• 1. Examination of deposit in commercial diluted phosphoric acid
  Analyst, 1880,5, 146-147
• 2. Distinction of trans–cis photoisomers with comparable optical properties in multiple-state photochromic systems – examining a molecule with three azobenzenes via in situ irradiation NMR spectroscopy?
  Jonas Kind,Lukas Kaltschnee,Martin Leyendecker,Christina M. Thiele Chem. Commun., 2016,52, 12506-12509
• 3. Excimer emission and magnetoluminescence of radical-based zinc(ii) complexes doped in host crystals?
  Shojiro Kimura,Tetsuro Kusamoto Chem. Commun., 2020,56, 11195-11198
• 4. Excellent lithium ion storage property of porous MnCo2O4 nanorods?
  Peiyuan Zeng,Xiaoxiao Wang,Ming Ye,Qiuyang Ma,Jianwen Li,Wanwan Wang,Baoyou Geng,Zhen Fang RSC Adv., 2016,6, 23074-23084
• 5. Ester-directed orthogonal dual C–H activation and ortho aryl C–H alkenylation via distal weak coordination?
  Manickam Bakthadoss,Tadiparthi Thirupathi Reddy,Vishal Agarwal,Duddu S. Sharada Chem. Commun., 2022,58, 1406-1409

Research Brief on (2S,5R,6R)-6-acetamido-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (CAS: 15493-53-5)

Recent advancements in the field of chemical biology and medicinal chemistry have highlighted the significance of (2S,5R,6R)-6-acetamido-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (CAS: 15493-53-5), a compound with notable pharmacological properties. This research brief synthesizes the latest findings on this molecule, focusing on its structural characteristics, synthetic pathways, biological activities, and potential therapeutic applications. The compound, a derivative of the penicillin core structure, has garnered attention for its role in antibiotic development and beyond.

Structural analysis reveals that (2S,5R,6R)-6-acetamido-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid features a bicyclic β-lactam ring, a hallmark of penicillin-related compounds. The presence of the acetamido and carboxylic acid functional groups enhances its reactivity and binding affinity to bacterial transpeptidases, which are critical targets in antibacterial therapy. Recent studies have explored modifications to this core structure to improve stability, bioavailability, and resistance to β-lactamases, addressing some of the limitations observed in traditional penicillin derivatives.

In terms of synthesis, innovative methodologies have been developed to produce this compound with higher yields and purity. A 2023 study published in the Journal of Medicinal Chemistry demonstrated a novel enzymatic approach that leverages engineered acylases to catalyze the formation of the β-lactam ring, significantly reducing the need for harsh chemical conditions. This green chemistry strategy not only improves the environmental footprint of the synthesis but also enhances the scalability of production, making it more feasible for industrial applications.

Biological evaluations of (2S,5R,6R)-6-acetamido-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid have revealed its potent activity against a range of Gram-positive and Gram-negative bacteria. Notably, its efficacy against methicillin-resistant Staphylococcus aureus (MRSA) has been a focal point of recent research. In vitro studies indicate that this compound inhibits cell wall synthesis by binding to penicillin-binding proteins (PBPs), with a particularly high affinity for PBP2a, a key mediator of β-lactam resistance in MRSA. These findings suggest its potential as a lead compound for next-generation antibiotics.

Beyond its antibacterial properties, emerging research has explored the compound's utility in other therapeutic areas. A 2024 study in ACS Chemical Biology reported its role as a modulator of inflammatory pathways, with potential applications in autoimmune diseases. The carboxylic acid moiety was found to interact with specific immune receptors, dampening pro-inflammatory cytokine production. This dual functionality—antibacterial and immunomodulatory—positions the compound as a versatile candidate for multifunctional drug development.

In conclusion, (2S,5R,6R)-6-acetamido-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (CAS: 15493-53-5) represents a promising scaffold in medicinal chemistry. Its structural features, synthetic accessibility, and broad biological activities make it a valuable subject for ongoing research. Future directions may include further optimization of its pharmacokinetic properties and exploration of its mechanisms in non-antibacterial applications. As resistance to existing antibiotics continues to rise, such innovative compounds will be critical in addressing global health challenges.

• 61477-96-1(Piperacillin)
• 65772-67-0(N-Piperacillinyl Ampicillin)
• 37091-66-0(Azlocillin)
• 64817-22-7(Piperacilloic Acid)
• 332062-08-5(Fmoc-S-3-amino-4,4-diphenyl-butyric acid)
• 1270529-38-8(1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol)
• 2680771-01-9(4-cyclopentyl-3-{(prop-2-en-1-yloxy)carbonylamino}butanoic acid)
• 2098070-20-1(2-(3-(Pyridin-3-yl)-1H-pyrazol-1-yl)acetimidamide)
• 1444113-98-7(N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide)
• 941977-17-9(N'-(3-chloro-2-methylphenyl)-N-2-(dimethylamino)-2-(naphthalen-1-yl)ethylethanediamide)