Synthesis and characterization of some penicillins modified with germanium‐containing moieties

Abstract

Penicillin derivatives, penicillin G (1), penicillin V (2) and ampicillin (3), were modified with germanium-containing moieties and their structures were confirmed based on NMR spectroscopy and MALDI-TOF. Their antibacterial ability was tested. None of these exhibited activity stronger than the parent penicillins.

Synthesis and characterization of several cephalothin derivatives modified with germanium‐containing moieties

“…In a previous communication 1 we reported the synthesis, characterization and pharmaceutical assay of three penicillins, i.e. 3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (penicillin G) (1), 3,3-dimethyl-7-oxo-6-[(phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (penicillin V) (2) and 6-[amino(phenyl)acetylamino]-3,3-dimethyl-7-oxo-4thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (ampicillin) (3) modified with germanium-containing moieties.…”

“…The synthesis of germyl iodides 3-(trimethylgermyl)-1-propyl iodide (5a), 3-(triethylgermyl)-1-propyl iodide (5b) and 3-(triphenylgermyl)-1-propyl iodide (5c) has been described previously. 1 The carboxy group of 4 was reacted with germylpropyl iodides 5 to afford the corresponding germyl esters 6. 1 A serious problem accompanying the esterification of 4 is a possible isomerization, e.g.…”

“…1 The carboxy group of 4 was reacted with germylpropyl iodides 5 to afford the corresponding germyl esters 6. 1 A serious problem accompanying the esterification of 4 is a possible isomerization, e.g. from 2 isomer to 3 isomer of the esters obtained as depicted in Scheme 2.…”

“…None of these, however, exhibited activity that was stronger than the parent penicillins. 1 We considered it important that a similar attempt be made with cephalosporins, which form one of the most important group of β-lactam antibiotics. For this purpose 3-[(acetyloxy)methyl]-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylic acid (cephalothin 4; Scheme 1) was chosen because it is a widely used commercially available antibiotic.…”

Synthesis of Novel Organogermanium Derivative Conjugated with Vitamin C and Study of its Antioxidant Effects

“…First, commercially available trichlorogermylpropionic acid (1) was converted to trimethylgermylpropionic acid (2) by a treatment with three equivalents of methyl magnesiumiodide according to the literature procedure. 7 Compound 2 was treated with N-hydroxysuccinimide (NHS) in the presence of dicyclohexylcarbodiimide (DCC) to produce the corresponding active ester 3. The vitamin C derivative 5 was prepared independently from bromide, which was synthesized from ascorbic acid (4) according to the literature procedure.…”