24255-23-0

Basic information

• Product Name: 5-Chloro-3-phenyl-1,2,4-thiadiazole
• Synonyms: 5-Chloro-3-phenyl-1,2,4-thiadiazole
• CAS NO: 24255-23-0
• Molecular Formula: C₈H₅ClN₂S
• Molecular Weight: 196.66
• Mol File: 24255-23-0.mol
• Article Data: 3

Chemical Properties

• Melting Point: 52 °C
• Boiling Point: 329.5°Cat760mmHg
• Flash Point: 153.1°C
• Appearance: /
• Density: 1.379g/cm³
• Vapor Pressure: 0.00034mmHg at 25°C
• Refractive Index: 1.623
• PKA: -2.43±0.30(Predicted)
• CAS DataBase Reference: 5-Chloro-3-phenyl-1,2,4-thiadiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Chloro-3-phenyl-1,2,4-thiadiazole(24255-23-0)
• EPA Substance Registry System: 5-Chloro-3-phenyl-1,2,4-thiadiazole(24255-23-0)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 24255-23-0(Hazardous Substances Data)

Usage

Description

5-Chloro-3-phenyl-1,2,4-thiadiazole is a heterocyclic chemical compound with the molecular formula C8H5ClN2S. It features a five-membered ring composed of alternating sulfur and nitrogen atoms, along with a chlorine atom and a phenyl group attached to it. 5-Chloro-3-phenyl-1,2,4-thiadiazole is known for its potential biological and pharmacological activities, including anti-inflammatory, antimicrobial, and antitumor properties. Its chemical reactivity and diverse biological activities make it a promising candidate for drug development and medicinal chemistry.

Uses

Used in Pharmaceutical Industry:
5-Chloro-3-phenyl-1,2,4-thiadiazole is used as a building block for the synthesis of various organic compounds and pharmaceuticals. Its unique structure and properties allow it to be incorporated into the development of new drugs with potential therapeutic applications.
Used in Drug Development:
Due to its anti-inflammatory, antimicrobial, and antitumor properties, 5-Chloro-3-phenyl-1,2,4-thiadiazole is used in drug development for the creation of novel therapeutic agents. Its potential to modulate biological processes and target specific pathways makes it a valuable component in the design of new medications.
Used in Medicinal Chemistry:
5-Chloro-3-phenyl-1,2,4-thiadiazole is utilized in medicinal chemistry for the study and development of compounds with potential therapeutic effects. Its chemical reactivity and diverse biological activities contribute to the advancement of research in this field, leading to the discovery of new treatments and interventions for various diseases and conditions.

InChI:InChI=1/C8H5ClN2S/c9-8-10-7(11-12-8)6-4-2-1-3-5-6/h1-5H

Upstream product

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• 594-42-3 chlorothio-trichloro-methane 
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• 73171-46-7 N-Nitroso-3-phenyl-1,2,4-thiadiazol-5-amin 

Downstream Products

• 108015-80-1 methyl-nitroso-(phenyl-[1,2,4]thiadiazol-5-yl)-amine 
• 93567-05-6 4-amino-N-(3-phenyl-[1,2,4]thiadiazol-5-yl)-benzenesulfonamide 
• 1158994-72-9 5-(4-methylpiperazin-1-yl)-3-phenyl-1,2,4-thiadiazole 
• 1158994-84-3 3-phenyl-5-[4-(pyrrolidin-1-yl)piperidin-1-yl]-1,2,4-thiadiazole 
• 1158994-88-7 3-phenyl-5-(4-phenylpiperazin-1-yl)-1,2,4-thiadiazole 
• 568591-60-6 (1-{[(3-phenyl-1,2,4-thiadiazol-5-yl)oxy]methyl}cyclobutyl)methanol 
• 83609-56-7 3-Oxo-2-(3-phenyl-[1,2,4]thiadiazol-5-yl)-butyric acid tert-butyl ester 
• 71879-86-2 2-oxo-8-(3-phenyl-[1,2,4]thiadiazol-5-yl)-nortrop-3-ene-6endo-carboxylic acid methyl ester 
• 71879-86-2 2-oxo-8-(3-phenyl-[1,2,4]thiadiazol-5-yl)-nortrop-3-ene-6exo-carboxylic acid methyl ester 
• 71879-88-4 2-oxo-8-(3-phenyl-[1,2,4]thiadiazol-5-yl)-nortrop-3-ene-6endo-carbonitrile 
• 71879-92-0 3,4-dimethyl-7-(3-phenyl-[1,2,4]thiadiazol-5-yl)-7-aza-bicyclo[4.3.1]deca-3,8-dien-10-one 
• 71880-12-1 8ξ-ethoxy-3,11-bis-(3-phenyl-[1,2,4]thiadiazol-5-yl)-(1rN,2tC¹²,6tC¹²,7cN)-3,11-diaza-tricyclo[5.3.1.1^2,6]dodec-4-ene-10,12-dione 
• 71879-90-8 6endo-phenyl-8-(3-phenyl-[1,2,4]thiadiazol-5-yl)-nortrop-3-en-2-one 
• 17467-34-4 5-(morpholin-4-yl)-3-phenyl-1,2,4-thiadiazole 

Relevant articles and documents

The optimization of xanthine derivatives leading to HBK001 hydrochloride as a potent dual ligand targeting DPP-IV and GPR119

A series of xanthine compounds derived from the previous hit 20i with modification on the terminal side chain was discovered through ring formation strategy. Systematic optimization of the compounds with rigid heterocycles in the hydrophobic side chain led to the new lead compound HBK001 (21h) with the improved DPP-IV inhibition and moderate GPR119 agonism activity in vitro. As a continuing work to further study the PK and PD profiles, 21h and its hydrochloride (22) were synthesized on grams scale and evaluated on the ADME/T and oral glucose tolerance test (OGTT) in ICR mice. Compound 22 showed the improved bioavailability and blood glucose-lowering effect in vivo compared to its free base 21h probably attributed to its improved solubility and permeability. The preliminary toxicity studies on compound 22 exhibited that the result of mini-Ames was negative and the preliminary acute toxicity LD50 in mice was above 1.5 g/kg, while it showed moderate inhibition on hERG channel with IC50 4.9 μM maybe due to its high lipophilicity. These findings will be useful for the future drug design for more potent and safer dual ligand targeting DPP-IV and GPR119 for the treatment of diabetes.

Synthesis, SAR study, and biological evaluation of a series of piperazine ureas as fatty acid amide hydrolase (FAAH) inhibitors

A series of piperazine ureas was designed, synthesized, and evaluated for their potential as novel orally available fatty acid amide hydrolase (FAAH) inhibitors that are therapeutically effective against pain. We carried out an optimization study of the l