204513-62-2

Usage

Uses

Used in Organic Synthesis:
4-bromo-2-(methylthio)thiazole is used as a key intermediate in organic synthesis for the production of various chemical compounds. Its unique structure allows for functional group transformations, facilitating the creation of a wide range of molecules with diverse applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-bromo-2-(methylthio)thiazole is utilized as a building block for the synthesis of potential drug candidates. Its presence in these compounds can contribute to their therapeutic properties, making it an essential component in drug discovery and development processes.
Used in Medicinal Chemistry:
4-bromo-2-(methylthio)thiazole is employed as an antimicrobial and antifungal agent in medicinal chemistry. Its ability to combat microorganisms makes it a valuable asset in the development of treatments for various infections and diseases.
Used in Agricultural Chemistry:
In agricultural chemistry, 4-bromo-2-(methylthio)thiazole is used for its antimicrobial and antifungal properties to protect crops from diseases and pests, thereby contributing to increased crop yields and food security.

InChI:InChI=1/C4H4BrNS2/c1-7-4-6-3(5)2-8-4/h2H,1H3

Upstream product

• 4175-77-3 2,4-dibromo-1,3-thiazole 
• 5188-07-8 sodium thiomethoxide 

Downstream Products

• 2103-93-7 2-methylmercapto-4-(4'-bromophenyl)thiazole 
• 41029-86-1 2-Methylthio-4-formylthiazol 

Relevant academic research and scientific papers

Small-molecule anticancer agents kill cancer cells by harnessing reactive oxygen species in an iron-dependent manner

In the course of generating a library of open-chain epothilones, we discovered a new class of small molecule anticancer agents that has no effect on tubulin but instead kills selected cancer cell lines by harnessing reactive oxygen species in an iron-dependent manner. Results of the preliminary studies are consistent with the recently described cell death mechanism ferroptosis. Studies are in progress to confirm ferroptosis as the cell death mechanism and to identify the specific molecular targets of these small molecule anticancer agents.

AZIRIDINE CONTAINING EPOTHILONE ANALOGS, METHODS OF SYNTHESIS, METHODS OF TREATMENT, AND DRUG CONJUGATES

In one aspect, the present disclosure provides epothilone analogs of the formula: (I) wherein the variables are as defined herein. In another aspect, the present disclosure also provides methods of preparing the compounds disclosed herein. In another aspect, the present disclosure also provides pharmaceutical compositions and methods of use of the compounds disclosed herein. Additionally, drug conjugates with cell targeting moieties of the compounds are also provided.

EPOTHILONE ANALOGS, METHODS OF SYNTHESIS, METHODS OF TREATMENT, AND DRUG CONJUGATES THEREOF

In one aspect, the present disclosure provides epothilone analogs of the formula (I) wherein the variables are as defined herein. In another aspect, the present disclosure also provides methods of preparing the compounds disclosed herein. In another aspect, the present disclosure also provides pharmaceutical compositions and methods of use of the compounds disclosed herein. Additionally, drug conjugates with cell targeting moieties of the compounds are also provided.

12,13-Aziridinyl Epothilones. Stereoselective Synthesis of Trisubstituted Olefinic Bonds from Methyl Ketones and Heteroaromatic Phosphonates and Design, Synthesis, and Biological Evaluation of Potent Antitumor Agents

The synthesis and biological evaluation of a series of 12,13-aziridinyl epothilone B analogues is described. These compounds were accessed by a practical, general process that involved a 12,13-olefinic methyl ketone as a starting material obtained by ozonolytic cleavage of epothilone B followed by tungsten-induced deoxygenation of the epoxide moiety. The attachment of the aziridine structural motif was achieved by application of the Ess-Kürti-Falck aziridination, while the heterocyclic side chains were introduced via stereoselective phosphonate-based olefinations. In order to ensure high (E) selectivities for the latter reaction for electron-rich heterocycles, it became necessary to develop and apply an unprecedented modification of the venerable Horner-Wadsworth-Emmons reaction, employing 2-fluoroethoxyphosphonates that may prove to be of general value in organic synthesis. These studies resulted in the discovery of some of the most potent epothilones reported to date. Equipped with functional groups to accommodate modern drug delivery technologies, some of these compounds exhibited picomolar potencies that qualify them as payloads for antibody drug conjugates (ADCs), while a number of them revealed impressive activities against drug resistant human cancer cells, making them desirable for potential medical applications.

Total synthesis of Epothilone E and related side-chain modified analogues via a stille coupling based strategy

A Stille coupling strategy has been utilized to complete a total synthesis of epothilone E from vinyl iodide 7 and thiazole-stannane 8h. The central core fragment 7 and its trans-isomer 11 were prepared from triene 15 using ring-closing metathesis (RCM),