55323-55-2

Upstream product

• 68360-39-4 2-(3-benzyloxy-4-methoxyphenyl)ethylene 
• 6346-05-0 3-benzyloxy-4-methoxybenzaldehyde 
• 50602-41-0 3-hydroxy-4-methoxyphenethyl alcohol 
• 100-39-0 benzyl bromide 
• 34016-03-0 2-(3-benzyloxy-4-merhoxyphenyl)acetaldehyde 
• 16249-43-7 methyl 2-(3-benzyloxy-4-methoxyphenyl)acetate 
• 15964-81-5 methyl 3-hydroxy-4-methoxyphenylacetate 
• 1131-94-8 homoisovanillic acid 
• 100-44-7 benzyl chloride 
• 63909-29-5 3-benzyloxy-4-methoxy-β-nitrostyrene 
• 55161-43-8 N-{2-[3-(benzyloxy)-4-methoxyphenyl]ethyl}acetamide 
• 23428-77-5 1‐(3‐(benzyloxy)‐4‐methoxyphenyl)ethanone 
• 23428-78-6 4-[(3-benzyloxy-4-methoxy-phenyl)-thioacetyl]-morpholine 
• 621-59-0 isovanillin 

Downstream Products

• 115262-36-7 3-benzyloxy-4-methoxyphenethyl bromide 
• 50602-41-0 3-hydroxy-4-methoxyphenethyl alcohol 
• 688011-27-0 [2-(3-benzyloxy-4-methoxy-phenyl)-ethoxy]-triisopropyl-silane 
• 160857-74-9 (3-benzyloxy-4-methoxyphenyl)ketene 
• 160857-71-6 (3-benzyloxy-4-methoxyphenethylimino)triphenylphosphorane 
• 945531-28-2 Acetic acid 2-(3-benzyloxy-4-methoxy-phenyl)-ethyl ester 
• 73053-73-3 (+/-)-trans-1-(3-benzyloxy-4-methoxyphenethyl)-5-ethyl-2-oxo-4-piperidineacetic acid ethyl ester 
• 115262-61-8 5-ethyl-1-(3-hydroxyphenethyl)-2-piperidone 
• 115262-51-6 5-ethyl-1-(3-hydroxy-4-methoxyphenethyl)-2-piperidone 
• 115262-49-2 5-acetyl-1-(3-hydroxy-4-methoxyphenethyl)-2-piperidone 
• 115262-56-1 1-(3-benzyloxy-4-methoxyphenethyl)-5-ethyl-5,6-dihydro-2(1H)-pyridinone 
• 115262-53-8 1-(3-benzyloxy-4-methoxyphenethyl)-5-ethyl-2-piperidone 
• 115288-08-9 1-(3-benzyloxy-4-methoxyphenethyl)-5-(1,1-ethylenedioxyethyl)-2-(1H)-pyridinone 
• 115262-57-2 1-(3-benzyloxy-4-methoxyphenethyl)-5-ethyl-2-oxo-4-piperidinemalonic acid 

Relevant academic research and scientific papers

TETRAHYDROISOQUINOLINE COMPOUNDS

The present invention relates to a novel class of tetrahydroisoquinoline compounds of formula I and to compositions comprising the same. The compounds and compositions of the present invention can be used as medicaments in the treatment of cancer.

Total synthesis of three natural phenethyl glycosides

Phenethyl glycosides having phenolic or methoxy functions at benzene rings are substances widely occurring in nature. This kind of compounds has been shown to have anti-oxidant, anti-inflammatory, and anticancer activities. However, some of them are not naturally abundant, thus the synthesis of such molecules is desirable. In this paper, natural phenethyl glycosides 3 and 4 were first totally synthesized from easily available materials with overall yields of 50.5% and 40.1%, respectively. And a new synthetic route to obtain natural phenethyl glycoside 2 in 46.2% yield was also described.

Convergent Total Synthesis of Lamellarins and Their Congeners

A convergent total synthesis of lamellarins S and Z is described. The synthesis features a halogen dance of an easily accessible α,β-dibromopyrrole promoted by an ester moiety. The resultant β,β′-dibromopyrrole undergoes a ligand-controlled Suzuki-Miyaura coupling to provide a range of diarylated pyrrole derivatives. The established synthetic method was also applicable to the synthesis of ningalin B and lukianols A and B.

Interrupted Pummerer Reaction in Latent-Active Glycosylation: Glycosyl Donors with a Recyclable and Regenerative Leaving Group

Latent O-glycosides, 2-(2-propylthiol)benzyl (PTB) glycosides, were converted into the corresponding active glycosyl donors, 2-(2-propylsulfinyl)benzyl (PSB) glycosides, by a simple and efficient oxidation. Treatment of the PSB donor and various acceptors with triflic anhydride provided the desired glycosides in good to excellent yields. The leaving group, which was activated by an interrupted Pummerer reaction, can be recycled (PSB-OH) and regenerated as the precursor (PTB-OH). A natural hepatoprotective glycoside, leonoside F, was efficiently synthesized in a convergent [3+1] manner with this newly developed method. The present total synthesis also led to a structural revision of this phenylethanoid glycoside.

Synthesis and Biological Evaluation of N-[2-(4-Hydroxyphenylamino)-pyridin-3-yl]-4-methoxy-benzenesulfonamide (ABT-751) Tricyclic Analogues as Antimitotic and Antivascular Agents with Potent in Vivo Antitumor Activity

Benzopyridothiadiazepine (2a) and benzopyridooxathiazepine (2b) were modified to produce tricyclic quinazolinone 15-18 or benzothiadiazine 26-27 derivatives. These compounds were evaluated in cytotoxicity and tubulin inhibition assays and led to potent inhibitors of tubulin polymerization. N-[2(4-Methoxyphenyl)ethyl]-1,2-dihydro-pyrimidino[2,1-b]quinazolin-6-one (16a) exhibited the best in vitro cytotoxic activity (GI50 10-66.9 nM) against the NCI 60 human tumor cell line and significant potency against tubulin assembly (IC50 0.812 μM). In mechanism studies, 16a was shown to block cell cycle in G2/M phase and to disrupt microtubule formation and displayed good antivascular properties as inhibition of cell migration, invasion, and endothelial tube formation. Compound 16a was evaluated in C57BL/6 mouse melanoma B16F10 xenograft model to validate its antitumor activity, in comparison with reference ABT-751 (1). Compound 16a displayed strong in vivo antitumor and antivascular activities at a dose of 5 mg/kg without obvious toxicity, whereas 1 needed a 10-fold higher concentration to reach similar effects.

A novel approach to erythrinan alkaloids by utilizing substituted biphenyl as building block

Aryl ortho-quinone monoacetal 6 possessing a carbamate group on the side chain was synthesized from the appropriate biphenyl precursor via selective oxidation of one of the aromatic rings. Under Lewis acidic conditions, the carbamate group underwent internal attack at the quinone acetal moiety to give the spiro tricycle 9 corresponding to the A-, C-, and D-rings of erythrinan alkaloids, from which O-methylerysodienone was synthesized via the B ring formation in an efficient manner.

Diastereoselective Synthesis of Cularine Alkaloids via Enium Ions and an Easy Entry to Isoquinolines by Aza-Wittig Electrocyclic Ring Closure

In preliminary communications, we reported the diastereoselective synthesis of cularine and sarcocapnine via the intramolecular ring closure of nitrenium and oxenium ions, a new highly diastereoselective reductive methylation with (+)-8-phenylmenthyl chloroacetate followed by reduction with sodium borohydride, and a facile entry to the isoquinoline precursors by aza-Wittig electrocyclic ring closure. We now report the full details of the syntheses of (+)-O-demethylcularine, (+)-cularine, (+)-sarcocapnidine, (+)-sarcocapnine, and (+)-crassifoline and describe different methods of synthesis of their precursors.

Quinolizidines. XXII. An Extension of the "3-Acetylpyridine Route" to the Syntheses of 9-Hydroxy-10-methoxy- and 10-Hydroxy-9-methoxybenzoquinolizidine-Type Alangium Alkaloids

Alternative syntheses of the Alangium alkaloids bearing the 9-hydroxy-10-methoxy- and 10-hydroxy-9-methoxybenzoquinolizidine skeletons (types 3 and 4) have now become feasible through generally applicable routes starting from 3-acetylpyridine.The route