(7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Base Information

• Chemical Name: (7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS No.: 91832-40-5
• Molecular Formula: C14H13N5O5S2
• Molecular Weight: 395.42
• Hs Code.: 2941906000
• European Community (EC) Number: 643-088-1
• Metabolomics Workbench ID: 42873
• NCI Thesaurus Code: C28914
• RXCUI: 25037
• Wikipedia: Cefdinir
• Mol file: 91832-40-5.mol

Synonyms:7-(2 (2-aminothiazol-4-yl)-2-hydroxyiminoacetamido)-3-vinyl-3-cephem-4-carboxylic acid;cefdinir;CI 983;CI-983;CI983;FK 482;FK-482;FK482;Omnicef;PD 134393;PD-134393

Chemical Property of (7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Chemical Property:

• Appearance/Colour: Pale yellow solid
• Melting Point: >180 °C dec
• Refractive Index: 1.861
• PKA: 9.70(at 25℃)
• PSA: 211.75000
• Density: 1.89 g/cm³
• LogP: 0.73820
• Storage Temp.: Room temp
• Solubility.: dilute HCl: slightly soluble
• Water Solubility.: Soluble in water
• XLogP3: 0
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 5
• Exact Mass: 395.03581088
• Heavy Atom Count: 26
• Complexity: 739

Purity/Quality:

99%, ^*data from raw suppliers

Cefdinir ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C=CC1=C(N2C(C(C2=O)NC(=O)C(=NO)C3=CSC(=N3)N)SC1)C(=O)O
• Isomeric SMILES: C=CC1=C(N2C([C@@H](C2=O)NC(=O)/C(=N\O)/C3=CSC(=N3)N)SC1)C(=O)O
• Recent ClinicalTrials: Trial to Evaluate Beta-Lactam Antimicrobial Therapy of Community Acquired Pneumonia in Children
• Description: Cefdinir is a cephalosporin antibiotic. It is active against numerous Gram-positive and Gram-negative bacteria, including β-lactamase-producing E. coli, K. oxytoca, K. pneumoniae, and P. aeruginosa clinical isolates (MICs = 0.25-16 μg/ml). Cefdinir is protective against sepsis induced by strains of S. aureus or H. influenzae in mice with 50% protective dose (PD50) values of 2.7-35 and 3.1-5.8 mg/kg, respectively. Formulations containing cefdinir have been used in the treatment of Gram-positive and Gram-negative infections. Cefdinir is an orally active, beta-lactamase stable cephalosporin with a broad spectrum of activity. Compared to other oral cephalosporins, cefdinir is more potent against Gram-positive bacteria, especially Staphylococci. Its activity against Gram-negative bacteria such as E.coli,K. pneumoniae and P.mirabilis is similar to cefixime, but superior to cefaclor and cephalexin.
• Uses: A Cephalosporin antibiotic structurally similar to Cefixime A broad spectrum antibiotic targeting both Gram-positive and Gram-negative pathogens
• Therapeutic Function: Antibiotic

Technology Process of (7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

There total 41 articles about (7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

7-amino-3-vinylcephalosporin-4-carboxylic acid p-nitrobenzyl ester + 1-[(Z)-2-(2-amino-4-thiazolyl)-2-(acetoxyimino)acetoxy]benzotriazole → cefdinir (91832-40-5,178601-88-2)

Guidance literature:

7-amino-3-vinylcephalosporin-4-carboxylic acid p-nitrobenzyl ester; With N-cyclohexyl-cyclohexanamine; In water; isopropyl alcohol; acetonitrile; at 5 - 10 ℃; for 0.166667h;

1-[(Z)-2-(2-amino-4-thiazolyl)-2-(acetoxyimino)acetoxy]benzotriazole; In water; isopropyl alcohol; acetonitrile; at 20 ℃; Further stages;

Reference yield: 90.0%

potassium syn-7-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylate tetrahydrate → cefdinir (91832-40-5,178601-88-2)

Guidance literature:

With hydrogenchloride; In water; at 25 - 30 ℃; for 2h; pH=2.4 - 2.5;

Reference yield: 88.6%

S-2-benzothiazolyl (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyimino thioacetate (104797-47-9) + (6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (79349-82-9) → cefdinir (91832-40-5,178601-88-2)

Guidance literature:

S-2-benzothiazolyl (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyimino thioacetate; (6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; With triethylamine; In tetrahydrofuran; at 20 - 23 ℃; for 5h;

With hydrogenchloride; methoxybenzene; In tetrahydrofuran; dichloromethane; at -25 - -20 ℃; for 1.5h;

upstream raw materials:

7β-[(Z)-2-(2-amino-4-thiazolyl)-2-(trityloxyamino)acetamido]-3-vinylcephem-4-carboxylic acid

C₁₆H₁₅N₅O₆S₂

S-2-benzothiazolyl (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyimino thioacetate

(Z)-2-(2-amino-4-thiazolyl)-2-(acetoxyimino)acetic acid

Downstream raw materials:

cefdinir lactone

cefdinir p-toluenesulphonic acid salt

2-((Z)-2-(2-aminothiazol-4-yl)-2-(hydroxyimino)acetamido)-2-(5-methyl-7-oxo-2,4,5,7-tetrahydro-1H-furan[3,4-d][1,3]thiazin-2-yl)acetic acid

Refernces

Synthesis and antibacterial activities of novel C(3)-aminopyrimidinyl substituted cephalosporins

10.7164/antibiotics.53.1305

The study focuses on the synthesis and antibacterial activities of novel C(3)-aminopyrimidinyl substituted cephalosporins. Cephalosporins are widely used antibiotics, but many have become ineffective against respiratory tract infections due to resistance issues, particularly from penicillin-resistant Streptococcus pneumoniae (PRSP). To address this, researchers introduced a vinyl spacer at the C-3 position of the cephem nucleus and synthesized new cephalosporins with a C(3) substituted aminopyrimidinyl group. The synthesis involved coupling acid 3 with 7-ACLE in the presence of pyridine and phosphorous oxychloride to form intermediate 5, which was then reacted with nucleophiles (pyrimidinylthiol group) in DMF. The protecting groups were removed using trifluoroacetic acid (TFA) and anisole to obtain the final cephalosporins. Another series of compounds was prepared from chloride 5 via allyl chloride 6, using a Wittig reagent and subsequent displacement reactions. The synthesized compounds were tested for their antibacterial activities against various bacterial strains, including Gram-positive and Gram-negative bacteria, and showed improved activities against respiratory tract pathogens compared to the reference antibiotic cefdinir.

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