Amsacrine hydrochloride

Base Information

• Chemical Name: Amsacrine hydrochloride
• CAS No.: 54301-15-4
• Molecular Formula: C21H19 N3 O3 S . Cl H
• Molecular Weight: 429.927
• Hs Code.: 2935009090
• European Community (EC) Number: 637-255-8
• NSC Number: 141549
• UNII: U66HX4K4CO
• DSSTox Substance ID: DTXSID2037186
• Wikidata: Q27290741
• ChEMBL ID: CHEMBL1256655
• Mol file: 54301-15-4.mol

Synonyms:AMSA;AMSA P D;AMSA P-D;AMSA PD;Amsacrina;Amsacrine;Amsidine;Amsidyl;Cain Acridine;Cain's Acridine;Cains Acridine;m-AMSA;meta AMSA;meta-AMSA;NSC 141549;NSC 156303;NSC 249992;NSC-141549;NSC-156303;NSC-249992;NSC141549;NSC156303;NSC249992;SN 11841;SN-11841;SN11841

Chemical Property of Amsacrine hydrochloride

Chemical Property:

• Vapor Pressure: 1.06E-12mmHg at 25°C
• Melting Point: 197-199 ºC
• Boiling Point: 563°C at 760 mmHg
• Flash Point: 294.3°C
• PSA: 88.70000
• LogP: 6.54050
• Storage Temp.: Refrigerator
• Solubility.: DMSO: 10 mg/mL with heat and sonication
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 429.0913904
• Heavy Atom Count: 29
• Complexity: 601

Purity/Quality:

99% ^*data from raw suppliers

Amsacrine Hydrochloride ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 25-36/37/38
• Safety Statements: 26-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)NS(=O)(=O)C)NC2=C3C=CC=CC3=NC4=CC=CC=C42.Cl
• Uses: Amsacrine hydrochloride has been used: as a topoisomerase poison in bacteriophage T4 topoisomerase assayas a topoisomerase inhibitor in Drosophila cell line, Kc167 as an antileukemia drug to test its effect on p53 transcriptional activity in tumor xenograftsas a topoisomerase II poison in dose-response assays in C elegans

Technology Process of Amsacrine hydrochloride

There total 4 articles about Amsacrine hydrochloride 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:

9-Chloroacridine (1207-69-8) + N-(4-amino-3-methoxyphenyl)methanesulfonamide (57165-06-7) → N-[4-(9-acridinylamino)-3-methoxyphenyl]methanesulfonamide hcrochloride (54301-15-4)

Guidance literature:

With hydrogenchloride; In methanol;

DOI:10.1021/jm00387a012

Reference yield:

3-methoxy-4-nitro-N-(methylsulfonyl)benzenamine (57165-05-6) → N-[4-(9-acridinylamino)-3-methoxyphenyl]methanesulfonamide hcrochloride (54301-15-4)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Pd/C / methanol / 0.25 h / 1520 Torr

2: HCl / methanol

With hydrogenchloride; hydrogen; palladium on activated charcoal; In methanol;

DOI:10.1021/jm00387a012

Reference yield:

3-methoxy-4-nitroanilin (16292-88-9) → N-[4-(9-acridinylamino)-3-methoxyphenyl]methanesulfonamide hcrochloride (54301-15-4)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / 4 h / 20 °C

2: H₂ / Pd/C / methanol / 0.25 h / 1520 Torr

3: HCl / methanol

With pyridine; hydrogenchloride; hydrogen; palladium on activated charcoal; In methanol;

DOI:10.1021/jm00387a012

upstream raw materials:

9-Chloroacridine

N-(4-amino-3-methoxyphenyl)methanesulfonamide

3-methoxy-4-nitro-N-(methylsulfonyl)benzenamine

3-methoxy-4-nitroanilin

Refernces

• 1、 -. "Multi-step process for the production of methanesulfon-m-anisidide, 4'-(9-acridinylamino)-". . . Retrieved 2008/06/13.