Acivicin

Base Information

• Chemical Name: Acivicin
• CAS No.: 42228-92-2
• Molecular Formula: C5H7ClN2O3
• Molecular Weight: 178.57
• NSC Number: 163501
• UNII: O0X60K76I6
• DSSTox Substance ID: DTXSID0046010
• Nikkaji Number: J16.742H
• Wikipedia: Acivicin
• Wikidata: Q4674217
• NCI Thesaurus Code: C986
• ChEMBL ID: CHEMBL1231101
• Mol file: 42228-92-2.mol

Synonyms:acivicin;alpha-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid;alpha-S,5S-alpha-amino-3-chloro-2-isoxazoline-5-acetic acid;AT 125;AT-125;L-(alphaS,5S)-alpha-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid;NSC 163501;U 42,126;U-42,126

Chemical Property of Acivicin

Chemical Property:

• Appearance/Colour: 36
• Vapor Pressure: 1.45E-05mmHg at 25°C
• Melting Point: >200°C (dec.)
• Refractive Index: 1.663
• Boiling Point: 341.6 °C at 760 mmHg
• PKA: 2.02±0.10(Predicted)
• Flash Point: 160.4 °C
• PSA: 84.91000
• Density: 1.85 g/cm³
• LogP: -0.12460
• Storage Temp.: 2-8°C
• Solubility.: H2O: soluble10mg/mL (warmed)
• Water Solubility.: Soluble in water at 10mg/ml with warming
• XLogP3: -2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 178.0145198
• Heavy Atom Count: 11
• Complexity: 206

Purity/Quality:

97% ^*data from raw suppliers

Acivicin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(ON=C1Cl)C(C(=O)O)N
• Isomeric SMILES: C1[C@H](ON=C1Cl)[C@@H](C(=O)O)N
• Uses: Inhibits glutamine amidotransferases in purine and pyrimidine synthetic pathways. Tumor growth inhibitor Azaserine and Acivicin are classical and irreversible inhibitors of γ-Glutamyltranspeptidase
• Therapeutic Function: Antineoplastic

Technology Process of Acivicin

There total 13 articles about Acivicin 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: 65.0%

erythro-DL-N-benzyloxycarbonyl-α-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid (76843-83-9,104754-65-6) → erythro-DL-α-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid <(+/-)-AT-125> (42228-92-2,52583-41-2,76898-56-1,80184-13-0,104832-77-1)

Guidance literature:

With oxalyl dichloride; N,N-dimethyl-formamide; In benzene; Heating;

DOI:10.1021/ja00394a039

Reference yield:

erythro-DL-N-benzyloxycarbonyl-α-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid o-nitrobenzyl ester (76843-81-7,76879-01-1) → erythro-DL-α-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid <(+/-)-AT-125> (42228-92-2,52583-41-2,76898-56-1,80184-13-0,104832-77-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / Al-Hg / diethyl ether

2: 65 percent / (COCl)2, DMF / benzene / Heating

With oxalyl dichloride; aluminium amalgam; N,N-dimethyl-formamide; In diethyl ether; benzene;

DOI:10.1021/ja00394a039

Reference yield:

(R)-((R)-3-chloro-4,5-dihydro-isoxazol-5-yl)-phthalimido-acetic acid (69977-84-0) → (R)-amino-((R)-3-chloro-4,5-dihydro-isoxazol-5-yl)-acetic acid (42228-92-2,52583-41-2,76898-56-1,80184-13-0,104832-77-1)

Guidance literature:

With hydrazine hydrate;

DOI:10.1021/ja00498a056

upstream raw materials:

N^δ-Hydroxyornithine

2,2,2-Trichloro-N-[(R)-1-((S)-3-chloro-4,5-dihydro-isoxazol-5-yl)-2-hydroxy-ethyl]-acetamide

erythro-DL-N-benzyloxycarbonyl-α-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid

(R)-Amino-((R)-3-chloro-4,5-dihydro-isoxazol-5-yl)-acetic acid; hydrochloride

Downstream raw materials:

(2S,3S)-β-hydroxyornithine

2,2-dimethyl-propionic acid 4-[((carboxy)-(3-chloro-4,5-dihydro-isoxazol-5-yl)-methyl)carbamoyloxymethyl]-2-[(2-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-ethyl)carbamoyl]-phenyl ester

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