N-[4-(9-acridinylmethyl)-3-methoxyphenyl]methanesulfonamide

Base Information

• Chemical Name: N-[4-(9-acridinylmethyl)-3-methoxyphenyl]methanesulfonamide
• CAS No.: 51264-14-3
• Molecular Formula: C₂₁H₁₉N₃O₃S
• Molecular Weight: 393.466
• Hs Code.: 2935009090
• NSC Number: 758423
• Wikidata: Q27165420
• ChEMBL ID: CHEMBL1624239
• Mol file: 51264-14-3.mol

Synonyms:N-[4-(9-acridinylmethyl)-3-methoxyphenyl]methanesulfonamide;N-[4-(acridin-9-ylmethyl)-3-methoxyphenyl]methanesulfonamide;KBio3_002781;Spectrum3_001860;BSPBio_003280;CHEMBL1624239;SCHEMBL14479866;CHEBI:93727;HMS2093A11;Pharmakon1600-01503256;NSC758423;CCG-213145;NSC-758423;SBI-0206714.P001;AB01562989_01;SR-05000001846;SR-05000001846-1;BRD-K98490050-001-01-8;BRD-K98490050-003-01-4;Q27165420

Chemical Property of N-[4-(9-acridinylmethyl)-3-methoxyphenyl]methanesulfonamide

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 4.07E-14mmHg at 25°C
• Melting Point: 230-240oC
• Refractive Index: 1.688
• Boiling Point: 563 °C at 760 mmHg
• PKA: 8.55±0.10(Predicted)
• Flash Point: 294.3 °C
• PSA: 88.70000
• Density: 1.398 g/cm³
• LogP: 5.73850
• Storage Temp.: 2-8°C(protect from light)
• Solubility.: Soluble in DMSO
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 392.11946368
• Heavy Atom Count: 28
• Complexity: 598

Purity/Quality:

99%, ^*data from raw suppliers

Amsacrine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)NS(=O)(=O)C)CC2=C3C=CC=CC3=NC4=CC=CC=C42
• Description: Amsacrine is a cytostatic reported to be active against adult lymphoblastic leukemia which has failed primary treatment or become resistant. Its clinical use, however, is associated with significant neuro-, gastro- and hepatotoxicity.
• Uses: Amsacrine (Amsidyl) is used as an Investigational drug. Amsacrine is a drug undergoing intensive trials for severe leukemia and lymphoma. It is a cytotoxic drug that binds with DNA with expressed specificity to the adenosine–tyrosine pair, thus inhibiting DNA synthesis. It has been suggested to be used for severe leukemia. A synonym of this drug is amsidyl. Antineoplastic.

Technology Process of N-[4-(9-acridinylmethyl)-3-methoxyphenyl]methanesulfonamide

There total 7 articles about N-[4-(9-acridinylmethyl)-3-methoxyphenyl]methanesulfonamide 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: 78.0%

9-Chloroacridine (1207-69-8) + N-(4-amino-3-methoxyphenyl)methanesulfonamide (57165-06-7) → 4'-(9-acridinylamino) methanesulfon-m-anisidine (349459-07-0,51264-14-3)

Guidance literature:

at 120 ℃; for 0.666667h;

DOI:10.1016/j.tet.2012.11.083

Reference yield: 42.8%

methanesulfonyl chloride (124-63-0) + N1-(acridin-9-yl)-2-methoxybenzene-1,4-diamine → 4'-(9-acridinylamino) methanesulfon-m-anisidine (349459-07-0,51264-14-3)

Guidance literature:

With triethylamine; In dichloromethane; for 4h;

Reference yield: 36.0%

methylthiol (74-93-1) + N(1')-(methylsulfonyl)-N(4')-(9-acridynyl)-3'-methoxy-2',5'-cyclohexadiene-1',4'-diimine (117252-49-0) → 4'-(9-acridinylamino) methanesulfon-m-anisidine (349459-07-0,51264-14-3) + N-<4'-(9-acridynylamino)-3'-methoxy-6'-(methylthio)phenyl>methanesulfonamide (117252-55-8) + N-<4'-(9-acridynylamino)-3'-methoxy-5'-(methylthio)phenyl>methanesulfonamide (117252-56-9)

Guidance literature:

In acetonitrile;

DOI:10.1021/jo00261a010

upstream raw materials:

9-Chloroacridine

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

methylthiol

N(1')-(methylsulfonyl)-N(4')-(9-acridynyl)-3'-methoxy-2',5'-cyclohexadiene-1',4'-diimine

Downstream raw materials:

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

4-[2-(Acridin-9-ylsulfanyl)-1-(carboxymethyl-carbamoyl)-ethylcarbamoyl]-2-amino-butyric acid

Refernces

• 1、 Staderini, Matteo,Cabezas, Nieves,Bolognesi, Maria Laura,Menéndez, J. Carlos. "Solvent- and chromatography-free amination of π-deficient nitrogen heterocycles under microwave irradiation. A fast, efficient and green route to 9-aminoacridines, 4-aminoquinolines and 4-aminoquinazolines and its application to the synthesis of the drugs amsacrine and bistacrine". . p. 1024 - 1030. Retrieved 2013/02/23.
• 2、 Rewcastle, Gordon W.,Baguley, Bruce C.,Atwell, Graham J.,Denny, William A.. "Potential Antitumor Agents. 52. Carbamate Analogues of Amsacrine with in Vivo Activity against Multidrug-Resistant P388 Leukemia". . p. 1576 - 1581. Retrieved 2007/10/02.