3-[[[(2S,4S)-4-Mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidinyl]carbonyl]amino]benzoic acid
[CAS# 202467-69-4]

Identification

• Classification: API >> Antibiotics >> Beta-lactamase inhibitor
• Name: 3-[[[(2S,4S)-4-Mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidinyl]carbonyl]amino]benzoic acid
• Synonyms: 2-[[(3-Carboxyphenyl)amino]carbonyl]-4-mercapto-1-pyrrolidinecarboxylic acid (2S-cis)-1-[(4-nitrophenyl)methyl] ester
• Molecular Formula: C₂₀H₁₉N₃O₇S
• Molecular Weight: 445.45
• CAS Registry Number: 202467-69-4
• SMILES: C1[C@@H](CN([C@@H]1C(=O)NC2=CC=CC(=C2)C(=O)O)C(=O)OCC3=CC=C(C=C3)[N+](=O)[O-])S

Properties

• Density: 1.5±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.676, Calc.^*
• Boiling Point: 749.6±60.0 ºC (760 mmHg), Calc.^*
• Flash Point: 407.1±32.9 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P305+P351+P338

Discovory and Applicatios

3-[[[(2S,4S)-4-Mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidinyl]carbonyl]amino]benzoic acid is a complex organic compound that plays a significant role in medicinal chemistry due to its unique structural features and reactivity. This compound consists of several functional groups, including a mercapto group, a nitrobenzyloxy group, and a pyrrolidinyl group, which contribute to its chemical and biological properties. The intricate structure of this molecule has made it an important subject of study in the context of drug design and the development of potential therapeutic agents.

The discovery of 3-[[[(2S,4S)-4-Mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidinyl]carbonyl]amino]benzoic acid can be attributed to the growing interest in compounds that combine different functional groups to enhance biological activity. The development of this molecule likely stemmed from the broader efforts in medicinal chemistry to create molecules with specific reactivity profiles, especially those that can interact with biological targets such as enzymes and receptors. The use of a mercapto group in this molecule is of particular interest because it can participate in various biochemical processes, including disulfide bond formation and redox reactions, which are critical for many biological functions.

The synthesis of 3-[[[(2S,4S)-4-Mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidinyl]carbonyl]amino]benzoic acid involves several synthetic steps, each designed to introduce the functional groups at precise locations on the molecular scaffold. One of the key steps in its synthesis is the formation of the pyrrolidinyl group, which is typically achieved through a reaction involving a chiral precursor. The mercapto group is introduced through a selective substitution reaction, while the nitrobenzyloxy group is incorporated via a carbonylation step. The careful control of reaction conditions during each step ensures that the final compound retains its desired structure and reactivity.

This compound is of significant interest in the field of medicinal chemistry due to its potential as a pharmacological agent. Its structure suggests that it could act as an inhibitor or modulator of various enzymes or proteins involved in cellular processes. The mercapto group, in particular, may interact with thiol groups in proteins, potentially altering their function. This makes the compound a candidate for the development of drugs targeting diseases where protein function is disrupted, such as in cancer or neurodegenerative diseases.

One of the key applications of 3-[[[(2S,4S)-4-Mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidinyl]carbonyl]amino]benzoic acid is in the development of enzyme inhibitors. Enzymes are essential for various biological functions, and the inhibition of specific enzymes can have therapeutic effects. The presence of the mercapto group in this compound may allow it to form covalent bonds with enzyme active sites, leading to enzyme inhibition. This property is particularly valuable in the design of drugs for conditions such as cancer, where inhibiting the activity of certain enzymes can slow down tumor growth or enhance the effects of other treatments.

In addition to its potential as an enzyme inhibitor, the compound may also serve as a starting point for the development of more selective and potent therapeutic agents. By modifying the structure of 3-[[[(2S,4S)-4-Mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidinyl]carbonyl]amino]benzoic acid, researchers can explore its interactions with different biological targets and optimize its pharmacological properties. This approach is commonly used in drug discovery to identify lead compounds that can be further developed into effective therapies.

Furthermore, the compound's nitrobenzyloxy group could also provide a useful handle for further chemical modifications, enabling the introduction of additional functional groups that could enhance its activity or selectivity. This makes 3-[[[(2S,4S)-4-Mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidinyl]carbonyl]amino]benzoic acid a versatile scaffold for drug design, with the potential to be developed into a range of novel therapeutics.

In conclusion, 3-[[[(2S,4S)-4-Mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidinyl]carbonyl]amino]benzoic acid is an important compound in the field of medicinal chemistry, with potential applications as an enzyme inhibitor and a precursor for drug development. Its unique structure, featuring a mercapto group, nitrobenzyloxy group, and pyrrolidinyl group, makes it a promising candidate for the design of therapeutic agents targeting a variety of diseases.