Penbritin-S

Base Information

• Chemical Name: Penbritin-S
• CAS No.: 69-53-4
• Molecular Formula: C16H19N3O4S
• Molecular Weight: 363.437
• Hs Code.: 29212900
• Mol file: 69-53-4.mol

Synonyms:Binotal sodium;Sodium binotal;Totacillin-N;Penbritin-S;Principen/N;Omnipen-N;Amcill-S;Alpen-N;Sodium P-50;(2S,5R,6R)-6-[[(2R)-2-azaniumyl-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;PEN A/N;C16H19N3O4S.Na;DRG-0074;C16-H19-N3-O4-S.Na;EINECS 200-708-1;4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-, monosodium salt, (2S-(2alpha,5alpha,6beta(S*)))-;4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[(aminophenylacetyl)amino]-3,3-dimethyl-7-oxo-, monosodium salt, [2S-[2alpha,5alpha,6beta(S*)]]-;4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[(aminophenylacetyl)amino]-3,3-dimethyl-7-oxo-, monosodium salt,[2S-[2.alpha.,5.alpha.,6.beta.(S*)]]-;4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(2R)-aminophenylacetyl]amino]-3,3-dimethyl-7-oxo-, monosodium salt, (2S,5R,6R)-;Monosodium (2S,5R,6R)-6-((R)-2-Amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate;natrium-[2S-[2alpha,5alpha,6beta(S*)]]-6-(aminophenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-2-carboxylat;Sodium [2S-[2alpha,5alpha,6beta(S*)]]-6-(aminophenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

Chemical Property of Penbritin-S

Chemical Property:

• Appearance/Colour: Crystalline solid
• Melting Point: 198-200 °C (dec.)(lit.)
• Refractive Index: 1.6320 (estimate)
• Boiling Point: 683.9 °C at 760 mmHg
• PKA: 2.5 (COOH)(at 25℃)
• Flash Point: 367.4 °C
• PSA: 138.03000
• Density: 1.45 g/cm³
• LogP: 1.34720
• Storage Temp.: 2-8°C
• Solubility.: NH4OH 1 M: 50 mg/mL, clear, colorless
• Water Solubility.: 0.1-1 g/100 mL at 21℃
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 349.10962727
• Heavy Atom Count: 24
• Complexity: 556

Purity/Quality:

96%, ^*data from raw suppliers

DDO ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,T
• Statements: 36/37/38-42/43-61
• Safety Statements: 22-26-36/37-45-53

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)[NH3+])C(=O)[O-])C
• Isomeric SMILES: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)[NH3+])C(=O)[O-])C
• Description: Ampicillin is an antibacterial antibiotic from the α-aminobenzyl penicillin group, which differs from penicillin by the presence of an amino group that facilitates penetration through the outer membrane of some gram-negative bacteria. Ampicillin is Semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic. Ampicillin acts by interfering directly with the biosynthesis of peptidoglycan, which constitutes the major component of the bacterial cell wall, leading to structural instability and death of bacteria. Ampicillin is a β-lactam antibiotic within the penicillin family. As a member of this family, Ampicillin is susceptible to β-lactamase, which hydrolyzes the β-lactam ring. This broad spectrum antibiotic is effective against gram-positive, gram-negative bacteria and anaerobic bacteria. Ampicillin is widely used in cell culture as a selective agent. As an antibiotic, Ampicillin binds to penicillin binding proteins (PBPs) on a susceptible organism and Inhibits bacterial cell-wall synthesis by inactivating transpeptidases on the inner surface of the bacterial cell membrane. After binding to the PBPs, Ampicilin acts as a structural analogue of acyl-D-alanyl-D-alanine, acylates the transpeptidase enzyme and thereby prevents the cross-linking of the peptidoglycan of the cell wall necessary for the growth of the bacterium. Ampicillin sodium can be used as a selective agent in several types of isolation media. Ampicillin sodium is routinely used to select for cells containing the pcDNA3.1 and pEAK10 resistance plasmids in cell line A904L at an effective concentration of 50 μg/ml.
• Uses: Ampicillin caused contact dermatitis in a nurse also sensitized to amoxicillin (with tolerance to oral phenoxymethylpenicillin), and in a pharmaceutical factory worker. β-lactam antibiotics Labelled Ampicillin. Orally active, semi-synthetic antibiotic; structurally related to penicillin. Antibacterial.
• Therapeutic Function: Antibacterial

Technology Process of Penbritin-S

There total 31 articles about Penbritin-S 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: 96.7%

6-Aminopenicillanic Acid (551-16-6) → ampicillin (69-53-4)

Guidance literature:

With (S)-Phenylglycine methyl ester; In ethylene glycol; at 20 ℃; for 48h; Enzymatic reaction;

DOI:10.1016/j.cclet.2010.02.015

Reference yield: 86.0%

6-Aminopenicillanic Acid (551-16-6) + (R)-phenylglycine amide (700-63-0,6485-52-5,6485-67-2,58429-87-1) → (R)-phenylglycine (875-74-1) + ampicillin (69-53-4)

Guidance literature:

With A_. faecalis; immobilised penicillin acylase (EC 3.5.1.11); In water; acetonitrile; at 0 ℃; Further Variations:; Solvents; reusing run; Product distribution; Kinetics; Enzymatic reaction;

DOI:10.1002/adsc.200303023

Reference yield: 70.0%

6-Aminopenicillanic Acid (551-16-6) + (R)-Phenylglycine methyl ester (24461-61-8) → ampicillin (69-53-4)

Guidance literature:

With phosphate buffer; Eupergit C-immobilized penicillin acylase (30 U/mg); sodium sulfate; at 20 ℃; pH=6.5; Further Variations:; Reagents; water content; Product distribution; Kinetics; solid phase reaction;

DOI:10.1002/1615-4169(200209)344:8<894::AID-ADSC894>3.0.CO;2-Q

upstream raw materials:

6-epi-hetacillin

hetacillin

6-Aminopenicillanic Acid

(+)-(S)-α-bromophenylacetic acid

Downstream raw materials:

2-(3,6-dioxo-5-phenylpiperazine-2-yl)-5,5-dimethylthiazolidine-4-carboxylic acid

6β-((Ξ)-2-hydroxy-2-phenyl-acetylamino)-penicillanic acid methyl ester

6β-[(R)-2-((R)-2-amino-2-phenyl-acetylamino)-2-phenyl-acetylamino]-penicillanic acid

6β-((R)-2-benzylideneamino-2-phenyl-acetylamino)-penicillanic acid; triethylamine salt

Refernces

Trimethylsilyl chloride catalyzed synthesis of substituted benzimidazoles using two phase system under microwave conditions, and their antimicrobial studies

10.4067/S0717-97072012000200014

The study explores a convenient method for synthesizing substituted benzimidazoles using Trimethylsilyl Chloride (TMSCl) as a catalyst in a microwave-induced two-phase system. The chemicals involved include o-phenylenediamine and various carboxylic acids as starting materials, TMSCl as the catalyst, and solvents such as DMF and water. The TMSCl catalyzes the cyclization of o-phenylenediamine with carboxylic acids to form benzimidazoles. The microwave conditions significantly reduce reaction time and enhance yield compared to conventional heating methods. The synthesized compounds were evaluated for their in vitro antibacterial and antifungal activities against several pathogenic strains, revealing that certain compounds, such as 3e, 3f, 3g, 3k, 3m, 3n, and 3o, demonstrated antimicrobial activity comparable to standard drugs like ampicillin and itraconazole, with the most effective compounds showing activity at a MIC of 6.25 μg/mL. The study concludes that the presence of a substituted phenyl ring at position 2 of the benzimidazole structure might be responsible for the enhanced antimicrobial activity.

Synthesis, biological evaluation and QSAR studies of new thieno[2,3-d]pyrimidin-4(3H)-one derivatives as antimicrobial and antifungal agents

10.1016/j.bioorg.2020.104509

The research focuses on the synthesis, biological evaluation, and QSAR studies of new thieno[2,3-d]pyrimidin-4(3H)-one derivatives as potential antimicrobial and antifungal agents. The purpose of the study was to develop new compounds that exhibit excellent activity against gram-positive and gram-negative bacteria, as well as fungal species, and to understand their structure-activity relationships. The majority of the synthesized compounds showed promising antimicrobial and antifungal activity, surpassing the potency of control compounds like streptomycin and ampicillin. Particularly, compound 22, with a m-methoxyphenyl group and an ethylenediamine side chain, demonstrated broad-spectrum antibacterial activity, while compound 15, with a m-methoxyphenyl group and a 2-(2-mercaptoethoxy)ethan-1-ol side chain, showed the best antifungal activity. Both compounds 15 and 22 showed no toxic effects in vitro on HFL-1 human embryonic primary cells and in vivo in the nematode C. elegans at their respective MIC concentrations.

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