54549-75-6

Upstream product

• 13575-74-1 4-(3,4-dimethoxyphenyl)butanoic acid 
• 13575-75-2 6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydronaphthalene 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 98799-43-0 trans-4-(3,4-dimethoxyphenyl)but-3-enoic acid 
• 91-16-7 1,2-dimethoxybenzene 
• 5333-34-6 3-(3,4-dimethoxybenzoyl)propionic acid 

Downstream Products

• 119034-87-6 6,7-bis(benzyloxy)-3,4-dihydronaphthalen-1(2H)-one 
• 41303-45-1 6,7-methylenedioxy-1-tetralone 
• 873296-52-7 6-benzyloxy-7-hydroxy-1-tetralone 
• 383382-48-7 6,7-dihydroxy-8-nitro-3,4-dihydro-2H-naphthalen-1-one 
• 383383-11-7 6-benzyloxy-7-hydroxy-8-nitro-1-tetralone 
• 205178-57-0 naphtho[2,3-d][1,3]dioxol-5-yl 6-iodo-2,3-dimethoxybenzoate 
• 207279-90-1 6,7-Bis-benzyloxy-2,3-dihydro-[1,4]naphthoquinone 
• 119034-85-4 6,7-diethoxy-1,2-dihydro-3-naphthoic acid 
• 15288-01-4 7-hydroxy-6-methoxy-3,4-dihydronaphthalen-1(2H)-one 
• 1262799-69-8 1-(4-(1-(4-fluorophenyl)-8-isopropoxy-7-methoxy-4,5-dihydro-1H-benzo[g]indazole-3-carbonyl)-1,4-diazepan-1-yl)ethanone 
• 1262799-71-2 C₂₄H₂₅FN₂O₄ 
• 1262799-72-3 C₂₂H₂₁FN₂O₄ 
• 1359946-26-1 8-(3-(Cyclohexylamino)propoxy)-9-methoxy-12-methyl-5,6-dihydro-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]acridin-12-ium chloride 

Relevant academic research and scientific papers

Synthesis and biological activity of conformationally restricted tricyclic analogs of the hormone melatonin

A serie of rotationally restricted tricyclic naphthalenic and tetrahydronathalenic analogs of the hormone melatonin has been synthesized, the C-7 oxygen being incorporated in a pyran, furan or dioxan heterocyclic ring. The receptor binding profile of these compounds is a function of the directionality of the lone pairs electrons of this C-7 oxygen. In these two studied analogous series the agonist activity seems to be correlated with the existence of a naphthalene nucleus.

12-N-Methylated 5,6-dihydrobenzo[c]acridine derivatives: A new class of highly selective ligands for c-myc G-quadruplex DNA

12-N-Methylated and non-methylated 5,6-dihydrobenzo[c]acridine derivatives were designed and synthesized as new series of c-myc G-quadruplex binding ligands. Their interactions with c-myc G-quadruplex were evaluated using fluorescence resonance energy tra

Dihydrobenzoindazoles

The invention relates to benzoindazole derivatives according to general Formula I or a pharmaceutically acceptable salt thereof. The compounds can be used for the treatment of infertility.

DIHYDROBENZOINDAZOLES

The invention relates to benzoindazole derivatives according to general Formula I or a pharmaceutically acceptable salt thereof. The compounds can be used for the treatment of infertility.

Synthesis and biological evaluation of a novel series of "ortho-nitrated" inhibitors of catechol-O-methyltransferase

Novel regioisomeric "ortho-nitrated" catechols related to the catechol-O-methyltransferase (COMT) inhibitors BIA 3-202 3 and BIA 3-335 4 were synthesized and biologically evaluated. Changing the position of the nitro group from the "classical" meta- to th

Cleavage of aromatic methyl ethers by chloroaluminate ionic liquid reagents

We have discovered serendipitously that chloroaluminate ionic liquids can cleave aromatic methyl ethers under surprisingly mild conditions. Three ionic liquids, viz. [TMAH]-[Al2Cl7], [BMIM][Al2Cl7], and [EMIM][Al2Cl6I], and aluminum chloride were compared in the selective demethylation of 4,5-dimethoxyindanone at the 4-methoxy-function. The ionic liquids exhibited a remarkably high selectivity (96:4) in comparison with aluminum chloride (70:30). In addition, the reaction time was drastically shortened when the ionic liquids were used. Interestingly, the three ionic liquids displayed the same reactivity in the demethylation of 4,5-dimethoxyindanone. Considering the lower cost and the bulk availability of the precursors of [TMAH][Al2Cl7], we conclude that this is the most attractive ionic liquid from an industrial point of view. To make the large-scale application of [TMAH][Al2Cl7] feasible, we have developed a safe upscalable method for its preparation. Furthermore, the scope of ether cleavage by the ionic liquid reagent [TMAH][Al2Cl7] was investigated and it was found that aromatic methyl-, al- lyl-, and benzyl-ether cleavage is applicable to a variety of heterocyclic compounds. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Aminomethylcarboxylic acid derivatives

The present invention relates to aminomethylcarboxylic acid derivatives general formula (I), wherein Z is (CH2)n, O, S, SO, SO2or N—R5; n is 0, 1 or 2; X represents 1-3 substituents independently selected from hydrogen, halogen, (C1-6)alkyloxy, (C3-6)cycloalkyloxy, (C6-12)aryloxy, (C6-12)aryl, thienyl, SR6, SOR6, SO2R6, NR6R6, NHR6, NH2, NHCOR6, NSO2R6, CN, COOR6and (C1-4)alkyl, optionally substituted with halogen, (C6-12)aryl, (C1-6)alkyloxy or (C6-12)aryloxy; or 2 substituents at adjacent positions together represent a fused (C5-6)aryl group, a fused (C5-6)cycloalkyl ring or O—(CH2)m—O; m is 1 or 2; Y represents 1-3 substituents independently selected from hydrogen, halogen, (C1-4)alkyloxy, SR6, NR6R6and (C1-4)alkyl, optionally substituted with halogen; R1is COOR7or CONR8R9; R2and R6are (C1-4)alkyl; R3, R4and R5are independently hydrogen or (C1-4)alkyl; R7, R8and R9are independently hydrogen, (C1-4)alkyl, (C6-12)aryl or arylalkyl; or a pharmaceutically acceptable salt thereof. The invention also relates to pharmaceutical compositions comprising said derivatives, as well as to the use of these aminomethylcarboxylic acid derivatives in therapy, more specifically for the treatment of CNS disorders.

Synthesis and reactivity of the catechol metabolites from the equine estrogen, 8,9-dehydroestrone

The risk factors for women developing breast and endometrial cancers are all associated with a lifetime of estrogen exposure. Estrogen replacement therapy in particular has been correlated with an increased cancer risk. Previously, we showed that the equine estrogens equilin and equilenin, which are major components of the widely prescribed estrogen replacement formulation Premarin, are metabolized to highly cytotoxic quinoids which caused oxidative stress and alkylation of DNA in vitro [Bolton, J. L., Pisha, E., Zhang, F., and Qiu, S. Chem. Res. Toxicol. 1998, 11, 1113-1127]. In this study, we have synthesized 8,9-dehydroestrone (a third equine estrogen component of Premarin) and its potential catechol metabolites, 4-hydroxy-8,9-dehydroestrone and 2-hydroxy-8,9-dehydroestrone. Both 2-hydroxy-8,9-dehydroestrone and 4-hydroxy-8,9-dehydroestrone were oxidized by tyrosinase or rat liver microsomes to o-quinones which reacted with GSH to give one mono-GSH conjugate and two di-GSH conjugates. Like endogenous estrogens, 8,9-dehydroestrone was primarily converted by rat liver microsomes to the 2-hydroxylated rather than the 4-hydroxylated o-quinone GSH conjugates; the ratio of 2-hydroxy-8,9-dehydroestrone versus 4-hydroxy-8,9-dehydroestrone was 6:1. Also in contrast to experiments with equilin, 4-hydroxyequilenin was not observed in microsomal incubations with 8,9-dehydroestrone or its catechols. The behavior of 2-hydroxy-8,9-dehydroestrone was found to be more complex than 4-hydroxy-8,9-dehydroestrone as GSH conjugates resulting from 2-hydroxy-8,9-dehydroestrone were detected even without oxidative enzyme catalysis. Under physiological conditions, 2-hydroxy-8,9-dehydroestrone isomerized to 2-hydroxyequilenin to form the very stable 2-hydroxyequilenin catechol; however, 4-hydroxy-8,9-dehydroestrone was found to be stable under similar conditions. Finally, preliminary studies conducted with the human breast tumor S-30 cell lines demonstrated that the catechol metabolites of 8,9-dehydroestrone were much less toxic than 4-hydroxyequilenin (20-40-fold). These results suggest that the catechol metabolites of 8,9-dehydroestrone may have the ability to cause cytotoxicity in vivo primarily through formation of o-quinones; however, most of the adverse effects of Premarin estrogens are likely due to formation of 4-hydroxyequilenin o-quinone from equilin and equilenin.

Synthesis of arnottin I through a palladium-mediated aryl-aryl coupling reaction

6H-Dibenzo[b,d]pyran-6-one, 6H-benzo[d]naphtho[1,2-b]pyran-6-one, and their derivatives were prepared via the palladium mediated aryl-aryl coupling reaction of aryl ortho-halobenzoate. The short step synthesis of arnottin I (1) was achieved by this method.

Catalytic asymmetric synthesis of halenaquinone and halenaquinol

A catalytic asymmetric synthesis of halenaquinone (1) and halenaquinol (2) has been achieved using an asymmetric Heck reaction or a cascade Suzuki cross-coupling and an asymmetric Heck reaction as a key step. This synthesis also features the one-pot construction of a unique pentacyclic ring system from a tricyclic system using palladium chemistry. Moreover, the use of Ph3As as an achiral ligand has been found to enhance both the cascade Suzuki cross-coupling and also the Heck reaction to a synthetically useful extent.