833-63-6

Basic information

• Product Name: 2-AMINO-5-(4-NITROPHENYL)-1 3 4-THIADIA&
• Synonyms: 1,3,4-Thiadiazol-2-aMine, 5-(4-nitrophenyl)-;5-(4-nitrophenyl)-1,3,4-thiadiazol-2-ammonium chloride;2-AMINO-5-(4-NITROPHENYL)-1 3 4-THIADIA&;2-amino-5-(p-nitrophenyl)-1,3,4-thiadiazole;2-amino-5-p-nitrofenil-1,3,4-tiadiazolo;4-thiadiazole,2-amino-5-(p-nitrophenyl)-3
• CAS NO: 833-63-6
• Molecular Formula: C₈H₆N₄O₂S
• Molecular Weight: 222.22384
• Product Categories: API intermediates;Building Blocks;Heterocyclic Building Blocks;Thiadiazoles
• Mol File: 833-63-6.mol
• Article Data: 65

Chemical Properties

• Melting Point: 257-261 °C(lit.)
• Boiling Point: 454.4°C at 760 mmHg
• Flash Point: 228.6°C
• Appearance: /
• Density: 1.535g/cm³
• Vapor Pressure: 1.91E-08mmHg at 25°C
• Refractive Index: 1.703
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-AMINO-5-(4-NITROPHENYL)-1 3 4-THIADIA&(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-5-(4-NITROPHENYL)-1 3 4-THIADIA&(833-63-6)
• EPA Substance Registry System: 2-AMINO-5-(4-NITROPHENYL)-1 3 4-THIADIA&(833-63-6)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: XI3603000
• Hazardous Substances Data: 833-63-6(Hazardous Substances Data)

Usage

General Description

2-Amino-5-(4-nitrophenyl)-1,3,4-thiadiazole is a chemical compound with the molecular formula C8H6N4O2S. It is a heterocyclic organic compound that contains nitrogen, sulfur, and oxygen atoms in its structure. 2-AMINO-5-(4-NITROPHENYL)-1 3 4-THIADIA& has potential applications in pharmaceuticals and agrochemicals due to its diverse biological activities, such as antimicrobial, antifungal, and antitumor properties. It is also used as a building block in the synthesis of various other compounds. Additionally, it has been studied for its potential use as a fluorescent probe for the detection of metal ions. The compound is included in the thiazole class of chemicals and is known for its versatile chemical and biological properties.

InChI:InChI=1/C8H6N4O2S/c9-8-11-10-7(15-8)5-1-3-6(4-2-5)12(13)14/h1-4H,(H2,9,11)

Upstream product

• 5470-48-4 para-nitrobenzaldehyde thiosemicarbazone 
• 836-16-8 1-(4-nitrobenzoyl)thiosemicarbazide 
• 40546-45-0 ethyl 4-nitrobenzenecarboximidoate hydrochloride 
• 79-19-6 thiosemicarbazide 
• 62-23-7 4-nitro-benzoic acid 
• 636-97-5 N-amino-(4-nitrophenyl)carboxamide 
• 555-16-8 4-nitrobenzaldehdye 
• 344885-00-3 C₈H₈N₄O₂S 
• 2290-65-5 trimethylsilyl isothiocyanate 
• 180864-33-9 (2E)-2-[(4-nitrophenyl)methylidene]hydrazine-1-carbothioamide 
• 619-72-7 4-nitrobenzonitrile 
• 4346-94-5 thiosemicarbazide hydrochloride 
• 333-20-0 potassium thioacyanate 
• 122-04-3 4-nitro-benzoyl chloride 

Downstream Products

• 51659-90-6 2-amino-5-(4-aminophenyl)-1,3,4-thiadiazole 
• 16430-12-9 2-[5-(4-nitro-phenyl)-[1,3,4]thiadiazol-2-ylamino]-ethanol 
• 36897-66-2 3-[5-(4-nitro-phenyl)-[1,3,4]thiadiazol-2-yl]-3H-quinazolin-4-one 
• 18378-71-7 2,2-dichloro-N-[5-(4-nitro-phenyl)-[1,3,4]thiadiazol-2-yl]-acetamide 
• 70038-92-5 N-[5-(4-nitro-phenyl)-[1,3,4]thiadiazol-2-yl]-benzamidine 
• 18378-70-6 2-chloro-N-[5-(4-nitrophenyl)-[1,3,4]-thiadiazol-2-yl]-acetamide 
• 101118-21-2 2-(2,4-dimethyl-phenylazo)-5-(4-nitro-phenyl)-[1,3,4]thiadiazole 
• 70038-99-2 N-[5-(4-nitro-phenyl)-[1,3,4]thiadiazol-2-yl]-acetamidine 
• 22926-47-2 2,2,2-trifluoro-N-[5-(4-nitro-phenyl)-[1,3,4]thiadiazol-2-yl]-acetamide 
• 1250-63-1 4-acetylamino-N-[5-(4-nitro-phenyl)-[1,3,4]thiadiazol-2-yl]-benzenesulfonamide 
• 18199-91-2 2,2,2-Trichloro-N-(5-(4-nitrophenyl)-1,3,4-thiadiazol-2-yl)acetamide 
• 16430-74-3 2-{4-[bis-(2-chloro-ethyl)-amino]-phenyl}-N-[5-(4-nitro-phenyl)-[1,3,4]thiadiazol-2-yl]-acetamide 
• 130672-14-9 2-(4-nitro-phenyl)-5-(2,4,6-trimethyl-phenylazo)-[1,3,4]thiadiazole 
• 19430-32-1 2-Chloro-5-(4-nitrophenyl)-1,3,4-thiadiazole 

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.]

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.

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.