125697-93-0

Basic information

• Product Name: LAVENDUSTIN C
• Synonyms: 2-HYDROXY-5-(2,5-DIHYDROXYBENZYLAMINO)BENZOIC ACID;[2-HYDROXY-5-[N-(2',5'-DIHYDROXYBENZYL)AMINO]BENZOIC ACID;5-(2,5-DIHYDROXYBENZYLAMINO)-2-HYDROXYBENZOIC ACID;5-(2,5-DIHYDROXYBENZYLAMINO)SALICYLIC ACID;5-(N-2',5'-DIHYDROXYBENZYL)AMINOSALICYLIC ACID;5-(N-2,5-DIHYDROXYBENZYL)AMINOSALICYLIC ACID;HDBA;COMPOUND 5
• CAS NO: 125697-93-0
• Molecular Formula: C₁₄H₁₃NO₅
• Molecular Weight: 275.26
• Product Categories: All Inhibitors;Inhibitors;Tyrosine Kinase Inhibitors;Other enzyme inhibitors and activators
• Mol File: 125697-93-0.mol
• Article Data: 4

Chemical Properties

• Melting Point: 193-195°C dec.
• Boiling Point: 597.5 °C at 760 mmHg
• Flash Point: 315.2 °C
• Appearance: /solid
• Density: 1.551 g/cm³
• Vapor Pressure: 4E-15mmHg at 25°C
• Refractive Index: 1.758
• Storage Temp.: −20°C
• Solubility: DMSO: soluble
• PKA: 2.32±0.10(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: LAVENDUSTIN C(CAS DataBase Reference)
• NIST Chemistry Reference: LAVENDUSTIN C(125697-93-0)
• EPA Substance Registry System: LAVENDUSTIN C(125697-93-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 125697-93-0(Hazardous Substances Data)

Usage

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.

Chemical Properties

Brown Solid

Uses

Different sources of media describe the Uses of 125697-93-0 differently. You can refer to the following data:
1. Shows potent tyrosine kinase inhibitory activity
2. Shows potent tyrosine kinase inhibitory activity.

InChI:InChI=1/C14H13NO5/c16-10-2-4-12(17)8(5-10)7-15-9-1-3-13(18)11(6-9)14(19)20/h1-6,15-18H,7H2,(H,19,20)

Upstream product

• 89-57-6 5-Aminosalicylic Acid 
• 1194-98-5 2,5-Dihydroxybenzaldehyde 

Downstream Products

• 188292-98-0 Acetic acid 4-acetoxy-2-{[(4-acetoxy-3-tetradecylcarbamoyl-phenyl)-tert-butoxycarbonyl-amino]-methyl}-phenyl ester 
• 188292-96-8 Acetic acid 4-acetoxy-2-{[(4-acetoxy-3-hexylcarbamoyl-phenyl)-tert-butoxycarbonyl-amino]-methyl}-phenyl ester 
• 188292-93-5 Acetic acid 4-acetoxy-2-{[(4-acetoxy-3-methylcarbamoyl-phenyl)-tert-butoxycarbonyl-amino]-methyl}-phenyl ester 
• 188292-91-3 2-Acetoxy-5-[tert-butoxycarbonyl-(2,5-diacetoxy-benzyl)-amino]-benzoic acid 
• 188293-04-1 (2,5-Dihydroxy-benzyl)-(4-hydroxy-3-tetradecylcarbamoyl-phenyl)-carbamic acid tert-butyl ester 
• 188293-01-8 (2,5-Dihydroxy-benzyl)-(3-hexylcarbamoyl-4-hydroxy-phenyl)-carbamic acid tert-butyl ester 
• 188293-00-7 (2,5-Dihydroxy-benzyl)-(4-hydroxy-3-methylcarbamoyl-phenyl)-carbamic acid tert-butyl ester 
• 188292-90-2 5-[tert-Butoxycarbonyl-(2,5-dihydroxy-benzyl)-amino]-2-hydroxy-benzoic acid 

Relevant articles and documents

A versatile solid phase synthesis of lavendustin A and certain biologically active analogs

Reaction of aminomethylated polystyrene resin (8) with succinic anhydride, followed by esterification of the free carboxylic acid of the product 9 with 2,5-dihydroxybenzaldehyde (4), afforded the resin-linked aldehyde intermediate 10. The key intermediate 10 was converted into the protein-tyrosine kinase inhibitor lavendustin A and certain analogs through reductive amination and reductive alkylation steps, followed by cleavage from the resin. This method enables the preparation of a wide variety of lavendustin A analogs using combinatorial chemistry and parallel synthesis techniques.

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

Potent inhibitors of EGF-dependent protein tyrosine kinase (PTK) activity were synthesized in a series of 5-[(2,5-dihydroxybenzyl)amino]salicylates. Several of these compounds inhibited EGF-dependent DNA synthesis in ER 22 cells with IC50 1 μ