52648-45-0

Basic information

• Product Name: 2-ISOTHIOCYANATOPYRIDINE
• Synonyms: 2-PYRIDYL ISOTHIOCYANATE;2-ISOTHIOCYANATOPYRIDINE;2-Pyridinyl isothiocyanate
• CAS NO: 52648-45-0
• Molecular Formula: C₆H₄N₂S
• Molecular Weight: 136.17
• EINECS: 258-068-4
• Mol File: 52648-45-0.mol

Chemical Properties

• Melting Point: 110-111 °C(Solv: acetone (67-64-1))
• Boiling Point: 253.8°Cat760mmHg
• Flash Point: 107.3°C
• Appearance: /
• Density: 1.14g/cm³
• Vapor Pressure: 0.0286mmHg at 25°C
• Refractive Index: 1.61
• PKA: 0.61±0.19(Predicted)
• CAS DataBase Reference: 2-ISOTHIOCYANATOPYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-ISOTHIOCYANATOPYRIDINE(52648-45-0)
• EPA Substance Registry System: 2-ISOTHIOCYANATOPYRIDINE(52648-45-0)

Safety Data

• Hazardous Substances Data: 52648-45-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
2-ISOTHIOCYANATOPYRIDINE is used as an intermediate in the synthesis of pharmaceuticals and agrochemicals due to its unique chemical reactivity and potential biological activities. Its presence in these industries is attributed to its ability to contribute to the development of new drugs and pesticides with enhanced efficacy.
Used in Fungicide Development:
In the agricultural sector, 2-ISOTHIOCYANATOPYRIDINE is utilized as a potential fungicide, leveraging its antifungal properties to protect crops from fungal infections and diseases, thereby ensuring higher crop yields and quality.
Used in Organic Synthesis and Medicinal Chemistry:
2-ISOTHIOCYANATOPYRIDINE is employed as a key component in organic synthesis and medicinal chemistry, where its unique chemical reactivity allows for the creation of novel compounds with potential therapeutic applications. Its exploration in these fields is driven by the pursuit of innovative treatments and chemical processes.

InChI:InChI=1/C6H4N2S/c9-5-8-6-3-1-2-4-7-6/h1-4H

Upstream product

• 110-89-4 piperidine 
• 1148020-80-7 4-methylphenyl N-(2-pyridyl)thionocarbamate 
• 504-29-0 2-aminopyridine 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 102368-13-8 1,1'-Thiocarbonyldi-2(1H)-pyridone 
• 1212-30-2 1,3-di-pyridin-2-yl-thiourea 
• 54026-17-4 3-(2-pyridyl)-pyrido<1,2-a>-1,3,5-triazine-2,4-dithione 
• 13037-46-2 pyridin-2-yl-dithiocarbamic acid methyl ester 
• 463-71-8 thiophosgene 

Downstream Products

• 1238148-53-2 N-(5-methylisoxazol-3-yl)-4-(3-pyridin-2-ylthioureido)benzenesulfonamide 
• 880-14-8 1-allyl-3-(pyridin-2-yl)thiourea 
• 1418013-03-2 C₁₉H₂₀N₄OS 
• 1418012-67-5 5-phenoxymethyl-4-pyridin-2-yl-4H-[1,2,4]triazole-3-thiol 
• 1289638-28-3 C₁₆H₁₃FN₄OS 
• 1289638-15-8 LDN-193594 
• 1105039-48-2 3-(1-(4-methoxybenzyl)-3-propyl-1H-pyrazol-4-yl)-N-(pyridin-2-yl)-1,2,4-thiadiazol-5-ylamine 
• 1105039-49-3 3-(1-(4-methoxybenzyl)-5-propyl-1H-pyrazol-4-yl)-N-(pyridin-2-yl)-1,2,4-thiadiazol-5-ylamine 
• 30006-95-2 3-Phenyl-pyrido<1,2-a>-1,3,5-triazin-2,4-dion 
• 67041-63-8 2,4-Bis(phenylimino)-3-phenyl-pyrido<1,2-a>-1,2,3-triazin 
• 886-60-2 1-(2'-pyridyl)-3-phenylthiourea 
• 113576-66-2 N-benzyl-N-(2-pyridinyl)benzoylthioacetamide 
• 113576-65-1 N-benzyl-N-(2-pyridinyl)acetothioacetamide 
• 113576-64-0 2-benzoylmethylidene-2H-pyrido<2,3-a><1,2,4>thiadiazole 

Relevant articles and documents

Design and synthesis of a novel series of 4-heteroarylamino-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octanes as α7 nicotinic receptor agonists 2. Development of 4-heteroaryl SAR

Quinuclidine-containing spirooxazolines, as described in the previous report in this series, were demonstrated to have utility as α7 nicotinic acetylcholine receptor (α7 nAChR) partial agonists. In this work, the SAR of this chemotype was expanded to include an array of diazine heterocyclic substitutions. Many of the heterocyclic analogs were potent partial agonists of the α7 receptor, selective against other nicotinic receptors and the serotinergic 5HT3A receptor. (1′S,3′R,4′S)-N-(6-phenylpyrimidin-4-yl)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octan]-2-amine, a potent and selective α7 nAChR partial agonist, was demonstrated to improve cognition in the mouse novel object recognition (NOR) model of episodic memory.

N-aryl-2-aminobenzimidazoles: Novel, efficacious, antimalarial lead compounds

From the phenotypic screening of the AstraZeneca corporate compound collection, N-aryl-2-aminobenzimidazoles have emerged as novel hits against the asexual blood stage of Plasmodium falciparum (Pf). Medicinal chemistry optimization of the potency against Pf and ADME properties resulted in the identification of 12 as a lead molecule. Compound 12 was efficacious in the P. berghei (Pb) model of malaria. This compound displayed an excellent pharmacokinetic profile with a long half-life (19 h) in rat blood. This profile led to an extended survival of animals for over 30 days following a dose of 50 mg/kg in the Pb malaria model. Compound 12 retains its potency against a panel of Pf isolates with known mechanisms of resistance. The fast killing observed in the in vitro parasite reduction ratio (PRR) assay coupled with the extended survival highlights the promise of this novel chemical class for the treatment of malaria.

Synthesis and biological evaluation of arylthiourea derivatives with antitubercular activity

Tuberculosis (TB) is a contagious disease caused by Mycobacterium tuberculosis (M. tuberculosis), and remains one of the most life-threatening plagues for public health in the world. The emergence of drug resistant strains of TB and co-infection with HIV has further complicated TB treatment. Here, the synthesis and characterizaton of a series of compounds were described, and these were followed by evaluating for their antibacterial activity against M. tuberculosis. Several novel arylthiourea derivatives exhibited excellent activity (lowest MIC=0.09 μg/ml) against M. tuberculosis including drug resistant strains of M. tuberculosis. The results suggest that these compounds are promising candidates for new anti-TB agent development.

Structure-activity relationships (SAR) research of thiourea derivatives as dual inhibitors targeting both HIV-1 capsid and human cyclophilin A

HIV-1 capsid (CA) and human cyclophilin A (CypA) play important roles in HIV-1 assembly and disassembly processes, which are critical in HIV-1 replication. Based on the discovery of thiourea derivatives targeting both of the two proteins and indicating effective inhibitory activities in our group, we designed and synthesized a new class of thiourea derivatives. Their abilities to bind to capsid and cyclophilin A were determined by ultraviolet spectroscopic analysis, fluorescence binding affinity, and PPIase inhibition assay. Furthermore, the newly synthesized compounds were tested for their antiviral activities and cytotoxicities using CEM cells. According to the biological evaluation and subsequent molecular docking analyses, we studied the structure-activity relationships of thiourea derivatives. Three optimal compounds (K17, K24, K25) based on the achieved structure-activity relationships would be the basis for future optimization.

Chemistry of aryl n -(2-pyridyi) thionocarbamates in basic media

Three aryl A/-pyridylthionocarbamates were synthesized by thioacylation of 2-aminopyridine and 2-methylaminopyridine with the respective chlorothionoformates. Their hydrolysis mechanism was studied in aqueous basic media. The aryl A/-(2-pyridyl)thionocarb

New potent imidazoisoquinolinone derivatives as anti-Trypanosoma cruzi agents: Biological evaluation and structure-activity relationships

A series of novel benzoimidazo and N-aryl-5-oxo-imidazo[1,2-b]isoquinoline-10-carbothioamides was developed. All the compounds were evaluated for their in vitro action against the epimastigote form of Trypanosoma cruzi. Four of them showed higher activity than Nifurtimox. Their unspecific cytotoxicity was evaluated using HeLa and L6 cells, being non-toxic at concentrations at least 15 and 200 times higher than that of T. cruzi IC50. To gain insight into the mechanism of action, their DNA binding properties and reactivity with glutathione were studied, and QSAR study was performed.

Catalytic enantioselective additions of indoles to nitroalkenes

A new design principle that provides access to more active thiourea catalysts is described. Highly enantioselective additions of indoles to nitroalkenes are reported using a new quinolinium thioamide catalyst. Copyright

BENZAZOLE DERIVATIVES, COMPOSITIONS, AND METHODS OF USE AS AURORA KINASE INHIBITORS

The present invention relates to compounds and methods from the treatment of cancer. The invention provides compounds that inhibit Aurora kinase, pharmaceutical compositions comprising compounds that inhibit Aurora kinase, and methods for the treatment of cancer using the compounds of the presentation invention or pharmaceutical compositions comprising compounds of the present invention.

2-[(2-Aminobenzyl)sulfinyl]-1-(2-pyridyl)-1,4,5,6- tetrahydrocyclopent[d]imidazoles as a novel class of gastric H+/K+-ATPase inhibitors

Substituted 2-sulfinylimidazoles were synthesized and investigated as potential inhibitors of gastric H+/K+-ATPase. The 4,5-unsubstituted imidazole series 6-11 and the 1,4,5,6-tetrahydrocyclopent[d]imidazole series 12 were found to be potent inhibitors of the acid secretory enzyme H+/K+- ATPase. Structure-activity relationships indicate that the substitution of 2- pyridyl groups at the 1-position of the imidazole moiety combined with (2- aminobenzyl)sulfinyl groups at the 2-position leads to highly active compounds with a favorable chemical stability. Other substitution patterns in the imidazole moiety result in reducing biological activities. 2-[(2- Aminobenzyl)sulfinyl]-1-[2-(3-methylpyridyl)]-1,4,5,6- tetrahydrocyclopent[d]imidazole (12h, T-776) was selected for further development as a potential clinical candidate. Extensive study on the acid degradation of 12h indicates a mechanism of action different from that of omeprazole, the first H+/K+-ATPase inhibitor introduced to the market.

Novel [2-(4-piperidinyl)ethyl](thio)ureas: Synthesis and antiacetylcholinesterase activity

A series of 1-ar(o)yl-3-[2-(1-benzyl-4-piperidinyl)ethyl](thio)urea derivatives was synthesized and evaluated for antiacetylcholinesterase activity. Most aroyl(thio)urea derivatives showed potent inhibitory activity in the sub-micromolar range. A comparable potency was obtained with the aryl(thio)urea analogues by replacing the phenyl with a 2-pyridyl group. The substituted guanidine variations proved to be almost inactive whereas the nitroethylene analogues appeared to be quite efficient. These results were interpreted in terms of the preferential cis-trans conformation of the aroyl(thio)urea and 2-pyridyl(thio)urea moieties involving the existence of hydrogen bonding. In vivo experiments showed that compound 7m had maximal antiamnestic activity at 0.03 mg/kg with a therapeutic ratio greater than 1000, while cholinergic side effects were only seen at doses 100-fold the maximally effective antiamnestic dose. Compound 7m represents a potentially interesting antidementia agent.