13838-08-9 Usage
Description
Azidamfenicol is a semi-synthetic chloramphenicol derivative, first synthesized at Bayer in 1959. It is characterized by the replacement of the nitro moiety with a methylsulphone and the dichloroacetamide with azidoacetamide. Azidamfenicol is a broad-spectrum antibiotic with potent activity against Gram-negative and anaerobic bacteria. It functions by binding to the 23S sub-unit of the 50S ribosome, thereby inhibiting protein synthesis. Despite its potential, azidamfenicol has received limited research attention, resulting in a modest number of literature citations.
Uses
Used in Pharmaceutical Industry:
Azidamfenicol is used as a broad-spectrum antibiotic for treating bacterial infections caused by Gram-negative and anaerobic bacteria. Its application is particularly valuable in scenarios where conventional antibiotics may be less effective or where bacterial resistance is a concern.
Used in Research and Development:
Due to its unique structure and mechanism of action, azidamfenicol serves as a valuable compound in the field of research and development. It can be utilized to study the interactions between antibiotics and bacterial ribosomes, as well as to develop new drugs with improved efficacy and reduced resistance potential.
Used in Veterinary Medicine:
Azidamfenicol is also employed in veterinary medicine as an antibiotic to treat bacterial infections in animals. Its broad-spectrum activity makes it a useful tool for managing various bacterial infections in livestock and pets, contributing to the overall health and well-being of the animals.
Originator
Berlicetin-,Chauvin
Manufacturing Process
21.2 g of D-(-)-threo-1-p-nitrophenyl-2-aminopropane-1,3-diol are stirred
with 10 g of azidoacetonitrile (B.P. 68°C/25 mm) in a mixture of 125 ml of
methanol and 125 ml of water at 30-40°C for a few days. The mixture is
filtered off from a little undissolved base and the solvent is distilled in vacuo.
The residue is treated with a little normal hydrochloric acid until acid to Congo
red and extracted with ethylacetate. By evaporating the solvent and
recrystallizing the residue from ethylene chloride is obtained D-(-)-threo-1-pnitrophenyl-
2-azidoacetylamino-propane-1,3-diol, M.P. 107°C.
Therapeutic Function
Antibiotic
Check Digit Verification of cas no
The CAS Registry Mumber 13838-08-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,8,3 and 8 respectively; the second part has 2 digits, 0 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 13838-08:
(7*1)+(6*3)+(5*8)+(4*3)+(3*8)+(2*0)+(1*8)=109
109 % 10 = 9
So 13838-08-9 is a valid CAS Registry Number.
InChI:InChI=1/C11H13N5O5/c12-15-13-5-10(18)14-9(6-17)11(19)7-1-3-8(4-2-7)16(20)21/h1-4,9,11,17,19H,5-6H2,(H,14,18)/t9-,11-/m1/s1
13838-08-9Relevant articles and documents
Catalytic Syn-Selective Nitroaldol Approach to Amphenicol Antibiotics: Evolution of a Unified Asymmetric Synthesis of (-)-Chloramphenicol, (-)-Azidamphenicol, (+)-Thiamphenicol, and (+)-Florfenicol
Chen, Fener,Cheng, Dang,Huang, Huashan,Jiang, Meifen,Liu, Minjie,Qu, Hongmin,Xia, Yingqi,Xiong, Tong,Zhang, Yan
, p. 11557 - 11570 (2021/09/02)
A unified strategy for an efficient and high diastereo- and enantioselective synthesis of (-)-chloramphenicol, (-)-azidamphenicol, (+)-thiamphenicol, and (+)-florfenicol based on a key catalytic syn-selective Henry reaction is reported. The stereochemistry of the ligand-enabled copper(II)-catalyzed aryl aldehyde Henry reaction of nitroethanol was first explored to forge a challenging syn-2-amino-1,3-diol structure unit with vicinal stereocenters with excellent stereocontrol. Multistep continuous flow manipulations were carried out to achieve the efficient asymmetric synthesis of this family of amphenicol antibiotics.
