Cefaclor monohydrate

Cefaclor monohydrate is an effective antibiotic agent, and specifically binds to penicillin-binding protein 3 (PBP 3)[1].

Cefaclor is a beta-lactam, second-generation cephalosporin antibiotic with bactericidal activity. Cefaclor binds to and inactivates penicillin-binding proteins (PBP) located in bacterial cytoplasmic membranes. PBPs are enzymes involved in the terminal stages of assembling the bacterial cell wall and in reshaping the cell wall during growth and division. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This results in the weakening of the bacterial cell wall and causes cell lysis.|Semisynthetic, broad-spectrum antibiotic derivative of CEPHALEXIN.

With penicillin G as raw material. First protect the carboxyl group on penicillin G with p-nitrobenzyl, and then oxidize to sulfoxide with hydrogen peroxide or peroxyacetic acid. Under the action of N-chlorosuccinimide or N-chlorophosphorphthalamide, etc., chlorination and ring expansion are carried out. After ozonation and reduction, the 3 position will form a hydroxyl group. Then, under phosphorus trichloride, the 3 position is converted to chloro; then under the action of phosphorus pentachloride and pyridine, the 7 position is then alcoholylated to form the free amino acid hydrochloride, namely 7-amino-3-chloro Hydrochloride salt of p-nitrobenzyl-3-cephem-4-carboxylate. It was dissolved in a solution of tetrahydrofuran and methanol, and a 5% palladium-carbon ethanol solution was added, followed by hydrogenation at room temperature and a hydrogen pressure of 0.35 MPa for 45 minutes. Filter, the filter cake was washed with tetrahydrofuran and water. Evaporate the solvent to dryness. The residue is dissolved in a mixture of water and ethyl acetate, the Ph value is adjusted to 3, a solid is precipitated, filtered, and soaked with acetone, and then dried to be 7-amino-3-chloro-3-cephem-4-carboxylic acid . It was dissolved in acetonitrile, and N, O-bis(trimethylsilyl)acetamide was added with stirring at room temperature to form a soluble disilyl ester. Cooled to 0℃, in the presence of two drops of N, N-dimethylbenzylamine, slowly add the sodium salt of methyl 3-(β-carboxybenzylamine) crotonate and methyl chloroformate in the reaction solution of acetonitrile . The mixture was continuously stirred in an ice bath for 2h, methanol was added, and insoluble materials were removed by filtration. Add water again, adjust the Ph value to 1.5, and then adjust to 4.5 with triethylamine. Stir for another 1 h on the water bath, filter the crystalline precipitate, wash with acetonitrile, and vacuum dry to obtain cefaclor. The hydrochloride of the free amino group obtained above can be directly reacted with azidophenylacetic acid, and then hydrogenolysis can also be used to obtain cefaclor, the reaction is relatively simple.

Second-generation cephalosporin antibiotic. Antibacterial

Molecular Weight:385.8
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:4
Exact Mass:385.0499195
Monoisotopic Mass:385.0499195
Topological Polar Surface Area:139
Heavy Atom Count:25
Complexity:606
Defined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes