2002-04-2

Basic information

• Product Name: 2-AMINO-5-(4-PYRIDINYL)-1,3,4-THIADIAZO&
• Synonyms: 1,3,4-Thiadiazol-2-amine, 5-(4-pyridinyl)-;2-Amino-5-(4-piridil)-1,3,4-tiadiazolo;2-Amino-5-(4-piridil)-1,3,4-tiadiazolo [Italian];2-Amino-5-(4-pyridyl)-1,3,4-thiodiazole;4-(2-Amino-1,3,4-thiadiazol-5-yl)pyridine;Pyridine, 4-(2-amino-1,3,4-thiadiazol-5-yl)-;Pyridine, 4-(5-amino-1,3,4-thiadiazol-2-yl)-;2-Amino-5-(pyridin-4-yl)-1,3,4-thiadiazole
• CAS NO: 2002-04-2
• Molecular Formula: C₇H₆N₄S
• Molecular Weight: 178.22
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Thiadiazoles
• Mol File: 2002-04-2.mol

Chemical Properties

• Melting Point: 242-248°C
• Boiling Point: 409.1°Cat760mmHg
• Flash Point: 201.2°C
• Appearance: /
• Density: 1.412g/cm³
• Vapor Pressure: 6.67E-07mmHg at 25°C
• Refractive Index: 1.681
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 1.66±0.10(Predicted)
• CAS DataBase Reference: 2-AMINO-5-(4-PYRIDINYL)-1,3,4-THIADIAZO&(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-5-(4-PYRIDINYL)-1,3,4-THIADIAZO&(2002-04-2)
• EPA Substance Registry System: 2-AMINO-5-(4-PYRIDINYL)-1,3,4-THIADIAZO&(2002-04-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• RTECS: US2168500
• Hazardous Substances Data: 2002-04-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-5-(4-pyridinyl)-1,3,4-thiadiazole is used as a potential active pharmaceutical ingredient for its diverse pharmacological activities. Its presence in the thiadiazole class suggests that it may exhibit antibacterial, antifungal, anti-inflammatory, and anticancer properties, making it a candidate for the development of new drugs in these therapeutic areas.
Used in Chemical Research:
2-Amino-5-(4-pyridinyl)-1,3,4-thiadiazole is used as a subject of study in chemical research to explore its chemical properties and potential applications. The 4-pyridinyl component may offer unique characteristics that could be harnessed in the synthesis of new compounds or materials with specific properties.
Used in Material Science:
2-Amino-5-(4-pyridinyl)-1,3,4-thiadiazole may be used in material science applications, where its chemical properties could be leveraged to develop new materials with tailored properties. The exploration of its potential in this field would require further investigation into its interactions with other compounds and its stability under various conditions.

InChI:InChI=1/C7H6N4S/c8-7-11-10-6(12-7)5-1-3-9-4-2-5/h1-4H,(H2,8,11)

Upstream product

• 14397-24-1 2-(pyridin-4-ylcarbonyl)hydrazinecarbothioamide 
• 3652-14-0 2-acetylamino-5-(4-pyridyl)-1,3,4-thiadiazole 
• 872-85-5 pyridine-4-carbaldehyde 
• 1200-00-6 isonicotinaldehyde thiosemicarbazone 
• 62236-04-8 N-[4-acetyl-5-(pyridin-4-yl)-4,5-dihydro-1,3,4-thiadiazol-2-yl]acetamide 
• 108103-05-5 dithioisonicotinic acid ; potassium-salt 
• 100-48-1 pyridine-4-carbonitrile 
• 79-19-6 thiosemicarbazide 
• 55-22-1 pyridine-4-carboxylic acid 
• 54-85-3 isoniazid 
• 14254-57-0 4-(chlorocarbonyl)pyridine 
• 2290-65-5 trimethylsilyl isothiocyanate 

Downstream Products

• 3652-14-0 2-acetylamino-5-(4-pyridyl)-1,3,4-thiadiazole 
• 1114795-42-4 N-(2,6-difluorobenzoyl)-N'-[5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl]urea 
• 1082430-49-6 1-(4-fluorobenzoyl)-3-[5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl]thiourea 
• 1240521-12-3 (S)-tert-butyl 1-oxo-3-phenyl-1-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-ylamino)propan-2-ylcarbamate 
• 1307738-34-6 C₂₃H₂₅N₅O₅S 
• 1240521-18-9 (S)-3-phenyl-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)-2-(thiazol-4-ylmethylamino)propanamide 
• 1240521-13-4 (S)-2-amino-3-phenyl-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)propanamide 
• 1459140-27-2 1-(4-chloro-3-cyanophenyl)-3-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)urea 
• 1459140-28-3 1-(4-chloro-3-methylphenyl)-3-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)urea 

Relevant articles and documents

Synthesis of a Series of Novel 2-Amino-5-substituted 1,3,4-oxadiazole and 1,3,4-thiadiazole Derivatives as Potential Anticancer, Antifungal and Anti-bacterial Agents

Objective: The objective of the present study was to prepare the 5-substituted 2-amino-1,3,4-oxadiazole and 2-amino-1,3,4-thiadiazole derivatives and evaluate their potential anticancer, antibac-terial and antifungal activities. Methods: Twenty-seven derivatives were synthesized by iodine-mediated cyclization of semicarba-zones or thiosemicarbazones obtained from condensation of semicarbazide or thiosemicarbazide and aldehydes. The structures were confirmed by1H-NMR,13C-NMR and MS spectra. The antibacterial and antifungal activities were evaluated by diffusion method and the anticancer activities were evaluated by MTT assay. Results: Twenty-seven derivatives have been synthesized in moderate to good yields. A number of derivatives exhibited potential antibacterial, antifungal and anticancer activities. Conclusion: Compounds (1b, 1e and 1g) showed antibacterial activity against Streptococcus faecal-is, MSSA and MRSA with MIC value ranging between 4 to 64 μg/mL. Compound (2g) showed anti-fungal activity against Candida albicans (8 μg/mL) and Aspergillus niger (64 μg/mL). Compound (1o) exhibited high cytotoxic activity against HepG2 cell line (IC50 value 8.6 μM) which is compara-ble to the activity of paclitaxel, and is non-toxic on LLC-PK1 normal cell line. The structure activity relationship and molecular docking study of the synthesized compounds have also been reported.

HERBICIDAL COMPOUNDS

Compounds of the formula (I) wherein the substituents are as defined in claim 1, useful as a pesticides, especially as herbicides.

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

Method for preparing 2-amino-5-substituted-1,3,4-thiadiazole

The invention relates to a method for preparing 2-amino-5-substituted-1,3,4-thiadiazole, The method comprises: adding choline chloride and urea into a reaction container according to a formula ratio,and stirring at 80 DEG C to obtain a colorless transparent solution, ie., a eutectic solvent DES; cooling to a room temperature, adding carboxylic acid and thiosemicarbazide according to a formula ratio, slowly heating, reacting at 80 DEG C, and carrying out TLC monitoring until the reaction is finished; cooling the reaction mixed liquid to a room temperature, adding ammonia water into the mixed liquid under ice bath cooling to adjust the pH value to 8-9, precipitating the solid, carrying out suction filtration, washing the filter cake with ice water, and drying to obtain the 2-amino-5-substituted-1,3,4-thiadiazole; and recovering the filtrate to obtain the eutectic solvent capable of being repeatedly used. According to the invention, the method has characteristics of simple operation, simple post-treatment, short reaction time, high efficiency, catalyst recycling, environmental protection, cost reducing and no requirement of organic solvents, and is a method for efficiently synthesizing 2-amino-5-substituted-1,3,4-thiadiazole.

Novel fatty acid-thiadiazole derivatives as potential antimycobacterial agents

The discovery of antibiotics around the middle twentieth century led to a decrease in the interest in antimycobacterial fatty acids. In order to re-establish the importance of naturally abundant fatty acid, a series of fatty acid-thiadiazole derivatives were designed and synthesized based on molecular hybridization approach. In vitro antimycobacterial potential was established by a screening of synthesized compounds against Mycobacterium tuberculosis H37Rv strain. Among them, compounds 5a, 5d, 5h, and 5j were the most active, with compound 5j exhibiting minimum inhibitory concentration of 2.34?μg/ml against M.tb H37Rv. Additionally, the compounds were docked to determine the probable binding interactions and understand the mechanism of action of most active molecules on enoyl-acyl carrier protein reductases (InhA), which is involved in the mycobacterium fatty acid biosynthetic pathway.

N-thiadiazole-4-hydroxy-2-quinolone-3-carboxamides bearing heteroaromatic rings as novel antibacterial agents: Design, synthesis, biological evaluation and target identification

Due to the occurrence of antibiotic resistance, bacterial infectious diseases have become a serious threat to public health. To overcome antibiotic resistance, novel antibiotics are urgently needed. N-thiadiazole-4-hydroxy-2-quinolone-3-carboxamides are a potential new class of antibacterial agents, as one of its derivatives was identified as an antibacterial agent against S. aureus. However, no potency-directed structural optimization has been performed. In this study, we designed and synthesized 37 derivatives, and evaluated their antibacterial activity against S. aureus ATCC29213, which led to the identification of ten potent antibacterial agents with minimum inhibitory concentration (MIC) values below 1 μg/mL. Next, we performed bacterial growth inhibition assays against a panel of drug-resistant clinical isolates, including methicillin-resistant S. aureus, and cytotoxicity assays with HepG2 and HUVEC cells. One of the tested compounds named 1-ethyl-4-hydroxy-2-oxo-N-(5-(thiazol-2-yl)-1,3,4-thiadiazol-2-yl)-1,2-dihydroquinoline-3-carboxamide (g37) showed 2 to 128-times improvement compared with vancomycin in term of antibacterial potency against the tested strains (MICs: 0.25–1 μg/mL vs. 1–64 μg/mL) and an optimal selective toxicity (HepG2/MRSA, 110.6 to 221.2; HUVEC/MRSA, 77.6–155.2). Further, comprehensive evaluation indicated that g37 did not induce resistance development of MRSA over 20 passages, and it has been confirmed as a bactericidal, metabolically stable, orally active antibacterial agent. More importantly, we have identified the S. aureus DNA gyrase B as its potential target and proposed a potential binding mode by molecular docking. Taken together, the present work reports the most potent derivative of this chemical series (g37) and uncovers its potential target, which lays a solid foundation for further lead optimization facilitated by the structure-based drug design technique.

Pyridine and nitro-phenyl linked 1,3,4-thiadiazoles as MDR-TB inhibitors

In the present study, a series of substituted 1,3,4-thiadiazole derivatives 4(a–o), 5(a–m) and 6(a–j) were synthesized and characterized by IR, 1H NMR, 13C NMR and mass spectroscopic technique. The synthesized compounds were evaluate

2-(4-pyridyl)-6-ferrocenyl-imidazo[2,1-b]-1,3,4-thiadiazole preparation method

The present invention discloses a 2-(4-pyridyl)-6-ferrocenyl-imidazo[2,1-b]-1,3,4-thiadiazole preparation method, which comprises: carrying out stirring mixing on 2-amino-5-(4-pyridyl)-1,3,4-thiadiazole, alpha-bromo-acetylferrocene and ethanol; placing the mixed solution in a microwave oven, and carrying out microwave irradiation; after the alpha-bromo-acetylferrocene completely reacts, carrying out a microwave reaction; adding water to the reaction solution, and adjusting the pH value of the reaction solution to 7-8 with a saturated sodium carbonate solution; carrying out suction filtration, washing the filter cake with water, and drying to obtain a crude product; and re-crystallizing with DMF to obtain the target product. According to the present invention, the microwave-assisted synthesis reaction is used so as to substantially shorten the reaction time and improve the reaction efficiency.

Thiadiazolodiazepine analogues as a new class of neuromuscular blocking agents: Synthesis, biological evaluation and molecular modeling study

The synthesis, biological evaluation and molecular modeling study of 6,7-dihydro-[1,3,4] thiadiazolo[3,2-a][1,3]diazepine analogues as new class of neuromuscular blocking agents are described. The new compounds act via competitive mechanism with ACh which

Natural product-inspired rational design, synthesis and biological evaluation of 2,3-dihydropyrano[2,3-f]chromen-4(8H)-one based hybrids as potential mitochondrial apoptosis inducers

Synthesis of novel pyranochromanone amide hybrids, by combining pyranochromanone pharmacophore and privileged scaffolds such as 2-amino-1,3,4-thiadiaole/2-aminothiazole/aminopyridine/aminonaphthalene and anti-cancer evaluation of a series led us to discover a series of new chemical entities (NCEs) showing broad spectrum of anti-cancer activity against three different human cancer cell lines (MCF-7, A549 and HeLa), at IC50values ranging from 14.3 to 97.8?μM. Among them, some compounds such as 15b, 15d, 20a and 20b displayed excellent activity against breast cancer cell line MCF-7. Detailed biological studies such as AO/EB dual staining, Hoechst 33342 staining, FACS analysis of mitochondrial membrane potential (Δψm) using JC-1 dye and DNA fragmentation confirmed the apoptosis induced by the hybrids. Gene expression studies by Real time RT-PCR has shown that these compounds are efficient regulator of anti-apoptotic gene Bcl-2. Western blot analysis also revealed that these compounds persuade apoptosis through intrinsic pathway by up-regulating the pro-apoptotic protein Bax and down-regulating the anti-apoptotic protein Bcl-2. Molecular docking studies reveal that compounds 15b and 20b binds efficiently with Bcl-2 promoter G-quadruplex.