942-91-6

Usage

Uses

Used in Polymer Synthesis:
2-(Benzothioylthio)acetic acid is used as a reversible addition-fragmentation chain transfer (RAFT) agent for the copolymerization of styrene and divinylbenzene. It is also employed as a chain-transfer agent for the RAFT polymerizations of styrene, methyl methacrylate, and butyl acrylate. Its use in these processes allows for better control over the polymerization reaction, resulting in polymers with desired molecular weights and architectures.
Used in Pharmaceutical Synthesis:
2-(Benzothioylthio)acetic acid is used as a key intermediate in the synthesis of various pharmaceutical compounds. It can be reacted with DL-threonine to produce N-Thiobenzoyl-DL-threonine ethyl ester, which may have potential applications in the development of new drugs. Additionally, it can be used to synthesize Thiobenzoic acid O-esters by reacting with alkoxides and N-Thiobenzoylamino acids by reacting with amino acids, further expanding its utility in the pharmaceutical industry.

InChI:InChI=1/C9H8O2S2/c10-8(11)6-13-9(12)7-4-2-1-3-5-7/h1-5H,6H2,(H,10,11)

Upstream product

• 98-07-7 Benzotrichlorid 
• 100-44-7 benzyl chloride 
• 79-08-3 bromoacetic acid 
• 3926-62-3 sodium monochloroacetic acid 
• 75-15-0 carbon disulfide 
• 108-86-1 bromobenzene 
• 79-11-8 chloroacetic acid 
• 121-68-6 dithiobenzoic acid 
• 100-58-3 phenylmagnesium bromide 
• 100-52-7 benzaldehyde 
• 15563-40-3 N-thiobenzoylpiperidine 

Downstream Products

• 15563-40-3 N-thiobenzoylpiperidine 
• 2032-36-2 Thiobenzmorpholid 
• 679397-19-4 N-nicotinoyl-N'-thiobenzoyl hydrazine 
• 440106-97-8 N-isonicotinoyl-N'-thiobenzoylhydrazine 
• 15482-60-7 N,N-dimethylthiobenzamide 
• 636-04-4 N-Phenylbenzothioamide 
• 13437-75-7 N-Phenyl-N'-thiobenzoyl-hydrazin 
• 10070-07-2 phenyl-thiobenzoylamino-acetic acid 
• 2584-64-7 N-(thiobenzoyl)glycine 
• 35960-95-3 methyl N-(thiobenzoyl)glycinate 
• 5310-14-5 N-methylthiobenzamide 
• 14309-89-8 N-benzyl-benzenecarbothioamide 
• 857942-97-3 N-thiobenzoyl-alanine amide 
• 855264-13-0 phenyl-thiobenzoylamino-acetic acid amide 

Relevant academic research and scientific papers

Interconvertible living radical and cationic polymerization through reversible activation of dormant species with dual activity

The polymerization of vinyl monomers generally requires the selection of an appropriate single intermediate whereas in copolymerization the selection of the comonomer is limited by the intermediate. Herein we propose interconvertible dual active species that can connect comonomers through different mechanisms to produce specific comonomer sequences in a single polymer chain. More specifically two different stimuli that is a radical initiator and a Lewis acid are used to activate the common dormant CSC(S)Z group into radical and cationic species thereby inducing interconvertible radical and cationic copolymerization of acrylate and vinyl ether to produce a copolymer chain that consists of radically and cationically polymerized segments. The dual reversible activation provides control over molecular weights and multiblock copolymers with tunable segment lengths.

Asymmetric catalytic alkynylation of thiazolones and azlactones for synthesis of quaternary α-amino acid precursors

Asymmetric alkynylation of thiazolones and azlactones with alkynylbenziodoxolones as the electrophilic alkyne source catalyzed by thiourea phosphonium salt is described. By using thiazolones as nucleophiles, the desired alkyne functionalized thiazolones were obtained in 55-89% yields with 31-86% ee. Azlactones gave the desired products in comparable yields with lower enantioselectivities. Ring-opening of the alkynylation products led to α,α-disubstituted α-amino acid derivatives efficiently without loss of enantioselectivity.

An efficient one-pot synthesis of 2,5-disubstituted-1,3,4-thiadiazoles from aldehydes and hydrazides using Lawesson’s reagent

Five-membered heterocyclic-ring systems, such as thiadiazoles, remain an important and prevalent scaffold in the development of novel leads in medicinal chemistry for a variety of therapeutic targets. A two-step, one-pot synthesis of 2,5-disubstituted-1,3,4-thiadiazole derivatives from aryl hydrazides and aryl aldehydes using Lawesson’s reagent is described, yielding 2,5-disubstituted-1,3,4-thiadiazoles in moderate-to-high yields. Based on preliminary biological experiments, some of the newly synthesized thiadiazoles show antioxidant activity.

Syntheses and antitumor activities of N′1, N′3-dialkyl-N′1,N′3-di- (alkylcarbonothioyl) malonohydrazide: The discovery of elesclomol

A series of N′1,N′3-dialkyl- N′1,N′3-di(alkylcarbonothioyl) malonohydrazides have been designed and synthesized as anticancer agents by targeting oxidative stress and Hsp70 induction. Structure-activity relationship (SAR) studies lead to the discovery of STA-4783 (elesclomol), a novel small molecule that has been evaluated in a number of clinical trials as an anticancer agent in combination with Taxol.

Synthesis and biological evaluation of 5′-phenyl-3′H-spiro- [indoline-3,2′-[1,3,4]oxadiazol]-2-one analogs

A series of 5′-phenyl-3′H-spiro[indoline-3,2′-[1,3,4] thiadiazol]-2-one analogs were synthesized and their Bcl-2 protein inhibitory activities were studied. The lead compound was originally identified using a fluorescence polarization-based competitive binding assay. Among the 10 compounds investigated, 1k showed good binding affinities to Bcl-xL and Mcl-1, with inhibition constants of 8.9 μmol/L and 3.4 μmol/L, respectively. While compound 1c achieved tight binding affinities to Bcl-xL (Ki = 0.16 μmol/L), has the potential to be a new lead compound.

THERAPEUTIC COMPOUNDS AND METHODS

The invention provides compounds of formula I: and salts thereof. The invention also provides pharmaceutical compositions comprising a compound of formula I, processes for preparing compounds of formula I, intermediates useful for preparing compounds of formula I and therapeutic methods for treating cancer using compounds of formula I.

Porphyrin and galactosyl conjugated micelles for targeting photodynamic therapy

Purpose: To study the targeting and photodynamic therapy efficiency of porphyrin and galactosyl conjugated micelles based on amphiphilic copolymer galactosyl and mono-aminoporphyrin (APP) incoporated poly(2-aminoethyl methacrylate)-polycaprolactone (Gal-APP-PAEMA-PCL). Methods: Poly(2-aminoethyl methacrylate)-polycaprolactone (PAEMA-PCL) was synthesized by the combination of ring opening polymerization and reversible addition-fragmentation chain transfer (RAFT) polymerization, and then Gal-APP-PAEMA-PCL was obtained after conjugation of lactobionic acid and 5-(4-aminophenyl)-10,15,20- triphenylporphyrin (APP) to PAEMA-PCL. The chemical structures of the copolymers were characterized, and their biological properties were evaluated in human laryngeal carcinoma (HEp2) and human hepatocellular liver carcinoma (HepG2) cells. Results: Both APP-PAEMA-PCL and Gal-APP-PAEMA-PCL did not exhibit dark cytotoxicity to HEp2 cells and HepG2 cells. However, Gal-APP-PAEMA-PCL was taken up selectively by HepG2 cells and had the higher phototoxicity effect. Both polymers preferentially localized within cellular vesicles that correlated to the lysosomes. Conclusions: The results indicated that porphyrin and galactosyl conjugated polymer micelles exhibited higher targeting and photodynamic therapy efficacy in HepG2 cells than in HEp2 cells.

5′-Phenyl-3′H-spiro[indoline-3,2′-[1,3,4]thiadiazol]-2-one inhibitors of ADAMTS-5 (Aggrecanase-2)

5′-Phenyl-3′H-spiro[indoline-3,2′-[1,3,4]thiadiazol]-2-one inhibitors of ADAMTS-5 (Aggrecanase-2) have been prepared via commercially available starting materials. Selected compounds 23, 33-35 show sub-micromolar ADAMTS-5 potency and strong SAR trends with selectivity over the related metalloproteases ADAMTS-4 (Aggrecanase-1), MMP12, and MMP13. This series of compounds represents progress toward a selective ADAMTS-5 inhibitor as a disease modifying osteoarthritis drug.

POLYMERIZATION WITH LIVING CHARACTERISTICS

This invention concerns a free radical polymerization process, selected chain transfer agents employed in the process and polymers made thereby, in which the process comprises preparing polymer of general Formula (A) and Formula (B) comprising contacting: (i) a monomer selected from the group consisting of vinyl monomers (of structure CH2═CUV), maleic anhydride, N-alkylmaleimide, N-arylmaleimide, dialkyl fumarate and cyclopolymerizable monomers; (ii) a thiocarbonylthio compound selected from Formula (C) and Formula (D) having a chain transfer constant greater than about 0.1; and (iii) free radicals produced from a free radical source; the polymer of Formula (A) being made by contacting (i), (ii) C and (iii) and that of Formula (B) by contacting (i), (ii) D, and (iii); and (iv) controlling the polydispersity of the polymer being formed by varying the ratio of the number of molecules of (ii) to the number of molecules of (iii); wherein Q, R, U, V, Z, Z′, m, p and q are as defined in the text.

Dithiocarboxylic Acids, Dithiocarboxylic Esters, or Thiocarboxylic Amides by Reaction of Methylene-active Chloromethyl Compounds with Sulfur

With a mixture of sulfur and amine in DMF at room temperature halomethyl compounds (1,5-10) can be oxidized to give thiocarboxylic acids (2,11-16) and their derivatives (3,4,17-35).We studied this reaction in detail especially with chloroacetic derivatives (11-15) or chloromethyl heterocycles (16) formally derived from chloroacetic acid.The resulting thiooxalic acid derivatives (11-27) represent activated acids and very useful C2-synthons, especially for the synthesis of heterocycles.Oxidation in the presence of triethylamine leads to dithiocarboxylates (11-16) which can be alkylated to dithioesters (17-27) in high yields.As a rule, with different primary and secondary amines instead of tertiary amines these dithiocarboxylates or dithiocarboxylic esters can be transformed already at low temperatures to thioamides (28-35).