58449-06-2

Usage

Definition

ChEBI: A natural product found particularly in Uvaria acuminata and Uvaria chamae.

InChI:InChI=1/C23H22O5/c1-28-21-14-20(26)17(13-16-9-5-6-10-18(16)24)23(27)22(21)19(25)12-11-15-7-3-2-4-8-15/h2-10,14,24,26-27H,11-13H2,1H3

Upstream product

• 102056-84-8 (2E)-1-[2,4-dihydroxy-3-(2-hydroxybenzyl)-6-methoxyphenyl]-3-phenylprop-2-en-1-one 
• 102104-06-3 (E)-1-[4-Benzyloxy-3-(2-benzyloxy-benzyl)-2-hydroxy-6-methoxy-phenyl]-3-phenyl-propenone 
• 103633-33-6 5'-C-(o-Benzyloxybenzyl)-4'-benzyloxy-6'-hydroxy-2'-methoxychalcone 
• 3602-54-8 4,6-dihydroxy-2-methoxyacetophenone 
• 3381-87-1 2-benzyloxybenzyl alcohol 
• 103633-30-3 2-bromomethylphenyl benzyl ether 
• 103633-31-4 5-C-(o-Benzyloxybenzyl)-4,6-dihydroxy-2-methoxyacetophenone 
• 102104-05-2 5-C-(o-Benzyloxybenzyl)-4-benzyloxy-6-hydroxy-2-methoxyacetophenone 
• 28752-82-1 2-(allyloxy)benzaldehyde 
• 404597-94-0 1-(2-methoxy-4,6-bis(methoxymethoxy)phenyl)ethan-1-one 
• 1013662-04-8 (E)-1-(2-methoxy-4,6-bis(methoxymethoxy)phenyl)-3-phenylprop-2-en-1-one 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 90-02-8 salicylaldehyde 
• 832-58-6 1-(2,4,6-trimethoxyphenyl)ethanone 

Downstream Products

• 61463-12-5 2-(2-Hydroxy-benzyl)-5-methoxy-benzene-1,3-diol 
• 58449-08-4 1-[2-Hydroxy-3-(2-hydroxy-benzyl)-4,6-dimethoxy-phenyl]-3-phenyl-propan-1-one 
• 61463-06-7 1-(3-(2-hydroxybenzyl)-2,4,6-trimethoxyphenyl)-3-phenylpropan-1-one 
• 58449-09-5 1-[2-Hydroxy-4,6-dimethoxy-3-(2-methoxy-benzyl)-phenyl]-3-phenyl-propan-1-one 
• 61463-07-8 Chamuvarin-trimethylaether 
• 61463-13-6 2,4-Bis-(2-hydroxy-benzyl)-5-methoxy-benzene-1,3-diol 

Relevant academic research and scientific papers

The winding road of the uvaretin class of natural products: From total synthesis to bioactive agent discovery

Herein, we disclose the development of a synthetic route to gain access to the uvaretin class of chalcone natural products. In this, the construction of a small library was achieved, and the collection was evaluated for cytotoxicity and other biological properties. Uvaretin (1) was accessed via a seven-step route in an overall yield of 15.1%. Within this route, the unsaturated enone variant of uvaretin (2), also a natural product, was accessed in a 16.7% yield over six steps. This route provides a nearly three-fold increase in yields of 1 and 2 in comparison to the previous synthetic route accessing them in 5.8% and 3.0% overall yields, respectively. Evaluation of 1 and 2 revealed IC50 values between 2.0 and 5.1 μM in the cancerous cell lines HeLa, U937, A549, and MIA PaCa-2. Screening of the whole chalcone library set led to the discovery of over 30 compounds, within six cancerous cell lines, possessing single digit μM IC50 activity as sole agents. Furthermore, multiple library members were found to possess promising potentiating properties with known chemotherapeutic agents.

SYNTHESIS OF UVARETIN, AN ANTITUMOUR AND ANTIMICROBIAL FLAVONOID

The flavonoid uvaretin (1-(2,4-dihydroxy-6-methoxy-3-((2-hydroxyphenyl)-methyl)-phenyl)-3-phenyl-1-propanone), known to be active against some tumours and several bacteria, has been synthesized in six steps from 2',4',6'-trimethoxyacetophenone, 2-hydroxybenzaldehyde and benzaldehyde.

Aromatic Benzylation: Part III - Synthesis of Uvaretin, Isouvaretin and Related Nuclear Benzylated Dihydrochalcones

Reaction of 2-O-methylphloroacetophenone (5) with either o-benzyloxybenzyl alcohol (3) in the presence of boron trifluoride etherate and dioxan or with o-benzyloxybenzyl bromide (4) in the presence of methanolic potash affords 5-C-(o-benzyloxybenzyl) derivative (6) and its 3-C-isomer (7).Their orientation has been arrived at from a general behaviour of the chemical shift of chelated hydroxyl group in C-benzylated o-hydroxyacetophenones when C-benzyl group is present ortho or para to the chelated hydroxyl.Partial benzyl ether (9) of 6 and the complete benzyl ether (12) of 7 undergo facile condensation with benzaldehyde in the presence of alkali to give 10 and 13 respectively.These chalcones on hydrogenation in the presence of 10percent Pd-C afford uvaretin (11) and isouvaretin (14) respectively possessing physical characteristics identical with those of the natural samples.A parallel series of reactions starting from resacetophenone (15) provides C-benzylated dihydrochalcones 22 and 25 as analogues of uvaretin and isouvaretin respectively.