37643-54-2

Basic information

• Product Name: N-[PHENYL-(TOLUENE-4-SULFONYL)METHYL]FORMAMIDE
• Synonyms: N-[PHENYL-(TOLUENE-4-SULFONYL)METHYL]FORMAMIDE;N-(phenyl(tosyl)methyl)formamide
• CAS NO: 37643-54-2
• Molecular Formula: C₁₅H₁₅NO₃S
• Molecular Weight: 289.3495
• Mol File: 37643-54-2.mol

Chemical Properties

• Melting Point: 144.9-145.2 °C
• Boiling Point: 566.8±50.0 °C(Predicted)
• Appearance: /
• Density: 1.249±0.06 g/cm3(Predicted)
• PKA: 13.15±0.23(Predicted)
• CAS DataBase Reference: N-[PHENYL-(TOLUENE-4-SULFONYL)METHYL]FORMAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-[PHENYL-(TOLUENE-4-SULFONYL)METHYL]FORMAMIDE(37643-54-2)
• EPA Substance Registry System: N-[PHENYL-(TOLUENE-4-SULFONYL)METHYL]FORMAMIDE(37643-54-2)

Safety Data

• Hazardous Substances Data: 37643-54-2(Hazardous Substances Data)

Upstream product

• 14328-12-2 N,N'-benzylidene-bis-formamide 
• 104-15-4 toluene-4-sulfonic acid 
• 100-52-7 benzaldehyde 
• 77287-34-4 formamide 
• 536-57-2 p-toluene sulfinic acid 
• 824-79-3 sodium 4-methylbenzenesulfinate 

Downstream Products

• 850011-53-9 3-formylamino-3-phenyl-propionic acid ethyl ester 
• 1398093-70-3 C₁₉H₂₀N₂O₄ 

Relevant articles and documents

Selective N-Terminal BET Bromodomain Inhibitors by Targeting Non-Conserved Residues and Structured Water Displacement**

Bromodomain and extra-terminal (BET) family proteins, BRD2-4 and T, are important drug targets; however, the biological functions of each bromodomain remain ill-defined. Chemical probes that selectively inhibit a single BET bromodomain are lacking, although pan inhibitors of the first (D1), and second (D2), bromodomain are known. Here, we develop selective BET D1 inhibitors with preferred binding to BRD4 D1. In competitive inhibition assays, we show that our lead compound is 9–33 fold selective for BRD4 D1 over the other BET bromodomains. X-ray crystallography supports a role for the selectivity based on reorganization of a non-conserved lysine and displacement of an additional structured water in the BRD4 D1 binding site relative to our prior lead. Whereas pan-D1 inhibitors displace BRD4 from MYC enhancers, BRD4 D1 inhibition in MM.1S cells is insufficient for stopping Myc expression and may lead to its upregulation. Future analysis of BRD4 D1 gene regulation may shed light on differential BET bromodomain functions.

THERAPEUTIC COMPOUNDS AND METHODS OF USE THEREOF

The invention provides a compound of formula I: or a salt thereof, wherein R1, R2, R3, A, B, D, E, F and G have any of the values described in the specification, as well as compositions comprising a compound of formula I.

Synthesis, characterization and biological activity of bromido[3-ethyl-4-aryl-5-(2-methoxypyridin-5-yl)-1-propyl-1,3-dihydro-2H-imidazol-2-ylidene]gold(i) complexes

Bromido[3-ethyl-4-aryl-5-(2-methoxypyridin-5-yl)-1-propyl-1,3-dihydro-2H-imidazol-2-ylidene]gold(i) complexes (8a-h) with methoxy, methyl and fluorine substituents at different positions of the 4-aryl ring were synthesized and characterized. The relevance of the 2-methoxypyridin-5-yl residue and the substituents at the 4-aryl ring with regard to the activity against a series of cell lines was determined. Particularly against the Cisplatin-resistant ovarian cancer cell line A2780cis, the most active bromido[3-ethyl-4-(4-methoxyphenyl)-5-(2-methoxypyridin-5-yl)-1-propyl-1,3-dihydro-2H-imidazol-2-ylidene]gold(i) complex8cwas more active than Auranofin. It also inhibited thioredoxin reductase more effectively and induced high amounts of reactive oxygen species in A2780cis cells. Furthermore, its influence on non-cancerous SV 80 lung fibroblasts was lower than that of Auranofin. This fact, together with a high accumulation rate in tumor cells, determined on the example of MCF-7 cells, makes this complex an interesting candidate for further extensive studies.

The base-free van Leusen reaction of cyclic imines on water: Synthesis of N-fused imidazo 6,11-dihydro β-carboline derivatives

Construction of imidazoles has been demonstrated on water under base-free conditions. The reaction of dihydro β-carboline imines and p-toluenesulfonylmethyl isocyanides furnished the corresponding substituted N-fused imidazo 6,11-dihydro β-carboline derivatives in very good yields under ambient conditions. The use of deuterium oxide (D2O) as a solvent enabled the incorporation of deuterium isotopes in the imidazole ring.

Catalytic Enantio- and Diastereoselective Mannich Addition of TosMIC to Ketimines

Chiral amines bearing a stereocenter in the α position are ubiquitous compounds with many applications in the pharmaceutical and agrochemical sectors, as well as in catalysis. Catalytic asymmetric Mannich additions represent a valuable method to access such compounds in enantioenriched form. This work reports the first enantio- and diastereoselective addition of commercially available p-toluenesulfonylmethyl isocyanide (TosMIC) to ketimines, affording 2-imidazolines bearing two contiguous stereocenters, one of which is fully-substituted, with high yields and excellent stereocontrol. The reaction, catalyzed by silver oxide and a dihydroquinine-derived N,P-ligand, is broad in scope, operationally simple, and scalable. Derivatization of the products provides enantioenriched vicinal diamines, precursors to NHC ligands and sp3-rich heterocyclic scaffolds. Computations are used to understand catalysis and rationalize stereoselectivity.

COMPOSITIONS FOR THE TREATMENT OF HYPERTENSION AND/OR FIBROSIS

The present invention relates to novel compounds and their use in the prophylactic and/or therapeutic treatment of hypertension and/or fibrosis.

In silico-driven multicomponent synthesis of 4,5- and 1,5-disubstituted imidazoles as indoleamine 2,3-dioxygenase inhibitors

Indoleamine 2,3-dioxygenase is involved in pathological immune escape and has recently become an attractive target for anti-cancer therapy. 4-Phenylimidazole (4-PI) provides a promising starting point for the development of IDO1 inhibitors. With the aim o

Organocatalytic asymmetric synthesis of β-aryl-β-isocyano esters

The asymmetric addition of malonates to in situ generated N-formylimines of aromatic aldehydes was achieved under phase-transfer catalysis using Cinchona alkaloids-derived quaternary ammonium salts. The resulting β- formamidomalonates have been efficientl

KINASE INHIBITORS

ABSTRACT The present invention provides kinase inhibitors of Formula I: .