832-79-1

Basic information

• Product Name: 1,3,4-Thiadiazol-2-amine, 5-(2-nitrophenyl)-
• CAS NO: 832-79-1
• Molecular Formula: C8H6N4O2S
• Molecular Weight: 222.227
• Mol File: 832-79-1.mol

Chemical Properties

• CAS DataBase Reference: 1,3,4-Thiadiazol-2-amine, 5-(2-nitrophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,4-Thiadiazol-2-amine, 5-(2-nitrophenyl)-(832-79-1)
• EPA Substance Registry System: 1,3,4-Thiadiazol-2-amine, 5-(2-nitrophenyl)-(832-79-1)

Safety Data

• Hazardous Substances Data: 832-79-1(Hazardous Substances Data)

Usage

Classification

Heterocyclic organic compound

Structure

Nitro-substituted derivative of 1,3,4-thiadiazol-2-amine

Potential applications

Medicinal chemistry and pharmaceuticals

Use

Synthesis of novel drugs and biologically active molecules

Therapeutic effects

Potential therapeutic effects

Additional applications

Material science and industrial processes

Versatility

Valuable compound in various fields of science and technology

Upstream product

• 835-14-3 N₂-(2-nitrobenzoyl)thiosemicarbazide 
• 606-26-8 o-nitrobenzohydrazide 
• 79-19-6 thiosemicarbazide 
• 552-89-6 2-nitro-benzaldehyde 
• 1489265-34-0 (2E)-2-[(2-nitrophenyl)methylidene]hydrazine-1-carbothioamide 
• 552-16-9 ortho-nitrobenzoic acid 
• 6072-63-5 2-(2-nitrobenzylidene)hydrazinecarbothioamide 
• 2290-65-5 trimethylsilyl isothiocyanate 

Downstream Products

• 19819-06-8 2-(2-nitro-phenyl)-[1,3,4]thiadiazolo[3,2-a]pyrimidine-5,7-dione 
• 59565-60-5 (4-chloro-benzylidene)-[5-(2-nitro-phenyl)-[1,3,4]thiadiazol-2-yl]-amine 
• 59565-59-2 4-{[5-(2-nitro-phenyl)-[1,3,4]thiadiazol-2-ylimino]-methyl}-phenol 
• 70038-90-3 N-[5-(2-nitro-phenyl)-[1,3,4]thiadiazol-2-yl]-benzamidine 
• 70038-97-0 N-[5-(2-nitro-phenyl)-[1,3,4]thiadiazol-2-yl]-acetamidine 
• 22926-56-3 2,2,2-trifluoro-N-[5-(2-nitro-phenyl)-[1,3,4]thiadiazol-2-yl]-acetamide 
• 1173-99-5 4-acetylamino-N-[5-(2-nitro-phenyl)-[1,3,4]thiadiazol-2-yl]-benzenesulfonamide 
• 26621-39-6 2-nitro-5-(2-nitro-phenyl)-[1,3,4]thiadiazole 
• 83530-84-1 α-(5-o-nitrophenyl-1,3,4-thiadiazol-2-yl-amino)-p-anisylacetonitrile 
• 83530-80-7 α-(5-o-nitrophenyl-1,3,4-thiadiazol-2-yl-amino)-2-hydroxyphenylacetonitrile 
• 83530-78-3 α-(5-o-nitrophenyl-1,3,4-thiadiazol-2-yl-amino)-m-nitrophenylacetonitrile 
• 83530-77-2 α-(5-o-nitrophenyl-1,3,4-thiadiazol-2-yl-amino)-phenylacetonitrile 
• 83530-83-0 α-(5-o-nitrophenyl-1,3,4-thiadiazol-2-yl-amino)-(5-bromo-4-hydroxy-3-methoxyphenyl)acetonitrile 
• 83530-82-9 α-(5-o-nitrophenyl-1,3,4-thiadiazol-2-yl-amino)-(4-hydroxy-3-methoxyphenyl)acetonitrile 

Relevant articles and documents

Synthesis, in vitro thymidine phosphorylase activity and molecular docking study of thiadiazole bearing isatin analogs

A series of seventeen analogs (1─17) were synthesized and characterized through different spectroscopic techniques such as 1H, 13CNMR, HR-EI-MS and were evaluated for in vitro thymidine phosphorylase inhibition. All compounds showed excellent to good thymidine phosphorylase activity having IC50 value ranging between 4.10 ± 0.20 and 54.60 ± 1.40?μM when compared with standard drug 7-deazaxanthine (IC50 = 38.68 ± 1.12?μM). Among the series, compounds 1 (IC50 = 8.30 ± 0.30?μM), 6 (IC50 = 6.30 ± 0.10?μM), 11 (IC50 = 8.40 ± 0.30?μM) and 16 (IC50 = 4.10 ± 0.20?μM) were found more potent. Potent compounds were further subjected to molecular docking study to identify their interactions with the active site of amino acid. Structure activity relationship was done for all analogs mostly based on substitution pattern on phenyl and isatin rings. Graphic abstract: [Figure not available: see fulltext.]

New biologically dynamic hybrid pharmacophore triazinoindole-based-thiadiazole as potent α-glucosidase inhibitors: In vitro and in silico study

Triazinoindole bearing thiadiazole derivatives (1–25) have been synthesized and characterized through different spectroscopic techniques such as 1H, 13C-NMR and HREI-MS. The purpose of the study was to investigate the anti-diabetic activity of the synthesized triazinoindole bearing thiadiazole derivatives by inhibition of α-glucosidase. All synthesized analogues showed outstanding inhibition of α-glucosidase enzyme with IC50 values ranging from 2.5 ± 0.10 to 38.10 ± 0.10 μM as compared to the standard drug acarbose (IC50 = 38.45 ± 0.80 μM). Analogue 4 (IC50 = 2.5 ± 0.10 μM) was identifies as the most potent analogue in the series with fifteen folds more active than standard acarbose. Structure activity relationship (SAR) studies suggested that α-glucosidase activities of triazinoindole bearing thiadiazole are primarily dependent upon on number and position of different substitutions present on phenyl parts. Molecular docking study were conducted of the optimized compounds (i.e., compound 4, 6, and 3 etc. using MOE default parameters), the results revealed that compound 4, 6, and 3 showed numerous key interactions with the target protein, which indicate the high potential of these compounds against the target compound. All these compounds were screened for cytotoxic activity against normal normal Vero cell line and found non-toxic.

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 antiviral activity of novel 1,3,4-thiadiazole inhibitors of DDX3x

The human ATPase/RNA helicase X-linked DEAD-box polypeptide 3 (DDX3X) emerged as a novel therapeutic target in the fight against both infectious diseases and cancer. Herein, a new family of DDX3X inhibitors was designed, synthesized, and tested for its inhibitory action on the ATPase activity of the enzyme. The potential use of the most promising derivatives it has been investigated by evaluating their anti-HIV-1 effects, revealing inhibitory activities in the low micromolar range. A preliminary ADME analysis demonstrated high metabolic stability and good aqueous solubility. The promising biological profile, together with the suitable in vitro pharmacokinetic properties, make these novel compounds a very good starting point for further development.

Synthesis, in vitro and in silico Anti-Proliferative Studies of Novel Piperiene-Oxadiazole and Thiadiazole Analogs

Piperine is a component of pepper which has earlier been reported as anticancer active compound. This work is emphasized on the design and synthesis of new hybrid piperine analogs by coupling piperine with the amine group of oxadiazoles and thiadiazoles.

Synthesis, in vitro α-glucosidase inhibitory potential and molecular docking study of thiadiazole analogs

α-Glucosidase is a catabolic enzyme that regulates the body's plasma glucose levels by providing energy sources to maintain healthy functioning. 2-Amino-thiadiazole (1–13) and 2-amino-thiadiazole based Schiff bases (14–22) were synthesized, characterized by 1H NMR and HREI-MS and screened for α-glucosidase inhibitory activity. All twenty-two (22) analogs exhibit varied degree of α-glucosidase inhibitory potential with IC50 values ranging between 2.30 ± 0.1 to 38.30 ± 0.7 μM, when compare with standard drug acarbose having IC50 value of 39.60 ± 0.70 μM. Among the series eight derivatives 1, 2, 6, 7, 14, 17, 19 and 20 showed outstanding α-glucosidase inhibitory potential with IC50 values of 3.30 ± 0.1, 5.80 ± 0.2, 2.30 ± 0.1, 2.70 ± 0.1, 2.30 ± 0.1, 5.50 ± 0.1, 4.70 ± 0.2, and 5.50 ± 0.2 μM respectively, which is many fold better than the standard drug acarbose. The remaining analogs showed good to excellent α-glucosidase inhibition. Structure activity relationship has been established for all compounds. The binding interactions of these compounds were confirmed through molecular docking.

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.

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

Synthesis and evaluation of the trypanocidal activity of a series of 1,3,4-thiadiazoles derivatives of R-(+)-limonene benzaldehyde-thiosemicarbazones

In this study, we synthesized a series of 1,3,4-thiadiazole derivatives of R-(+)-limonene benzaldehyde-thiosemicarbazones (2a–k). We also determined the cytotoxicity in LLCMK2 cells and the activity against epimastigote and trypomastigote forms

Synthesis, bioevaluation and docking study of 5-substitutedphenyl-1,3,4-thiadiazole-based hydroxamic acids as histone deacetylase inhibitors and antitumor agents

Since the first histone deacetylase (HDAC) inhibitor (Zolinza, widely known as suberoylanilide hydroxamic acid; SAHA) was approved by the Food and Drug Administration for the treatment of T-cell lymphoma in 2006, the search for newer HDAC inhibitors has attracted a great deal of interest of medicinal chemists worldwide. As a continuity of our ongoing research in this area, we designed and synthesized a series of 5-substitutedphenyl-1,3,4-thiadiazole-based hydroxamic acids as analogues of SAHA and evaluated their biological activities. A number of compounds in this series, for example, N1-hydroxy-N8-(5-(2-chlorophenyl)-1,3,4-thiadiazol-2-yl)octandiamide (5b), N1-hydroxy-N8-(5-(3-chlorophenyl-1,3,4-thiadiazol-2-yl)octandiamide (5c) and N1-hydroxy-N8-(5-(4-chlorophenyl)-1,3,4-thiadiazol-2-yl)octandiamide (5d), were found to possess potent anticancer cytotoxicity and HDAC inhibition effects. Compounds 5b-d were generally two- to five-fold more potent in terms of cytotoxicity compared to SAHA against five cancer cell lines tested. Docking studies revealed that these hydroxamic acid displayed higher affinities than SAHA toward HDAC8.