13618-49-0

Upstream product

• 5446-02-6 4-methoxymethylsalicylate 
• 100-44-7 benzyl chloride 
• 2237-36-7 4-methoxysalicylic acid 
• 32884-23-4 2-benzyloxy-4-methoxybenzaldehyde 
• 100-39-0 benzyl bromide 
• 13618-48-9 methyl-2-(benzyloxy)-4-methoxybenzoate 
• 89-86-1 4-hydroxysalicylic acid 
• 673-22-3 2-Hydroxy-4-methoxybenzaldehyde 
• 2150-47-2 methyl 2,4-dihydroxybenzoate 

Downstream Products

• 112649-72-6 2,5-bis(2-benzyloxy-4-methoxybenzoyloxy)-4-methoxytoluene 
• 112649-73-7 2,5-bis(2-hydroxy-4-methoxybenzoyloxy)-4-methoxytoluene 
• 112649-74-8 2,5-bis(2-acetoxy-4-methoxybenzoyloxy)-4-methoxytoluene 
• 112649-75-9 2,5-bis(2-acetoxy-4-methoxybenzoyloxy)-4-methoxybenzyl bromide 
• 1323988-59-5 (2R,3R,6S)-2-(acetoxymethyl)-6-(2-(benzyloxy)-4-methoxyphenyl)-3,6-dihydro-2H-pyran-3,4-diyl diacetate 
• 1323988-62-0 (2R,3S,6S)-2-(acetoxymethyl)-6-(2-(benzyloxy)-4-methoxyphenyl)-3,6-dihydro-2H-pyran-3,4-diyl diacetate 
• 1374020-64-0 C₂₉H₂₆O₅ 
• 1374020-65-1 C₁₅H₁₄O₅ 
• 1374020-86-6 C₃₂H₃₂O₆ 
• 1374020-88-8 C₁₈H₂₀O₆ 
• 107777-40-2 2-benzyloxy-4-methoxy-phenol 
• 1448816-36-1 1-(2-(benzyloxy)-3,4,5-trimethoxyphenyl)-5-(2-(benzyloxy)-4-methoxyphenyl)-1H-tetrazole 
• 1448816-38-3 5-(2-(benzyloxy)-4-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)-1H-tetrazole 
• 1448816-24-7 5-methoxy-2-(1-(3,4,5-trimethoxyphenyl)-1H-tetrazol-5-yl)phenol 

Relevant academic research and scientific papers

Synthesis of p-O-Alkyl Salicylanilide Derivatives as Novel EGFR Inhibitors

(Table Presented) Epidermal growth factor receptor (EGFR), a validated target for anticancer drugs, plays a critical role in tumorigenesis and tumor development. A series of p-O-alkyl salicylanilide derivatives were designed and synthesized as novel EGFR inhibitors using a salicylic acid scaffold. A simulated six-membered ring strategy formed through intramolecular hydrogen bonds was employed to mimic the planar quinazoline of the EGFR antagonist, gefitinib. The derived compounds with hydroxyl at the ortho position were more potent than ones with methoxyl group. In particular, compounds 5d and 5b displayed significant EGFR inhibitory (IC50 values = 0.30 and 0.45 μM, respectively) activity as well as potent antiproliferative activity in A431 and HCT-116 tumor cells. These salicylanilides could be considered as promising lead compounds for developing novel EGFR inhibitors.

Total synthesis of Neocosmosin A

An alternative synthetic route to (?)-Neocosmosin A has been synthesized from commercially available (R)-propylene oxide and 4-Methoxysalicylic acid as starting materials. The key steps involved in the synthesis are alkylation of 1,3-dithiane and Yamaguchi macrolactonization.

BRARTEMICIN ANALOGUES

The invention relates to brartemicin analogues of Formula (IV) and their uses. These compounds are potent Mincle agonists and Th1-stimulating vaccine adjuvants.

Second-Generation Synthesis of the Northern Fragment of Mandelalide A: Role of π-Stacking on Sharpless Dihydroxylation of cis-Enynes

The development of a π-stacking-based approach for increased stereoselectivity in Sharpless asymmetric and diastereomeric dihydroxylation of cis-enynes is disclosed. The use of neighboring, electron-rich benzoate esters proved key to the success of this process. Density functional theory study suggests that the substrate benzoate ester group rigidifies the dihydroxylation transition states by forming a favorable π-stacking interaction in both Major-TS and Minor-TS. The energetic preference for the Major-TS was found in part because of the favorable eclipsing conformation of the alkene substituent as opposed to the disfavored bisecting conformation found in the Minor-TS. The application to a second-generation synthesis of the C15-C24 northern portion of mandelalide A is demonstrated.

Lipidated Brartemicin Analogues Are Potent Th1-Stimulating Vaccine Adjuvants

Effective Th1-stimulating vaccine adjuvants typically activate antigen presenting cells (APCs) through pattern recognition receptors (PRRs). Macrophage inducible C-type lectin (Mincle) is a PRR expressed on APCs and has been identified as a target for Th1-stimulating adjuvants. Herein, we report on the synthesis and adjuvanticity of rationally designed brartemicin analogues containing long-chain lipids and demonstrate that they are potent Mincle agonists that activate APCs to produce inflammatory cytokines in a Mincle-dependent fashion. Mincle binding, however, does not directly correlate to a functional immune response. Mutation studies indicated that the aromatic residue of lead compound 9a has an important interaction with Mincle Arg183. In vivo assessment of 9a highlighted the capability of this analogue to augment the Th1 response to a model vaccine antigen. Taken together, our results show that lipophilic brartemicin analogues are potent Mincle agonists and that 9a has superior in vivo adjuvant activity compared to TDB.

Correlation of hydrogen-bonding propensity and anticancer profile of tetrazole-tethered combretastatin analogues

A series of 1,5-disubstituted tetrazole-tethered combretastatin analogues with extended hydrogen-bond donors at the ortho-positions of the aryl A and B rings were developed and evaluated for their antitubulin and antiproliferative activity. We wanted to test whether intramolecular hydrogen-bonding used as a conformational locking element in these analogues would improve their activity. The correlation of crystal structures with the antitubulin and antiproliferative profiles of the modified analogues suggested that hydrogen-bond-mediated conformational control of the A ring is deleterious to the bioactivity. In contrast, although there was no clear evidence that intramolecular hydrogen bonding to the B ring enhanced activity, we found that increased substitution on the B ring had a positive effect on antitubulin and antiproliferative activity. Among the various analogues synthesized, compounds 5d and 5e, having hydrogen-bonding donor groups at the ortho and meta-positions on the 4-methoxy phenyl B ring, are strong inhibitors of tubulin polymerization and antiproliferative agents having IC50 value in micromolar concentrations.

Psoromic acid is a selective and covalent rab-prenylation inhibitor targeting autoinhibited rabggtase

Post-translational attachment of geranylgeranyl isoprenoids to Rab GTPases, the key organizers of intracellular vesicular transport, is essential for their function. Rab geranylgeranyl transferase (RabGGTase) is responsible for prenylation of Rab proteins

Natural Benzofurans. Synthesis of Methylsainfuran and Sainfuran

2-(2,4-Dimethoxyphenyl)-5-hydroxy-6-methoxybenzofuran (methylsainfuran) and 2-(2-hydroxy-4-methoxyphenyl)-5-hydroxy-6-methoxybenzofuran (sainfuran).Insect feeding deterrent extractives of sainfoin, have been synthesized by a pathway in which the benzofuran heterocycle is formed by an interamolecular Wittig reaction.

Benzamide derivatives

Benzamide derivatives of the formula:- STR1 wherein R1 represents a fluorine, chlorine or bromine atom, or an alkyl, alkoxy, alkylthio, alkylsulphonyl, alkanoylamino, alkylamino or alkylsulphamoyl group, each such group containing from 1 to 6 carbon atoms, a dialkylsulphamoyl, dialkylamino or dialkylcarbamoyl group (wherein the two alkyl groups may be the same or different and each contains from 1 to 4 carbon atoms), an alkanoyl, alkoxycarbonyl, alkoxycarbonylamino or alkylcarbamoyl group containing from 2 to 6 carbon atoms, or a hydroxy, formyl, nitro, trifluoromethyl, aryl, benzyloxycarbonylamino, amino, sulphamoyl, cyano, tetrazol-5-yl, carboxy, carbamoyl or aroyl group, and n represents an integer 1, 2 or 3, are new compounds possessing pharmacological properties, in particular properties of value in the treatment of respiratory disorders manifested by the interaction of tissue-fixed antibodies with specific antigens.