1138-41-6

Upstream product

• 99-96-7 4-hydroxy-benzoic acid 
• 101511-34-6 methyl-4-methoxy-3-(3’-methyl-2’-butenyl)benzoate 
• 99-76-3 methyl 4-hydroxylbenzoate 
• 107743-98-6 4-methoxy-3-(3'-methyl-2'-butenyl)-benzoic acid 
• 870-63-3 prenyl bromide 
• 123-08-0 4-hydroxy-benzaldehyde 
• 54730-30-2 4-hydroxy-3-C-prenylbenzaldehyde 
• 120-47-8 Ethyl 4-hydroxybenzoate 
• 918164-15-5 methyl 4-acetoxy-3-allylbenzoate 
• 35750-24-4 methyl 4-allyloxybenzoate 
• 918164-16-6 methyl 4-acetoxy-3-(3-methylbut-2-enyl)benzoate 
• 150-13-0 4-amino-benzoic acid 
• 89-86-1 4-hydroxysalicylic acid 
• 1145-42-2 ethyl 4-hydroxy-3-(3-methylbut-2-en-1-yl)benzoate 

Downstream Products

• 102012-55-5 4-acetoxy-3-(3-methyl-but-2-enyl)-benzoic acid anilide 
• 5919-91-5 prenylhydroquinone 
• 22944-03-2 Siccayne 
• 107743-98-6 4-methoxy-3-(3'-methyl-2'-butenyl)-benzoic acid 
• 121007-19-0 4-hydroxy-3-(3′-methylbut-3′-en-1′-ynyl)-benzoic acid 
• 1489296-36-7 C₃₈H₄₂N₂O₁₂ 
• 485-23-4 N-(4,7-dihydroxy-8-methyl-2-oxo-2H-chromen-3-yl)-4-hydroxy-3-(3-methylbut-2-en-1-yl)benzamide 
• 534600-69-6 3-[(E)-5-Benzenesulfonyl-3-methyl-5-((4aR,8aR)-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-pent-2-enyl]-4-benzyloxy-benzoic acid benzyl ester 
• 534600-70-9 4-benzyloxy-3-{(2'E)-3'-methyl-5'-[(4aR,8aR)-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydronaphthyl]-2'-pentenyl}benzoic acid 
• 534600-68-5 benzyl 3-(3'-bromomethyl-2'-butenyl)-4-benzyloxybenzoate 
• 534600-67-4 benzyl 3-(3'-hydroxymethyl-2'-butenyl)-4-benzyloxybenzoate 
• 92194-92-8 4-(chlorocarbonyl)-2-(3-methylbut-2-en-1-yl)phenyl acetate 
• 918164-17-7 4-((7-((3aR,4R,7R,7aR)-7-methoxy-6,6-dimethyl-2-oxotetrahydro-3aH-[1.3]dioxolo[4,5-c]pyran-4-yloxy)-8-methyl-2-oxo-2H-chromen-3-ylcarbamoyl)-2-(3-methylbut-2-enyl) phenyl acetate 
• 1990-85-8 4-acetoxy-3-(3-methylbut-2-en-1-yl)benzoic acid 

Relevant academic research and scientific papers

A Monooxygenase from Boreostereum vibrans Catalyzes Oxidative Decarboxylation in a Divergent Vibralactone Biosynthesis Pathway

The oxidative decarboxylation of prenyl 4-hydroxybenzoate to prenylhydroquinone has been frequently proposed for the biosynthesis of prenylated (hydro)quinone derivates (sometimes meroterpenoids), yet no corresponding genes or enzymes have so far been reported. A FAD-binding monooxygenase (VibMO1) was identified that converts prenyl 4-hydroxybenzoate into prenylhydroquinone and is likely involved in the biosynthesis of vibralactones and other meroterpenoids in the basidiomycete Boreostereum vibrans. Feeding of 3-allyl-4-hydroxybenzylalcohol, an analogue of the vibralactone pathway intermediate 3-prenyl-4-hydroxybenzylalcohol, generated 20 analogues with different scaffolds. This demonstrated divergent pathways to skeletally distinct compounds initiating from a single precursor, thus providing the first insight into a novel biosynthetic pathway for 3-substituted γ-butyrolactones from a shikimate origin.

Antibacterial Prenylated p-Hydroxybenzoic Acid Derivatives from Oberonia myosurus and Identification of Putative Prenyltransferases

Twelve hitherto unknown tandem prenylated p-hydroxybenzoic acid derivatives, namely, oberoniamyosurusins A-L, together with five known derivatives, were isolated from an EtOH extract of the whole parts of the plant Oberonia myosurus. Compounds 10, 13, and 17 exhibited moderate inhibitory activity against Staphylococcus aureus subsp. aureus ATCC29213 with MIC50 values ranging from 7.6 to 23 μg/mL. To determine the biosynthetic pathway of this class of tandem prenyl-substituted compounds, the full-length transcriptome of O. myosurus was sequenced, yielding 19.09 Gb of clean data and 10 949 nonredundant sequences. Two isoforms of p-hydroxybenzoic acid prenyltransferases were annotated and functionally characterized as the enzymes that might be involved in the biosynthesis of nervogenic acid (13) in Pichia pastoris.

Biosynthesis of Biscognienyne B Involving a Cytochrome P450-Dependent Alkynylation

The alkyne is a biologically significant moiety found in many natural products and a versatile functional group widely used in modern chemistry. Recent studies have revealed the biosynthesis of acetylenic bonds in fatty acids and amino acids. However, the

Discovery of a Dual Function Cytochrome P450 that Catalyzes Enyne Formation in Cyclohexanoid Terpenoid Biosynthesis

The 1,3-enyne moiety is commonly found in cyclohexanoid natural products produced by endophytic and plant pathogenic fungi. Asperpentyn (1) is a 1,3-enyne-containing cyclohexanoid terpenoid isolated from Aspergillus and Pestalotiopsis. The genetic basis and biochemical mechanism of 1,3-enyne biosynthesis in 1, and other natural products containing this motif, has remained enigmatic despite their potential ecological roles. Identified here is the biosynthetic gene cluster and characterization of two crucial enzymes in the biosynthesis of 1. A P450 monooxygenase that has a dual function, to first catalyze dehydrogenation of the prenyl chain to generate a cis-diene intermediate and then serve as an acetylenase to yield an alkyne moiety, and thus the 1,3-enyne, was discovered. A UbiA prenyltransferase was also characterized and it is unusual in that it favors transferring a five-carbon prenyl chain, rather than a polyprenyl chain, to a p-hydroxybenzoic acid acceptor.

NOVOBIOCIN ANALOGUES AND TREATMENT OF POLYCYSTIC KIDNEY DISEASE

Novobiocin analogues are useful in methods of treating, inhibiting, and/or preventing cyst formation in autosomal dominant polycystic kidney disease (ADPKD) in a subject. The disclosure provides methods of treating ADPKD comprising administering a therapeutically effective amount of a coumarin-3-carboxamide novobiocin analogue. Accordingly, the method can include administering a novobiocin analogue in a therapeutically effective amount for reducing levels of mTOR pathway phosphoproteins P-mTOR, P-Akt and P-S6K, or combinations thereof. Further, the method can include administering a novobiocin analogue in a therapeutically effective amount for reducing levels of Hsp-90 client proteins CFTR, ErbB2, c-Raf and Cdk4, or combinations thereof.

PHENYL-PRENYL DERIVATIVES, OF MARINE AND SYNTHETIC ORIGIN, FOR THE TREATMENT OF COGNITIVE, NEURODEGENERATIVE OR NEURONAL DISEASES OR DISORDERS

The present invention is related to a family of phenyl-prenyl derivatives of formula (I), and to their use in the treatment of cognitive, neurodegenerative or neuronal diseases or disorders, such as Alzheimer's disease or Parkinson's Disease. The present

Novobiocin: Redesigning a DNA gyrase inhibitor for selective inhibition of Hsp90

Novobiocin is a member of the coumermycin family of antibiotics and is a well-established inhibitor of DNA gyrase. Recent studies have shown that novobiocin binds to a previously unrecognized ATP-binding site at the C-terminus of Hsp90 and induces degradation of Hsp90-dependent client proteins at ～700 μM. In an effort to develop more efficacious inhibitors of the C-terminal binding site, a library of novobiocin analogues was prepared and initial structure-activity relationships revealed. These data suggested that the 4-hydroxy moiety of the coumarin ring and the 3′-carbamate of the noviose appendage were detrimental to Hsp90 inhibitory activity. In an effort to confirm these findings, 4-deshydroxy novobiocin (DHN1) and 3′-descarbamoyl-4- deshydroxynovobiocin (DHN2) were prepared and evaluated against Hsp90. Both compounds were significantly more potent than the natural product, and DHN2 proved to be more active than DHN1. In an effort to determine whether these moieties are important for DNA gyrase inhibition, these compounds were tested for their ability to inhibit DNA gyrase and found to exhibit significant reduction in gyrase activity. Thus, we have established the first set of compounds that clearly differentiate between the C-terminus of Hsp90 and DNA gyrase, converted a well-established gyrase inhibitor into a selective Hsp90 inhibitor, and confirmed essential structure-activity relationships for the coumermycin family of antibiotics.

Synthesis and absolute configuration of (-)-subersic acid, a sponge-derived, terpenoidal inhibitor of human 15-lipoxygenase

(-)-Subersic acid (1), a new derivative of p-hydroxybenzoic acid in which the m-position is substituted with a bicyclic diterpenoid was synthesized from (S)-3-hydroxy-2,2-dimethylcyclohexanone and p-hydroxybenzoic acid. The stereochemistry of this sponge-

HYDROXY-(METHYLBUTENYNYL)-BENZOIC ACID AND DERIVATIVES FROM CURVULARIA FALLAX

4-Hydroxy-3-(3'-methyl-2'-butenyl)-benzoic acid, 4-hydroxy-3-(3'-methyl-3'-buten-1'-inyl)-benzoic acid, 2-isopropenylbenzofuran-5-carboxylic acid, anofinic acid and its 3,4-trans-dihydroxy derivative were isolated from the fungus Curvularia fallax.Biotransformation with p-amino-benzoic acid led to the corresponding 3-prenylbenzoic acid while 2,4-dihydroxybenzoic acid was alkylated in 5-position.Other related substrates were not prenylated by the microorganism.The biosynthesis of these compounds in C. fallax and Streptomyces niveus is compared.