103499-27-0

Basic information

• Product Name: 3-phenyl-5-(broMoMethyl)-1,2,4-oxadiazole
• Synonyms: 3-phenyl-5-(broMoMethyl)-1,2,4-oxadiazole;1,2,4-Oxadiazole, 5-(broMoMethyl)-3-phenyl-
• CAS NO: 103499-27-0
• Molecular Formula: C₉H₇BrN₂O
• Molecular Weight: 239.06868
• Mol File: 103499-27-0.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-phenyl-5-(broMoMethyl)-1,2,4-oxadiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-phenyl-5-(broMoMethyl)-1,2,4-oxadiazole(103499-27-0)
• EPA Substance Registry System: 3-phenyl-5-(broMoMethyl)-1,2,4-oxadiazole(103499-27-0)

Safety Data

• Hazardous Substances Data: 103499-27-0(Hazardous Substances Data)

Upstream product

• 22118-09-8 2-bromoacetyl chloride 
• 613-92-3 N-hydroxyl-benzamidine 
• 100-47-0 benzonitrile 
• 598-21-0 2-Bromoacetyl bromide 
• 613-92-3 N-hydroxybenzenecarboximidamide 

Downstream Products

• 4915-89-3 3-phenyl-5-(thiocyanatomethyl)-1,2,4-oxadiazole 
• 1352576-29-4 Br^(1-)*C₃₀H₃₇N₄O₃⁽¹⁺⁾ 
• 92440-02-3 3-phenyl-5-(piperidin-1-ylmethyl)-1,2,4-oxadiazole 
• 93475-44-6 5-[(N-butyl)aminomethyl]-3-phenyl-1,2,4-oxadiazole 

Relevant articles and documents

Design, semisynthesis and cytotoxic activity of novel ester derivatives of betulinic acid-1,2,4 oxadiazoles

Taking into consideration of the biological activity of betulinic acid derivatives containing a oxadiazole ring, the semisynthetic betulinic acid-1,2,4-oxadiazole esters (14–25) were synthesized starting from betulinic acid (1) and 5-(bromomethyl)-3-aryl-1,2,4-oxadiazoles (2–13) and final compounds were tested for cytotoxic activity on three human cancer cell lines in vitro. All tested compounds showed good cytotoxic activity. The structures of synthesized compounds are established based on infrared (IR), nuclear magnetic resonance (NMR), and mass spectrometry.

Development of hydroxamate-based histone deacetylase inhibitors containing 1,2,4-oxadiazole moiety core with antitumor activities

Histone deacetylases (HDACs) has proved to be promising target for the development of antitumor drugs. In this study, we reported the design and synthesis of a class of novel hydroxamate-based bis-substituted aromatic amide HDAC inhibitors with 1,2,4-oxadiazole core. Most newly synthesized compounds displayed excellent HDAC1 inhibitory effects and significant anti-proliferative activities. Among them, compounds 11a and 11c increased acetylation of histone H3 and H4 in dose-dependent manner. Furthermore, 11a and 11c remarkably induced apoptosis in HepG2 cancer cells. Finally, the high potency of compound 11a was rationalized by molecular docking studies.

Development of 1,2,4-Oxadiazoles as Potent and Selective Inhibitors of the Human Deacetylase Sirtuin 2: Structure–Activity Relationship, X-ray Crystal Structure, and Anticancer Activity

Sirt2 is a target for the treatment of neurological, metabolic, and age-related diseases including cancer. Here we report a series of Sirt2 inhibitors based on the 1,2,4-oxadiazole scaffold. These compounds are potent Sirt2 inhibitors active at single-digit μM level by using the Sirt2 substrate a-tubulin-acetylLys40 peptide and inactive up to 100 μM against Sirt1, -3, and -5 (deacetylase and desuccinylase activities). Their mechanism of inhibition is uncompetitive toward both the peptide substrate and NAD+, and the crystal structure of a 1,2,4-oxadiazole analog in complex with Sirt2 and ADP-ribose reveals its orientation in a still unexplored subcavity useful for further inhibitor development. Tested in leukemia cell lines, 35 and 39 induced apoptosis and/or showed anti proliferative effects at 10 or 25 μM after 48 h. Western blot analyses confirmed the involvement of Sirt2 inhibition for their effects in NB4 and in U937 cells. Our results provide novel Sirt2 inhibitors with a compact scaffold and structural insights for further inhibitor improvement.