87-53-6

Usage

Uses

Used in Pharmaceutical Industry:
(2S-cis)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid is used as an antibiotic for the treatment of various bacterial infections. Its antimicrobial properties make it effective against a wide range of gram-positive and some gram-negative bacteria, including Staphylococcus, Streptococcus, and Neisseria species. It works by inhibiting bacterial cell wall synthesis, leading to cell lysis and death.
Used in Research and Development:
(2S-cis)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid is also used as a research compound in the development of new antibiotics and pharmaceuticals. Its unique structure and properties make it a valuable tool for studying the mechanisms of action and resistance to penicillin-class antibiotics, as well as for designing new drugs with improved efficacy and reduced side effects.
Used in Veterinary Medicine:
In addition to human medicine, (2S-cis)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid is also used in veterinary medicine for the treatment of bacterial infections in animals. Its broad-spectrum antimicrobial activity makes it suitable for treating various infections in pets, livestock, and other animals, contributing to their overall health and well-being.

InChI:InChI=1/C8H11NO3S/c1-8(2)6(7(11)12)9-4(10)3-5(9)13-8/h5-6H,3H2,1-2H3,(H,11,12)/t5-,6+/m1/s1

Upstream product

• 20097-86-3 6-chloropenicillanic acid 
• 24158-88-1 6,6-dibromopenicillanic acid 
• 5187-94-0 ampicillin trihydrate 
• 2153-89-1 6α-chloropenicillanic acid 
• 205320-26-9 6α-Bromopenicillanic acid 
• 205320-24-7 6,6-dibromopenicillanic acid 
• 79-37-8 oxalyl dichloride 
• 38313-33-6 3-phenyl-2-(2-thienyl)acrylic acid 
• 551-16-6 6-Aminopenicillanic Acid 
• 24138-28-1 6-bromopenicillanic acid 
• 551-16-6 6-aminopenicillanic acid 
• 139595-42-9 6,6-dibromopenicillanic acid 
• 24138-28-1 (S)-6-Bromo-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 
• 2153-89-1 (S)-6-Chloro-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 

Downstream Products

• 69388-89-2 penicillanic acid 4-nitro-benzyl ester 
• 122692-67-5 para-methoxybenzyl penicillinate 
• 122692-70-0 (2R,4S)-2-Hydroxycarbamoylmethyl-5,5-dimethyl-thiazolidine-4-carboxylic acid 4-methoxy-benzyl ester 
• 68373-14-8 sulbactum 
• 20425-27-8 (2S,5R,6R)-6-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 
• 69388-84-7 sodium sulbactam 
• 793625-09-9 C₈H₁₁NO₄S 
• 89786-04-9 tazobactam acid 

Relevant academic research and scientific papers

Method for preparing sulbactam acid

The invention discloses a preparation method of sulbactam acid, hypophosphorous acid is used as a diazotization reaction reagent and a reduction reagent at the same time, a diazotization and reductionreaction one-pot method is realized, and an obtained intermediate is oxidized by potassium permanganate to obtain the sulbactam acid. The product is the sulbactam acid, the generation amount of wastesalt is greatly reduced compared with that of a traditional process, the production cost and the reaction danger coefficient are obviously reduced, and good economic benefits and social values are achieved.

Synthetic method for tazobactam chiral isomer

The invention discloses a synthetic method for a tazobactam chiral isomer. The method comprises the following steps of: using 6-APA as a raw material, through diazotization, deaminizing by using sodium hypophosphite to obtain a compound 1, and performing mono-oxidation through a hydrogen peroxide solution, reacting with iodomethane, and reacting with 2-mercaptobenzothiazole, so as to obtain a compound 4; in hydrochloric acid, enabling the compound 4 to react with sodium nitrite to obtain a compound 5; enabling the compound 5 to react with triazole, after oxidizing by using potassium permanganate, performing column chromatography to obtain a compound 7-1; performing hydrolysis and de-protection on the compound 7-1 to obtain the tazobactam chiral isomer. According to the method, a carboxyl is ptotected by using a methyl with smaller steric hindrance, thereby generating more R configurations while constructing a No. 2 carbon atom, and the three configurations of compounds are separated byusing the column chromatography. The method has the advantages of low raw material cost, convenient and rapid post-treatment, and high yield. Reaction reagents in each step are easily obtained. The compounds are shown in the description.

Synthesis method of tazobactam acid

The invention provides a synthesis method of tazobactam acid, and the method comprises the following steps: performing deamination reaction on 6-APA to obtain a compound A; selectively oxidizing the compound A by a Ce(OTf)4/H2O2 oxidation system to obtain a compound B; reacting the compound B with acetic anhydride to obtain a compound C; reacting the compound C with hydrazine hydrate to obtain a compound D; reacting the compound D with methanesulfonyl chloride to obtain a compound E, reacting the compound E with triazole to obtain a compound F, and performing oxidation reaction on the compoundF to obtain the tazobactam acid. The method has the advantages of simple operation steps, cheap and easily available reaction raw materials, short reaction steps, high purity of obtained intermediateproducts and products, purity of the final product tazobactam acid white solid powder of more than 99.5%, high total molar yield, suitability for industrial production, and wide application prospect.

Synthesis and antibacterial evaluation of sulbactam derivatives against Acinetobacter baumannii

Sulbactam, a known β-lactamase inhibitor, was found to own potent antimicrobial activity against Acinetobacter baumannii in clinical practice. Based on clinical evidence, a series of sulbactam derivatives were designed, synthesized and evaluated for antibacterial activity against Acinetobacter baumannii, taking sulbactam as the lead. Among them, compound 9 exhibited a good antibacterial activity against Acinetobacter baumannii with a MIC value of 4 μg/mL, slightly lower than that of sulbactam of 1 μg/mL. Especially, compound 9 displayed outstanding oral pharmacokinetic profiles with a maximum plasma concentration (Cmax) of 19.6 μg/mL and area under the curve (AUC) of 10.8 μg?h/mL, much higher than those of sulbactam, and thus held the potential of being developed into an oral medication. These results provided the useful information for further structural modification and optimization of its kind, and compound 9 has been selected for the further investigation.

Sulbactam sodium preparation method

The invention relates to a sulbactam sodium preparation method belongs to the technical field of synthesis of beta-lactamase inhibitors. The sulbactam sodium preparation method comprises the steps that 6-amino penicillanic acid (6-APA) is used as a raw material, reacts in strong acid and a sodium nitrite water solution, then reacts under the effects of copper powder and hypophosphorous acid, and then a target product sulbactam sodium is prepared through oxidation and substitution reaction. The reaction process is simple in operation, the method includes few reaction steps, a by-product is reduced, the final reaction yield is high, the treatment difficulty and cost after wastewater production are reduced, the pressure of environmental protection is reduced for enterprises, the product production cost is reduced, and the sulbactam sodium preparation method is suitable for industrial production.

BICYCLIC IMIDAZOLIDINONES AS POTENTIAL ANTIBIOTICS

The bicyclic imidazolidinones 5 topologically related to the penicillin family, are susceptible to form a stable carbamate with serine-D,D-peptidases.A series of N-7 acylated or sulfonylated (2R,5R)-3,3-dimethyl-8-oxo-4-thia-7,1-diazabicyclooctane-2-carboxylates 12-21 have been prepared.None of these novel penicillin analogs exhibited antibacterial activity.

β-Lactam antibiotics

A 3-β-(vic-dihydroxyphenylmethyleneamino-2-oxo-imidazolidine)- or 3-β-(vic-dihydroxyphenyl-methyleneamino-2,3-dioxo-piperazine)-1-carbonylamino-acetamidoazetidin-2-one having an acidic grouping on 1 N, e.g. of the formula STR1 The compounds are antibiotically active, especially against Pseudomonas bacteria and can be used in combating bacterial infection, as a preservative and as a growth promoting agent in animal feeds.

Formation of β-lactams from 3-phenylthiopropionamide derivatives. A possible model for penicillin biosynthesis

The Cu-catalysed reaction of the substituted 3-phenylthiopropianamide with di-t-butyl peroxide gives the β-lactam via oxidative cyclisation of the α-thioalkyl radical. Similar reactions of the propionamides with t-butyl perbenzoate give benzoates which can be readily converted into the β-lactams, but neither β-lactams nor benzoates can be obtained from the thiazepines. Dimethyl disulfide is benzoyloxylated on treatment with t-butyl perbenzoate. The relevance of these results to penicillin biosynthesis is discussed.