174502-99-9

Basic information

• Product Name: (1Z)-1-(5-bromothiophen-2-yl)ethanone thiosemicarbazone
• CAS NO: 174502-99-9
• Molecular Formula: C₇H₈BrN₃S₂
• Molecular Weight: 278.1925
• Mol File: 174502-99-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 379.2°C at 760 mmHg
• Flash Point: 183.1°C
• Density: 1.76g/cm³
• Vapor Pressure: 5.95E-06mmHg at 25°C
• Refractive Index: 1.726
• CAS DataBase Reference: (1Z)-1-(5-bromothiophen-2-yl)ethanone thiosemicarbazone(CAS DataBase Reference)
• NIST Chemistry Reference: (1Z)-1-(5-bromothiophen-2-yl)ethanone thiosemicarbazone(174502-99-9)
• EPA Substance Registry System: (1Z)-1-(5-bromothiophen-2-yl)ethanone thiosemicarbazone(174502-99-9)

Safety Data

• Hazardous Substances Data: 174502-99-9(Hazardous Substances Data)

Upstream product

• 5370-25-2 2-Acetyl-5-bromothiophene 
• 79-19-6 thiosemicarbazide 

Relevant articles and documents

M-STAGE KINESIN INHIBITOR

A mitotic kinesin Eg5 inhibitor which comprises a thiadiazoline derivative represented by the general formula (I) or a pharmacologically acceptable salt thereof as an active ingredient: [wherein R1 represents a hydrogen atom and the like, R2 represents a hydrogen atom, -C(=W)R6 (wherein W represents an oxygen atom or a sulfur atom, and R6 represents substituted or unsubstituted lower alkyl and the like) and the like, R3 represents -C(=Z)R19 (wherein Z represents an oxygen atom or a sulfur atom, and R19 represents substituted or unsubstituted lower alkyl and the like) and the like, R4 represents substituted or unsubstituted lower alkyl and the like, and R5 represents substituted or unsubstituted aryl and the like] and the like are provided.

Synthesis and structure-activity relationship study of potent trypanocidal thio semicarbazone inhibitors of the trypanosomal cysteine protease cruzain

American trypanosomiasis, or Chagas' disease, is the leading cause of heart disease in Latin America. Currently there is an urgent need to develop antitrypanosomal therapy due to the toxicity of existing agents and emerging drug resistance. A novel series of potent thio semicarbazone small-molecule inhibitors of the Trypanosoma cruzi cysteine protease cruzain have been identified. Some of these inhibitors have been shown to be trypanocidal. We initially discovered that 3′-bromopropiophenone thio semicarbazone (1i) inhibited cruzain and could cure mammalian cell cultures infected with T. cruzi. 3′-Bromopropiophenone thio semicarbazone showed no toxicity for mammalian cells at concentrations that were trypanocidal. Following this lead, more than 100 compounds were designed and synthesized. A specific structure-activity relationship (SAR) was established, and many potent analogues with IC50 values in the low nanomolar range were identified. Eight additional analogues were trypanocidal in a cell culture assay, and this indicates that aryl thio semicarbazone is a productive scaffold for killing the parasites. Kinetic studies show that these are time-dependent inhibitors. Molecular modeling studies of the enzyme-inhibitor complex have led to a proposed mechanism of interaction as well as insight into the SAR of the thio semicarbazone series. The nonpeptide nature of this series, small size, and extremely low cost of production suggest this is a promising direction for the development of new antitrypanosome chemotherapy.