally to compounds having the formula (I): wherein each of X, Y, R1, R2, R3, R4, and n are as defined herein. Compounds of formula (I) may act as inhibitors of the thioredoxin reductase enzyme system. The subject matter also relates to use, formulation and preparation of the compounds. The compounds may be useful in the treatment of inflammatory and oxidative diseases and conditions. The compounds may also provide useful anti-proliferative and anti- apoptotic effects.

Synthesis of nitric oxide probes with fluorescence lifetime sensitivity

We present the rationale, synthesis and evaluation of the first activatable fluorescent probe that utilizes fluorescence lifetime change for detection of nitric oxide. The new probe DAP-LT1 features a near-infrared polymethine skeleton with a diaminobenzene functionality incorporated into the meso-position. The probe is partially quenched, and upon reaction with nitric oxide shows an increase in the fluorescence lifetime from 1.08 ns to 1.24 ns.