5737-78-0

Basic information

• Product Name: 2-{[(Z)-(3-methoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]amino}-6,7-dihydro-1H-indeno[6,7,1-def]isoquinoline-1,3(2H)-dione
• CAS NO: 5737-78-0
• Molecular Formula: C₁₄H₁₁NO₄
• Molecular Weight: 372.3734
• Mol File: 5737-78-0.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 640.8°C at 760 mmHg
• Flash Point: 341.4°C
• Density: 1.47g/cm³
• Vapor Pressure: 2.56E-16mmHg at 25°C
• Refractive Index: 1.746
• CAS DataBase Reference: 2-{[(Z)-(3-methoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]amino}-6,7-dihydro-1H-indeno[6,7,1-def]isoquinoline-1,3(2H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-{[(Z)-(3-methoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]amino}-6,7-dihydro-1H-indeno[6,7,1-def]isoquinoline-1,3(2H)-dione(5737-78-0)
• EPA Substance Registry System: 2-{[(Z)-(3-methoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]amino}-6,7-dihydro-1H-indeno[6,7,1-def]isoquinoline-1,3(2H)-dione(5737-78-0)

Safety Data

• Hazardous Substances Data: 5737-78-0(Hazardous Substances Data)

Upstream product

• 577-19-5 2-nitrophenyl bromide 
• 99768-12-4 4-methoxycarbonylphenylboronic acid 

Downstream Products

• 5737-79-1 methyl 2′-amino-[1,1′-biphenyl]-4-carboxylate 
• 26000-33-9 methyl 9H-carbazole-2-carboxylate 
• 5730-77-8 methyl 2'-amino-[1,1'-biphenyl]-4-carboxylate 

Relevant articles and documents

Design, synthesis, and evaluation of N-phenyl-4-(2-phenylsulfonamido)-benzamides as microtubule-targeting agents in drug-resistant cancer cells, displaying HDAC inhibitory response

Microtubule-targeting agents (MTA) have enjoyed significant clinical success for decades. However, several mechanisms may cause inactivation of such drugs, leading to acquired resistance in patients treated with them. Therefore, drugs containing a stilbene-like skeleton and possessing dual inhibitory activity may provide a new and differentiated treatment for patients to overcome challenging acquired resistance. A new compound (16c) displays promising anticancer activity with GI50 of 22 ± 2 and 12 ± 0.1 nM in vincristine-resistant nasopharyngeal (KB-Vin) cancer cells and etoposide-resistant nasopharyngeal (KB-7D) cancer cells and is better than vincristine, etoposide, ABT-751, and MS-275. A mechanistic study revealed that 16c interferes with the cell cycle distribution and induces cell cycle arrest at the G2/M phase and severe mitotic spindle defects followed by apoptosis. In addition, it produces much more significant cytotoxicity than vincristine and etoposide in the corresponding resistant cells, indicating that it may be a promising candidate to overcome drug resistance in cancer cells. Compound 16c also displays inhibitory activity against HDAC 1 and HDAC 2 with IC50 values of 1.07 μM, and 1.47 μM, respectively. These findings may lead to a new type of structural motif for future development of drugs that could overcome acquired resistance to MTAs.

N-Sulfonyl-aminobiaryls as Antitubulin Agents and Inhibitors of Signal Transducers and Activators of Transcription 3 (STAT3) Signaling

A series of N-sulfonyl-aminobiaryl derivatives have been examined as novel antitubulin agents. Compound 21 [N-(4′-cyano-3′-fluoro-biphenyl-2-yl)-4-methoxy-benzenesulfonamide] exhibits remarkable antiproliferative activity against four cancer cell lines (pancreatic AsPC-1, lung A549, liver Hep3B, and prostate PC-3) with a mean GI50 value of 57.5 nM. Additional assays reveal that 21 inhibits not only tubulin polymerization but also the phosphorylation of STAT3 inhibition with an IC50 value of 0.2 μM. Four additional compounds (8, 10, 19, and 35) are also able to inhibit this phosphorylation. This study describes novel N-sulfonyl-aminobiaryl (biaryl-benzenesulfonamides) as potent anticancer agents targeting both STAT3 and tubulin. (Chemical Equation Presented).