64920-21-4

Basic information

• Product Name: Benzenesulfonamide, N-(4-hydroxy-1-naphthalenyl)-4-methyl-
• CAS NO: 64920-21-4
• Molecular Formula: C17H15NO3S
• Molecular Weight: 313.377
• Mol File: 64920-21-4.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Benzenesulfonamide, N-(4-hydroxy-1-naphthalenyl)-4-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenesulfonamide, N-(4-hydroxy-1-naphthalenyl)-4-methyl-(64920-21-4)
• EPA Substance Registry System: Benzenesulfonamide, N-(4-hydroxy-1-naphthalenyl)-4-methyl-(64920-21-4)

Safety Data

• Hazardous Substances Data: 64920-21-4(Hazardous Substances Data)

Upstream product

• 605-62-9 4-nitro-1-naphthol 
• 86-57-7 1-Nitronaphthalene 
• 2834-90-4 4-amino-1-naphthol 
• 98-59-9 p-toluenesulfonyl chloride 
• 236739-37-0 N-(2,3-dibromo-4-oxo-3,4-dihydro-2H-naphthalen-1-ylidene)-4-methyl-benzenesulfonamide 

Downstream Products

• 139739-77-8 4-p-tolylsulfonylimino-2,2,3,3-tetrachloro-1,2,3,4-tetrahydronaphthalen-1-one 
• 124052-35-3 N-p-tolylsulfonyl-2-chloro-1,4-aminonaphthol 
• 117-80-6 2,3-Dichloro-1,4-naphthoquinone 
• 152509-81-4 N-p-methylbenzenesulfonyl-2-bromo-1,4-naphthoquinone imine 
• 146463-29-8 N-(3-bromo-4-hydroxynaphthalen-1-yl)-4-methylbenzenesulfonamide 
• 139719-08-7 2,3-Dichloro-N-p-tolylsulfonyl-1,4-naphthoquinonemonoimine 
• 70249-49-9 N-(3-chloro-4-oxonaphthalen-1(4H)-ylidene)-4-methyl benzenesulfonamide 
• 36062-30-3 N-p-tolylsulfonyl-1,4-naphthoquinone-4-imine 

Relevant articles and documents

Inhibition of mutated isocitrate dehydrogenase 1 in cancer

Background: R132H mutation of isocitrate dehydrogenase 1 (IDH1) is found in ~75% of low-grade gliomas and secondary glioblastomas as well as in several other types of cancer. More chemotypes of inhibitors of IDH1(R132H) are therefore needed. Objective: The study aimed to develop a new class of IDH1(R132H) inhibitors as potent antitumor agents. Method: A biochemical assay was developed to find inhibitors of IDH1(R132H) mutant enzyme. Chemical synthesis and structure-activity relationship studies were used to find compounds with improved potency. Antitumor activities of selected compounds were evaluated. Results: A series of aromatic sulfonamide compounds was found to be novel, potent inhibitors of IDH1(R132H) with Ki values as low as 0.6 μM. Structure-activity relationships of these compounds are discussed. Enzyme kinetics studies showed that one compound is a competitive inhibitor against the substrate α-KG and a non-competitive inhibitor against the cofactor NADPH. Several inhibitors were found to have no activity against wild-type IDH1, showing a high selectivity. Two potent inhibitors exhibited strong activity against proliferation of BT142 glioma cells with IDH1 R132H mutation, while these compounds did not significantly affect the growth of glioma cells without IDH1 mutation. Conclusion: This novel series of IDH1(R132H) inhibitors have potential to be further developed for the treatment of glioma with IDH1 mutation.

Potential therapeutic application of small molecule with sulfonamide for chondrogenic differentiation and articular cartilage repair

The restoration of damaged articular cartilage is a long-pursued goal in regenerative medicine. Chondrocyte-specific differentiation of mesenchymal stem cells (MSCs) may be an effective means of repairing damaged cartilage. We identified small molecule 6

Discovery of N-(3-((7H-purin-6-yl)thio)-4-hydroxynaphthalen-1-yl)- sulfonamide derivatives as novel protein kinase and angiogenesis inhibitors for the treatment of cancer: Synthesis and biological evaluation. Part III

A novel series of N-(3-((7H-purin-6-yl)thio)-4-hydroxynaphthalen-1-yl)- sulfonamides were designed and synthesized. Biological characterization revealed that several compounds exerted enhanced anti-proliferative activity against human umbilical vein endothelial cells (HUVECs) and several cancer cell lines and high specific protein kinase and angiogenesis inhibitory activities. Compared with our previously synthesized compounds, the substitution of sulfonamide structure for amide fragment played an essential role for the advance of inhibitory activities. In addition, the replacement of 1H-1,2,4-triazole ring by 7H-purine did not result in obvious decrease of inhibition efficacy, indicating that the sulfonamide structure contributes even more to the inhibition efficacy than the 1H-1,2,4-triazole ring. Among these compounds, compound 9n demonstrated comparable in vitro antiangiogenic activities to pazopanib in both HUVEC tube formation assay and the rat thoracic aorta rings (TARs) test. Meanwhile, compound 9n was identified to inhibit Akt1 (IC50 = 1.73 μM) and Abl tyrosine kinase (IC50 = 1.53 μM) effectively.