129271-98-3

Basic information

• Product Name: 1-(PHENYLSULFONYL)-1H-INDOL-3-YLBORONIC ACID
• Synonyms: AKOS BRN-0396;1-PHENYLSULPHONYLINDOLE-3-BORONIC ACID;1-(PHENYLSULFONYL)-1H-INDOL-3-YLBORONIC ACID;1-(PHENYLSULFONYL)-3-INDOLEBORONIC ACID;1-PHENYLSULFONYLINDOLE-3-BORONIC ACID;1-(Phenylsulphonyl)-1H-indole-3-boronic acid;1-(PHENYLSULFONYL)-3-INDOLEBORONIC ACI&;1-(Phenylsulphonyl)-1H-indole-3-boronic acid 97%
• CAS NO: 129271-98-3
• Molecular Formula: C₁₄H₁₂BNO₄S
• Molecular Weight: 301.13
• Product Categories: Boronic acids;Boronic Acids;Boronic Acids and Derivatives;Heteroaryl
• Mol File: 129271-98-3.mol

Chemical Properties

• Melting Point: 144 °C (dec.)(lit.)
• Boiling Point: 581.384 °C at 760 mmHg
• Flash Point: 305.41 °C
• Appearance: /
• Density: 1.35 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.633
• Storage Temp.: 2-8°C
• PKA: 7.98±0.30(Predicted)
• CAS DataBase Reference: 1-(PHENYLSULFONYL)-1H-INDOL-3-YLBORONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(PHENYLSULFONYL)-1H-INDOL-3-YLBORONIC ACID(129271-98-3)
• EPA Substance Registry System: 1-(PHENYLSULFONYL)-1H-INDOL-3-YLBORONIC ACID(129271-98-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26
• WGK Germany: 3
• Hazardous Substances Data: 129271-98-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-(PHENYLSULFONYL)-1H-INDOL-3-YLBORONIC ACID is used as a key intermediate in the synthesis of various pharmaceutical compounds for its ability to form carbon-carbon bonds through chemoselective cross-coupling reactions. This allows for the creation of complex molecular structures that are essential in the development of new drugs with improved efficacy and selectivity.
Used in Organic Synthesis:
In the realm of organic synthesis, 1-(PHENYLSULFONYL)-1H-INDOL-3-YLBORONIC ACID serves as a versatile building block for the construction of a wide range of organic molecules. Its reactivity in cross-coupling reactions enables the formation of new carbon-carbon bonds, which is crucial for the synthesis of complex organic compounds with potential applications in various fields, such as materials science, agrochemicals, and specialty chemicals.
Used in Chemical Research:
1-(PHENYLSULFONYL)-1H-INDOL-3-YLBORONIC ACID is also utilized in academic and industrial research settings for the investigation of new reaction mechanisms, the development of novel synthetic methods, and the exploration of structure-activity relationships in biologically active molecules. Its unique reactivity and selectivity make it a valuable tool for advancing the understanding of organic chemistry and its applications.

InChI:InChI=1/C14H12BNO4S/c17-15(18)13-10-16(14-9-5-4-8-12(13)14)21(19,20)11-6-2-1-3-7-11/h1-10,17-18H

Upstream product

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• 121-43-7 Trimethyl borate 

Downstream Products

• 183544-32-3 1-Benzenesulfonyl-3-pyridin-3-yl-1H-indole 
• 944347-26-6 C₃₄H₂₄N₂O₄S₂ 
• 1031342-07-0 ethyl N-(tert-butoxycarbonyl)-4-[1-(phenylsulfonyl)-1H-indol-3-yl]-L-phenylalaninate 
• 1050623-68-1 C₂₈H₂₀N₂O₅S 
• 1296269-87-8 4-(1-benzenesulfonyl-1H-indol-3-yl)-3-(methylthio)-1,5-diphenyl-1H-pyrazole 
• 1265905-05-2 N-methoxy-N-methyl-2-(3-(1-(phenylsulfonyl)-1H-indol-3-yl)phenyl)acetamide 
• 1257306-97-0 4-(1-((9-methyl-6-morpholino-2-(1-(phenylsulfonyl)-1H-indol-3-yl)-9H-purin-8-yl)methyl)piperidin-4-yl)morpholine 
• 1257307-09-7 5-(1-benzenesulfonyl-1H-indol-3-yl)-7-morpholin-4-yl-2-(3-morpholin-4-yl-azetidin-1-ylmethyl)-thiazolo[5,4-d]pyrimidine 

Relevant articles and documents

FUNCTIONALISED AND SUBSTITUTED INDOLES AS ANTI-CANCER AGENTS

The present invention relates to anti-tropomyosin compounds, processes for their preparation, and methods for treating or preventing a proliferative disease, preferably cancer, using compounds of the invention.

Computer-aided rational drug design: A novel agent (SR13668) designed to mimic the unique anticancer mechanisms of dietary indole-3-carbinol to block Akt signaling

Indole-3-carbinol (I3C) is a naturally occurring anticancer agent and has entered clinical trials for cancer prevention. However, the clinical development of I3C has been impeded by its poor metabolic profile. The active components of I3C were used to develop a novel class of indole analogs to optimize I3C's anticancer actions, including blocking growth factor-stimulated Akt activation. The most promising of these analogs, SRI3668, exhibited potent oral anticancer activity against various cancers and no significant toxicity.

HETEROARYL SUBSTITUTED PHENYL ISOXAZOLE SULFONAMIDE ENDOTHELIN ANTAGONISTS

Compounds of the formula STR1 inhibit the activity of endothelin.