7659-02-1

Basic information

• Product Name: 5-(3-NITROPHENYL)-1,3,4-OXADIAZOL-2-AMINE
• Synonyms: 1,3,4-oxadiazol-2-amine, 5-(3-nitrophenyl)-; 5-(3-Nitrophenyl)-1,3,4-oxadiazol-2-amine
• CAS NO: 7659-02-1
• Molecular Formula: C₈H₆N₄O₃
• Molecular Weight: 206.1582
• Mol File: 7659-02-1.mol

Chemical Properties

• Boiling Point: 422°Cat760mmHg
• Flash Point: 209°C
• Appearance: /
• Density: 1.493g/cm³
• Vapor Pressure: 2.5E-07mmHg at 25°C
• Refractive Index: 1.645
• CAS DataBase Reference: 5-(3-NITROPHENYL)-1,3,4-OXADIAZOL-2-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(3-NITROPHENYL)-1,3,4-OXADIAZOL-2-AMINE(7659-02-1)
• EPA Substance Registry System: 5-(3-NITROPHENYL)-1,3,4-OXADIAZOL-2-AMINE(7659-02-1)

Safety Data

• Hazardous Substances Data: 7659-02-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H6N4O3/c9-8-11-10-7(15-8)5-2-1-3-6(4-5)12(13)14/h1-4H,(H2,9,11)

Upstream product

• 5346-31-6 3-nitro-benzaldehyde semicarbazone 
• 4426-72-6 hydrazine carboxamide 
• 121-92-6 3-nitrobenzoic acid 
• 563-41-7 semicarbazide hydrochloride 
• 99-61-6 3-nitro-benzaldehyde 

Downstream Products

• 159888-87-6 2,2,2-Trichloro-N-[5-(3-nitro-phenyl)-[1,3,4]oxadiazol-2-yl]-acetamide 
• 201343-22-8 [1,3]dithiolan-2-ylidene-[5-(3-nitro-phenyl)-[1,3,4]oxadiazol-2-yl]-amine 
• 1335198-58-7 C₈H₄ClN₃O₃ 
• 1335198-37-2 C₂₅H₂₁FN₆O₆ 
• 1335198-44-1 C₂₇H₂₅FN₆O₇ 
• 1335198-51-0 C₂₄H₂₁FN₆O₆ 
• 191531-35-8 C₁₅H₉N₅O₅ 

Relevant articles and documents

Synthesis, telomerase inhibitory and anticancer activity of new 2-phenyl-4H-chromone derivatives containing 1,3,4-oxadiazole moiety

Based on previous studies, 66 2-phenyl-4H-chromone derivatives containing amide and 1,3,4-oxadiazole moieties were prepared as potential telomerase inhibitors. The results showed most of the title compounds exhibited significantly inhibitory activity on telomerase. Among them, some compounds demonstrated the most potent telomerase inhibitory activity (IC50 50 = 6.41 μM). In addition, clear structure–activity relationships were summarised, indicating that the substitution of the methoxy group and the position, type and number of the substituents on the phenyl ring had significant effects on telomerase activity. Among them, compound A33 showed considerable inhibition against telomerase. Flow cytometric analysis showed that compound A33 could arrest MGC-803 cell cycle at G2/M phase and induce apoptosis in a concentration-dependent way. Meanwhile, Western blotting revealed that this compound could reduce the expression of dyskerin, which is a fragment of telomerase.

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Background: In the recent past, we have synthesized and reported different derivatives of oxadiazoles as potential α-glucosidase inhibitors, keeping in mind, the pharmacological aspects of oxadiazole moiety and in continuation of our ongoing research on the chemistry and bioactivity of new heterocyclic compounds. Methods: 1,3,4-Oxadiazole derivatives (1-14) have been synthesized and characterized by different spectroscopic techniques such as1 H-,13 C-NMR and HREI-MS. Results: The synthetic derivatives were screened for α-glucosidase inhibitory potential. All compounds exhibited good inhibitory activity with IC50 values ranging between 0.80 ± 0.1 to 45.1 ± 1.7 μM in comparison with the standard acarbose having IC50 value 38.45 ± 0.80 μM. Conclusion: Thirteen compounds 1-6 and 8-14 showed potential inhibitory activity as compared to the standard acarbose having IC50 value 38.45 ± 0.80 μM, however, only one compound 7 (IC50 = 45.1 ± 1.7 μM) was found to be less active. Compound 14 (IC50 = 0.80 ± 0.1 μM) showed promising inhibitory activity among all synthetic derivatives. Molecular docking studies were also conducted for the active compounds to understand the ligand-enzyme binding interactions.

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