13178-12-6

Usage

Uses

Used in Pharmaceutical Industry:
2-AMINO-5-(4-BROMOPHENYL)-1,3,4-THIADIAZOLE is used as a synthetic intermediate for the development of new pharmaceuticals. Its unique structure allows it to be a key component in the creation of various drug molecules, potentially leading to the discovery of novel therapeutic agents.
Used in Organic Synthesis:
In the field of organic chemistry, 2-AMINO-5-(4-BROMOPHENYL)-1,3,4-THIADIAZOLE is utilized as a building block for the synthesis of a wide range of organic compounds. Its reactive functional groups facilitate its incorporation into complex molecular structures, broadening its applications in material science and chemical research.
Used in Research and Development:
2-AMINO-5-(4-BROMOPHENYL)-1,3,4-THIADIAZOLE is employed as a subject of interest in research settings. Its potential biological and pharmacological activities are being explored, which could lead to advancements in understanding its mechanisms of action and its possible uses in treating various diseases or conditions.

InChI:InChI=1/C8H6BrN3S/c9-6-3-1-5(2-4-6)7-11-12-8(10)13-7/h1-4H,(H2,10,12)

Upstream product

• 586-76-5 4-Bromobenzoic acid 
• 79-19-6 thiosemicarbazide 
• 333-20-0 potassium thioacyanate 
• 1122-91-4 4-bromo-benzaldehyde 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 39631-30-6 2-(4-bromobenzoyl)hydrazinecarbothioamide 
• 586-75-4 4-chlorobenzoyl chloride 
• 623-00-7 4-bromobenzenecarbonitrile 
• 36449-43-1 2-(4-bromobenzylidene)hydrazine carbothioamide 
• 94794-27-1 (2E)-2-[(4-bromophenyl)methylidene]hydrazine-1-carbothioamide 

Downstream Products

• 128627-69-0 2--5-(4-bromophenyl)-1,3,4-thiadiazole 
• 128627-72-5 3-[5-(4-Bromo-phenyl)-[1,3,4]thiadiazol-2-ylamino]-butyric acid 
• 128627-70-3 3-[5-(4-Bromo-phenyl)-[1,3,4]thiadiazol-2-ylamino]-2-methyl-propionic acid 
• 91660-18-3 2-Chloro-5-(4-bromophenyl)-1,3,4-thiadiazole 
• 1060691-87-3 C₂₀H₁₇BrN₄O₃S 
• 1060691-74-8 C₂₀H₁₇BrN₄O₂S 
• 1140322-85-5 C₁₃H₁₅BrN₄O₄S₂ 
• 1073557-80-8 (2R)-N-[5-(4-bromophenyl)-1,3,4-thiadiazol-2-yl]-2-[(benzoyl)-amino]propanamide 
• 1073557-86-4 (2R)-N-[5-(4-bromophenyl)-1,3,4-thiadiazol-2-yl]-2-[(phenylacetyl)amino]propanamide 
• 1072008-41-3 (2R)-N-[5-(4-bromophenyl)-1,3,4-thiadiazol-2-yl]-2-[(phenylsulfonyl)amino]propanamide 
• 1220708-60-0 5-(4-bromophenyl)-N-butyl-1,3,4-thiadiazol-2-amine 
• 1293376-75-6 3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethyl-N-[5-(4-bromophenyl)-1,3,4-thiadiazol-2-yl]cyclopropanecarboxamide 
• 1341231-14-8 (E)-5-(4-bromophenyl)-N-(4-chlorobenzylidene)-1,3,4-thiadiazol-2-amine 
• 1253523-93-1 C₁₅H₁₀BrN₃OS 

Relevant academic research and scientific papers

The balance between hydrogen bonds, halogen bonds, and chalcogen bonds in the crystal structures of a series of 1,3,4-chalcogenadiazoles

In order to explore how specific atom-to-atom replacements change the electrostatic potentials on 1,3,4-chalcogenadiazole derivatives, and to deliberately alter the balance between inter-molecular interactions, four target molecules were synthesized and characterized. DFT calculations indicated that the atom-to-atom substitution of Br with I, and S with Se enhanced the σ-hole potentials, thus increasing the structure directing ability of halogen bonds and chalcogen bonds as compared to intermolecular hydrogen bonding. The delicate balance between these intermolecular forces was further underlined by the formation of two polymorphs of 5-(4-iodophenyl)-1,3,4-thiadiazol-2-amine; Form I displayed all three interactions while Form II only showed hydrogen and chalcogen bonding. The results emphasize that the deliberate alterations of the electrostatic potential on polarizable atoms can cause specific and deliberate changes to the main synthons and subsequent assemblies in the structures of this family of compounds.

Gramine-based structure optimization to enhance anti-gastric cancer activity

Gramine is a natural indole alkaloid with a wide range of biological activities, but its anti-gastric cancer activity is poor. Herein, a pharmacophore fusion strategy was adopted to design and synthesize a new series of indole-azole hybrids on the structural basis of gramine. Based on our previous studies, different nitrogen-containing five-membered heterocyclic rings and terminal alkyne group were introduced into the indole-based scaffold to investigate their effect on improving the anti-gastric cancer activity of gramine derivatives. Structure-activity relationship (SAR) studies highlighted the role played by terminal alkyne in enhancing the inhibitory effect, and compound 16h displayed the best antiproliferative activity against gastric cancer MGC803 cells with IC50 value of 3.74 μM. Further investigations displayed compound 16h could induce mitochondria-mediated apoptosis, and caused cell cycle arrest at G2/M phase. Besides, compound 16h could inhibit the metastasis ability of MGC803 cells. Our studies may provide a new strategy for structural optimization of gramine to enhance anti-gastric cancer activity, and provide a potential candidate for the treatment of gastric cancer.

Synthesis of Emodin Amide Derivatives Containing 1,3,4-Thiadiazole and Their Inhibitory Activity on Vibrio harveyi

A series of new 1,3,4-thiadiazole Emodin amide derivatives were synthesized through the connection of 5-substituted-1,3,4-thiadiazole-2-amine and Emodin carboxylic acids which were obtained by a two-step procedure starting from Emodin. Vibrio harveyi inhibition activities of the newly prepared compounds were evaluated. Results revealed that all compounds showed different degrees of inhibition on V. harveyi. Among them, compound 7a showed the best V. harveyi inhibition effect and the minimum inhibitory concentration (MIC) was 0.0625 mg/mL.

Aryl or heteroaryl substituted thiadiazole compound and antibacterial application thereof

The invention belongs to the technical field of medicines, and particularly relates to an aryl or heteroaryl substituted thiadiazole compound, a preparation method and application thereof as an antibacterial drug. The compound is represented by formula (1

N-(5-phenyl-1, 3, 4-thiadiazole-2-yl) benzamide compound

The invention belongs to the technical field of medicines, relates to a compound with antitumor activity and a specific chemical structure, and in particular relates to an N-((6, 7-dimethoxyquinoline-4-yl) oxy) methyl)-N-(5-phenyl-1, 3, 4-thiadiazole-2-yl) benzamide compound and a preparation method and an application thereof. The structural general formula of the compound is shown in the specification, wherein an R group is mono-substituted or double-substituted phenyl, fluorophenyl, chlorphenyl, bromophenyl, benzyl, benzyloxy, benzene nitro or trifluoromethyl substituted at 2-position, 3-position or 4-position. Pharmacological studies show that the compound provided by the invention has a relatively remarkable proliferation inhibition effect on HER-2 positive breast cancer cells SK-Br-3, the effect is obviously superior to that of HER-2 negative breast cancer cells MCF-7, the compound can be used for preparing antitumor drugs, and a new way is opened up for deep research and development of tumor drugs in the future. The preparation method provided by the invention is simple and feasible, relatively high in yield and easy for large-scale production.

Further insight into the dual COX-2 and 15-LOX anti-inflammatory activity of 1,3,4-thiadiazole-thiazolidinone hybrids: The contribution of the substituents at 5th positions is size dependent

Herin we report the design, synthesis, full characterization and biological investigation of new 15-LOX/COX dual inhibitors based on 1,3-thiazolidin-4-one (15-lipoxygenase pharmacophore) and 1,3,4-thiadiazole (COX pharmacophore) scaffolds. This series of molecular modifications is an extension of a previously reported series to further explore the structural activity relationship. Compounds 3a, 4e, 4n, 4q, 7 and 8 capable of inhibiting 15-LOX at (2.74, 4.2, 3.41, 10.21, 3.71 and 3.36 μM, respectively) and COX-2 at (0.32, 0.28, 0.28, 0.1, 0.28 and 0.27 μM, respectively). The results revealed that binding to 15-LOX and COX is sensitive to the bulkiness of the substituents at the 5 positions. 15-LOX bind better with small substituents, while COXs bind better with bulky substituents. Compounds 3a, 4r and 4q showed comparable in vivo anti-inflammatory activity to the reference drug (celecoxib). The ulcer liability test showed no sign of ulceration which ensures the safe gastric profile. Docking study was performed to explore the possible mode of interaction of the new compounds with the active site of human 15-LOX and COX-2. This study discloses some structural features for binding to 15-LOX and COX, thus pave the way to design anti-inflammatory agents with balanced dual inhibition of these enzymes.

Synthesis of indole-tethered [1,3,4]thiadiazolo and [1,3,4]oxadiazolo[3,2-a]pyrimidin-5-one hybrids as anti-pancreatic cancer agents

New indole-tethered [1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one (8a-j) and [1,3,4]oxadiazolo[3,2-a]pyrimidin-5-one hybrids (9a-e) were synthesized using [4+2] cycloaddition reactions of functionalized 1,3-diazabuta-1,3-dienes with indole-ketenes. All molecul

Design and development of 1,3,5-triazine-thiadiazole hybrids as potent adenosine A2A receptor (A2AR) antagonist for benefit in Parkinson's disease

Various studies showed adenosine A2A receptors (A2ARs) antagonists have profound therapeutic efficacy in Parkinsons Disease (PD) by improving dopamine transmission, thus being active in reversing motor deficits and extrapyramidal symptoms related to the disease. Therefore, in the presents study, we have showed the development of novel 1,3,5-triazine-thiadiazole derivative as potent A2ARs antagonist. In the radioligand binding assay, these molecules showed excellent binding affinity with A2AR compared to A1R, with significant selectivity. Results suggest, compound 7e as most potent antagonist of A2AR among the tested series. In docking analysis with A2AR protein model, compound 7e found to be deeply buried into the cavity of receptor lined via making numerous interatomic contacts with His264, Tyr271, His278, Glu169, Ala63, Val84, Ile274, Met270, Phe169. Collectively, our study demonstrated 1,3,5-triazine-thiadiazole hybrid as a highly effective scaffold for the design of new A2A antagonists.

1,3,4-Thiadiazole-Containing Azo Dyes: Synthesis, Spectroscopic Properties and Molecular Structure

Three series of azo dyes derived from 2-amino-5-aryl-1,3,4-thiadiazoles and aniline, N,N-dimethylaniline and phenol were synthesized in high yields by a conventional diazotization-coupling sequence. The chemical structures of the prepared compounds were confirmed by 1H-NMR, 13C-NMR, IR, UV-Vis spectroscopy, mass spectrometry and elemental analysis. In addition, the X-ray single crystal structure of a representative azo dye was presented. For explicit determination of the influence of a substituent on radiation absorption in UV-Vis range, time-dependent density functional theory calculations were performed.