- Preparation, gram-negative antibacterial activity, and hydrolytic stability of novel siderophore-conjugated monocarbam diols
-
A novel series of monocarbam compounds exhibiting promising antibacterial activity against multidrug resistant Gram-negative microorganisms is reported, along with the synthesis of one such molecule MC-1 (1). Also reported are structure-activity relationships associated with the in vitro and in vivo efficacy of 1 and related analogues in addition to the hydrolytic stability of such compounds and possible implications thereof.
- Flanagan, Mark E.,Brickner, Steven J.,Lall, Manjinder,Casavant, Jeffrey,Deschenes, Laura,Finegan, Steven M.,George, David M.,Granskog, Karl,Hardink, Joel R.,Huband, Michael D.,Hoang, Thuy,Lamb, Lucinda,Marra, Andrea,Mitton-Fry, Mark,Mueller, John P.,Mullins, Lisa M.,Noe, Mark C.,O'Donnell, John P.,Pattavina, David,Penzien, Joseph B.,Schuff, Brandon P.,Sun, Jianmin,Whipple, David A.,Young, Jennifer,Gootz, Thomas D.
-
scheme or table
p. 385 - 390
(2011/07/09)
-
- Exploring the potential of the β-thiolactones in bioorganic chemistry
-
A series of novel peptide-based β-thiolactones were synthesized and assayed for cytotoxicity against several human cancer cell lines, where they showed greater activity than the corresponding β-lactones and β-lactams. Several of the β-thiolactones prepare
- Aubry, Sylvain,Sasaki, Kaname,Eloy, Laure,Aubert, Genevieve,Retailleau, Pascal,Cresteil, Thierry,Crich, David
-
supporting information; experimental part
p. 7134 - 7143
(2011/11/14)
-
- MONOCARBAMS
-
The invention relates to compounds of formula (I): wherein R1, R2, R3, R4, Rs, and R6 as defined herein. The invention also relates to pharmaceutical compositions and methods of treating bacterial infections using compounds of formula (I)
- -
-
Page/Page column 15
(2010/07/04)
-
- Studies on stereoselective [2+2] cycloadditions between N,N-dialkylhydrazones and ketenes
-
Staudinger-like cycloadditions between chiral, non-racemic N,N-dialkylhydrazones 1 and functionalized ketenes constitute an efficient methodology for the stereoselective construction of the β-lactam ring. The potential for fine tuning of the dialkylamino
- Martin-Zamora, Eloisa,Ferrete, Ana,Llera, Jose M.,Munoz, Jesus M.,Pappalardo, Rafael R.,Fernandez, Rosario,Lassaletta, Jose M.
-
p. 6111 - 6129
(2007/10/03)
-
- 3-Acylamino-azetidin-2-one as a novel class of cysteine proteases inhibitors
-
A new class of inhibitors for cysteine proteases cathepsin B, L, K and S is described. These inhibitors are based on the β-lactam ring designed to interact with the nucleophilic thiol of the cysteine in the active site of cysteine proteases. Some 3-acylamino-azetidin-2-one derivatives showed very potent inhibition activities for cathepsins L, K and S at the nanomolar or subnanomolar IC50 values.
- Zhou, Nian E.,Guo, Deqi,Thomas, George,Reddy, Andhe V. N.,Kaleta, Jadwiga,Purisima, Enrico,Menard, Robert,Micetich, Ronald G.,Singh, Rajeshwar
-
p. 139 - 141
(2007/10/03)
-
- Enantioselective synthesis of 4-unsubstituted 3-alkoxy- and 3-aminoazetidin-2-ones from formaldehyde N,N-dialkylhydrazones
-
Playing two roles at once, chiral amines from L-proline or D-mannitol act as protecting groups and as chiral auxiliaries in the [2+2] cyclo-addition of formaldehyde hydrazones, such as 1, to ketenes. This strategy, based on the stability of the hydrazones
- Fernandez, Rosario,Ferrete, Ana,Lassaletta, Jose M.,Llera, Jose M.,Monge, Angeles
-
p. 2893 - 2897
(2007/10/03)
-
- Penicillin G acylase mediated synthesis of the enantiopure (S)-3-amino-azetidinl-2-one
-
A detailed study of the influence of temperature, pH and enzyme amount on the enantiomeric excess in the enzymatic resolution of N-1 protected 3-amino-azetidin-2-ones with supported PGA is presented. Both enantiomers could be obtained in good enantiomeric
- Cainelli, Gianfranco,Giacomini, Daria,Galletti, Paola,DaCol, Marco
-
p. 3231 - 3235
(2007/10/03)
-
- 2-OXO-1-AZETIDINESULFONIC ACID SALTS
-
Antibacterial activity is exhibited by beta-lactams having a sulfonic acid salt substituent in the 1-position and an amino or acylamino substituent in the 3-position.
- -
-
-
- Reduction process for the preparation of 4-unsubstituted azetidin-2-ones
-
Novel process for the preparation of azetidin-2-ones of the formula STR1 wherein R1 and R2 independently from each other are hydrogen, or an organic group linked to the ring carbon via a carbon atom, a nitrogen atom or an oxygen atom, characterized in that a corresponding 4-acyloxyazetidin-2-one, which is substituted by a group --O--CO--R3 at the 4-position, wherein R3 is hydrogen or an organic radical stable at the reaction conditions, is reacted with a complex metal hydride comprising reactive hydride ions, such as, lithium borohydride, sodium borohydride, potassium borohydride, zinc borohydride or tetraorganoammonium borohydride.
- -
-
-
- The Synthesis of Substituted thio>acetic Acids
-
The synthesis of substituted thio>acetic acids (6, thiamazins) is described.Various substituted 3(S)-(acylamino)-2-azetidinones were sulfenylated with tert-butyl (phtalimidothio)acetate.Deprotection of the tert-butyl ester with trifluoroacetic acid provided the title compounds.In sharp contrast to their oxygen analogues (oxamazins), the thiamazins were devoid of biological activity.
- Woulfe, Steven R.,Miller, Marvin J.
-
p. 3133 - 3139
(2007/10/02)
-
- 2-oxo-1-[[(substituted sulfonyl)amino]-carbonyl]azetidines
-
Antibacterial activity is exhibited by β-lactams having a STR1 substituent in the 1-position and an acylamino substituent in the 3-position wherein Z is oxygen or sulfur, and R is alkyl, alkenyl, alkynyl, substituted alkyl, phenyl, substituted phenyl, a 5
- -
-
-
- A NOVEL PREPARATION OF 4-UNSUBSTITUTED β-LACTAMS
-
The key intermediate (1) for monobacyam synthesis has been prepared from 6-aminopenicillanic acid (6-APA) without using Raney nickel.Desulfurization was accomplished by a two step process, involving a novel reduction reaction.
- Pfaendler, Hans Rudolf,Hoppe, Heike
-
p. 265 - 272
(2007/10/02)
-
- Synthesis and antibacterial activity of 3-acylamino-2-azetidinone-1-sulfonic acid derivatives
-
Sulfazecin is a monocyclic β-lactam antibiotic isolated from strain G-6302, Pseudomonas acidophila. As a key intermediate for the synthesis of sulfazecin derivatives, 3-amino-2-azetidinone was synthesized from penicillins, and various new compounds were s
- Matsuo,Sugawara,Masuya,Kawano,Noguchi,Ochiai
-
p. 1874 - 1884
(2007/10/02)
-
- Process for 3β-aminoazetidin-2-ones
-
1-[α-(Carboxy)-4-hydroxybenzyl]-3β-aminoazetidin-2-one esters are prepared by converting 2-acyl-3,3-dialkyl-7-oxo-α-[4-(benzyloxy)phenyl]-4-thia-2,6-diazabicyclo[3.2.0]-heptane-6-acetic acid esters with mercuric acetate in an aqueous organic solvent mixture, e.g., in aqueous methanol, to 7-oxo-3-phenyl-α-[4-(benzyloxy)phenyl]-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-ene-1-acetic acid esters and the latter are reacted with PCl5 and pyridine to provide the monocyclic 1-[α-(carboxy)-4-benzyloxybenzyl]-3β-(α-chlorobenzylideneamino)-4-chloroazetidin-2-one esters. Reduction of the dichloro azetidin-2-one with an organo tin hydride and azobisisobutyronitrile affords the deschloro, 1-[α-(carboxy)-4-benzyloxybenzyl]-3β-benzylideneaminoazetidin-2-one ester. The latter is hydrolyzed and the 4-benzyloxy group is cleaved via catalytic hydrogenolysis to yield an ester of 1-[α-(carboxy)-4-hydroxybenzyl]-3β-aminoazetidin-2-one. The 3β-amino ester is useful for the preparation of the antibiotic FR 1923 (nocardicin).
- -
-
-