73282-11-8

Basic information

• Product Name: [1-(PHENYLSULFONYL)-1H-INDOL-2-YL]METHANOL
• Synonyms: 1-PHENYLSULPHONYLINDOLE-2-METHANOL;[1-(PHENYLSULFONYL)-1H-INDOL-2-YL]METHANOL;RARECHEM AL BD 1292;[1-(phenylsulphonyl)-1H-indol-2-yl]methanol;[1-(Phenylsulfonyl)-1h-indol-2-yl]methanol, 95+%
• CAS NO: 73282-11-8
• Molecular Formula: C₁₅H₁₃NO₃S
• Molecular Weight: 287.33
• Mol File: 73282-11-8.mol
• Article Data: 2

Chemical Properties

• Melting Point: 76℃
• Boiling Point: 529.5°C at 760 mmHg
• Flash Point: 274°C
• Appearance: /
• Density: 1.32g/cm³
• Vapor Pressure: 4.84E-12mmHg at 25°C
• Refractive Index: 1.644
• CAS DataBase Reference: [1-(PHENYLSULFONYL)-1H-INDOL-2-YL]METHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: [1-(PHENYLSULFONYL)-1H-INDOL-2-YL]METHANOL(73282-11-8)
• EPA Substance Registry System: [1-(PHENYLSULFONYL)-1H-INDOL-2-YL]METHANOL(73282-11-8)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 73282-11-8(Hazardous Substances Data)

Usage

Description

[1-(PHENYLSULFONYL)-1H-INDOL-2-YL]METHANOL is a chemical compound characterized by a phenylsulfonyl group attached to an indole ring, with a methanol group also connected to the indole ring. [1-(PHENYLSULFONYL)-1H-INDOL-2-YL]METHANOL is known for its unique structure and versatile reactivity, which makes it a valuable intermediate in medicinal chemistry and pharmaceutical research.

Uses

Used in Medicinal Chemistry:
[1-(PHENYLSULFONYL)-1H-INDOL-2-YL]METHANOL is used as a building block for the synthesis of various bioactive molecules. Its phenylsulfonyl group and indole ring contribute to its diverse chemical reactivity, allowing it to participate in a wide range of chemical reactions.
Used in Pharmaceutical Research:
In the field of pharmaceutical research, [1-(PHENYLSULFONYL)-1H-INDOL-2-YL]METHANOL serves as an important intermediate for the preparation of drug candidates and other biologically active compounds. Its unique structure and potential biological activity make it a promising compound for further study and exploration in drug discovery and development.

InChI:InChI=1/C15H13NO3S/c17-11-13-10-12-6-4-5-9-15(12)16(13)20(18,19)14-7-2-1-3-8-14/h1-10,17H,11H2

Upstream product

• 50-00-0 formaldehyd 
• 99275-44-2 2-iodo-1-(phenylsulfonyl)-1H-indole 
• 80360-23-2 1-(phenylsulfonyl)-1H-indole-2-carbaldehyde 
• 40899-71-6 1-benzenesulfonylindole 

Downstream Products

• 143774-54-3 <1-(phenylsulfonyl)indol-2-yl>methyl acetate 
• 337508-54-0 2-(N-benzenesulfonyl)indolyl methyl bromide 
• 773056-59-0 carbamic acid 1-benzenesulfonyl-1H-indol-2-ylmethyl ester 
• 400626-27-9 ethyl (2R,4R)-1-(tert-butoxycarbonyl)-4-[2-(N-benzenesulfonyl)indolyl]methyl D-pyroglutamate 
• 1082828-63-4 C₃₃H₃₂N₂O₃S 

Relevant articles and documents

4-Substituted D-glutamic acid analogues: The first potent inhibitors of glutamate racemase (MurI) enzyme with antibacterial activity

The first potent inhibitors of glutamate racemase (MurI) enzyme that show whole cell antibacterial activity are described. Optically pure 4-substituted D-glutamic acid analogues with (2R,4S) stereochemistry and bearing aryl-, heteroaryl-, cinnamyl-, or biaryl-methyl substituents represent a novel class of glutamate racemase inhibitors. Exploration of the D-Glu core led to the identification of lead compounds (-)-8 and 10. 2-Naphthylmethyl derivative 10 was found to be a potent competitive inhibitor of glutamate racemase activity (Ki = 16 nM, circular dichroism assay; IC50 = 0.1 μg/mL high-performance liquid chromatography (HPLC) assay). Thorough structure-activity relationship (SAR) studies led to benzothienyl derivatives such as 69 and 74 with increased potency (IC50 = 0.036 and 0.01 μg/mL, respectively, HPLC assay). These compounds showed potent whole cell antibacterial activity against S. pneumoniae PN-R6, and good correlation with the enzyme assay. Compounds 69, 74 and biaryl derivative 52 showed efficacy in an in vivo murine thigh infection model against Streptococcus pneumoniae. Data described herein suggest that glutamate racemase may be a viable target for developing new antibacterial agents.