Cyclazosin

Base Information

• Chemical Name: Cyclazosin
• CAS No.: 139953-73-4
• Molecular Formula: C₂₃H₂₇N₅O₄
• Molecular Weight: 437.498
• DSSTox Substance ID: DTXSID701112809
• Nikkaji Number: J981.319E
• Wikidata: Q27076939
• Pharos Ligand ID: 79DM9PJKKZ6R
• Metabolomics Workbench ID: 63057
• ChEMBL ID: CHEMBL423294
• Mol file: 139953-73-4.mol

Synonyms:(4-(4-amino-6,7-dimethoxyquinazolin-2-yl)octahydroquinoxalin-1-yl)furan-2-ylmethanone hydrochloride;cyclazosin;cyclazosin, (trans)-isomer

Chemical Property of Cyclazosin

Chemical Property:

• Vapor Pressure: 4.74E-18mmHg at 25°C
• Boiling Point: 674.5°Cat760mmHg
• Flash Point: 361.7°C
• PSA: 106.95000
• Density: 1.304g/cm³
• LogP: 3.67990
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 437.20630436
• Heavy Atom Count: 32
• Complexity: 668

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C2C(=C1)C(=NC(=N2)N3CCN(C4C3CCCC4)C(=O)C5=CC=CO5)N)OC
• Isomeric SMILES: COC1=C(C=C2C(=C1)C(=NC(=N2)N3CCN([C@@H]4[C@H]3CCCC4)C(=O)C5=CC=CO5)N)OC

Technology Process of Cyclazosin

There total 7 articles about Cyclazosin 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:

benzyl (4aR,8aS)-4-(4-amino-6,7-dimethoxyquinazolin-2-yl)octahydroquinoxaline-1(2H)-carboxylate hydrochloride → (+)-Cyclazosin (139953-73-4)

Guidance literature:

Multi-step reaction with 2 steps

1: cyclohexene / Pd/C / methanol; ethanol / 6 h / 80 °C

2: triethylamine / CH₂Cl₂ / 3 h / 20 °C

With triethylamine; cyclohexene; palladium on activated charcoal; In methanol; ethanol; dichloromethane;

DOI:10.1016/j.bmc.2007.01.028

Reference yield:

benzyl (4aS,8aR)-4-(4-amino-6,7-dimethoxyquinazolin-2-yl)octahydroquinoxaline-1(2H)-carboxylate hydrochloride → 2-[(4aR,8aS)-4-(2-furoyl)octahydroquinoxalin-1(2H)-yl]-6,7-dimethoxyquinazolin-4-amine (139953-73-4)

Guidance literature:

Multi-step reaction with 2 steps

1: cyclohexene / Pd/C / methanol; ethanol / 6 h / 80 °C

2: triethylamine / CH₂Cl₂ / 3 h / 20 °C

With triethylamine; cyclohexene; palladium on activated charcoal; In methanol; ethanol; dichloromethane;

DOI:10.1016/j.bmc.2007.01.028

Reference yield:

(-)-6,7-dimethoxy-2-[(4aS,8aR)-octahydroquinoxalin-1(2H)-yl]quinazolin-4-amine (944767-72-0) + 2-furancarbonyl chloride (527-69-5) → (+)-Cyclazosin (139953-73-4)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1016/j.bmc.2007.01.028

upstream raw materials:

2-chloro-6,7-dimethoxyquinazolin-4-amine

2-furancarbonyl chloride

(+/-)-trans-decahydroquinoxaline

(-)-6,7-dimethoxy-2-[(4aS,8aR)-octahydroquinoxalin-1(2H)-yl]quinazolin-4-amine

Refernces

• 1、 Giardina, Dario,Gulini, Ugo,Massi, Maurizio,Piloni, Maria G.,Pompei, Pierluigi,et al.. "Structure-Activity Relationships in Prazosin-Related Compounds. 2. Role of the Piperazine Ring on α-Blocking Activity". . p. 690 - 698. Retrieved 2007/10/02.