4-PHENYL-1,2,3-THIADIAZOLE Chemical Properties

Melting point:

78°C

Boiling point:

100°C 1,5mm

Density 

1.241±0.06 g/cm3(Predicted)

Flash point:

100°C/1.5mm

storage temp. 

Store at -20°C

solubility 

DMF: 3 mg/ml; DMSO: 30 mg/ml; DMSO:PBS (pH 7.2) (1:1): 0.5 mg/ml; Ethanol: 10 mg/ml

form 

A crystalline solid

pka

-4.23±0.22(Predicted)

BRN 

119480

Safety Information

Hazard Codes 

Xi

Safety Statements 

22-24/25

HazardClass 

IRRITANT

HS Code 

29420000

MSDS

• Language:English Provider:ALFA

4-PHENYL-1,2,3-THIADIAZOLE Usage And Synthesis

Description

Cytochrome P450 (CYP450) enzymes are a superfamily of oxidative catalysts important in the biosynthesis and metabolism of a wide range of endogenous molecules as well as the metabolism of xenobiotics. For example, CYP2B4 metabolizes substituted amines, CYP2E1 metabolizes various alcohols and halogenated alkenes, and CYP1A2 catalyzes the oxygenation of aromatic compounds and polycyclic hydrocarbons. 4-phenyl-1,2,3-Thiadiazole is, at 100 μM, a selective inhibitor of certain CYP450 enzymes (CYP2B4, CYP2E1), but not others (CYP1A2), with inactivation occurring in a mechanism-based manner. 1,2,3-Thiadiazole compounds and their derivatives, including 4-phenyl-1,2,3-thiadiazole, are also commonly used as fungicides, herbicides, and plant growth regulators.

Chemical Properties

Off-white to light brown solid

Uses

4-Phenyl-1,2,3-thiadiazole is an CYP2B4 and CYP2E1 inhibitor. 4-Phenyl-1,2,3-thiadiazole inhibits the oxidation of 1-phenylethanol to acetophenone by CYP2B4 and CYP2E1[1].

Synthesis Reference(s)

Journal of Medicinal Chemistry, 28, p. 442, 1985 DOI: 10.1021/jm00382a009

References

[1] Babu BR, et al. 1,2,3-Thiadiazole: a novel heterocyclic heme ligand for the design of cytochrome P450 inhibitors. Biochemistry. 1997 Jun 10;36(23):7209-16. DOI:10.1021/bi9623183

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