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26973-24-0

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  • 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid,8-oxo-7-[[2-(1H-tetrazol-1-yl)acetyl]amino]-3-[(1,3,4-thiadiazol-2-ylthio)methyl]-,(6R,7R)- 26973-24-0

    Cas No: 26973-24-0

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26973-24-0 Usage

Description

Ceftezole is a β-lactam, cephem antibiotic that possesses potent α-glucosidase inhibitory activity and demonstrates significant antidiabetic effects in streptozotocin-induced mice. It is a direct bandgap semiconductor with a band gap that varies from approximately 1.4 to 2.2 eV, depending on its composition. Ceftezole, also known as Cadmium zinc telluride (Cd1-xZnxTe or CZT), is capable of detecting nuclear radiation, making it a versatile compound with applications in various industries.

Uses

Used in Pharmaceutical Industry:
Ceftezole is used as an antibiotic for treating bacterial infections due to its β-lactam, cephem structure, which aids in disrupting bacterial cell wall synthesis.
Used in Diabetes Management:
Ceftezole is used as an α-glucosidase inhibitor and antidiabetic agent for managing blood sugar levels in streptozotocin-induced mouse models, potentially offering a therapeutic approach for diabetes treatment.
Used in Semiconductor Industry:
Ceftezole, as a direct bandgap semiconductor, is used in various applications such as radiation detectors, photorefractive gratings, electro-optic modulators, solar cells, and terahertz generation and detection. Its tunable band gap makes it a valuable material for these advanced technologies.
Used in Radiation Detection:
Ceftezole, specifically in the form of Cadmium zinc telluride (CZT) with Zn concentrations between 0.1-0.2, is used in the making of radiation detectors for X-ray and gamma-ray spectrometers, providing a means to detect and measure nuclear radiation.

Originator

Ceftezole,Arocor Holdings Inc.

Manufacturing Process

To a solution of 1 equivalent (eq.) of 1H-tetrazole-1-acetic acid and 1 eq. of triethylamine in 20 ml of tetrahydrofuran cooled to -20°C was added 1 eq. of pivaloyl chloride. After thirty-minute stirring of the mixture 20 ml of a chloroform solution containing 1 eq. of and 1 eq. of triethylamine was poured into the solution cooled at -10°C during a period of 30 minutes. The resulting mixed solution was stirred for 30 minutes at the same temperature, for 1 hour in an ice-water mixture and for 3 hours at room temperature. Removal of a solvent from the reaction mixture afforded an oily residue, which was dissolved into 15 ml of 10% sodium bicarbonate aqueous solution. The resulting aqueous layer was adjusted to pH 1.0-2.0 with 10% hydrochloric acid, washed with ether and extracted with ethyl acetate. The extract was washed with water, dried over sodium sulfate and concentrated under reduced pressure leaving a residue which was triturated with ethyl acetate to obtain 3- acetoxymethyl-8-oxo-7-(2-tetrazol-1-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid. A solution of 1 eq. of sodium salt of 3-acetoxymethyl-8-oxo-7-(2-tetrazol-1- acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (it may be prepared with equivalent of sodium bicarbonate and above named acid) and 1 eq. of [1.3.4]-thiadiazole-2-thiol in 20 ml of phosphate buffer (pH 6.4) was stirred for 5.5 hours at 60°C. The reaction mixture was adjusted to pH 2.0 with 5% hydrochloric acid and treated with ethyl acetate to form a title compound - ceftezole.

Therapeutic Function

Antibiotic

Check Digit Verification of cas no

The CAS Registry Mumber 26973-24-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,6,9,7 and 3 respectively; the second part has 2 digits, 2 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 26973-24:
(7*2)+(6*6)+(5*9)+(4*7)+(3*3)+(2*2)+(1*4)=140
140 % 10 = 0
So 26973-24-0 is a valid CAS Registry Number.
InChI:InChI=1/C13H12N8O4S3/c22-7(1-20-4-14-18-19-20)16-8-10(23)21-9(12(24)25)6(2-26-11(8)21)3-27-13-17-15-5-28-13/h4-5,8,11H,1-3H2,(H,16,22)(H,24,25)/t8-,11-/m1/s1

26973-24-0Downstream Products

26973-24-0Relevant articles and documents

A head spore for preparation method of the acidic

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Paragraph 0029-0031; 0033-0040, (2018/01/13)

The invention discloses a preparation method of ceftezole acid. The preparation method comprises the following steps: in a reaction container, adding cyclohexanone, 7-amino-3-chloromethyl-3-cephalosporin-4-carboxylic acid 2-sulfydryl-1,3,4-thiadiazole shown in a formula (IV),, solid alkali and an alkaline hyamine catalyst, stirring to facilitate the reaction for 1 to 10 hours at the temperature of 20 to 100 DEG C, then adding 1H-1-tetrazole tert-butyl acetate shown in a formula (V), stirring to facilitate the reaction for 1 to 10 hours at the temperature of 20 to 100 DEG C, cooling, and performing posttreatment to obtain the target product ceftezole acid shown in a formula (I). (See the specification).

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