71089-19-5

Upstream product

• 1226467-43-1 (Z)/(E)-5-(3-methoxyphenyl)pent-4-enoic acid 
• 17857-14-6 (3-carboxypropyl)(triphenyl)phosphonium bromide 
• 1378238-56-2 5-(3'-methoxy-2'-nitrophenyl)pent-4-enoic acid 
• 6500-65-8 2-methoxy-6,7,8,9-tetrahydro-benzocyclohepten-5-one 
• 53055-05-3 3-methoxy 2-nitrobenzaldehyde 
• 6500-64-7 5-(3'-methoxyphenyl)pentanoic acid 
• 1378238-57-3 5-(3'-methoxy-2'-nitrophenyl)pentanoic acid 

Downstream Products

• 1378238-58-4 2-methoxy-1-nitro-5-(3',4',5'-trimethoxyphenyl)-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-ol 
• 1378238-59-5 3-methoxy-4-nitro-9-(3',4',5'-trimethoxyphenyl)-6,7-dihydro-5H-benzo[7]annulene 
• 1378238-60-8 3-methoxy-9-(3',4',5'-trimethoxyphenyl)-6,7-dihydro-5H-benzo[7]annulen-4-amine 

Relevant academic research and scientific papers

Design, synthesis, and biological evaluation of water-soluble amino acid prodrug conjugates derived from combretastatin, dihydronaphthalene, and benzosuberene-based parent vascular disrupting agents

Targeting tumor vasculature represents an intriguing therapeutic strategy in the treatment of cancer. In an effort to discover new vascular disrupting agents with improved water solubility and potentially greater bioavailability, various amino acid prodru

An amino-benzosuberene analogue that inhibits tubulin assembly and demonstrates remarkable cytotoxicity

The recent discovery of a small-molecule benzosuberene-based phenol that demonstrates remarkable picomolar cytotoxicity against selected human cancer cell lines and strongly inhibits tubulin polymerization (1-2 μM) inspired the design and synthesis of a variety of new, structurally diverse benzosuberene derivatives. An efficient synthetic route to functionalized benzosuberenes was developed. This methodology utilized a Wittig reaction, followed by a selective alkene reduction and ring-closing cyclization to form the core benzosuberone structure. This synthetic route facilitated the preparation of a 4-nitro-1-(3′,4′,5′-trimethoxyphenyl) benzosuberene derivative and its corresponding 4-amino analogue in good yield. The 4-amino analogue was a strong inhibitor of tubulin polymerization (1.2 μM), demonstrated enhanced cytotoxicity against the human cancer cell lines examined (GI50 = 33 pM against SK-OV-3 ovarian cancer, for example), and exhibited a concentration dependent disruption of a pre-established capillary-like network of tubules formed from human umbilical vein endothelial cells.

Efficient Method for Preparing Functionalized Benzosuberenes

The disclosed process can efficiently synthesize functionalized benzosuberenes. The process provides an improved method of production of benzosuberene and compounds containing a benzosuberene moiety, which is characterized by a ring closing methodology comprising reaction of a 5-phenylpentanoic acid with Eaton's reagent to form the benzosuberone. The process, optionally, further includes steps for adding a functional group at the ketone position.