1531-80-2

Usage

Uses

Used in Organic Synthesis:
2-(Benzylsulfanyl)benzenecarboxylic Acid is used as a building block for the synthesis of more complex organic molecules. Its benzyl and carboxylic acid functional groups allow for a variety of reactions, making it a valuable intermediate in the creation of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
2-(Benzylsulfanyl)benzenecarboxylic Acid is used as a key component in the development of new drugs. Its unique structure can be exploited to design molecules with specific biological activities, potentially leading to the discovery of novel therapeutic agents.
Used in Material Science:
2-(Benzylsulfanyl)benzenecarboxylic Acid is used as a precursor in the synthesis of advanced materials, such as polymers and composites, with tailored properties for various applications, including electronics, coatings, and adhesives.

InChI:InChI=1/C14H12O2S/c15-14(16)12-8-4-5-9-13(12)17-10-11-6-2-1-3-7-11/h1-9H,10H2,(H,15,16)/p-1

Upstream product

• 623-11-0 1-methyl-4-nitrosobenzene 
• 855469-12-4 2-(4'-methoxy-3'-nitro-α'-oxo-bibenzyl-α-ylmercapto)-benzoic acid 
• 100-44-7 benzyl chloride 
• 147-93-3 Thiosalicylic acid 
• 5651-35-4 2-phenylbenzo[d]-1,3-oxathiin-4-one 
• 100-39-0 benzyl bromide 
• 88-65-3 2-bromobenzoic-acid 
• 100-53-8 phenylmethanethiol 
• 620-05-3 iodomethylbenzene 
• 100-51-6 benzyl alcohol 
• 98-88-4 benzoyl chloride 
• 65-85-0 benzoic acid 
• 58435-43-1 2-methoxycarbonyl-1-benzylthiobenzene 
• 100-47-0 benzonitrile 

Downstream Products

• 1531-81-3 2-(Benzylsulfanyl)benzoyl chloride 
• 14188-04-6 <2-Dimethylaminoethyl>-2--benzoat 
• 14187-99-6 <3-Dimethylaminopropyl>-2-benzylthiobenzoat 
• 104351-55-5 2-Benzylsulfanyl-N-hydroxy-benzamide 
• 13536-21-5 2-phenylmethanesulfonyl-benzoic acid 
• 54705-19-0 2-(benzylthio)-N-methylbenzamide 
• 58435-43-1 2-methoxycarbonyl-1-benzylthiobenzene 
• 861215-49-8 5-(2-benzylsulfanyl-phenyl)-[1,3,4]oxadiazole-2-thiol 
• 51471-69-3 2-Benzylmercapto-benzoesaeure-hydrazid 
• 15150-04-6 2-(Mercaptobenzyl)-phenylessigsaeure 
• 14200-05-6 <2-Dimethylaminoethyl>-2--phenylacetat 
• 15150-21-7 (3-Dimethylaminopropyl)-2-benzylthio-benzoat 
• 1225284-28-5 [Ru(2,2'-bipyridine)2(2-benzylsulfanyl-benzoato)]PF₆ 
• 1242951-61-6 (2-benzylthiobenzoyl)ferrocene 

Relevant academic research and scientific papers

Synthesis, characterization and antimicrobial activity of copper(II) complexes with some S-alkyl derivatives of thiosalicylic acid. Crystal structure of the binuclear copper(II) complex with S-methyl derivative of thiosalicylic acid

The five new copper(II) complexes with some S-alkyl derivatives of thiosalicylic acid (alkyl = benzyl (L1), methyl (L2), ethyl (L3), propyl (L4), butyl (L5)) have been synthesized and characterized by microanalysis and infrared spectra. The spectroscopica

Cytotoxicity of copper(II)-complexes with some S-alkyl derivatives of thiosalicylic acid. Crystal structure of the binuclear copper(II)-complex with S-ethyl derivative of thiosalicylic acid

The spectroscopically predicted structure of the obtained copper(II)-complex with S-ethyl derivative of thiosalicylic acid was confirmed by X-ray structural study and compared to previously reported crystal structure of the Cu complex with S-methyl deriva

DNA binding and antitumor activities of platinum(IV) and zinc(II) complexes with some S-alkyl derivatives of thiosalicylic acid

A series of complexes of platinum(IV) (C1–C5) and zinc(II) (C6–C10) with S-alkyl derivatives of thiosalicylic acid were prepared and characterized. The interactions of the complexes with calf thymus DNA were analyzed by absorption (UV–Vis) and emission spectral studies (ethidium bromide displacement studies). The cytotoxic activities of complexes C1–C10 were determined against mouse B cell lymphocytic leukemia cells (BCL1), human B-prolymphocytic leukemia (JVM-13), mouse mammary carcinoma cells (4T1), and human mammary carcinoma cells (MDA-MB-468) and compared to the activities of the free ligand precursors and cisplatin. The cytotoxicities of the platinum(IV) and zinc(II) complexes toward mouse tumor cell lines were higher compared with their effects on human tumor cell lines. The zinc(II) complex C9 showed the highest antitumor activity toward the tested human cell lines, while the platinum(IV) complex C4 exhibited the highest antitumor activity toward mouse BCL1 and 4T1 cells. Both C4 and C9 have ligands derived from S-propyl thiosalicylic acid.

Sequential C-H activation enabled expedient delivery of polyfunctional arenes

Modular construction of polyfunctional arenes from abundant feedstocks stands as an unremitting pursue in synthetic chemistry, accelerating the discovery of drugs and materials. Herein, using the multiple C-H activation strategy with versatile imidate esters, the expedient delivery of molecular libraries of densely functionalized sulfur-containing arenes was achieved, which enabled the concise construction of biologically active molecules, such as Bipenamol.

METHOD FOR SYNTHESIZING THIOAURONES

An embodiment of the present invention is a process for producing 2 - benzoic acid compound by reacting a thiosalicylic acid with a strongly basic substance and a benzylhalide. The 2 - methoxy - N N-methyl -2 - benzamides, which are reacted with N - methoxy - N N-methylcarbamoyl chloride to produce N - methoxy-N-methylbenzamides. The N - methoxy - N N-methyl -2 - (benzocyclohexyl) benzamide is treated with arylethynyl salt to prepare 1 - (2- benzocyclohexyl) phenyl -3 - phenyl -2 - profin -1 . The 1 - (2-) phenyl -3 - phenyl -2 - profin -1 - one is treated with an acid material. Provided is a method for preparing a thiouronone compound.

Repositioning Salirasib as a new antimalarial agent

Malaria is a serious tropical disease that kills thousands of people every year, mainly in Africa, due to Plasmodium falciparum infections. Salirasib is a promising cancer drug candidate that interferes with the post-translational modification of Ras. This S-farnesyl thiosalicylate inhibits isoprenylcysteine carboxyl methyltransferase (ICMT), a validated target for cancer drug development. There is a high homology between the human and the parasite enzyme isoforms, in addition to being a druggable target. Looking to repurpose its structure as an antimalarial drug, a collection of S-substituted derivatives of thiosalicylic acid were prepared by introducing 1,2,3-triazole as a diversity entry point or by direct alkylation of the thiol. We further investigated the in vitro toxicity of FTS analogues to Plasmodium falciparum in the asexual stages and in Vero cells. An antiplasmodial activity assay was performed using a simple, high-sensitivity methodology based on nanoluciferase (NLuc)-transfected P. falciparum parasites. The results showed that some of the analogs were active at low micromolar concentration, including Salirasib. The most potent member of the series has S-farnesyl and the 1,2,3-triazole moiety substituted with phytyl. However, the compound substituted with methyl-naphthyl shows promising physicochemical and activity values. The low cytotoxicity in eukaryotic cells of the most active analogs provided good therapeutic indices, being starting-point candidates for future antimalarial drug development.

Design, synthesis and biological activity of selective hCAs inhibitors based on 2-(benzylsulfinyl)benzoic acid scaffold

A large library of derivatives based on the scaffold of 2-(benzylsulfinyl)benzoic acid were synthesised and tested as atypical inhibitors against four different isoforms of human carbonic anhydrase (hCA I, II, IX and XII, EC 4.2.1.1). The exploration of the chemical space around the main functional groups led to the discovery of selective hCA IX inhibitors in the micromolar/nanomolar range, thus establishing robust structure-activity relationships within this versatile scaffold. HPLC separation of some selected chiral compounds and biological evaluation of the corresponding enantiomers was performed along with molecular modelling studies on the most active derivatives.

Synthesis and Crystal Structures of Diaryl Thioethers and Aryl Benzyl Thioethers Derived from Thiosalicylic Acid

Abstract: Reaction of thiosalicylic acid and iodobenzene or 1-fluoro-2-nitrobenzene in the presence of two equiv. of K2CO3 in acetone–water afforded the according diaryl thioethers 1 and 2 bearing carboxyl groups. Treatment of thiosalicylic acid with benzyl bromide-type compounds under similar reaction conditions gave aryl benzyl thioethers 3–8 in excellent yields. Moreover, reactions of thiosalicylic acid and benzyl bromide in the presence of excess K2CO3 led to isolation of compound 9 (Leka et al. in Acta Cryst E69:o285–0286, 2013) through further esterification of the carboxyl group. Crystal structures of 2, 5–7 and 9 (Leka et al. in Acta Cryst E69:o285–0286, 2013), along with their spectroscopic properties are reported. Weak hydrogen-bonding interactions exist in compound 2 and isomers 5–7. Compounds 2 and 7 crystallize in the monoclinic space group P21/n and C2/c, respectively, with a = 12.04(3), b = 7.311(19), C=14.22(4) ?, β = 93.94(3)°, and Z = 4 for 2, and a = 14.934(13), b = 5.116(5), C=33.76(3) ?, β = 91.523(12)°, and Z = 8 for 7. The unit cell of 5 has triclinic P-1 symmetry with the cell parameters a = 5.4334(14), b = 7.7787(19), C=16.488(4) ?, α = 76.601(3)°, β = 86.078(3)°, γ = 70.772(3)°, and Z = 2 for 5. Compound 6 crystallizes in the orthorhombic space group Pbca with a = 15.1881(12), b = 7.3288(6), C=23.7366(19) ?, and Z = 8. Graphical Abstract: Reactions of thiosalicylic acid and a series of aryl- or benzyl halides in the presence of K2CO3 in acetone–water resulted in the formation of according diaryl thioethers and aryl benzyl thioethers in excellent yields.

Cyclic analogue of S-benzylisothiourea that suppresses kynurenine production without inhibiting indoleamine 2,3-dioxygenase activity

Kynurenine is biosynthesised from tryptophan catalysed by indoleamine 2,3-dioxygenase (IDO). The abrogation of kynurenine production is considered a promising therapeutic target for immunological cancer treatment. In the course of our IDO inhibitor programme, formal cyclisation of the isothiourea moiety of the IDO inhibitor 1 afforded the 5-Cl-benzimidazole derivative 2b-6, which inhibited both recombinant human IDO (rhIDO) activity and cellular kynurenine production. Further derivatisation of 2b-6 provided the potent inhibitor of cellular kynurenine production 2i (IC50 = 0.34 μM), which unexpectedly exerted little effect on the enzymatic activity of rhIDO. Elucidation of the mechanism of action revealed that compound 2i suppresses IDO expression at the protein level by inhibiting STAT1 expression in IFN-γ-treated A431 cells. The kynurenine-production inhibitor 2i is expected to be a promising starting point for a novel approach to immunological cancer treatment.

Cytotoxicity of palladium(II) complexes with some alkyl derivates of thiosalicylic acid. Crystal structure of the bis(S-butyl-thiosalicylate)palladium(II) complex, [Pd(S-bu-thiosal)2]

The spectroscopically predicted structure of the obtained bis(S-butyl-thiosalicylate)palladium(II) complex, [Pd(S-bu-thiosal)2], was confirmed by an X-ray structural study. The asymmetric unit of [Pd(S-bu-thiosal)2] consists of neutr