59092-94-3

Usage

Uses

Used in Oncology:
Phadodendrol is used as an anti-cancer agent for its potent cytotoxicity against various cancer cell lines, such as breast, lung, and colon cancer. It induces apoptosis and inhibits cell proliferation, making it a promising lead compound for the development of new cancer therapies.
Used in Drug Development:
Phadodendrol is used as a lead compound in the development of new cancer therapies due to its promising in vivo anti-tumor activity in xenograft models and unique chemical structure and mechanism of action. Further research and development in the field of oncology are necessary to fully explore its potential as a novel cancer treatment.

Upstream product

• 146609-83-8 (2R)-4-(4-Hydroxyphenyl)-2-butanol 2-O-β-D-apiofuranosyl-(1->6)-β-D-glucopyranoside 
• 69617-84-1 rac-rhododendrol 
• 5597-50-2 3-(4-hydroxyphenyl)propionic acid methyl ester 
• 108-05-4 vinyl acetate 
• 544-97-8 dimethyl zinc(II) 
• 147974-20-7 3-[4-(tert-butyl-dimethyl-silanyloxy)phenyl]propionaldehyde 
• 152339-86-1 (S)-4-(4′-methoxyphenyl)-2-butanol 
• 501-97-3 4-hydroxyphenylpropionic acid 
• 5471-51-2 4-(4-hydroxyphenyl)-2-oxobutane 
• 944335-23-3 (2S)-4-[4-(benzyloxy)phenyl]-2-hydroxybutyl 4-methyl-1-benzenesulfonate 
• 944335-22-2 (2S)-4-[4-(benzyloxy)phenyl]butane-1,2-diol 
• 944335-21-1 (4S)-4-[4-(benzyloxy)phenethyl]-2,2-dimethyl-1,3-dioxolane 
• 944335-20-0 4-{2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethyl}phenol 
• 85120-75-8 (R)-(+)-4-(4'-acetoxyphenyl)-2-butyl acetate 

Downstream Products

• 1195113-90-6 (R)-4-(3-hydroxybutyl)-4-hydroxy-2,5-cyclohexadien-1-one 
• 1195113-83-7 (R)-4-(3-hydroxybutyl)-4-hydroperoxy-2,5-cyclohexadien-1-one 
• 5471-51-2 4-(4-hydroxyphenyl)-2-oxobutane 
• 1000019-92-0 (S)-4-[3-hydroxybutyl]-4-hydroperoxy-2,5-cyclohexadien-1-one 
• 69617-84-1 rac-rhododendrol 
• 59092-94-3 (R)-rhododendrol 
• 152339-87-2 (S)-4-(p-pivaloyloxyphenyl)butan-2-ol 
• 129752-69-8 (R)-(+)-4-(4'-hydroxyphenyl)-2-butyl acetate 
• 1482494-92-7 C₂₂H₄₂O₂Si₂ 
• 1482494-94-9 C₁₆H₂₈O₃Si 
• 1482494-93-8 C₁₆H₂₈O₂Si 
• 152339-90-7 rhododendrin pentapivalate 
• 65982-27-6 (1R)-3-(4-hydroxyphenyl)-1-methylpropyl β-D-glucopyranoside 
• 2344-70-9 1-phenyl-3-butanol 

Relevant academic research and scientific papers

Characterization of phenolic compounds from Rhododendron alutaceum

A new phenolic glycoside, 3′-keto rhododendrin (1) and a new sesquilignan, alutaceuol (2), together with twelve known phenolic compounds, were isolated from the leaves of Rhododendron alutaceum. Their structures were elucidated by extensive spectroscopic data analysis and comparison with literature values. In addition, the detailed analysis of 2D NMR data led us to conclude that the chemical shifts of dihydrobuddlenol B (5) need to be revised.

STEREOSPECIFIC SYNTHESIS AND ABSOLUTE CONFIGURATION OF (+)-RHODODENDROL

The stereospecific synthesis of (+)-rhododendrol, a constituent of Rhododendron maximum and Acer nikoense, by enzymatic reduction of 4-(4'-hydroxyphenyl)-2-butanone has shown that the absolute configuration of the molecule is S.

Deracemization and Stereoinversion of Alcohols Using Two Mutants of Secondary Alcohol Dehydrogenase from Thermoanaerobacter pseudoethanolicus

We developed a one-pot sequential two-step deracemization approach to chiral alcohols using two mutants of Thermoanaerobacter pseudoethanolicus secondary alcohol dehydrogenase (TeSADH). This approach relies on consecutive non-stereospecific oxidation of alcohols and stereoselective reduction of their prochiral ketones using two mutants of TeSADH with poor and good stereoselectivities, respectively. More specifically, W110G TeSADH enables a non-stereospecific oxidation of alcohol racemates to their corresponding prochiral ketones, followed by W110V TeSADH-catalyzed stereoselective reduction of the resultant ketone intermediates to enantiopure (S)-configured alcohols in up to > 99 percent enantiomeric excess. A heat treatment after the oxidation step was required to avoid the interference of the marginally stereoselective W110G TeSADH in the reduction step; this heat treatment was eliminated by using sol-gel encapsulated W110G TeSADH in the oxidation step. Moreover, this bi-enzymatic approach was implemented in the stereoinversion of (R)-configured alcohols, and (S)-configured alcohols with up to > 99 percent enantiomeric excess were obtained by this Mitsunobu-like stereoinversion reaction.

New glycosides from the twigs and leaves of Rhododendron latoucheae

Six new glycosides (1?6), together with three known ones, were isolated from the twigs and leaves of Rhododendron latoucheae. Their structures were elucidated based on the spectroscopic data, including infrared spectrometry, mass spectrometry, and nuclear magnetic resonance experiments, along with Mosher's method. In addition, all compounds were tested their antiviral (herpes simplex virus-1 and influenza A/95-359) activities.

Expanding the Substrate Specificity of Thermoanaerobacter pseudoethanolicus Secondary Alcohol Dehydrogenase by a Dual Site Mutation

Here, we report the asymmetric reduction of selected phenyl-ring-containing ketones by various single- and dual-site mutants of Thermoanaerobacter pseudoethanolicus secondary alcohol dehydrogenase (TeSADH). The further expansion of the size of the substrate binding pocket in the mutant W110A/I86A not only allowed the accommodation of substrates of the single mutants W110A and I86A within the expanded active site but also expanded the substrate range of the enzyme to ketones bearing two sterically demanding groups (bulky–bulky ketones), which are not substrates for the TeSADH single mutants. We also report the regio- and enantioselective reduction of diketones with W110A/I86A TeSADH and single TeSADH mutants. The double mutant exhibited dual stereopreference to generate the Prelog products most of the time and the anti-Prelog products in a few cases.

Deracemization of Secondary Alcohols by using a Single Alcohol Dehydrogenase

We developed a single-enzyme-mediated two-step approach for deracemization of secondary alcohols. A single mutant of Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase enables the nonstereoselective oxidation of racemic alcohols to ketones, followed by a stereoselective reduction process. Varying the amounts of acetone and 2-propanol cosubstrates controls the stereoselectivities of the consecutive oxidation and reduction reactions, respectively. We used one enzyme to accomplish the deracemization of secondary alcohols with up to >99 % ee and >99.5 % recovery in one pot and without the need to isolate the prochiral ketone intermediate.

Asymmetric synthesis of enantiomerically pure zingerols by lipase-catalyzed transesterification and efficient synthesis of their analogues

The achiral zingerone 1, readily available from ginger, can be easily transformed into chiral derivatives. Zingerol 2, a reduced product of zingerone 1 is expected to be an important new medicinal lead compound. We have achieved a concise synthesis of optically active zingerol (R)-2 and (S)-2 by the lipase-catalyzed stereoselective transesterification of racemic 2. Under the optimized conditions, a lipase from Alcaligenes sp. (Meito QLM) and vinyl acetate in i-Pr2O or hexane at 35 C within 1 h gave the alcohol (S)-2 and the acetate (R)-9 with high enantioselectivity without producing acetylated by-products. Since optically active (S)-2 and (R)-9 were obtained through lipase-catalyzed transesterification, other enantiomerically pure novel compounds could all be synthesized.

Cephalosporolide B serving as a versatile synthetic precursor: Asymmetric biomimetic total syntheses of cephalosporolides C, E, F, G, and (4-OMe-)G

Cephalosporolide B (Ces-B) was efficiently synthesized and exploited for the first time as a versatile biomimetic synthetic precursor for the chemical syntheses of not only cephalosporolides C, G, and (4-OMe-) G via a challenging diastereoselective oxa-Michael addition but also the structurally unprecedented cephalosporolides E and F via a novel biomimetic ring-contraction rearrangement. These findings provide the first direct chemical evidence that Ces-B may be the true biosynthetic precursor of cephalosporolides.

Concise enantioselective synthesis of the ten-membered lactone cephalosporolide G and its C-3 epimer

A short and highly stereo-selective sequence for the first enantioselective total synthesis of the naturally occurring 10-membered lactone, which was obtained in only eight steps, was reported. The macrolactone ring was carried out by the use of a high-yielding pyridinium chlorochromate (PCC)-mediated oxidative cleavage of a bicyclic intermediate, generated in a domino sequence from a p-peroxyquinol. The synthesis was started with (-)-rhododendrol, which was obtained by enzymatic resolution of the racemic derivative. Phenol (R)-5 was submitted to an oxidative dearomatisation process with singlet oxygen, generated from Oxone in the presence of NaHCO3. The treatment of compound peroxyquinol with para-toluene sulfonic acid followed by Triton B gave, in one step and 49% yield, the tricyclic epoxide bicyclic derivative. A similar route was employed for the synthesis of the C-3 diastereoisomer of the natural product, which was obtained in only 7 steps and 15.2% overall yield.

Orchestration of concurrent oxidation and reduction cycles for stereoinversion and deracemisation of sec-alcohols

Black and white are opposites as are oxidation and reduction. Performing an oxidation, for example, of a sec-alcohol and a reduction of the corresponding ketone in the same vessel without separation of the reagents seems to be an impossible task. Here we show that oxidative cofactor recycling of NADP + and reductive regeneration of NADH can be performed simultaneously in the same compartment without significant interference. Regeneration cycles can be run in opposing directions beside each other enabling one-pot transformation of racemic alcohols to one enantiomer via concurrent enantioselective oxidation and asymmetric reduction employing defined alcohol dehydrogenases with opposite stereo- and cofactor-preference. Thus, by careful selection of appropriate enzymes, NADH recycling can be performed in the presence of NADP+ recycling to achieve overall, for example, deracemisation of sec-alcohols or stereoinversion representing a possible concept for a "green" equivalent to the chemical-intensive Mitsunobu inversion.