1-(4-Fluorophenyl)-3-(phenylsulfonyl)-1H-pyrrolo[2,3-b]quinoxalin-2-amine - ≥95% , CAS No.374922-43-7

CAS: 374922-43-7 Cat. No.: C274737 Molecular Weight: 418.44

GRADE & PURITY ≥95%

Synonyms

SCHEMBL3483653 | ZPA92243 | Oprea1_667095 | SIRT1 Activator II | BDBM50193077 | F1204 | BCP32626 | MFCD02236691 | STL303186 | 3-(benzenesulfonyl)-1-(4-fluorophenyl)pyrrolo[3,2-b]quinoxalin-2-amine | AKOS016397864 | DTXSID00365601 | CAY-10602; CAY 10602 |

Storage

Protected from light,Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

Overview

A cell-permeable pyrroloquinoxaline compound that acts as a reversible SIRT1 activator (10 µM causes ~2.3-fold fluorescent enhancement in a fluorescent assay using hrSIRT1) and enhances fat mobilization in fully differentiated 3T3L1 fibroblasts. Shown to inhibit LPS-induced TNF-α release in THP-1 cells by ~10-fold more potent than resveratrol

Specifications

Synonyms

SCHEMBL3483653 | ZPA92243 | Oprea1_667095 | SIRT1 Activator II | BDBM50193077 | F1204 | BCP32626 | MFCD02236691 | STL303186 | 3-(benzenesulfonyl)-1-(4-fluorophenyl)pyrrolo[3, 2-b]quinoxalin-2-amine | AKOS016397864 | DTXSID00365601 | CAY-10602; CAY 10602 |

Specifications & Purity

≥95%

Biochemical and Physiological Mechanisms

SIRT1 Activator. Suppresses NF-κB-dependent induction of TNF-α by LPS (IC 70 = 60 μM, THP-1 cells). Upregulates PPARδ-mediated transcription in ECs.

Storage

Protected from light, Store at -20°C, Desiccated

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

ACTIVATOR

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥95%

Names and Identifiers

• Pubchem Sid: 504760653
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504760653
• Canonical Smiles: C1=CC=C(C=C1)S(=O)(=O)C2=C(N(C3=NC4=CC=CC=C4N=C23)C5=CC=C(C=C5)F)N
• IUPAC Name: 3-(benzenesulfonyl)-1-(4-fluorophenyl)pyrrolo[3,2-b]quinoxalin-2-amine
• InChIKey: CSFVFDHRYKBBPD-UHFFFAOYSA-N
• INCHI: 1S/C22H15FN4O2S/c23-14-10-12-15(13-11-14)27-21(24)20(30(28,29)16-6-2-1-3-7-16)19-22(27)26-18-9-5-4-8-17(18)25-19/h1-13H,24H2
• Isomeric SMILES: C1=CC=C(C=C1)S(=O)(=O)C2=C(N(C3=NC4=CC=CC=C4N=C23)C5=CC=C(C=C5)F)N
• Molecular Weight: 418.44
• Reaxy-Rn: 33537479
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=33537479&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Pyrroles
      • Subclass Substituted pyrroles

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Pyrroles
• Subclass: Substituted pyrroles
• Intermediate Tree Nodes: Not available
• Direct Parent: Phenylpyrroles
• Alternative Parents: Quinoxalines Pyrrolopyrazines Benzenesulfonyl compounds Fluorobenzenes Pyrazines Aryl fluorides Sulfones Heteroaromatic compounds Azacyclic compounds Primary amines Organopnictogen compounds Organofluorides Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: 1-phenylpyrrole - Diazanaphthalene - Quinoxaline - Benzenesulfonyl group - Pyrrolopyrazine - Fluorobenzene - Halobenzene - Aryl fluoride - Aryl halide - Monocyclic benzene moiety - Benzenoid - Pyrazine - Heteroaromatic compound - Sulfonyl - Sulfone - Azacycle - Amine - Primary amine - Organosulfur compound - Organonitrogen compound - Organofluoride - Organohalogen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as phenylpyrroles. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrole ring through a CC or CN bond.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

AOX1 Tchem Aldehyde oxidase (429 Activities)

Discover Target: AOX1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in DMSO to 25 mM
• Sensitivity: light & heat sensitive
• Melt Point(°C): 270 °C
• Molecular Weight: 418.400 g/mol
• XLogP3: 4.500
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 418.09 Da
• Monoisotopic Mass: 418.09 Da
• Topological Polar Surface Area: 99.300 Ų
• Heavy Atom Count: 30
• Formal Charge: 0
• Complexity: 702.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1