6326-79-0

Basic information

• Product Name: 6-Bromoisatin
• Synonyms: BUTTPARK 50\07-95;BROMOISATIN(6-);AKOS B018432;6-BROMOINDOLE-2,3-DIONE;6-BROMOINDOLINE-2,3-DIONE;6-BROMOISATIN;6-BROMO ISATINIC ANHYDRIDE;6-BROMO-1H-INDOLE-2,3-DIONE
• CAS NO: 6326-79-0
• Molecular Formula: C₈H₄BrNO₂
• Molecular Weight: 226.03
• EINECS: 1592732-453-0
• Product Categories: Indane/Indanone and Derivatives;Halides;Aminomethyl's;Phenyls & Phenyl-Het;Heterocyclic Compounds;Indoles;Simple Indoles;Heterocycles;Phenyls & Phenyl-Het;Fused Ring Systems
• Mol File: 6326-79-0.mol
• Article Data: 15

Chemical Properties

• Melting Point: 274°C
• Appearance: Orange powder
• Density: 1.826 g/cm³
• Refractive Index: 1.649
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 8.83±0.20(Predicted)
• CAS DataBase Reference: 6-Bromoisatin(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Bromoisatin(6326-79-0)
• EPA Substance Registry System: 6-Bromoisatin(6326-79-0)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22-41-43
• Safety Statements: 22-24/25-36/37/39-26
• HazardClass: IRRITANT
• Hazardous Substances Data: 6326-79-0(Hazardous Substances Data)

Usage

Chemical Properties

Orange Powder

Uses

Antimicrobial

Purification Methods

6-Bromoisatin recrystallises from AcOH (yellow needles). It is a plant growth substance. IR in CHCl3 has 1320 and 3440cm-1. [Sadler J Org max Chem 21 169 1956, Beilstein 21 III/IV 5012.]

InChI:InChI=1/C8H4BrNO2/c9-4-1-2-5-6(3-4)10-8(12)7(5)11/h1-3H,(H,10,11,12)

Upstream product

• 65971-74-6 (E)-N-(3-bromophenyl)-2-(hydroxyimino)acetamide 
• 65971-74-6 N-(3-bromophenyl)-2-(hydroxyimino)ethanamide 
• 99365-40-9 6-bromo-2,3-dihydro-1H-indole-2-one 
• 302-17-0 chloral hydrate 
• 591-19-5 m-Bromoaniline 

Downstream Products

• 20776-50-5 2-amino-4-bromobenzoic acid 
• 124028-89-3 7-bromo-3-(2-methoxyphenyl)-2-oxo-1,2-dihydroquinoline-4-carboxylic acid 
• 667463-68-5 6-Bromo-5-nitroisatin 
• 667463-62-9 (2'Z,3'E)-6-bromoindirubin-3'-oxime 
• 667463-95-8 MeBIO 
• 76561-16-5 7-bromo-1,2-dihydro-3,1-4H-benzoxazine-2,4-dione 
• 1147124-21-7 1,1'-dihydro-6,6'-dibromoisoindigo 
• 1253579-24-6 6-bromo-1-tritylindoline-2,3-dione 
• 99365-40-9 6-bromo-2,3-dihydro-1H-indole-2-one 
• 1236255-71-2 C₂₉H₁₈Br₂N₆O 
• 1236255-61-0 C₃₀H₂₁BrN₆O 
• 1236255-58-5 C₂₉H₁₉BrN₆O 
• 1236255-64-3 C₃₀H₂₁BrN₆O 
• 854923-38-9 5,6-dibromo-1H-indole 

Relevant articles and documents

Saccharomonosporine A inspiration; synthesis of potent analogues as potential PIM kinase inhibitors

Saccharomonosporine A was recently reported as a natural anti-cancer agent working through inhibition of a Proviral integration site for Moloney murine leukemia virus-1 (PIM-1) kinase. Structural bioisosteres of this natural product were synthesized and t

Methylisoindigo and its bromo-derivatives are selective tyrosine kinase inhibitors, repressing cellular stat3 activity, and target CD133+ cancer stem cells in PDAC

Indirubin is an active component of the herbal ingredient 'Danggui Longhui wan', which was used for the treatment of inflammation and chronic myeloid leukemia in China. The recent study showed its derivative methylisoindigo (also known as meisoindigo) preferentially targeting cancer stem cells (CSCs) in interference with AMPK and LKB1, the cellular metabolic sensors. In this study, we screened the effect of meisoindigo on a panel of 300 protein kinases and found that it selectively inhibited Stat3-associated tyrosine kinases and further confirmed its activity in cell based assays. To gain a deeper insight into the structure-activity relationship we produced 7 bromo-derivatives exhausting the accessible positions on the bisindole backbone except for in the 4-position due to the space limitation. We compared their anti-proliferative effects on tumor cells. We found that 6-bromomeisoindigo showed improved toxicity in company with increased Stat3 inhibition. Moreover, we detected that 6-bromomeisoindigo induced apoptosis of 95% of CD133+ pancreatic cancer cells. Considering that CD133 is a common marker highly expressed in a range of CSCs, our results imply the potential application of 6-bromomeisoindigo for the treatment of CSCs in different types of cancers.

Novel synthesis of 4-or 6-substituted indirubin derivatives

A simple and convenient route for synthesis of a series of 4-or 6-substituted indirubin derivatives by oxidation and subsequent condensation of indoxyl and isatin is described. Acidic reaction conditions are crucial to the condensation of 4-substituted derivatives, whereas for the condensation of 6-substituted derivatives, both acidic and basic conditions work well. Copyright Taylor & Francis Group, LLC.