942-70-1

Basic information

• Product Name: 2-AMINO-5-(4-FLUOROPHENYL)-1 3 4-THIADI&
• Synonyms: 2-AMINO-5-(4-FLUOROPHENYL)-1 3 4-THIADI&;1,3,4-Thiadiazol-2-amine, 5-(4-fluorophenyl)-;5-(4-fluorophenyl)-1,3,4-thiadiazol-2-amine(SALTDATA: FREE);5-(4-Fluorophenyl)-1,3,4-thiadiazol-2-amine, 1-(5-Amino-1,3,4-thiadiazol-2-yl)-4-fluorobenzene;2-Amino-5-(4-fluorophenyl)-1,3,4-thiadiazole 97%
• CAS NO: 942-70-1
• Molecular Formula: C₈H₆FN₃S
• Molecular Weight: 195.22
• Product Categories: API intermediates;Building Blocks;Chemical Synthesis;Fluorinated Building Blocks;Heterocyclic Building Blocks;Heterocyclic Fluorinated Building Blocks;Other Fluorinated Heterocycles;Thiadiazoles
• Mol File: 942-70-1.mol

Chemical Properties

• Melting Point: 238-243 °C
• Boiling Point: 351.9 °C at 760 mmHg
• Flash Point: 166.6 °C
• Appearance: /
• Density: 1.423 g/cm³
• Vapor Pressure: 3.98E-05mmHg at 25°C
• Refractive Index: 1.643
• CAS DataBase Reference: 2-AMINO-5-(4-FLUOROPHENYL)-1 3 4-THIADI&(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-5-(4-FLUOROPHENYL)-1 3 4-THIADI&(942-70-1)
• EPA Substance Registry System: 2-AMINO-5-(4-FLUOROPHENYL)-1 3 4-THIADI&(942-70-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 942-70-1(Hazardous Substances Data)

Usage

Uses

Used in Dye Synthesis:
2-Amino-5-(4-fluorophenyl)-1,3,4-thiadiazole is used as a substrate in the preparation of bithiophene-based azo dyes, which possess potential nonlinear optical (NLO) properties. These dyes can be utilized in various applications, such as optical data storage, optical communication, and photonic devices, due to their ability to manipulate light at the molecular level.
Used in Pharmaceutical Industry:
2-Amino-5-(4-fluorophenyl)-1,3,4-thiadiazole is used as a key intermediate in the synthesis of 4-thiazolidinone derivatives. These derivatives have been identified as potent inhibitors of the Hepatitis C Virus (HCV) NS5B polymerase, an essential enzyme in the viral replication process. By inhibiting this enzyme, these derivatives can help in the development of antiviral drugs to treat Hepatitis C.
Used in Antitubercular Drug Development:
2-Amino-5-(4-fluorophenyl)-1,3,4-thiadiazole is also used in the synthesis of 1,3,4-thiadiazole and phenothiazine hybrids, which have shown potential as antitubercular agents. These hybrids target Mycobacterium tuberculosis, the causative agent of tuberculosis, and can be used in the development of new drugs to combat this infectious disease.

InChI:InChI=1/C8H6FN3S/c9-6-3-1-5(2-4-6)7-11-12-8(10)13-7/h1-4H,(H2,10,12)

Upstream product

• 459-57-4 4-fluorobenzaldehyde 
• 79-19-6 thiosemicarbazide 
• 403-43-0 4-fluorobenzoyl chloride 
• 403-33-8 methyl 4-flurobenzoate 
• 456-22-4 4-Fluorobenzoic acid 
• 2290-65-5 trimethylsilyl isothiocyanate 
• 456-06-4 4-fluorobenzoyl hydrazide 
• 333-20-0 potassium thioacyanate 
• 459-38-1 (4-fluorobenzylidenehydrazinyl)thiocarboxamide 
• 831-38-9 2-(4-fluorobenzoyl)hydrazinecarbothioamide 

Downstream Products

• 70038-95-8 N-[5-(4-fluoro-phenyl)-[1,3,4]thiadiazol-2-yl]-acetamidine 
• 980-45-0 4-acetylamino-N-[5-(4-fluoro-phenyl)-[1,3,4]thiadiazol-2-yl]-benzenesulfonamide 
• 1374152-05-2 C₁₅H₈FN₃OSSe 
• 1313411-39-0 C₂₄H₁₈FN₃OS₂ 
• 1313411-40-3 C₂₄H₁₈FN₃O₂S 
• 1313411-41-4 C₂₃H₁₆FN₃OS 
• 1402070-33-0 (E)-2-(2,2'-bithiophen-5-yldiazenyl)-5-(4-fluorophenyl)-1,3,4-thiadiazole 
• 1431555-43-9 4-[[5-(4-fluorophenyl)-1,3,4-thiadiazol-2-ylimino]-methyl]phenol 
• 1338084-08-4 C₁₃H₈FN₅O₂S 
• 1338083-74-1 C₁₃H₉FN₆O₂S 
• 1338084-29-9 C₁₈H₁₇FN₆O₃S 
• 1338083-96-7 C₁₅H₁₂FN₅O₂S 
• 954142-31-5 C₁₉H₂₁FN₃O₃PS 
• 907178-54-5 C₁₅H₁₀FN₃S 

Relevant articles and documents

COMPOUNDS HAVING PDE9A INHIBITORY ACTIVITY, AND PHARMACEUTICAL USES THEREOF

The present invention provides a compound having a specific chemical structure and having PDE9A inhibitory activity, or a pharmaceutically acceptable salt thereof. The present invention provides a composition containing the compound or a pharmaceutically acceptable salt thereof. The present invention provides a pharmaceutical use, for treating or preventing PDE9A-related diseases, of the compound according to the present invention, a salt thereof, and a composition containing the compound or salt. The present invention also provides a method for treating or preventing PDE9A-related diseases, the method comprising administering an effective amount of the compound according to the present invention, a salt thereof, or a composition containing the compound or salt to a subject in need of treatment.

Synthesis and preliminary anticancer activity assessment of n-glycosides of 2-amino-1,3,4-thiadiazoles

The addition of 2-amino-1,3,4-thiadiazole derivatives with parallel iodination of differ-ently protected glycals has been achieved using a double molar excess of molecular iodine under mild conditions. The corresponding thiadiazole derivatives of N-glycosides were obtained in good yields and anomeric selectivity. The usage of iodine as a catalyst makes this method easy, inexpen-sive, and successfully useable in reactions with sugars. Thiadiazole derivatives were tested in a panel of three tumor cell lines, MCF-7, HCT116, and HeLa. These compounds initiated biological response in investigated tumor models in a different rate. The MCF-7 is resistant to the tested com-pounds, and the cytometry assay indicated low increase in cell numbers in the sub-G1 phase. The most sensitive are HCT-116 and HeLa cells. The thiadiazole derivatives have a pro-apoptotic effect on HCT-116 cells. In the case of the HeLa cells, an increase in the number of cells in the sub-G1-phase and the induction of apoptosis was observed.

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.

Synthesis, docking, and biological evaluation of thiazolidinone derivatives against hepatitis C virus genotype 4a

Hepatitis C virus (HCV) genotype 4a (GT4a) is prevalent in Egypt. It did not gain the necessary scientific focus despite its high resistance. Since the crystal structure NS5B (RNA-dependent RNA polymerase) of HCV GT4a has not been resolved until now, homology modeling was conducted to build and validate the 3D model of the enzyme. Ligand binding sites including the allosteric thumb II pocket were detected and used in lead optimization. Sixty new 4-thiazolidinone derivatives have been virtually designed and docked into thumb II site of HCV NS5B GT4a using rigid docking approach. Eighteen compounds (7a–r) that show good docking scores were synthesized and tested in vitro against NS5B GT4a. Compounds 7b and 7n showed the best inhibitory activity (IC50 = 0.338 and 0.342 μM, respectively). Compounds 7a, 7b, 7c, 7d, 7k, 7n, 7q, and 7r that have IC50 values less than 2 μM were assessed for cellular anti-HCV GT4a activity using human hepatoma cell line (Huh 7.5). The percentages of viral growth inhibition are between 79.67 and 94.77%. Compound 7b is the most active in the in vitro and cellular assays and could be considered a potential new lead for future anti-HCV studies. [Figure not available: see fulltext.]

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.

Antitubercular polyhalogenated phenothiazines and phenoselenazine with reduced binding to CNS receptors

Targeting energy metabolism in Mycobacterium tuberculosis (Mtb) is a new paradigm in the search for innovative anti-TB drugs. NADH:menaquinone oxidoreductase is a non-proton translocating type II NADH dehydrogenase (NDH-2) that is an essential enzyme in the respiratory chain of Mtb and is not found in mammalian mitochondria. Phenothiazines (PTZs) represent one of the most known class of NDH-2 inhibitors, but their use as anti-TB drugs is currently limited by the wide range of potentially serious off-target effects. In this work, we designed and synthesized a series of new PTZs by decorating the scaffold in an unconventional way, introducing various halogen atoms. By replacing the sulfur atom with selenium, a dibromophenoselenazine 20 was also synthesized. Among the synthesized poly-halogenated PTZs (HPTZs), dibromo and tetrachloro derivatives 9 and 11, along with the phenoselenazine 20, emerged with a better anti-TB profile than the therapeutic thioridazine (TZ). They targeted non-replicating Mtb, were bactericidal, and synergized with rifampin and bedaquiline. Moreover, their anti-TB activity was found to be related to the NDH-2 inhibition. Most important, they showed a markedly reduced affinity to dopaminergic and serotonergic receptors respect to the TZ. From this work emerged, for the first time, as the poly-halogenation of the PTZ core, while permitting to maintain good anti-TB profile could conceivably lead to fewer CNS side-effects risk, making more tangible the use of PTZs for this alternative therapeutic application.

Synthesis and trypanocidal activity of novel pyridinyl-1,3,4-thiadiazole derivatives

Herein, we present the design, synthesis and trypanocidal evaluation of sixteen new 1,3,4-thiadiazole derivatives from N-aminobenzyl or N-arylhydrazone series. All derivatives were assayed against the trypomastigote form of Trypanosoma cruzi, showing IC50 values ranging from 3 to 226 μM, and a better trypanocidal profile was demonstrated for the 1,3,4-thiadiazole-N-arylhydrazones (3a-g). In this series, the 2-pyridinyl fragment bound to the imine subunit of the hydrazine moiety presented pharmacophoric behavior for trypanocidal activity. Compounds 2a, 11a and 3e presented remarkable activity and excellent selectivity indexes. Compound 2a was also active against the intracellular amastigote form of T. cruzi. Moreover, its corresponding hydrochloride, compound 11a, showed the most promising profile, producing phenotypic changes similar to those caused by posaconazole, a well-known inhibitor of sterol biosynthesis. Thus, 1,3,4-thiadiazole derivative 11a could be considered a good prototype for the development of new drug candidates for Chagas disease therapy.

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.

I2 Promoted Synthesis of 2-Aminothiadiazoles Employing KSCN as a Sulfur Source Under Metal-Free Conditions

A new three-component strategy from aldehyde, p-toluenesulfonyl hydrazide and potassium thiocyanate for the synthesis of 2-aminothiadiazoles promoted by I2 under metal-free conditions has been described. Potassium thiocyanate was used as an odo

Novel synthesized SLC-0111 thiazole and thiadiazole analogues: Determination of their carbonic anhydrase inhibitory activity and molecular modeling studies

In the presented work, we report the design and synthesis of novel SLC-0111 thiazole and thiadiazole analogues (11a–d, 12a–d, 16a–c and 17a–d). A bioisosteric replacement approach was adopted to replace the 4-fluorophenyl tail of SLC-0111 with thiazole and thiadiazole ones, which were thereafter extended with lipophilic un/substituted phenyl moieties. All the newly synthesized SLC-0111 analogues were evaluated in vitro for their inhibitory activity towards a panel of the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1) isoforms (hCA I, II, IX and XII), using a stopped-flow CO2 hydrase assay. All the examined isoforms were inhibited by the primary sulfonamide derivatives (11a–d and 12a–d) in variable degrees with the following KI ranges: 162.6–7136 nM for hCA I, 9.0–833.6 nM for hCA II, 7.9–153.0 nM for hCA IX, and 9.4–94.0 nM for hCA XII. In particular, compounds 12b and 12d displayed 5.5-fold more potent inhibitory activity (KIs = 8.3 and 7.9 nM, respectively) than SLC-0111 (KI = 45 nM) towards hCA IX. Molecular docking study was carried out for 12d within the hCA IX (PDB 3IAI) active site, to justify its inhibitory activity.