60774-07-4

Upstream product

• 106-44-5 p-cresol 
• 83485-32-9 4-methoxy-3-methylsulfanyl-toluene 
• 95-84-1 3-amino-4-hydroxytoluene 
• 15062-74-5 5-methylbenzo[d][1,3]oxathiol-2-one 
• 83485-33-0 2-methoxy-5-methylbenzenethiol 
• 33931-37-2 bis(2-hydroxy-5-methylphenyl) disulfide 

Downstream Products

• 77065-45-3 2-(5-tert-Butyl-benzo[1,3,2]oxathiaphosphol-2-ylsulfanyl)-4-methyl-phenol 
• 112632-42-5 (2-Cyanomethoxy-5-methyl-phenylsulfanyl)-acetonitrile 
• 99203-96-0 methyl 2-methoxycarbonylmethylthio-4-methylphenoxyacetate 
• 149139-87-7 1-allyloxy-2-allylthio-4-methylbenzene 
• 85591-44-2 3-<(2-hydroxy-5-methylphenyl)thio>-1,2-epoxypropane 
• 7431-33-6 2-methylthio-4-methylphenol 
• 38527-90-1 O-ethyl-S-n-propyl-O-(4-methylmercapto-phenyl)-thiophosphate 
• 172483-48-6 triethylammonium bis(triphenylphosphine)iminium tris(2-mercapto-4-methylphenolato)vanadate(IV) 
• 81717-64-8 1-chloro-3-(2-hydroxy-5-methylphenylthio)-2-propanol 

Relevant academic research and scientific papers

Exploring the influence of the protein environment on metal-binding pharmacophores

The binding of a series of metal-binding pharmacophores (MBPs) related to the ligand 1-hydroxypyridine-2-(1H)-thione (1,2-HOPTO) in the active site of human carbonic anhydrase II (hCAII) has been investigated. The presence and/or position of a single methyl substituent drastically alters inhibitor potency and can result in coordination modes not observed in small-molecule model complexes. It is shown that this unexpected binding mode is the result of a steric clash between the methyl group and a highly ordered water network in the active site that is further stabilized by the formation of a hydrogen bond and favorable hydrophobic contacts. The affinity of MBPs is dependent on a large number of factors including donor atom identity, orientation, electrostatics, and van der Waals interactions. These results suggest that metal coordination by metalloenzyme inhibitors is a malleable interaction and that it is thus more appropriate to consider the metal-binding motif of these inhibitors as a pharmacophore rather than a "chelator". The rational design of inhibitors targeting metalloenzymes will benefit greatly from a deeper understanding of the interplay between the variety of forces governing the binding of MBPs to active site metal ions.

Regiocontrolled carbonylsulfanylations at ortho-position of phenols and at α-position of ketones using chlorocarbonylsulfenyl chloride

Bu3N/AlCl3-promoted [3+2] cyclocondensation between phenols and chlorocarbonylsulfenyl chloride (CCSC; 3) gave 1,3-benzoxathiol-2-ones (2), wherein the acylation of phenols with CCSC (3) and the intramolecular and regioselective ortho-sulfenylation successively proceeded in a one-pot manner. 2-Sulfanylphenols (1) were produced from 2 by mild hydrolysis using NaOH. An analogous Bu3N-promoted [3+2] cyclocondensation between ketones and 3 gave 1,3-oxathioles (7), wherein the α-CH2- position of the ketones was regioselectively sulfenylated.

FORMATION OF BENZOTHIA CROWNS IN REACTION OF THE DIALLYL DERIVATIVE OF 2-MERCAPTO-4-METHYLPHENOL WITH SCl2

The reaction of SCl2 with 1-allyloxy-2-allylthio-4-methylbenzene gave a mixture of 2,9,11,18-tetrachloromethyldi(4-methylbenzo)-1,7,10,13-tetrathia-18-crown-6- and 2,9,11,18-tetrachloromethyldi-(4-methylbenzo)-1,7,10,15-tetrathia-18-crown-6.

SHORT COMMUNICATION SULFONATION AND SULFATION IN THE REACTION OF 4-METHYLPHENOL WITH CONCENTRATED SULFURIC ACID

The sulfonation of 4-methylphenol in concentrated sulfuric acid ranging in concentration from 81.6-112.2percent H2SO4 has been studied.In ca. 98.5percent H2SO4 the initial product is exclusively the 2-sulfonic acid (1-2-S) and the eventual one 1-2,6-S2.In fuming sulfuric acid, the additional products are the cyclic sulfate sulfonate anhydride 2, 2-5-S, and 2-3, 5-S2.Theprecursor of 2-5-S is 2 and that of 2-6-S 1-2,6-S2.In 112.2percent H2SO4 2-5-S yields slowly 2-3,5-S2 (cf.Scheme 1)