1012054-59-9

Basic information

• Product Name: CUDC-101
• Synonyms: CUDC101;CUDC-101;7-[[4-(3-Ethynylphenylamino)-7-methoxyquinazolin-6-yl]oxy]-N-hydroxyheptanamide;HeptanaMide, 7-[[4-[(3-ethynylphenyl)aMino]-7-Methoxy-6-quinazolinyl]oxy]-N-hydroxy-;7-[[4-[(3-Ethynylphenyl)aMino]-7-Methoxy-6-quinazolinyl]oxy]-N-hydroxyheptanaMide;7-[[4-(3-Ethynylphenylamino)-7-methoxyquinazolin-6-yl]oxy]-N-hydroxyheptanamide CUDC-101;7-[4-(3-ethynylanilino)-7-methoxyquinazolin-6-yl]oxy-N-hydroxyheptanamide;CUDC-101, >=98%
• CAS NO: 1012054-59-9
• Molecular Formula: C₂₄H₂₆N₄O₄
• Molecular Weight: 434.48764
• EINECS: -0
• Product Categories: Inhibitor;Antineoplastic;Inhibitors
• Mol File: 1012054-59-9.mol

Chemical Properties

• Melting Point: 174-177℃
• Appearance: white/
• Density: 1.28
• Storage Temp.: ?20°C
• Solubility: DMSO: soluble
• PKA: 9.47±0.20(Predicted)
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.
• CAS DataBase Reference: CUDC-101(CAS DataBase Reference)
• NIST Chemistry Reference: CUDC-101(1012054-59-9)
• EPA Substance Registry System: CUDC-101(1012054-59-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 1012054-59-9(Hazardous Substances Data)

Usage

Uses

Used in Cancer Treatment:
CUDC-101 is used as a potent multi-acting HDAC, EGFR, and HER2 inhibitor for the treatment of cancer. It displays potent antiproliferative and proapoptotic activities against cultured and implanted tumor cells that are sensitive or resistant to several approved single-targeted drugs. This makes it a promising candidate for the treatment of various cancer types, including those that have developed resistance to conventional therapies.

References

1) Lai?et al. (2010),?CUDC-101, a multitargeted inhibitor of histone deacetylase, epidermal growth factor receptor, and human epidermal growth factor receptor 2, exerts potential anticancer activity; Cancer Res.,?70?3647 2) Cai?et al.?(2010), Discovery of 7-(4-(3-ethynylphenylamino)-7-methoxyquinazolin-6-yloxy)-N-hydroxyheptanamide (CUDc-101) as a potent multi-acting HDAC, EGFR, and HER2 inhibitor for the treatment of cancer; J. Med. Chem.,?53?2000

Upstream product

• 1012920-21-6 ethyl 6-(4-(3-ethynylphenylamino)-7-methoxyquinazolin-6-yloxy)heptanoate 
• 905306-05-0 4-[(3-acetylenephenyl)amino]-7-methoxyquinazolin-6-ol 
• 1012057-22-5 ethyl 3-(7-ethoxy-7-oxoheptyloxy)-4-methoxybenzoate 
• 1012057-25-8 ethyl 7-(7-methoxy-4-oxo-3,4-dihydroquinazolin-6-yloxy)heptanoate 
• 1012067-93-4 ethyl 2-amino-5-(7-ethoxy-7-oxoheptyloxy)-4-methoxybenzoate 
• 1012067-92-3 ethyl 5-(7-ethoxy-7-oxoheptyloxy)-4-methoxy-2-nitrobenzoate 
• 1012057-17-8 4-(3-ethynylphenylamino)-7-methoxyquinazolin-6-yl acetate hydrochloride 
• 29823-18-5 ethyl 7-bromoheptanoate 
• 3943-89-3 Ethyl protocatechuate 
• 26759-46-6 methyl 2-amino-4,5-dimethoxybenzoate 
• 148527-38-2 ethyl 3-hydroxy-4-methoxybenzoate 
• 179688-53-0 6-acetoxy-7-methoxy-3,4-dihydroquinazolin-4-one 
• 230955-75-6 6-acetoxy-4-chloro-7-methoxyquinazoline 
• 13794-72-4 3H-6,7-dimethoxyquinazolin-4-one 

Downstream Products

• 1012054-99-7 N-(cyclohexanecarbonyloxy)-7-(4-(3-ethynylphenylamino)-7-methoxyquinazolin-6-yloxy)heptanamide 
• 1012920-29-4 7-(4-(3-ethynylphenylamino)-7-methoxyquinazolin-6-yloxy)-N-hydroxyheptanamide citrate 
• 1133147-76-8 CUDC-101 hydrochloride 
• 1449289-03-5 7-(4-(3-(1-(6-aminohexyl)-1H-1,2,3-triazol-4-yl)phenylamino)-7-methoxyquinazolin-6-yloxy)-N-hydroxyheptanamide 

Relevant articles and documents

Discovery of 7-(4-(3-Ethynylphenylamino)-7-methoxyquinazolin-6-yloxy)-N- hydroxyheptanamide (CUDC-101) as a potent multi-acting HDAC, EGFR, and HER2 inhibitor for the treatment of cancer

By incorporating histone deacetylase (HDAC) inhibitory functionality into the pharmacophore of the epidermal growth factor receptor (EGFR) and human epidermal growth factor receptor 2 (HER2) inhibitors, we synthesized a novel series of compounds with potent, multiacting HDAC, EGFR, and HER2 inhibition and identified 7-(4-(3-ethynylphenylamino)-7-methoxyquinazolin-6-yloxy)-N- hydroxyheptanamide 8 (CUDC-101) as a drug candidate, which is now in clinical development. 8 displays potent in vitro inhibitory activity against HDAC, EGFR, and HER2 with an IC50 of 4.4, 2.4, and 15.7 nM, respectively. In most tumor cell lines tested, 8 exhibits efficient antiproliferative activity with greater potency than vorinostat (SAHA), erlotinib, lapatinib, and combinations of vorinostat/erlotinib and vorinostat/lapatinib. In vivo, 8 promotes tumor regression or inhibition in various cancer xenograft models including nonsmall cell lung cancer (NSCLC), liver, breast, head and neck, colon, and pancreatic cancers. These results suggest that a single compound that simultaneously inhibits HDAC, EGFR, and HER2 may offer greater therapeutic benefits in cancer over single-acting agents through the interference with multiple pathways and potential synergy among HDAC and EGFR/HER2 inhibitors.

FORMULATION OF QUINAZOLINE BASED EGFR INHIBITORS CONTAINING A ZINC BINDING MOIETY

The present invention relates to a composition comprising an inclusion complex of a cyclodextrin and quinazoline containing zinc-binding moiety based derivatives. The cyclodextrin is preferable a β-cyclodextrin or a derivative thereof. The quinazolines have enhanced and unexpected properties as inhibitors of epidermal growth factor receptor tyrosine kinase (EGFR-TK) and their use in the treatment of EGFR-TK related diseases and disorders such as cancer. The said derivatives may further act as HDAC inhibitors.

TARTRATE SALTS OF QUINAZOLINE BASED EGFR INHIBITORS CONTAINING A ZINC BINDING MOIETY

The present invention relates to tartrate salts of quinazoline containing zinc-binding moiety based derivatives that are inhibitors of epidermal growth factor receptor tyrosine kinase (EGFR-TK) and their use in the treatment of EGFR-TK related diseases and disorders such as cancer. The tartrate salts may further act as HDAC inhibitors.

MULTI-FUNCTIONAL SMALL MOLECULES AS ANTI-PROLIFERATIVE AGENTS

The present invention relates to the compositions, methods, and applications of a novel approach to selective inhibition of several cellular or molecular targets with a single small molecule. More specifically, the present invention relates to multi-functional small molecules wherein one functionality is capable of inhibiting histone deacetylases (HDAC) and the other functionality is capable of inhibiting a different cellular or molecular pathway involved in aberrant cell proliferation, differentiation or survival.