828-81-9

Basic information

• Product Name: 2-AMINO-5-(2-CHLOROPHENYL)-1,3,4-THIADIAZOLE
• Synonyms: VITAS-BB TBB000090;IFLAB-BB F1386-0067;5-(2-CHLOROPHENYL)-1,3,4-THIADIAZOL-2-AMINE;5-(2-CHLORO-PHENYL)-[1,3,4]THIADIAZOL-2-YLAMINE;2-AMINO-5-(2-CHLOROPHENYL)-1,3,4-THIADIAZOLE;1,3,4-Thiadiazol-2-aMine, 5-(2-chlorophenyl)-;5-(2-Chlorophenyl)
• CAS NO: 828-81-9
• Molecular Formula: C₈H₆ClN₃S
• Molecular Weight: 211.67
• Mol File: 828-81-9.mol

Chemical Properties

• Melting Point: 192-195 °C
• Boiling Point: 393.8±44.0 °C(Predicted)
• Appearance: /
• Density: 1.461±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 2.28±0.10(Predicted)
• CAS DataBase Reference: 2-AMINO-5-(2-CHLOROPHENYL)-1,3,4-THIADIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-5-(2-CHLOROPHENYL)-1,3,4-THIADIAZOLE(828-81-9)
• EPA Substance Registry System: 2-AMINO-5-(2-CHLOROPHENYL)-1,3,4-THIADIAZOLE(828-81-9)

Safety Data

• Hazard Codes: Xi,T
• Statements: 25
• Safety Statements: 45
• HazardClass: IRRITANT
• Hazardous Substances Data: 828-81-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-5-(2-chlorophenyl)-1,3,4-thiadiazole is used as a potential bioactive agent for its possible anti-microbial properties, making it a candidate for the development of new antimicrobial drugs to combat resistant infections.
Used in Pharmaceutical Industry:
2-Amino-5-(2-chlorophenyl)-1,3,4-thiadiazole is used as a potential bioactive agent for its possible anti-inflammatory properties, which could be harnessed in the development of new treatments for inflammatory conditions.
Used in Pharmaceutical Industry:
2-Amino-5-(2-chlorophenyl)-1,3,4-thiadiazole is used as a potential bioactive agent for its possible anti-tubercular properties, indicating its potential use in the development of new anti-tubercular drugs to treat tuberculosis.
Used in Pharmaceutical Industry:
2-Amino-5-(2-chlorophenyl)-1,3,4-thiadiazole is used as a potential bioactive agent for its possible anti-cancer properties, suggesting its potential role in the development of new cancer therapeutics.

Upstream product

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Downstream Products

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• 1430197-23-1 N-(5-(2-chlorophenyl)-1,3,4-thiadiazol-2-yl)-4-methyl-1,2,3-thiadiazole-5-carboxamide 

Relevant articles and documents

Diversity-Oriented Synthesis of 1,2,4-Triazols, 1,3,4-Thiadiazols, and 1,3,4-Selenadiazoles from N-Tosylhydrazones

The diversity-oriented synthesis of 1,2,4-triazols, 1,3,4-thiadiazols, and 1,3,4-selenadiazoles from N-tosylhydrazones was developed, and the reactions were general for a wide range of substrates, in which NH2CN, KOCN, KSCN, and KSeCN were used as odorless sources. Two different pathways were proposed, and N-tosylhydrazonoyl chlorides were formed in situ in the presence of NCS.

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.]

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 and Biological Evaluation of Oxadiazole Clubbed Thiadiazole Derivatives as Antimicrobial Agents

A series of 1,3,4-oxadiazole clubbed 1,3,4-thiadiazole derivatives were synthesized and assessed in vitro for their activity as antimicrobial agents. The target compounds 2-(5-(substituted aryl)-1, 3, 4-oxadiazol-2-ylthio)-N-(5-(substituted aryl)-1, 3, 4-thiadiazol-2-yl) acetamides (5a-5s) were synthesized using a basic condensation reaction between 5-(substituted aryl)-1,3,4-oxadiazole-2-thiol and 2-chloro-N-(5-(substituted aryl)-1,3,4-thiadiazol-2-yl)acetamide in presence of K2CO3 as a scavenging agent and acetone as reaction solvent. The titled compounds synthesized here, exhibited excellent to moderate antimicrobial activity against a broad panel of antibacterial strains of Gram-positive and Gram-negative bacteria and fungi.

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

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.

Synthesis of (1,3,4-thiadiazol-2-yl)-acrylamide derivatives as potential antitumor agents against acute leukemia cells

A lead compound with the (1,3,4-thiadiazol-2-yl)-acrylamide scaffold was discovered to have significant cytotoxicity on several tumor cell lines in an in-house cell-based screening. A total of 60 derivative compounds were then synthesized and tested in a CCK-8 cell viability assay. Some of them exhibited improved cytotoxic activities. The most potent compounds had IC50 values of 1–5 μM on two acute leukemia tumor cell lines, i.e. RS4;11 and HL-60. Flow cytometry analysis of several active compounds and detection of caspase activation indicated that they induced caspase-dependent apoptosis. It was also encouraging to observe that these compounds did not have obvious cytotoxicity on normal cells, i.e. IC50 > 50 μM on HEK-293T cells. Although the molecular targets of this class of compound are yet to be revealed, our current results suggest that this class of compound represents a new possibility for developing drug candidates against acute leukemia.

Intrabacterial Metabolism Obscures the Successful Prediction of an InhA Inhibitor of Mycobacterium tuberculosis

Tuberculosis, caused by Mycobacterium tuberculosis (M. tuberculosis), kills 1.6 million people annually. To bridge the gap between structure- A nd cell-based drug discovery strategies, we are pioneering a computer-aided discovery paradigm that merges stru

Novel 1,3,4-thiadiazole conjugates derived from protocatechuic acid: Synthesis, antioxidant activity, and computational and electrochemical studies

A series of 15 novel 1,3,4-thiadiazole amide derivatives containing a protocatechuic acid moiety were synthesized and structurally characterized. In addition, the corresponding imino (4) and amino (5) analogues of a phenyl-substituted 1,3,4-thiadiazole am

Metal-free synthesis of 2-aminothiadiazoles via TBHP-Mediated oxidative C-S bond formation

An efficient one-pot synthesis of 2-amino-1,3,4-thiadiazoles from easily available aldehydes and thiosemicarbazide using TBHP as an oxidant has been described. Notably, these reactions were carried out at room temperature using ethanol as solvent. This is the first example for one-pot synthesis of 2-amino-1,3,4-thiadiazole derivatives from aldehydes. This new synthetic methodology provides a simple procedure utilizing a safer oxidizing system that affords the target products in mild reaction condition with satisfactory yields and wide substrate scope.