Nocardamine

Base Information

• Chemical Name: Nocardamine
• CAS No.: 26605-16-3
• Molecular Formula: C₂₇H₄₈N₆O₉
• Molecular Weight: 600.713
• UNII: Q645668975
• DSSTox Substance ID: DTXSID00181161
• Nikkaji Number: J34.318H
• Wikidata: Q27122069
• Metabolomics Workbench ID: 57426
• ChEMBL ID: CHEMBL505734
• Mol file: 26605-16-3.mol

Synonyms:deferrioxamine E;nocardamin;nocardamine

Chemical Property of Nocardamine

Chemical Property:

• Melting Point: 192-195°
• Boiling Point: °Cat760mmHg
• PKA: 8?+-.0.20(Predicted)
• Flash Point: °C
• PSA: 208.92000
• Density: 1.162g/cm³
• LogP: 1.65360
• Storage Temp.: -20°C
• Solubility.: Soluble in DMSO (5 mg/ml)
• XLogP3: -2.2
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 0
• Exact Mass: 600.34827713
• Heavy Atom Count: 42
• Complexity: 764

Purity/Quality:

98%Min ^*data from raw suppliers

Nocardamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCNC(=O)CCC(=O)N(CCCCCNC(=O)CCC(=O)N(CCCCCNC(=O)CCC(=O)N(CC1)O)O)O
• Description: Nocardamine is a ferrioxamine siderophore that has been found in Streptomyces and has diverse biological activities. It chelates iron in a chrome azurol S assay (IC50 = 9.9 μM). Nocardamine inhibits M. smegmatis and M. bovis biofilm formation (MIC = 10 μM for both), an effect that can be reversed by iron. It is cytotoxic to T47D, SK-MEL-5, SK-MEL-28, and RPMI-7951 cancer cells (IC50s = 6, 18, 12, and 14 μM, respectively). Nocardamine also induces morphological changes in BM-N4 insect cells.
• Uses: Nocardamine is a cyclic siderophore.

Technology Process of Nocardamine

There total 19 articles about Nocardamine 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: 100.0%

1,12,23-tris(benzyloxy)-1,6,12,17,23,28-hexaazacyclotritriacontane-2,5,13,16,24,27-hexone (130946-44-0) → nocardamine (26605-16-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 7h;

DOI:10.1016/S0040-4020(01)87913-8

Reference yield:

5,16,27-tris(benzyloxy)-32-amino-4,12,15,23,26-pentaoxo-5,11,16,22,27-pentaazadotriacontanoic acid (130946-43-9) → nocardamine (26605-16-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 54 percent / diphenylphosphoryl azide / dimethylformamide / 96 h / -1 - 8 °C

2: 100 percent / H₂ / 10percent Pd-C / methanol / 7 h

With diphenylphosphoranyl azide; hydrogen; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)87913-8

Reference yield:

O-benzyl-N-(5-aminopentyl)-N-(tert-butoxycarbonyl)hydroxylamine (129245-21-2) → nocardamine (26605-16-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 44 percent / DCC, DMAP / CH₂Cl₂ / 96 h / 0 deg C to r.t.

2: 2.46 g / TFA / CH₂Cl₂ / 1) 3 min, 0 deg C, 2) 17 min, without cooling

3: 78 percent / pyridine / 1.87 h / 101 °C

4: 21 percent / H₂, NH₃, conc.NH₄OH / Raney nickel W-2 / methanol / 3 h / 0 °C / 2947.7 - 3102.9 Torr

5: 54 percent / diphenylphosphoryl azide / dimethylformamide / 96 h / -1 - 8 °C

6: 100 percent / H₂ / 10percent Pd-C / methanol / 7 h

With pyridine; dmap; ammonium hydroxide; diphenylphosphoranyl azide; hydrogen; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; Raney nickel W-2; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)87913-8

upstream raw materials:

1,12,23-tris(benzyloxy)-1,6,12,17,23,28-hexaazacyclotritriacontane-2,5,13,16,24,27-hexone

O-benzyl-N-(5-aminopentyl)-N-(tert-butoxycarbonyl)hydroxylamine

5,16-bis(benzyloxy)-20-cyano-4,12,15-trioxo-5,11,16-triazaeicosanoic acid

27--6,17-bis(benzyloxy)-7,10,18,21-tetraoxo-6,11,17,22-tetraazaheptacosanenitrile

Refernces

• 1、 Chiu, Cheng-Hsin,Chung, Wen-Sheng,Jheng, Ting-Cian,Mong, Kwok-Kong Tony,Peng, Bo-Chun. "Convergent Synthesis of Macrocyclic and Linear Desferrioxamines". supporting information. . Retrieved 2020/06/17.