30225-82-2

Upstream product

• 2103-57-3 2,3,4-trimethoxybenzaldehyde 
• 634-36-6 1,2,3-trimethoxybenzene 

Downstream Products

• 19676-64-3 2,3,4-trimethoxyphenol 
• 478-01-3 nobiletin 
• 30225-96-8 1-(2-hydroxy-3,4,5-trimethoxyphenyl)ethan-1-one 
• 30225-98-0 2,3,4,5-Tetramethoxy-acetoxybenzol 
• 86475-21-0 2,3,4,5-tetramethoxyphenylformate 
• 65884-12-0 2,3,4,5-tetramethoxybenzaldehyde 
• 30225-99-1 2,3,4,5-Tetramethoxyphenol 
• 30225-97-9 1-(2,3,4,5-tetramethoxyphenyl)ethan-1-one 
• 3117-05-3 2,3,5-trimethoxy-1,4-benzoquinone 
• 634905-58-1 2-[1-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-meth-(Z)-ylidene]-5,6,7-trimethoxy-benzofuran-3-one 
• 527750-39-6 (Z)-3'-hydroxy-5,6,7,4'-tetramethoxyaurone 
• 527750-69-2 2-[1-(3-Fluoro-4-methoxy-phenyl)-meth-(Z)-ylidene]-5,6,7-trimethoxy-benzofuran-3-one 
• 527751-66-2 5,6,7-Trimethoxy-2-[1-(4-methoxy-phenyl)-meth-(Z)-ylidene]-benzofuran-3-one 
• 29877-56-3 6,7,8-trimethoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one 

Relevant academic research and scientific papers

Practical Synthesis of Polymethylated Flavones: Nobiletin and Its Desmethyl Derivatives

We present a practical synthesis of the polymethoxylated citrus flavone nobiletin that is suitable for use on a hundred gram scale. Ready availability of this compound and its derivatives will aid detailed chemical-biological investigations of their biological activities, including activation of signaling via the cAMP-dependent protein kinase A/extracellular signal-related protein kinase/cAMP response element-binding protein pathway.

Rational design, synthesis and biological evaluation of ubiquinone derivatives as IDO1 inhibitors

Indoleamine 2,3-dioxygenase 1 (IDO1) is an attractive therapeutic target for the treatment of cancer, chronic viral infections and neurological disorders characterized by pathological immune stimulation. Herein, a series of known metal-chelating ubiquinone derivatives were designed, synthesized and evaluated for the IDO1 inhibiting activities. The docking studies showed that the compounds 11, 16, 18 and coenzyme-Q1 exhibited different binding modes to IDO1 protein. Among these compounds, the most active compound is 16d with an IC50 of 0.13 μM in enzymatic assay. The results reveal that a possible halogen bonding interaction between the bromine atom (3-Br) and Cys129 significantly enhances the inhibition activity against IDO1. This study provides structural insights of the interactions between ubiquinone analogues and IDO1 protein for the further modification and optimization.

Polygala tenuifolia-Acori tatarinowii herbal pair as an inspiration for substituted cinnamic α-asaronol esters: Design, synthesis, anticonvulsant activity, and inhibition of lactate dehydrogenase study

Inspired by the traditional Chinese herbal pair of Polygala tenuifolia-Acori Tatarinowii for treating epilepsy, 33 novel substituted cinnamic α-asaronol esters and analogues were designed by Combination of Traditional Chinese Medicine Molecular Chemistry (CTCMMC) strategy, synthesized and tested systematically not only for anticonvulsant activity in three mouse models but also for LDH inhibitory activity. Thereinto, 68–70 and 75 displayed excellent and broad spectra of anticonvulsant activities with modest ability in preventing neuropathic pain, as well as low neurotoxicity. The protective indices of these four compounds compared favorably with stiripentol, lacosamide, carbamazepine and valproic acid. 68–70 exhibited good LDH1 and LDH5 inhibitory activities with noncompetitive inhibition type, and were more potent than stiripentol. Notably, 70, as a representative agent, was also shown as a moderately positive allosteric modulator at human α1β2γ2 GABAA receptors (EC50 46.3 ± 7.3 μM). Thus, 68–70 were promising candidates for developing into anti-epileptic drugs, especially for treatment of refractory epilepsies such as Dravet syndrome.

Bioinspired Total Synthesis of Bussealin e

The first total synthesis of bussealin E, a natural product with a unique cycloheptadibenzofuran scaffold, is reported. A strategy inspired by a proposed biosynthesis was employed whereby a diphenylpropane derivative underwent an oxidative phenolic coupling to forge the tetracyclic ring system. The synthesis of the diphenylpropane featured a key sp2-sp3 Hiyama coupling between a vinyldisiloxane and a benzylic bromide.

TUBULIN BINDING AGENTS

The invention provides combretastatin A-4 like compounds that are modified to have enhanced tubulin binding activity and in some embodiments the ability to promote accumulation in the vasculature undergoing angiogenesis (homing activity). The compounds are based on the combretastatin A-4 skeletal structure having a tubulin-binding pharmacophore comprising two fused rings (A and B rings) in which the B ring is substituted with (a) an aromatic ring structure (C ring) and (b) a second substituent/functional group that comes off the B ring. The aromatic ring structure is typically a six membered ring phenolic or aniline structure, or may also be a fused ring structure such as a substituted or unsubstituted naphthalene. The second substituent on the B ring may for example be a substituent which has been found to provide enhanced tubulin binding activity (for example a carbonyl group), or may be a substituent that facilitates functionalisation of the B ring (for example an hydroxyl or amine group), or it may be a binding agent for a target that is preferentially expressed on vasculature undergoing angiogenesis, and not expressed on quiescent vasculature.

PET imaging of nobiletin based on a practical total synthesis

A practical synthesis of nobiletin, a polymethoxylated citrus flavone, was accomplished by utilizing our novel flavone synthesis. Synthetic nobiletin was labelled by selective demethylation and rapid incorporation of 11C atom. Positron emission tomography images successfully visualized the brain distribution, which may provide therapeutic benefits in the treatment of Alzheimer's disease. The Royal Society of Chemistry.

Quinol fatty alcohols as promoters of axonal growth

The synthesis of three series of quinol fatty alcohols (QFAs) and their biological activities on the promotion of axonal growth are described. Interestingly, the 15-(2,5-dimethoxyphenyl)pentadecan-1-ol, the QFA bearing 15 carbon atoms on the side chain (n = 15), shows the most potent promotion of axonal growth in the presence of both permissive and non-permissive naturally occurring substrates such as Sema3A and myelin proteins.

An efficient synthesis of benzofurans and their application in the preparation of natural products of the genus Calea

The intramolecular cyclization of the β-substituted olefins methyl 2-aryloxy-3-dimethylaminopropenoates 3a-3f catalyzed by Lewis acids leads to a short and novel synthesis of benzofurans 2a-2f. When the olefins 4-dimethylamino-3-aryloxy-3-buten-2-ones 4a-4f were used, the cyclization process was faster and provided the corresponding substituted 2-acetylbenzofurans 1a-1f. Among the latter, naturally occurring compounds calebertin (1a), caleprunin A (1b), and caleprunin B (1c) were prepared in good overall yields. These benzofurans were also obtained by direct treatment under MW irradiation of the precursors 1-aryloxypropan-2-ones 7a-7c with DMFDMA, followed by addition of the catalyst, resulting in a route that was one step shorter.

The total synthesis of an aurone isolated from Uvaria hamiltonii: Aurones and flavones as anticancer agents

The naturally occurring aurone 1, isolated from Uvaria hamiltonii, and a series of aurones analogues based structurally on known tubulin binding agents were prepared and evaluated for anticancer activity. Aurone 20 was the most active (IC50 K562 50 nM) and caused significant G2/M cell-cycle arrest.