39088-65-8

Usage

Uses

Used in Pharmaceutical Industry:
4-(mercaptomethyl)benzoic acid is used as a building block for the synthesis of pharmaceuticals due to its ability to form complexes with metals and its reactivity in chemical processes. Its presence in drug molecules can enhance their therapeutic effects and improve their pharmacokinetic properties.
Used in Dye Industry:
In the dye industry, 4-(mercaptomethyl)benzoic acid is utilized as a key intermediate in the production of various dyes. Its chemical structure allows for the creation of dyes with specific color properties and improved stability.
Used in Agrochemical Industry:
4-(mercaptomethyl)benzoic acid serves as a crucial component in the development of agrochemicals, such as pesticides and herbicides. Its metal-complexing ability and reactivity contribute to the effectiveness of these products in agricultural applications.
Used in Chemical and Biological Research:
Due to its unique properties, 4-(mercaptomethyl)benzoic acid is employed in various chemical and biological research applications. It can be used to study the interactions between metal ions and organic compounds, as well as to develop new methods for the synthesis of complex molecules.

InChI:InChI=1/C8H8O2S/c9-8(10)7-3-1-6(5-11)2-4-7/h1-4,11H,5H2,(H,9,10)/p-1

Upstream product

• 26496-94-6 Ethyl 4-(bromomethyl)benzoate 
• 263758-16-3 C₉H₁₀N₂O₂S*ClH 
• 1032290-97-3 4-tritylsulfanylmethyl-benzoic acid 
• 2417-72-3 Methyl 4-(bromomethyl)benzoate 
• 99-94-5 p-Toluic acid 
• 383400-99-5 4-[(4-methoxy-phenyl)-diphenyl-methylsulfanylmethyl]-benzoic acid 
• 75472-97-8 4-(ethoxythiocarbonylthiomethyl)benzoic acid 
• 1642-81-5 p-(chloromethyl)benzoic acid 
• 6232-88-8 4-bromomethylbenzoic Acid 
• 51776-12-6 4-(sulfanylmethyl)benzonitrile 

Downstream Products

• 63684-45-7 C₁₆H₁₄O₄S₂ 
• 1236136-49-4 4-(((2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methylthio)methyl)benzoic acid 
• 1057704-56-9 4-((4-chlorobenzylthio)methyl)benzoic acid 
• 619-66-9 4-Carboxybenzaldehyde 
• 142650-25-7 4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthoylthiomethyl)benzoic acid 
• 132055-68-6 1,10,19,28-tetra<4-(acetylthiomethyl)benzoyl>-1,10,19,28-tetra-azacyclohexatriacontane 
• 132035-68-8 1,10,19,28-tetra<4-(mercaptomethyl)benzoyl>-1,10,19,28-tetra-azacyclohexatriacontane 
• 129018-27-5 4-(acetylthiomethyl)benzoyl chloride 
• 81509-60-6 2,5-bis-(p-bromomethylphenylmethylthiomethyl)thiophen 
• 81509-59-3 2,5-bis-(p-hydroxyphenylmethylthiomethyl)thiophen 
• 149280-80-8 4-{6-((E)-2-Methoxycarbonyl-vinyl)-5-[8-(4-methoxy-phenyl)-octyloxy]-pyridin-2-ylmethanesulfinylmethyl}-benzoic acid methyl ester 
• 149280-79-5 4-{6-((E)-2-Methoxycarbonyl-vinyl)-5-[8-(4-methoxy-phenyl)-octyloxy]-pyridin-2-ylmethylsulfanylmethyl}-benzoic acid methyl ester 
• 536710-95-9 4-tert-butyldisulfanylmethyl-benzoic acid tert-butyl ester 

Relevant academic research and scientific papers

Synthesis and structure-activity relationship of new cytotoxic agents targeting human glutathione-S-transferases

The 6-((7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)thio)hexan-1-ol (NBDHEX, 1), a "suicide inhibitor" of the glutathione-S-transferase GSTP1-1, showed pro-apoptotic properties in tumor cells, but in vivo studies were limited by poor bioavailability and high af finity towards GSTM2-2, expressed in many noncancerous tissues. Here we describe the synthesis and biological characterization of new 1 analogs (2-40), in which the hydroxyhexyl portion at the C4-sulfur atom has been replaced with phenylcontaining moieties as well as substituted alkyl chains. Some of the new compounds displayed 10-100 times increased water-solubility (8, 11, 17, 26-28, 34, 35), and most of them showed higher GSTP1- 1 selectivity (2-20, 23-26, 31-33, 35) than 1. The presence of a phenyl ring with polar substituents is in general associated, with some exceptions (23, 24) to low cytotoxicity in osteosarcoma U-2OS cells. Differently, some alkyl derivatives possess cytotoxicity comparable (26, 34, 35) or higher (30, 32) than 1. Among the novel compounds, selected ones (26, 27, 34, and 35) deserve further investigation for their anticancer potential.

A flexizyme that selectively charges amino acids activated by a water-friendly leaving group

We have developed a new flexizyme (a flexible de novo tRNA acylation ribozyme) system, a pair of amino-derivatized benzyl thioester (ABT) and amino flexizyme (aFx). ABT bearing the ammonium ion was designed to render the acyl-donor substrates better water

Exploring the differential recognition of DNA G-quadruplex targets by small molecules using dynamic combinatorial chemistry

Tuning affinities: Dynamic combinatorial chemistry has been employed to explore the effect of chemical modifications on the DNA G-quadruplex binding properties of anoxazole-based peptide macrocycle. Two dynamic libraries of molecules, containing cationic and carbohydrate motifs, respectively, were screened by using structurally diverse nucleic acid targets (see scheme; each colored shape represents a cation or carbohydrate). (Chemical Equation Presented).

Sulfonylethyl phosphorodiamidates

Sulfonylethyl and thioethyl phosphorodiamidates, their preparation and intermediates in their preparation, formulations containing them, and their pharmaceutical use. The compounds are useful for treating cancer, alone and in combination with other anticancer therapies.

Parallel synthesis of glycomimetic libraries: targeting a C-type lectin.

We have developed methods for the parallel synthesis of two libraries of non-carbohydrate-based analogues of mannose on a solid support. The natural product shikimic acid was used as a key building block. The ability of the compounds to block the binding of the C-type lectin MBP-A to a mannosylated surface was assessed in a high-throughput assay. Ten library members with inhibitory activities equivalent to that of alpha-methyl mannopyranoside were identified. [reaction: see text]

S-4-Methoxytrityl mercapto acids: Synthesis and application

4-Methoxytrityl (Mmt)-mercapto acids were obtained either by the reaction of mercapto acids with Mmt-chloride or by the reaction of halo acids with Mmt-thiol. The derivatives obtained were used in the solid-phase synthesis of small libraries of mercaptoacylamino acids and mercaptoacyl peptides. The removal of the Mmt-group was performed by treatment with trifluoroacetic acid (TFA) in dichloromethane (DCM) using triethylsilane (TES) as scavenger.

(E)-3-[[[[6-(2-Carboxyethenyl)-5-[[8-(4-methoxyphenyl)octyl]oxy]-2- pyridinyl]-methyl]thio]methyl]benzoic acid and related compounds: High affinity leukotriene B4 receptor antagonists

(E)-3-[[[[6-(2-Carboxyethenyl)-5-[[8-(4-methoxyphenyl)octyl]oxy]-2- pyridinyl]-methyl]thio]methyl]benzoic acid (11, SB 201993) is a novel, potent LTB4 receptor antagonist. Compound 11 arose from a structure-activity study of a series of trisubstituted pyridines that demonstrated LTB4 receptor antagonist activity. The placement of an additional methylene unit in the sulfur containing chain linking the pyridine and benzoic acid moieties of lead compound 8 (K(i) = 80 nM) resulted in a greater than 10-fold increase in receptor affinity. Additionally, in this new series of compounds, the oxidation state of the sulfur was found to be critical to the activity, i.e., the sulfoxide and sulfone showed substantially lower affinity for the LTB4 receptor. Compound 11 competitively inhibits the binding of [3H]LTB4 to LTB4 receptors on human polymorphonuclear leukocutes with a K(i) of 7.1 nM and blocks both the LTB4-induced calcium mobilization and the LTB4-induced degranulation responses in these cells with IC50 values of 131 and 271 nM, respectively. Compound 11 demonstrated oral LTB4 antagonist activity as well as topical antiinflammatory activity in the mouse.

Synthesis of Tetranuclear Iron-Sulphur Protein Analogues with Tetrathiol Ligands attached to Macrocycles which provide Intramolecular Hydrophobic Domains

A new type of active-site analogues for 4Fe-4S iron-sulphur proteins is introduced, where the active site core is surrounded by an intramolecular hydrophobic domain formed by a 36-membered ring consisting of a methylene backbone.An efficient synthesis of the macrocyclic ligands 1,10,19,28-tetra(4-mercaptobenzoyl)-1,10,19,28-tetra-azacyclohexatriacontane and 1,10,19,28--1,10,19,28-tetra-azacyclohexatriacontane and 1,10,19,28-tetra-(3-mercapto-3-methylbutanoyl)-1,10,19,28-tetra-azacyclohexatriacontane is described.Their reaction with t)4>2- afforded novel clusters in good yields (70 - 90percent) as black powders with m.p. > 300 deg C.They dissolve in dimethylformamide, dimethyl sulphoxide, and propylene carbonate.Complex formation with Fe4S4 clusters was mainly demonstrated by u.v.-visible and n.m.r. studies and the properties of the new clusters are discussed.

ALKYLAMIDE DERIVATIVES WITH H2-RECEPTOR ANTAGONISTIC AND CYTOPROTECTIVE ACTION

Alkylamide derivatives having the formula, These compounds have a strong antiulcer action depend on histamine H 2-receptor antagonistic action and a cytoprotective action upon gastric mucous membrance.

MACROCYCLIC RING FORMATION IN MICELLES

The influence SDS micelles exert on the course of the chemical reaction initiated by excimer laser photolysis of long-chain bis-dibenzylsulfone detergent molecules is evaluated.In the presence of SDS 3-paracyclophane forms, in the absence of SDS it does not.