7159-68-4

Usage

Type of compound

Synthetic intermediate

Industry application

Pharmaceutical industry

Potential applications

Treatment of cancer, inflammation, and neurological disorders

Structure significance

Valuable building block for synthesis of novel compounds with therapeutic uses

Additional properties

Studied for antibacterial and antifungal properties

Importance

Versatile and significant chemical in medicinal chemistry research

Upstream product

• 62-53-3 aniline 
• 127-17-3 2-oxo-propionic acid 
• 5351-69-9 4-Phenyl-3-thiosemicarbazide 
• 13153-00-9 N⁴-phenyl acetic acid thio-semicarbazide 
• 103-72-0 phenyl isothiocyanate 
• 142-04-1 aniline hydrochloride 
• 75-36-5 acetyl chloride 

Downstream Products

• 110180-40-0 [5-(4-dimethylamino-styryl)-[1,3,4]thiadiazol-2-yl]-phenyl-amine 
• 110439-72-0 5-anilino-2-(4-dimethylamino-styryl)-3-methyl-[1,3,4]thiadiazolium; iodide 

Relevant academic research and scientific papers

Crystal structure of 5-methyl-N-phenyl-1,3,4-thiadiazole-2-amine

The crystal structure of 5-methyl-N-phenyl-1,3,4-thiadiazole-2-amine (I) is determined. The molecule of compound I is non-planar; the mean square plane of its phenyl cycle is located at an angle of 22.8° with respect to the planar thiadiazole fragment. Th

Diazole heterocyclic compound and preparation method and application thereof

The invention relates to the technical field of pesticides, in particular to a diazole heterocyclic compound and a preparation method and application thereof. The diazole heterocyclic compound has anexcellent prevention and treatment effect on plant diseases such as plutella xylostella, myzus persicae and tetranychus urticae, and particularly has a remarkable prevention and treatment effect on plutella xylostella. The compound can be used for preparing insecticides in the fields of agriculture, horticulture and the like and developing novel insecticides without cross resistance, and has goodresearch value and market development prospect.

Selective Functionalization of Aminoheterocycles by a Pyrylium Salt

The functionalization of aminoheterocycles by using a pyrylium tetrafluoroborate reagent (Pyry-BF4) is presented. This reagent efficiently condenses with a great variety of heterocyclic amines and primes the C?N bond for nucleophilic aromatic substitution. More than 60 examples for the formation of C?O, C?N, C?S, or C?SO2R bonds are disclosed herein. In contrast to C?N activation through diazotization and polyalkylation, this method is characterized by its mild conditions and impressive functional-group tolerance. In addition to small-molecule derivatization, Pyry-BF4 allows the introduction of functional groups in a late-stage fashion to furnish highly functionalized structures.

Synthesis of some 1,3,4-thiadiazole derivatives as inhibitors of Entamoeba histolytica

In the quest for potent anti-amoebic agents, some 1,3,4-thiadiazole derivatives were synthesized and characterized by spectral data. The purity of the compounds was confirmed by elemental analysis. All the compounds were screened in vitro against HM1:IMSS strain of Entamoeba histolytica by microdilution method. The results revealed that compounds 1 (IC50 = 0.670 μM), 3 (IC50 = 1.60 μM) and 8 (IC50 = 0.522 μM) had much better anti-amoebic activity than the reference drug metronidazole (IC50 = 1.80 μM). Further, cytotoxicity of the compounds having IC50 value less than metronidazole was assessed by MTT assay on human breast cancer MCF-7 cell line and all the compounds were found low cytotoxic in the concentration range of 2.5-250 μM. Preliminary results indicate that these three compounds (1, 3 and 8) may be subjected to further investigations and it may be hoped that the present study will stimulate efforts towards the development of novel effective anti-amoebic agents.

Bis(1,3,4-thiadiazolo)-1,3,5-triazinium halides: Access to highly substituted aromatic guanidines

The reaction of bis(1,3,4-thiadiazolo)-1,3,5-triazinium halides with primary aromatic amines in CHCl3/Et3N yields new highly substituted aromatic guanidines (up to 90% yield).

Cyclization Reactions of Tricarbonylmethane Thiosemicarbazones: Formation of 1,3,4-Thiadiazole Derivatives with Concomitant C-C Bond Cleavage

Under acylating conditions 3-acetyl-4-hydroxy-2H-pyran-2-one thiosemicarbazones (1a, b and 2a, b) are transformed into 2-(acylamino)-5-methyl-1,3,4-thiadiazoles 3b, c, e, f and 2H-pyran-2-ones 1c and 2c via C-C bond cleavage.Similarly, the reaction of 1b with RCO2H/EtOH (R = Me, Et) affords 2-anilino-5-methyl-1,3,4-thiadiazole (3d) and triacetic acid lactone 1c.Upon treatment with Ac2O/Et3N the dehydroacetic acid derivative 1b is transformed into the thiadiazoline 4, while the benzo derivative 2b is converted into thiadiazole 3e and 4-acetoxycoumarin (2c). - Key Words: 2H-Pyran-2-ones / Coumarins / 1,3,4-Thiadiazoles / Thiosemicarbazones