| Identification | Back Directory | [Name]
2-AMINO-5-(4-CHLOROBENZYLTHIO)1,3,4-THIADIAZOLE | [CAS]
72836-33-0 | [Synonyms]
TIMTEC-BB SBB005594
2-AMINO-5-(4-CHLOROBENZYLTHIO)1,3,4-THIADIAZOLE
5-((4-CHLOROBENZYL)THIO)-1,3,4-THIADIAZOL-2-AMINE
5-[(4-CHLOROBENZYL)SULFANYL]-1,3,4-THIADIAZOL-2-AMINE
[5-[(4-chlorobenzyl)thio]-1,3,4-thiadiazol-2-yl]amine
5-[(4-CHLOROBENZYL)SULFANYL]-1,3,4-THIADIAZOL-2-YLAMINE
5-[(4-chlorophenyl)methylthio]-1,3,4-thiadiazol-2-amine
1,3,4-Thiadiazol-2-amine, 5-[[(4-chlorophenyl)methyl]thio]-
5-[(4-chlorophenyl)methylsulfanyl]-1,3,4-thiadiazol-2-amine | [Molecular Formula]
C9H8ClN3S2 | [MDL Number]
MFCD00114062 | [MOL File]
72836-33-0.mol | [Molecular Weight]
257.76 |
| Chemical Properties | Back Directory | [Melting point ]
168-169 °C(Solv: ethyl acetate (141-78-6)) | [Boiling point ]
443.8±47.0 °C(Predicted) | [density ]
1.50±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
DMSO: 100mg/mL | [form ]
powder | [pka]
2.41±0.10(Predicted) | [color ]
pale yellow | [InChI]
1S/C9H8ClN3S2/c10-7-3-1-6(2-4-7)5-14-9-13-12-8(11)15-9/h1-4H,5H2,(H2,11,12) | [InChIKey]
SPABJFQNGHSGMG-UHFFFAOYSA-N |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [WGK Germany ]
WGK 3 | [Hazard Note ]
Irritant | [HS Code ]
2934999090 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [Uses]
An orally bioavailable, non-toxic, thio-thiadiazolamine compound that specifically inhibits the DNA-binding capacity of virulence regulator, RegA (IC50 = 1.7 µM in E. coli strain MC4100 (kfc-lacZ, pACYC184-regA), by interacting with amino acid residues within a conserved region of the DNA-binding domain, but without affecting RegA dimerization. Interacts with the double helix-turn-helix (HTH) domain that results in a loss of binding affinity of RegA for its DNA targets. This interaction appears to involve W188 and R223 residues that are conserved in several RegA homologs including ToxT, AggR, RegR, and Rns. Shown to be highly effective in reducing Citrobacter rodentium colonization when administered perorally to mice (~50 mg/kg) either 15 minutes before or 12 hours after bacterial inoculation. Reduces the ability of Rns and RegR to activate the transcription of their target promoters, but does not affect the activity of AggR and ToxT.
Please note that the molecular weight for this compound is batch-specific due to variable water content. | [Definition]
ChEBI: 5-[(4-chlorophenyl)methylthio]-1,3,4-thiadiazol-2-amine is an aryl sulfide. | [General Description]
An orally bioavailable, non-toxic, thio-thiadiazolamine compound that specifically inhibits the DNA-binding capacity of virulence regulator, RegA (IC50 = 1.7 μM in E. coli strain MC4100 (kfc-lacZ, pACYC184-regA), by interacting with amino acid residues within a conserved region of the DNA-binding domain, but without affecting RegA dimerization. Interacts with the double helix-turn-helix (HTH) domain that results in a loss of binding affinity of RegA for its DNA targets. This interaction appears to involve W188 and R223 residues that are conserved in several RegA homologs including ToxT, AggR, RegR, and Rns. Shown to be highly effective in reducing Citrobacter rodentium colonization when administered perorally to mice (~50 mg/kg) either 15 minutes before or 12 hours after bacterial inoculation. Reduces the ability of Rns and RegR to activate the transcription of their target promoters, but does not affect the activity of AggR and ToxT.
Please note that the molecular weight for this compound is batch-specific due to variable water content. | [Biochem/physiol Actions]
Cell permeable: yes |
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