Lavendustin c

Base Information

• Chemical Name: Lavendustin c
• CAS No.: 125697-93-0
• Molecular Formula: C14H13 N O5
• Molecular Weight: 275.261
• Hs Code.: 2922509090
• European Community (EC) Number: 635-029-3
• NSC Number: 666251
• UNII: HJM06BIW5M
• DSSTox Substance ID: DTXSID60154856
• Nikkaji Number: J568.039E
• Wikidata: Q27166541
• NCI Thesaurus Code: C1487
• Metabolomics Workbench ID: 130711
• ChEMBL ID: CHEMBL319620
• Mol file: 125697-93-0.mol

Synonyms:2-hydroxy-5-(2,5-dihydrobenzyl) aminobenzoic acid;2-hydroxy-5-(2,5-dihydrobenzyl)aminobenzoic acid;HBABA

Chemical Property of Lavendustin c

Chemical Property:

• Appearance/Colour: Yellow to tan powder
• Vapor Pressure: 4E-15mmHg at 25°C
• Melting Point: 193-195°C dec.
• Boiling Point: 597.5 °C at 760 mmHg
• PKA: 2.32±0.10(Predicted)
• Flash Point: 315.2 °C
• PSA: 110.02000
• Density: 1.551 g/cm³
• LogP: 2.18670
• Storage Temp.: −20°C
• Solubility.: DMSO: soluble
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 275.07937252
• Heavy Atom Count: 20
• Complexity: 338

Purity/Quality:

98%Min ^*data from raw suppliers

5-(2,5-Dihydroxybenzylamino)-2-hydroxybenzoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=C(C=C1NCC2=C(C=CC(=C2)O)O)C(=O)O)O
• Description: Lavendustin C, a derivative of a Streptomyces griseolavendus butyl acetate extract, is a potent inhibitor of epidermal growth factor (EGF) receptor-associated tyrosine kinase with an IC50 value of 0.012 μM. Lavendustin C also inhibits pp60c-src(+) kinase and Ca2+ calmodulin-dependent kinase II with IC50 values of 0.5 and 0.2 μM, respectively. At a concentration of 10-150 μM, lavendustin C inhibits tyrosine kinase-associated neutrophil degranulation and superoxide generation.
• Uses: Shows potent tyrosine kinase inhibitory activity Shows potent tyrosine kinase inhibitory activity.

Technology Process of Lavendustin c

There total 5 articles about Lavendustin c 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:

5-{[1-(2,5-Dihydroxy-phenyl)-meth-(E)-ylidene]-amino}-2-hydroxy-benzoic acid → lavendustin C (125697-93-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 4h; under 760 Torr;

DOI:10.1021/jm00077a014 DOI:10.1021/jm00032a020

Reference yield:

2,5-Dihydroxybenzaldehyde (1194-98-5) → lavendustin C (125697-93-0)

Guidance literature:

Multi-step reaction with 2 steps

1: methanol / Heating

2: NaBH₃CN / methanol / 4 h / Ambient temperature

With sodium cyanoborohydride; In methanol;

DOI:10.1021/jm00050a005

Reference yield:

5-Aminosalicylic Acid (89-57-6) → lavendustin C (125697-93-0)

Guidance literature:

Multi-step reaction with 2 steps

1: methanol / Heating

2: NaBH₃CN / methanol / 4 h / Ambient temperature

With sodium cyanoborohydride; In methanol;

DOI:10.1021/jm00050a005

upstream raw materials:

2,5-Dihydroxybenzaldehyde

5-Aminosalicylic Acid

Downstream raw materials:

5-[tert-Butoxycarbonyl-(2,5-dihydroxy-benzyl)-amino]-2-hydroxy-benzoic acid

Acetic acid 4-acetoxy-2-{[(4-acetoxy-3-tetradecylcarbamoyl-phenyl)-tert-butoxycarbonyl-amino]-methyl}-phenyl ester

Acetic acid 4-acetoxy-2-{[(4-acetoxy-3-hexylcarbamoyl-phenyl)-tert-butoxycarbonyl-amino]-methyl}-phenyl ester

Acetic acid 4-acetoxy-2-{[(4-acetoxy-3-methylcarbamoyl-phenyl)-tert-butoxycarbonyl-amino]-methyl}-phenyl ester

Refernces

• 1、 Chen,Boiziau,Parker,Mailliet,Commercon,Tocque,Le Pecq,Roques,Garbay. "Structure-activity relationships in a series of 5-[(2,5- dihydroxybenzyl)amino]salicylate inhibitors of EGF-receptor-associated tyrosine kinase: Importance of additional hydrophobic aromatic interactions". . p. 845 - 859. Retrieved 2007/10/02.
• 2、 Chen, Huixiong,Boiziau, Janine,Parker, Fabienne,Maroun, Rachid,Tocque, Bruno,et al.. "Synthesis and Structure-Activity Studies of a Series of salicylates as Inhibitors of EGF Receptor-Associated Tyrosine Kinase Activity". . p. 4094 - 4098. Retrieved 2007/10/02.