104146-10-3

Usage

Uses

Used in Pharmaceutical Industry:
GCLE is used as a key intermediate for the synthesis of cephem compounds, which are a class of beta-lactam antibiotics. These antibiotics are essential in treating a wide range of bacterial infections, making GCLE a crucial component in the development of life-saving medications.
Used in Chemical Industry:
GCLE is used as a white solid in the chemical industry for various purposes. Its unique properties make it suitable for use in the production of various chemicals, including cosmetics, personal care products, and industrial chemicals.
Used in Cosmetics and Personal Care Industry:
GCLE is used as a humectant, moisturizer, and solvent in the cosmetics and personal care industry. Its ability to attract and retain moisture makes it an ideal ingredient for skincare products, hair care products, and oral care products. Additionally, its solubility properties allow it to act as a solvent for various active ingredients in these products.
Used in Food Industry:
GCLE is used as a humectant, emulsifier, and sweetener in the food industry. It helps to retain moisture in foods, preventing them from drying out and extending their shelf life. It is also used in the production of confectionery, baked goods, and as a component in the manufacturing of artificial sweeteners.
Used in Energy Industry:
GCLE is used as a component in the production of biodiesel, an alternative fuel source derived from renewable resources. Its compatibility with diesel engines and lower environmental impact make it a valuable component in the development of sustainable energy solutions.
Used in Textile Industry:
GCLE is used as a humectant, plasticizer, and lubricant in the textile industry. It helps to improve the softness, flexibility, and durability of fabrics, making it an essential component in the production of various textile products.

InChI:InChI=1/C24H23ClN2O5S/c1-31-18-9-7-16(8-10-18)13-32-24(30)21-17(12-25)14-33-23-20(22(29)27(21)23)26-19(28)11-15-5-3-2-4-6-15/h2-10,20,23H,11-14H2,1H3,(H,26,28)/t20-,23-/m1/s1

Upstream product

• 106773-36-8 4-methoxybenzyl-7-amino-3-chloromethyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate hydrochloride 
• 103-80-0 phenylacetyl chloride 
• 131903-39-4 1-<2-chloromethyl-1-(p-methoxybenzyloxycarbonyl)-2-propen-1-yl>-3-(phenylacetamido)-4-(phenylsulfonylthio)-2-azetidinone 
• 824-94-2 p-methoxybenzyl chloride 
• 105-13-5 4-Methoxybenzyl alcohol 
• 30200-14-7 benzylpenicillin 4-methoxybenzyl ester 
• 53956-74-4 penicillin sulfoxide p-methoxybenzyl ester 
• 106773-36-8 p-methoxybenzyl 7-amino-3-chloromethyl-ceph-3-em-4-carboxylate 
• 95361-36-7 C₃₀H₂₉ClN₂O₇S₂ 

Downstream Products

• 29126-11-2 (6R,7R)-3-Methyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester 
• 101156-43-8 (2R,6R,7R)-3-Methylene-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid 4-methoxy-benzyl ester 
• 129849-22-5 (6R,7R)-8-Oxo-7-phenylacetylamino-3-(4-trifluoromethyl-benzyl)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester 
• 129849-23-6 C₅₂H₄₈N₄O₁₀S₂ 
• 129849-20-3 (6R,7R)-3-Allyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester 
• 113479-65-5 (6R,7R)-4-methoxybenzyl 7-amino-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate hydrochloride 
• 29126-11-2 (6R,7R)-3-Methyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester 
• 112020-52-7 p-methoxybenzyl 3-exo-methylene-7-(phenylacetamido)-cepham-4-carboxylate 
• 101156-40-5 (6R,7R)-4-methoxybenzyl-3-(iodomethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 
• 143488-25-9 1-cyclopropyl-6-fluoro-7-{4-[2-(4-methoxy-benzyloxycarbonyl)-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.3.0]oct-2-en-3-ylmethyl]-piperazin-1-yl}-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid 
• 917470-57-6 3-[tert-butyldimethylsilyloxy-(4-methylbenzoyl)amino]methyl-7-phenylacetamido-3-cephem-4-carboxylic acid p-methoxybenzyl ester 

Relevant academic research and scientific papers

Fluorescence Resonance Energy Transfer-Mediated Immunosensor Based on Design and Synthesis of the Substrate of Amp Cephalosporinase for Biosensing

The traditional enzyme-linked immunosorbent assay (ELISA) has some disadvantages, such as insufficient sensitivity and low stability of the labeled enzyme, which limit its further applications. In this study, a more stable enzyme, Amp cephalosporinase (AmpC), was selected as the labeled enzyme, and its substrate was designed and synthesized. This substrate contained the cephalosporin ring core as the enzymatic recognition section and the structural motif of the 3-hydroxyflavone (3-HF) as the reporter molecule. AmpC can specifically catalyze the substrate and release 3-HF, which can enter the cavity of β-cyclodextrin (β-CD) on the surface of ZnS quantum dots and form a fluorescence resonance energy transfer (FRET) signal amplification system. An AmpC-catalyzed, FRET-mediated ultrasensitive immunosensor (ACF immunosensor) for procalcitonin (PCT) was developed by combining the signal amplification system of the polystyrene microspheres and effective immune-based magnetic separation. The ACF immunosensor has high sensitivity and specificity for the detection of PCT: its linear range is from 0.1 ng mL-1 to 70 ng mL-1, and the limit of detection can reach 0.03 ng mL-1. The spiking recoveries of PCT in human serum samples range from 98.3% to 107%, with relative standard deviations ranging from 2.14% to 12.0%. This approach was applied to detect PCT in real patient serum samples, and the results are consistent with those obtained with a commercial ELISA kit.

Design, syntheses, and anti-tuberculosis activities of conjugates of piperazino-1,3-benzothiazin-4-ones (pBTZs) with 2,7-dimethylimidazo [1,2-a]pyridine-3-carboxylic acids and 7-phenylacetyl cephalosporins

Tuberculosis (TB) remains one of the most threatening diseases in the world and the need for development of new therapies is dire. Herein we describe the rationale for the design and subsequent syntheses and studies of conjugates between pBTZ and both the imidazopyridine and cephalosporin scaffolds. Overall some compounds exhibited notable anti-TB activity in the range of 2-0.2 μM in the Microplate Alamar Blue (MABA) Assay.

A fluorogenic probe using a catalytic reaction for the detection of trace intracellular zinc

Labile zinc plays various roles in cells at low concentrations which most fluorescent probes are not able to detect. Here we report a cephem-based probe which coordinates to zinc and zinc-bound water cleaves the scaffold and releases the fluorophore. In addition, the zinc is recycled and reacts with multiple probes, amplifying the signal. This signal amplification system is useful for the detection of intracellular zinc at low concentrations and has potential for further development of probes with a similar molecular design. This journal is

Metal β - lactamase inhibitor cyclic amino dithio carboxylic acid salt derivative and its preparation method

The invention belongs to the field of medicinal chemistry, in particular to a metal β - lactamase inhibitor cyclic amino dithio carboxylic acid salt derivative and its preparation method, The invention through a low-temperature reaction and the combined effect of the alkali catalyst, and effectively increases the 7 - phenylacetylamino - 3 - chloromethyl - 4 - cephalosporanic acid-methoxybenzyl ester yield.

Antibacterial drug for targeted therapy of staphylococcal infection by synergizing with antibiotic as well as synthesis method and application of antibacterial drug

The invention designs and synthesizes a novel antibacterial drug ASC for staphylococcus aureus based on a beta-lactam ring of a parent nucleus structure of beta-lactam antibiotic molecules, wherein the ASC is an antibacterial reagent and is also a broad-spectrum inhibitor of beta-lactam antibiotic drug-resistant target protein metal beta-lactamase; the ASC can synergize with three kinds of 7 to 8antibiotics such as beta-lactams, aminoglycosides and tetracyclines to carry out targeted therapy on the staphylococcal infection. The vitality of the antibiotics is increased by 4 to 128 times by combining with 1 [mu]g/ml dosage of ASC.

Preparation of 7-phenylacetamide-3-chloromethyl-cephalosporanic acid p-methoxybenzyl ester

The invention belongs to the field of synthesis of cephalosporin drug intermediates and disclosesa preparation method of 7-phenylacetamide-3-chloromethyl-cephalosporanic acid p-methoxybenzyl ester (short for GCLE). According to the method, penicillin G potassium salt taken as an initial raw material reacts with 4-methoxybenzylchloride firstly, penicillin sulfoxide ester is prepared through oxidation with peracetic acid and reacts with 2-mercaptobenzothiazole firstly, then a product reacts with benzene sulfinic acid, a ring opening product is obtained and reacts with chlorine, sodium methoxide is used for ring closing under the action of a methanol solvent, and 7-phenylacetamide-3-chloromethyl-cephalosporanic acid p-methoxybenzyl ester is obtained. The solvent is simple and easy to recover, reaction conditions are mild, operation is simple and convenient, and industrial production is easy.

ANTIMICROBIAL PROCHELATORS TO TARGET DRUG-RESISTANT BACTERIA AND METHODS OF MAKING AND USING THE SAME

The present disclosure provides antibacterial prodrugs and methods of making and using the same.

PROCESS FOR PRODUCING 3-CHLOROMETHYL-3-CEPHEM DERIVATIVE

An industrially advantageous process for producing 3-chloromethyl-3-cephem derivative crystals. The process for 3-chloromethyl-3-cephem derivative production comprises: a first step in which a thiazolineazetidinone derivative (1) is reacted with a sulfonyl halide (2) in the presence of an acid in a solvent to obtain an azetidinone derivative (3); a second step in which the azetidinone derivative (3) is reacted with a chlorinating agent in an organic solvent to obtain a chlorinated azetidinone derivative (4); and a third step in which the chlorinated azetidinone derivative (4) is reacted with an alcoholate (5) at a pH of 8 or lower in a solvent comprising an alcohol and an ether and a 3-chloromethyl-3-cephem derivative (6) is recovered in the form of crystals.

Process for preparing crystalline 3-chloromethyl-3-cephem derivatives

A chlorinated azetidinone derivative expressed by Formula (1) and an alcoholate are allowed to react in a solvent containing at least one of alcohols and an ether at a pH of 8 or less. Thus a 3-chloromethyl-3-cephem derivative expressed by formula (2) is prepared. In the formulas, R1 represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic residue, and R2 and R3 each represent a substituted or unsubstituted aromatic hydrocarbon group.

AN IMPROVED PROCESS FOR THE PREPARATION OF CHLORO METHYL CEPHEM DERIVATIVES

The present invention provides an improved process to produce the chloromethylcephem derivatives of the formula (I), wherein R1 represents a carboxy-protecting group viz., substituted methyl group, which can be deprotected easily, such as t-butyl group, diphenylmethyl, 4-methoxybenzyl, 2-methoxybenzyl, 2-chlorobenzyl or benzyl group; R2 represents hydrogen, (C1-C4)alkyl, substituted or unsubstituted phenyl or substituted or unsubstituted phenoxy group.