892873-58-4

Basic information

• Product Name: 4-HYDROXY-3'-METHOXY[1,1'-BIPHENYL]-3-CARBALDEHYDE
• Synonyms: AKOS BAR-0853;4-HYDROXY-3'-METHOXY[1,1'-BIPHENYL]-3-CARBALDEHYDE;[1,1-BIPHENYL]-3-CARBOXALDEHYDE,4-HYDROXY-3-METHOXY-
• CAS NO: 892873-58-4
• Molecular Formula: C₁₄H₁₂O₃
• Molecular Weight: 228.24
• Mol File: 892873-58-4.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-HYDROXY-3'-METHOXY[1,1'-BIPHENYL]-3-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-HYDROXY-3'-METHOXY[1,1'-BIPHENYL]-3-CARBALDEHYDE(892873-58-4)
• EPA Substance Registry System: 4-HYDROXY-3'-METHOXY[1,1'-BIPHENYL]-3-CARBALDEHYDE(892873-58-4)

Safety Data

• Hazardous Substances Data: 892873-58-4(Hazardous Substances Data)

Upstream product

• 10365-98-7 3-methoxyphenylboronic acid 
• 1761-61-1 5-bromosalicyclaldehyde 

Downstream Products

• 1318166-03-8 6-(3-methoxyphenyl)-2H-chromen-2-one 
• 1318165-31-9 ethyl 2-amino-4-(2-ethoxy-2-oxoethyl)-6-(3-methoxyphenyl)-4H-chromene-3-carboxylate 

Relevant articles and documents

Carbohydrate hydrolyzing enzymes inhibitory and free radical scavenging activities of substituted 2H-chromene-3-carboxylates, 2H-chromenyl Knoevenagel derivatives and 6H-chromenoquinolinones

Three series of compounds namely ethyl 2-hydroxy-2-(trifluoromethyl)-2H-chromene-3-carboxylates 3a-q, 2H-chromenyl Knoevenagel derivatives 7a-j and 6H-chromenoquinolinones 9a-l have been prepared. The synthesized compounds 3a-q, 7a-j and 9a-g have been screened for anti-oxidant and anti-diabetic activity. Compound 3i shows the most potent ABTS inhibitory activity when compared to trolox. Compounds 3b, 3d, 3j and 3l show α-amylase inhibitory activity.

Structure-activity relationship and molecular mechanisms of ethyl 2-amino-6-(3,5-dimethoxyphenyl)-4-(2-ethoxy-2-oxoethyl)-4H -chromene-3- carboxylate (CXL017) and its analogues

Multidrug resistance (MDR) in cancer is a phenomenon in which administration of a single chemotherapeutic agent causes cross-resistance of cancer cells to a variety of therapies even with different mechanisms of action. Development of MDR against standard therapies is a major challenge in the treatment of cancer. Previously we have demonstrated a unique ability of CXL017 (5) to selectively target MDR cancer cells and synergize with mitoxantrone (MX) in HL60/MX2 MDR cells. Here we expand its scope and demonstrate that 5 can synergize with both vincristine and paclitaxel in three different MDR cell lines (HL60/DNR, K562/HHT300, and CCRF-CEM/VLB100). We also demonstrate that 5 has potent cytotoxicity in the NCI-60 panel of cell lines with an average IC 50 of 1.04 μM. In addition, 5 has a unique mechanism of action in comparison with standard agents in the NCI database based on COMPARE analysis. Further structure-activity relationship study led to the development of a more potent analogue, compound 7d, with an IC50 of 640 nM in HL60/MX2. Additionally, one enantiomer of 5 is 13-fold more active than the less active enantiomer. Taken together, our study has led to the discovery of a series of analogues that selectively target drug-resistant cancer cells with the potential for the treatment of drug-resistant cancers.