59115-47-8

Upstream product

• 109393-80-8 6-methoxy-2-(4-methoxy-phenyl)-1,2-dihydro-naphthalene 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 120-44-5 1,4-di(4-methoxyphenyl)ethanone 
• 60-29-7 diethyl ether 
• 74-86-2 acetylene 
• 71-43-2 benzene 
• 5111-65-9 2-Bromo-6-methoxynaphthalene 
• 5720-07-0 4-methoxyphenylboronic acid 
• 101743-58-2 7-Methoxy-3-(4-methoxy-phenyl)-1,2,3,4-tetrahydro-[1]naphthol 
• 177937-97-2 4-methoxy-2-(2-trimethylsilylethynyl)benzaldehyde 
• 1145-93-3 diethyl 4-methoxybenzylphosphonate 
• 416857-85-7 10-hydroxy-10-methyl-2,2-diphenyl-2H-pyrano[6,5-b]fluorene 
• 13139-86-1 4-methoxyphenyl magnesium bromide 

Downstream Products

• 380861-01-8 6-hydroxy-2-(4′-hydroxyphenyl)naphthalene 
• 550998-03-3 1-chloro-2-methoxy-6-(4-methoxyphenyl)naphthalene 
• 550998-02-2 1-bromo-2-methoxy-6-(4-methoxyphenyl)naphthalene 
• 132041-62-4 2-(4-methoxyphenyl)-6-methylnaphthalene 
• 132041-61-3 2-methyl-6-p-tolylnaphthalene 
• 102001-81-0 2-acetoxy-6-(4-acetoxy-phenyl)-naphthalene 
• 550998-07-7 2-methoxy-6-(4-methoxyphenyl)-1-phenylnaphthalene 
• 550998-06-6 2-methoxy-6-(4-methoxyphenyl)-1-naphthonitrile 
• 550997-76-7 1-bromo-6-(4-hydroxyphenyl)-2-naphthol 
• 550998-05-5 2-methoxy-6-(4-methoxyphenyl)-1-fluoronaphthalene 
• 550998-08-8 2-methoxy-6-(4-methoxyphenyl)-1-methylnaphthalene 
• 933066-96-7 6-(6-methoxy-naphthalen-2-yl)-2,2-diphenyl-2H-chromene 

Relevant academic research and scientific papers

Substituent effects on the iodine-catalyzed thermal cyclization of 3,4-diphenylbuta-1,3-dienyl isocyanates: Mechanistic studies

The thermal cyclization of 3,4-diphenylbuta-1,3-dienyl isocyanates 1, generated in situ from the corresponding azides, was investigated using iodine as a catalyst. Diphenylpyridinones 2, phenylnaphthalenes 3, and indenes 4 were produced via intramolecular ring closure. The nature of the substituents on the phenyl rings was found to be crucial to the distribution of cyclized products 2 - 4. The mechanism of the reaction is also discussed.

17BETA-HYDROXYSTEROID DEHYDROGENASE TYPE 1 INHIBITORS FOR THE TREATMENT OF HORMONE-RELATED DISEASES

The invention relates to the use of non-steroidal 17beta-hydroxysteroid dehydrogenase type 1 inhibitors for the treatment and prophylaxis of hormone-dependent, particularly estrogen-dependent, diseases.The invention further relates to suitable inhibitors and to a method for the production thereof.

Design, synthesis, and biological evaluation of (hydroxyphenyl)naphthalene and -quinoline derivatives: Potent and selective nonsteroidal inhibitors of 17β-hydroxysteroid dehydrogenase type 1 (17β-HSD1) for the treatment of estrogen-dependent diseases

Human 17β-hydroxysteroid dehydrogenase type 1 (17β-HSD1) catalyzes the reduction of the weak estrogen estrone (E1) to the highly potent estradiol (E2). This reaction takes place in the target cell where the estrogenic effect is exerted via the estrogen receptor (ER). Estrogens, especially E2, are known to stimulate the proliferation of hormone-dependent diseases. 17β-HSD1 is overexpressed in many breast tumors. Thus, it is an attractive target for the treatment of these diseases. Ligand- and structure-based drug design led to the discovery of novel, selective, and potent inhibitors of 17β-HSD1. Phenyl-substituted bicyclic moieties were synthesized as mimics of the steroidal substrate. Computational methods were used to obtain insight into their interactions with the protein. Compound 5 turned out to be a highly potent inhibitor of 17β-HSD1 showing good selectivity (17β-HSD2, ERα and β), medium cell permeation, reasonable metabolic stability (rat hepatic microsomes), and little inhibition of hepatic CYP enzymes.

Photochromism of arylchromenes: Remarkable modification of absorption properties and lifetimes of o-quinonoid intermediates

(Chemical Equation Presented) A significant π-conjugation in 6- and 7-arylchromenes manifests dramatically in the absorption properties of their photogenerated o-quinonoid intermediates. This in conjunction with facile synthesis via Suzuki coupling may render a myriad of photochromic arylchromenes with wide-ranging spectrokinetic properties readily accessible.

ERβ ligands. 3. Exploiting two binding orientations of the 2-phenylnaphthalene scaffold to achieve ERβ selectivity

The 2-phenylnaphthalene scaffold was explored as a simplified version of genistein in order to identify ER selective ligands. With the aid of docking studies, positions 1, 4, and 8 of the 2-phenylnaphthalene template were predicted to be the most potentially influential positions to enhance ER selectivity using two different binding orientations. Both orientations have the phenol moiety mimicking the A-ring of genistein. Several compounds predicted to adopt orientations similar to that of genistein when bound to ERβ were observed to have slightly higher ER affinity and selectivity than genistein. The second orientation we exploited, which was different from that of genistein when bound to ERβ, resulted in the discovery of several compounds that had superior ER selectivity and affinity versus genistein. X-ray structures of two ER selective compounds (i.e., 15 and 47) confirmed the alternate binding mode and suggested that substituents at positions 1 and 8 were responsible for inducing selectivity. One compound (i.e., 47, WAY-202196) was further examined and found to be effective in two models of inflammation, suggesting that targeting ER may be therapeutically useful in treating certain chronic inflammatory diseases.

Substituted phenyl naphthalenes as estrogenic agents

This invention provides estrogen receptor modulators of formula I, having the structure 1wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, and R10, are as defined in the specification, or a pharmaceutically acceptable salt thereof.

α-OXOKETENE DITHIOACETALS AS INTERMEDIATES FOR AROMATIC ANNELATION

The α-oxoketene dithioacetals of general formula 1 (Scheme 2), undergo regioselective 1,2-addition with allyl anions to afford the corresponding carbinol acetals 6 in quantitative yields, which on treatment with BF3*Et2O in refluxing benzene yield the corresponding aromatic systems.The method has been shown to be widely applicable as exemplified by a large number of allyl anions (Scheme 3) reacting with α-oxoketene dithioacetals with wide structural variation.However, when 1 carry the α-substituent the intermediate carbinol acetals 14 (Scheme 4) follow, different path to yield the corresponding indenes 15 in good yields.The cinnamoylketene dithioacetals 16 react with allyl anions to afford the corresponding methylthiostilbenes 18 (Scheme 5), while the homologous dithioacetal 20 failed to yield the corresponding 1,4-biaryl-1,3-diene 22 (Scheme 6).This limitation was circumvented by reacting 23 with allyl anions to afford the corresponding stilbenes 24, dienes 25 and triene 26 respectively.The method was successfully extended for naphthoannelation.Thus naphthalenes 28 (Scheme 7) were prepared by reacting benzylmagnesium chloride with 1.In this case the reaction followed a sequential 1,4- and 1,2-addition mode and yielded the corresponding benzyl substituted naphthalenes.This problem was solved by reacting benzylmagnesium chloride with 8 to afford the corresponding naphthalenes 31 (Scheme 8) in excellent yields.Similarly the lithio derivatives derived from toluene followed 1,2-addition mode with 1 to afford the derived methylthionaphthalenes 39 (Scheme 9) in high yields.The other alkyl substituted naphthalenes 41, 43 (Scheme 9), 45, 47 (Scheme 10) were similarly prepared.Also 1 and β-oxodithioacetals 8 reacted with 1-naphthylmethylmagnesium chloride to afford the corresponding phenanthrenes 49 and 51 respectively in good yields.The method was extended to benzanthracene 56 (Scheme 11) synthesis successfully.The 2-naphthylmethyl magnesium chloride reacted in a sequential 1,4- and 1,2-fasion to afford the corresponding naphthylmethyl hydrocarbons 58 while it reacted with β-oxodithioacetals to give expected condensed aromatics 60, 61 and 62 (Scheme 12) in high yields.The 1-naphthylmethylmagnesium chloride also reacted with β-oxodithioacetals 23 to afford the corresponding styrylphenanthrenes 65, dienes 66 and triene 67 respectively in high yields.The intermediate 69 precursor in the synthesis of hexahelicine was also obtained by reacting 68 with 1-naphthylmethylmagnesium chloride (Scheme 13).The oxygenated benzylmagnesium halides reacted with 1 in 1,2-fasion (Scheme 14) with the exception of the formation of 79.Five fold excess of Reformatsky reagent reacted with 1 to afford the corresponding salicylates 82 (Scheme 15) in high yields.Similarly 84 (Scheme 16) was formed.Propargylmagnesium chloride also reacted with 1 with the participation of solvent methanol to afford the corresponding thioresolcinol dimethylethers 86 ...