CAS 72836-33-0 5-(((4-Chlorophenyl)methyl)thio)-1,3,4-thiadiazol-2-amine (HCID 351887)

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Basic information

CAS: 72836-33-0
Standard SMILES: Nc1nnc(SCc2ccc(Cl)cc2)s1
InChIKey: SPABJFQNGHSGMG-UHFFFAOYSA-N
Molecular formula: C9H8ClN3S2
Average molar mass: 257.8 g/mol
Monoisotopic mass: 256.98481694

Overview

5-[(4-chlorophenyl)methylthio]-1,3,4-thiadiazol-2-amine is an aryl sulfide.

Names & identifiers

Preferred name: 5-(((4-Chlorophenyl)methyl)thio)-1,3,4-thiadiazol-2-amine
IUPAC: 5-[(4-chlorophenyl)methylsulfanyl]-1,3,4-thiadiazol-2-amine
English name: 2-Amino-5-(4-chlorobenzylthio)1,3,4-thiadiazole
Molecular formula: C9H8ClN3S2
Molecular weight: 257.76

Names & synonyms

72836-33-05-(((4-Chlorophenyl)methyl)thio)-1,3,4-thiadiazol-2-amine5-[[(4-Chlorophenyl)methyl]thio]-1,3,4-thiadiazol-2-amineRefChem:2990202-Amino-5-[(4-chlorobenzyl)thio]-1,3,4-thiadiazoleRegacin5-[(4-chlorophenyl)methylsulfanyl]-1,3,4-thiadiazol-2-amine5-{[(4-chlorophenyl)methyl]sulfanyl}-1,3,4-thiadiazol-2-amineMFCD001140625-[(4-chlorobenzyl)thio]-1,3,4-thiadiazol-2-amine5-((4-Chlorobenzyl)thio)-1,3,4-thiadiazol-2-amineNSC-523933

Show more names

TIMTEC-BB SBB0055942-Amino-5-(4-chlorobenzylthio)1,3,4-thiadiazole[5-[(4-chlorobenzyl)thio]-1,3,4-thiadiazol-2-yl]amine5-[(4-chlorophenyl)methylthio]-1,3,4-thiadiazol-2-amine

5-[(4-chlorobenzyl)sulfanyl]-1,3,4-thiadiazol-2-ylamine2-amino-5-(4-chlorobenzylthio)-1,3,4-thiadiazole5-[(4-chlorobenzyl)sulfanyl]-1,3,4-thiadiazol-2-amine5-[(4-chlorophenyl)methylthio]-1,3,4-thiadiazole-2-ylamine1,3,4-Thiadiazol-2-amine, 5-[[(4-chlorophenyl)methyl]thio]-NSC523933Oprea1_370904Oprea1_807956

Properties

Computed structural properties

XLogP: 3
Topological polar surface area: 105 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 5
Rotatable bonds: 3
Heavy atoms: 15
Formal charge: 0
Complexity: 200

Physicochemical properties

Melting point: 168 · 168-169 °C(Solv: ethyl acetate (141-78-6))
Boiling point: 443.8 · 443.8±47.0 °C(Predicted)
Density: 1.5 · 1.50±0.1 g/cm3(Predicted)
storage temp.: 2 · 2-8°C
solubility: 100 mg/mL · DMSO: 100mg/mL
pka: 2.41 · 2.41±0.10(Predicted)
form: powder
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
UNSPSC Code: 12352200 · 12352200
Hazard Codes: Xi
WGK Germany: 3 · WGK 3
Hazard Note: Irritant
HS Code: 2934999090 · 2934999090
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Safety data

wgk: WGK 3
hs_code: 2934999090
hazard_code: Xi
hazard_note: Irritant
Storage Class: 11 - Combustible Solids

Chemistry & industry

Applications · 2 items

UsesAn 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.

General DescriptionAn 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.