Cycloserine

Base Information

• Chemical Name: Cycloserine
• CAS No.: 68-41-7
• Molecular Formula: C3H6N2O2
• Molecular Weight: 102.093
• Hs Code.: 29419090
• European Community (EC) Number: 200-688-4
• NSC Number: 756712
• UNII: 95IK5KI84Z
• DSSTox Substance ID: DTXSID8022870
• Nikkaji Number: J8.592H
• Wikipedia: Cycloserine
• Wikidata: Q418508
• NCI Thesaurus Code: C47466
• RXCUI: 3007
• Metabolomics Workbench ID: 27997
• ChEMBL ID: CHEMBL771
• Mol file: 68-41-7.mol

Synonyms:Cycloserine;R-4-Amino-3-isoxazolidinone;Seromycin

Chemical Property of Cycloserine

Chemical Property:

• Appearance/Colour: White to pale yellow cryst. powder
• Melting Point: 147ºC
• Refractive Index: 1.5110 (estimate)
• Boiling Point: 267ºC
• PKA: pKa 4.5 (Uncertain)
• PSA: 64.35000
• Density: 1.278 g/cm³
• LogP: -0.59580
• Storage Temp.: −20°C
• Sensitive.: Air Sensitive
• Solubility.: water: soluble50mg/mL, clear, colorless to light yellow
• Water Solubility.: SOLUBLE
• XLogP3: -1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 102.042927438
• Heavy Atom Count: 7
• Complexity: 92.9

Purity/Quality:

99% ^*data from raw suppliers

D-Cycloserine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 5-20
• Safety Statements: 38-36/37-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Antituberculosis Agents
• Canonical SMILES: C1C(C(=O)NO1)N
• Isomeric SMILES: C1[C@H](C(=O)NO1)N
• Recent ClinicalTrials: Treating Urological Chronic Pelvic Pain Syndrome (UCPPS) Pain
• Recent EU Clinical Trials: Manipulating NMDA-dependent learning to alter nocebo effects: A pharmacological fMRI study on pain and itch.
• General Description: D-Cycloserine (DCS) is a partial agonist at the strychnine-insensitive glycine site of the NMDA receptor, known for its rigid framework and pharmacophore orientation, which makes it a valuable template for designing glycine receptor ligands. It has been used as a reference compound in studies targeting cognitive deficits, epilepsy, schizophrenia, pain, depression, and stroke due to its affinity and efficacy at this site. Structural modifications to DCS-like compounds often result in reduced activity, highlighting the importance of its specific molecular configuration for receptor interaction.

Technology Process of Cycloserine

There total 39 articles about Cycloserine 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: 94.25%

Methyl (2R)-2-amino-3-chloropropionate hydrochloride (17136-54-8) → cycloserine (68-41-7)

Guidance literature:

With hydrogenchloride; acetone oxime; In methanol; at 65 ℃; for 1h; Temperature;

Reference yield: 80.0%

methyl (2R)-2-amino-3-(aminooxy)propanoate (29491-80-3) → cycloserine (68-41-7)

Guidance literature:

methyl (2R)-2-amino-3-(aminooxy)propanoate; With sodium hydroxide; In water; at -5 - 0 ℃; for 3h;

With acetic acid; In water; isopropyl alcohol; at -12 - -8 ℃; for 1h; pH=6.7 - 6.9;

DOI:10.1007/s10593-018-2197-y

Reference yield: 65.0%

D-cycloserine-L-tartrate (72270-01-0) → cycloserine (68-41-7)

Guidance literature:

With Amberlite IR-120 PLUS ion exchange resin (sodium form); In water; Inert atmosphere;

DOI:10.3987/COM-12-12553

upstream raw materials:

3-chloro-D-alanine hydroxyamide

N-benzyloxycarbonyl-O-(toluene-4-sulfonyl)-D-serine benzyloxyamide

(R)-4-benzyloxycarbonylamino-3-oxo-isoxazolidine-2-carboxylic acid benzyl ester

tert-butyl N-[(4R)-3-oxoisoxazolidin-4-yl]carbamate

Downstream raw materials:

(R)-3-acetoxy-4-acetylamino-4,5-dihydro-isoxazole

N-acetyl-D-cycloserine

(3R,6R)-3,6-bis[(aminooxy)methyl]piperazine-2,5-dione

(R)-4-benzyloxycarbonylamino-3-oxo-isoxazolidine-2-carboxylic acid benzyl ester

Refernces

Design, synthesis and structure-activity relationships of novel strychnine-insensitive glycine receptor ligands

10.1016/S0960-894X(99)00194-8

The research aimed to design, synthesize, and investigate the structure-activity relationships of novel ligands that act at the strychnine-insensitive glycine site of the NMDA receptor. This site is of interest due to its potential therapeutic relevance in various disorders, including cognitive deficits, epilepsy, schizophrenia, pain, depression, and stroke. The study focused on 3-hydroxy-imidazolidin-4-one derivatives, using D-cycloserine (DCS) and L-687,414 as templates due to their rigid framework and spatial orientation of pharmacophores. The researchers synthesized a series of compounds and evaluated their affinities and efficacies at the target site. The most active compound, 3a, exhibited affinity and efficacy similar to DCS, a known partial agonist. However, modifications to the structure of 3a, such as the addition of methyl or hydroxymethyl groups, expansion of the ring size, or replacement of the basic nitrogen with a sulfur atom, generally led to a loss of activity.