865488-72-8

Basic information

• Product Name: 4-methyl-N'-(5,6-dichloro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)benzenesulfonylhydrazide
• Synonyms: 4-methyl-N'-(5,6-dichloro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)benzenesulfonylhydrazide
• CAS NO: 865488-72-8
• Molecular Weight: 384.243
• Mol File: 865488-72-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 4-methyl-N'-(5,6-dichloro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)benzenesulfonylhydrazide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-methyl-N'-(5,6-dichloro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)benzenesulfonylhydrazide(865488-72-8)
• EPA Substance Registry System: 4-methyl-N'-(5,6-dichloro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)benzenesulfonylhydrazide(865488-72-8)

Safety Data

• Hazardous Substances Data: 865488-72-8(Hazardous Substances Data)

Upstream product

• 6341-92-0 6-chloroisatin 
• 1677-48-1 5,6-dichloroisatin 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 

Relevant articles and documents

1-Substituted pyrazolo[1,5-c]quinazolines as novel Gly/NMDA receptor antagonists: Synthesis, biological evaluation, and molecular modeling study

A new set of 5,6-dihydro-pyrazolo[1,5-c]quinazoline-2-carboxylates (2-18), bearing different substituents (COOEt, Cl, Br, CH3, and COOH) at position-1, were synthesized in order to investigate the influence of various groups at this specific position on Gly/NMDA receptor affinity and/or selectivity. All the herein reported compounds were evaluated for their binding at the Gly/NMDA, AMPA, and KA receptors. Some selected compounds were also tested for their functional antagonistic activity at both the AMPA and NMDA receptor-ion channels. The results obtained in this study have highlighted that a C-1 lipophilic substituent on the pyrazolo[1,5-c]quinazoline-2-carboxylate core shifts selectivity toward the Gly/NMDA receptor, while a C-1 anionic carboxylate residue is able to increase affinity toward this receptor subtype. In particular, the 2-carboxylic acids 15 and 16, bearing a chlorine atom at position-1, are not only potent (Ki = 0.18 and 0.16 μM, respectively), but also highly Gly/NMDA versus AMPA selective (selectivity ratio > 500). Furthermore, the 1,2-dicarboxylic acids 13 and 14 are endowed with the highest Gly/NMDA receptor binding activity (Ki = 0.09 and 0.059 μM, respectively), among the pyrazoloquinazoline series of derivatives. A molecular modeling study has been carried out to better understand receptor affinity and selectivity of these new pyrazoloquinazoline derivatives.